https://www.islandsothebysrealty.com/blog/ Learn more about the Maui real estate market, new listings, market trends, and more, with an emphasis on Wailea, Kapalau, Upcountry, Makena, Kaanapali, and more. https://www.islandsothebysrealty.com/blog/kapalua-canvases-and-kula-nights-august-on-maui.html https://www.islandsothebysrealty.com/blog/kapalua-canvases-and-kula-nights-august-on-maui.html leads@islandsothebysrealty.com (Island Sotheby's International Realty) August on Maui moves at its own unhurried pace — obon drums echo from Lahaina to Lānaʻi, Upcountry ropers dust off their saddles, and our own Island Sothebys International Realty Kapalua office has a new artist in residence filling the space with color. Heres where to find the months best gatherings, from a Friday night town party to an evening with a Grammy-winning songwriter. Jules Trowbridge, Artist in Residence at Island Sothebys Kapalua Mondays 9:00 am 1:00 pm & Fridays 2:00 5:00 pm, throughout August Island Sothebys International Realty, Kapalua office Our Island Sothebys International Realty Kapalua office has a new artist in residence this month: Maui fine artist Jules Trowbridge, known for bold, emotionally expressive acrylic and oil work inspired by the islands. Jules has set up her easel right in our newly opened Kapalua Drive office, filling the space with color and giving the community a reason to stop by beyond real estate. Take a look through Jules Trowbridges portfolio before you go, and youll have a good sense of the color and movement waiting for you in person. Maui Obon Season: August Bon Dances FriSat, August 1429, 2026 Lahaina Community Bon Dance (Lahaina Hongwanji, Lahaina Jodo & Lahaina Shingon) — Fri, Aug 14, 59 pm, 12 Ala Moana St., Lahaina Kula Shofukuji Mission — Sat, Aug 15, service 5 pm / dance 7 pm, 113 Puanani Pl., Kula Pāʻia Rinzai Zen Mission — Sat, Aug 22, service 6 pm / dance 7 pm, 120 Alawai Rd., Pāʻia Lānaʻi Hongwanji Mission — Fri, Aug 28 service only / Sat, Aug 29 dance only, 7 pm, 1364 Frasier Ave., Lānaʻi City Obon season carries into August with temple dances honoring loved ones and embracing gratitude, each one built around taiko drumming, lantern light, and community food booths. Find the full rundown, including which temples serve dinner before the dancing starts, at the full 2026 Maui Bon Dance schedule. Photo courtesy of ProArts Playhouse ProArts Playhouse August Lineup Throughout August 2026 Azeka Plaza Makai, Kihei Kaulike Pescaia Good Fun Album Release Concert — Aug 1, 7:30 pm Magic in Paradise (David Kuraya) — Aug 2, 9, 23 & 30, 2:00 pm Omi Tutu: Cool Waters — Aug 5, 6:30 pm The Jazz Maui Modern Quintet — Aug 6, 7:30 pm John Cruz Island Style Series — Aug 12 & 26, 7:00 pm Sheryl Renee Cabaret Series presents DUETS — Aug 13, 7:30 pm Lo Wolf: Vocal Velvet — Aug 15, 7:30 pm Anthony Pfluke with Pohai and Stephen Henderson — Aug 20, 7:30 pm Amy Hānaialii: One Voice, One Guitar — Aug 21, 7:30 pm Free Range Comedy — Aug 22, 7:30 pm Kanekoa — Aug 28, 7:30 pm Lokahi Trio — Aug 29, 7:00 pm Spectacular Journeys: The Wizard of Oz in 3D — Aug 30, 2:00 pm Kiheis little theater packs an entire season into one month, swinging from an album release party to a magic show to an evening with Nā Hōkū Hanohano honoree Amy Hānaialii. Whether youre after music, comedy, or sleight-of-hand, theres a night for it on this stage. Browse ProArts Playhouses full August lineup and pick your night. Photo courtesy of The Ritz-Carlton Maui Kapalua Wine & Chef Series ft. Kristen Kish Saturday, August 8, 2026 · 5:30 8:30 pm The Ritz-Carlton Maui, Kapalua James Beard Award winner and Top Chef alum Kristen Kish headlines this intimate wine and chef dinner, pairing a tasting menu with the kind of sunset only Kapalua delivers. Its a 21-and-up evening, with tickets at $245 (or $215 for kamaʻāina). Reserve your seat at the Kapalua Wine & Chef Series before it fills up. Oskie Rice Arena Roping Weekend August 1516, 2026 Oskie Rice Event Center, Makawao The Hooey Jr. Patriot Super Qualifier — Sat, Aug 15, 9:00 am Maui ACTRA Roping — Sun, Aug 16, 10:00 am Upcountrys roping community turns out for back-to-back days at the Oskie Rice arena — young ropers chasing a spot on the national Hooey Jr. Patriot circuit on Saturday, then seasoned team roping pairs vying for the ACTRA National Finals on Sunday. Both days are free to watch from the stands, and theres no better excuse to spend a weekend up in Makawao. Get the details on the full roping weekend schedule. Photo courtesy of The Ritz-Carlton Maui Maui Songwriters Festival Summer Series ft. Kristian Bush & Payton Sullivan Friday, August 21, 2026 · 6:00 9:00 pm Alaloa Lounge, The Ritz-Carlton Maui, Kapalua Grammy-winning Sugarland co-founder Kristian Bush shares the stage with rising songwriter Payton Sullivan, opened by Hawaii artists Kamalani Kawaa and 94Tunez, for a night that blends Nashville storytelling with island sound against the Pacific backdrop. Its complimentary for resort guests, with just a $10 entertainment fee for everyone else. Details on the Maui Songwriters Festival Summer Series are worth a look if youre free that Friday. PC: J. Anthony Martinez Photography Maui Calls, 28th Annual Saturday, August 22, 2026 · 6:00 pm Maui Arts & Cultural Center, Kahului The MACCs signature gala leans into a nostalgic, old-Hawaii theme for its 28th year, pairing award-winning wines with dishes from Mauis top chefs and a silent and live auction stacked with one-of-a-kind island experiences. This is a night the whole community shows up for, knowing the funds raised will keep arts and culture alive on Maui all year long. Tickets and details for this years Maui Calls gala are live now. Kīhei 4th Friday Town Party Friday, August 28, 2026 · 6:00 9:00 pm Azeka Shopping Center, Kīhei The largest of Mauis Friday Town Parties fills both sides of Azeka with live music, food trucks, a keiki zone, and local vendors, closing out the month the way South Maui always does. Bring the whole family and plan to stay past sunset. See the Maui Friday Town Parties schedule for parking and vendor info. 2026 Huliau Food & Film Festival Saturday, August 29, 2026 · Evening Kapuakukui Farm, Kula Maui Huliau Foundations farm-to-table benefit moves to a beautiful new outdoor setting at Kapuakukui Farm this year, with sunset and ocean views over Upcountry, chef stations from Mauis top culinary talent, live music, hula, and student-produced films spotlighting the Kula moku. Its BYOB, with reserved tables for eight at $925 or Mix & Mingle passes at $75 per person, and every dollar raised supports Huliaus environmental education programs for Maui youth. Get the Huliau Food & Film Festivals ticket options before seats fill up. Photo courtesy of Pacific Cancer Foundation Battle of the Badges: MPD vs. MFD Softball Saturday, August 29, 2026 · 4:00 10:00 pm Ichiro Iron Maehara Baseball Stadium, Wailuku Maui Police and Maui Fire face off in a friendly softball showdown that kicks off the 2026 Battle of the Badges campaign benefiting Pacific Cancer Foundation. Its a family-friendly evening with food, refreshments, and official campaign merchandise on hand, marking the start of a two-month fundraising push that carries into September and October in support of Maui County families facing cancer. Get the full rundown on the Battle of the Badges event page. Thats the month, Maui — from a bon dances last drumbeat to a brand-new easel in Kapalua. Get out and catch a few of these while the islands at its August best. ]]> Tue, 28 Jul 2026 11:19:00 -1000 https://www.islandsothebysrealty.com/blog/the-soundtrack-of-south-maui-where-to-find-live-music-across-wailea-kihei-makena.html https://www.islandsothebysrealty.com/blog/the-soundtrack-of-south-maui-where-to-find-live-music-across-wailea-kihei-makena.html mapuanamarie@gmail.com (Mapuana Andrade)   Photo: Musician, Sunny Kalama South Maui has always had a rhythm of its own. Maybe its the sound of waves rolling into the shoreline, the golden glow of sunset over the ocean, or the way island life naturally slows people down enough to enjoy the moment.  One of the many perks of living in South Maui is that live music is never far away. Whether youre looking for a sunset cocktail with a view, a casual evening with local food and island tunes, or a special cultural experience, there are plenty of ways to enjoy the sounds of Maui. Here are some favorite places to experience live music in South Maui. Monkeypod Kitchen | Wailea A longtime South Maui favorite, Monkeypod Kitchen in Wailea is the perfect spot to enjoy local music, island-inspired dining, and one of Mauis most iconic Mai Tais. With open-air seating, ocean views, and a lively atmosphere, its a place where you can easily settle in for an afternoon or evening. Live music is offered daily, with performances typically scheduled around 12:00 p.m., 3:00 p.m., and 6:30 p.m. The lineup changes regularly and features talented Maui musicians including Sunny Kalama, Mike Stills, Elua, and many more. Guests can check their live music calendar for the latest schedule. Beyond the music, Monkeypod is known for its craft cocktails, 36 craft beers on tap, wood-fired pizzas, fresh day boat fish, and signature desserts like their famous cream pie. Their daily happy hour from 3:30 p.m. to 5:00 p.m. includes drink specials on draft beers, wine, and cocktails, along with food specials. Open daily from 11:00 a.m. to 10:00 p.m., Monkeypod Kitchen is a must-stop for anyone looking to experience the flavors, sounds, and easygoing energy of South Maui. Lehua Lounge at Andaz Maui | Wailea For a more elevated evening experience, Lehua Lounge at Andaz Maui offers live music in one of Waileas most beautiful resort settings. Located steps from the beach, this open-air lounge features live entertainment on select evenings, currently including performances Monday, Wednesday, Friday, and Saturday from 6:00 p.m. to 9:00 p.m. With handcrafted cocktails, island-inspired bites, and the peaceful atmosphere of the Andaz grounds, its an ideal spot for enjoying live music without the crowds. Lobby Lounge at Four Seasons Resort Maui | Wailea Theres something timeless about enjoying live music at a Maui resort lounge, and the Lobby Lounge at Four Seasons Maui delivers exactly that. Located in the heart of the resort with sweeping ocean views, the lounge features live music nightly from 5:30 p.m. to 10:30 p.m. Guests can enjoy a craft cocktail, pupus made with fresh local ingredients, sunset views, and the sounds of talented island musicians throughout the evening. The lounge also features a nightly hula performance and sunset torch lighting, creating a true sense of place. Nalus South Shore Grill | Kihei For a more casual, local-style evening, Nalus South Shore Grill is a must. Known for its relaxed atmosphere, island-inspired menu, and commitment to featuring local musicians, Nalus offers live music every evening. Their weekly lineup features a variety of Maui entertainers, with performances generally beginning around 7:00 p.m. (and some earlier sets throughout the week). The schedule changes regularly, so guests are encouraged to check their current lineup before visiting. Beyond the music, Nalus is a favorite for local comfort food, cocktails, breakfast, and dishes like fresh poke, island-style favorites, and their popular chicken and waffles. Wailea Wednesdays at The Shops at Wailea | Wailea For a family-friendly way to enjoy live entertainment, check out Wailea Wednesdays at The Shops at Wailea. This weekly live music series features local entertainers and takes place on the lower level of The Shops at Wailea every Wednesday. Its an easy way to enjoy island music while strolling through shops, grabbing a bite, or spending an evening in one of Waileas most popular gathering places. Special performances often feature well-known Maui musicians, including Kayson Gomes, a Maui-based singer-songwriter and 2017 Falsetto winner, who will perform on July 22 from 4:30 p.m. to 6:00 p.m. The Shops at Wailea also hosts a Polynesian cultural performance every Tuesday from 5:30 p.m. to 6:30 p.m., featuring Hawaiian hula and dances from across Polynesia. Maui Ocean Center: Mele, The Hawaiian Music Experience | Maalaea For a deeper connection to Hawaiʻis musical heritage, Mele: The Hawaiian Music Experience at the Maui Ocean Center offers a truly unique experience. Held inside the Sphere Theater, this immersive 360-degree visual and musical journey celebrates the history, stories, and traditions of Hawaiian music. The experience combines breathtaking visuals of Hawaiʻis landscapes and ocean environment with live performances from talented island musicians. The show takes place Tuesday evenings, with check-in at 5:30 p.m. and the performance beginning at 6:00 p.m. Led by renowned Maui entertainer Eric Gilliom, the experience brings together powerful storytelling, Hawaiian classics, and the spirit of aloha. Local musician Vince Esquire has also been part of this special musical experience, helping showcase the depth and talent of Mauis creative community. General admission is approximately $100 per person, with kamaʻāina discounts available. Photo: Musician, Dwight of Kai Kanani  Kai Kanani Sunset Cruise | Makena For something a little different, take your live music experience out on the water. Kai Kanani offers sunset sailing adventures departing from Maluaka Beach in Makena, just south of the Wailea resorts. Their two-hour sunset cruise combines ocean views, live music, food, and drinks for a memorable Maui evening. Guests can enjoy a three-course appetizer experience, an open bar, a sunset sparkling wine toast, and live music performed aboard the boat as you cruise along Mauis south shore. Its a beautiful way to experience the coastline from a completely different perspective. Photo: Musician, Kevin Coloso Maui Brewing Company | Kihei For a casual South Maui evening filled with local flavor, Maui Brewing Company in Kihei is a favorite gathering spot for both residents and visitors. With brewery-to-table dining, outdoor garden seating, a relaxed beer garden atmosphere, and games to enjoy, its the perfect place to settle in with friends and family. Guests can enjoy a rotating selection of craft and specialty beers on tap, along with island-inspired dishes and classic favorites. Happy hour runs daily from 3:00 p.m. to 5:00 p.m. with specials on draft beers, cocktails, and pizza. Live music and special events are offered regularly, featuring talented Maui musicians including Ikaika Cosma, Kevin Coloso, Sunny Kalama, Peter & Josh, M.I.G., and more. Entertainment schedules vary, so checking their event calendar is the best way to plan your visit. Open daily from 11:00 a.m. to 10:00 p.m., Maui Brewing Company is an easy spot to enjoy a local beer, great food, and the sounds of Mauis talented music community. South Shore Tiki Lounge | Kihei For a fun, laid-back night out in Kihei, South Shore Tiki Lounge brings together island vibes, live music, great food, and a little nightlife energy. Located in Kihei Kalama Village across from the whale statue and Kalama Park playground, this local favorite offers a relaxed open-air setting with lanai seating, tropical cocktails, and a lively atmosphere. Live music is featured daily from 4:00 p.m. to 6:00 p.m., with DJs and dancing on select nights from 9:00 p.m. to midnight. The kitchen is open daily from 11:00 a.m. to 10:00 p.m., and the bar stays open until midnight, making it a great spot for everything from afternoon pau hana to a late-night outing. The menu features island-inspired favorites, including pupus, coconut shrimp, tiki fries, burgers, pizza, and creative cocktails. With a kid- and dog-friendly atmosphere, outdoor seating, and a regular lineup of local entertainers, South Shore Tiki Lounge captures the playful, community-focused energy that makes Kihei so much fun. Recognized locally for favorites like Best Pizza, Best Pau Hana, and Best Bar on Maui, its an easy place to add to your South Maui music lineup.   From intimate lounges to oceanfront sunsets, live music is woven into everyday life in South Maui. Its one of the things that makes this community feel so special: the ability to slow down, gather with friends, and enjoy talented local artists surrounded by the beauty of the island. Whether youre a longtime resident or discovering Maui for the first time, theres always another song waiting to be heard. ]]> Wed, 08 Jul 2026 09:54:00 -1000 https://www.islandsothebysrealty.com/blog/rodeo-dust-ribbon-cuttings-and-reggae-mauis-july-lineup.html https://www.islandsothebysrealty.com/blog/rodeo-dust-ribbon-cuttings-and-reggae-mauis-july-lineup.html leads@islandsothebysrealty.com (Island Sotheby's International Realty) Blessing for Front Street Railing & Walkway Project Wed, Jul 1, 2026, 34pm 700 block of Front Street, Lahaina (between Lahainaluna Rd & Dickenson St) Lahaina marks another milestone in its wildfire recovery with a community blessing for the newly completed Front Street Railing and Walkway Project. The work rebuilt roughly 1,450 feet of sidewalk and 700 feet of stainless-steel, ipe-topped railing along the makai side of Front Street, plus new light poles, benches, bike racks, and planters filled with milo trees and ʻākai ground cover. Mayor Richard Bissen has called it another step toward bringing commercial life and jobs back to the heart of town. The block remains closed to through traffic, so plan to park at the Lahaina Aquatic Center — full project details and shuttle info explain how the 1:30pm shuttles work. Maui County Free Movie Nights — Park & Recreation Month Jul 124, 2026 · most screenings begin at sunset (times noted where they differ) July 1 East Maui: Hāna Ball Park, 7pm July 2 West Maui: Lahaina Civic Center Amphitheater, sunset July 10 South Maui: Kamaʻole III Beach Park (south end), sunset July 10 Molokaʻi: Kaunakakai Gymnasium, 7pm July 16 West Maui: Lahaina Civic Center Amphitheater, sunset July 17 Upcountry: Mayor Eddie Tam Memorial Complex, Makawao, sunset July 22 Lānaʻi: Lānaʻi Park Complex Gymnasium, 6:30pm July 24 Central Maui: War Memorial Complex, Wailuku, sunset Every July, Maui Countys Department of Parks and Recreation marks National Park and Recreation Month with a free outdoor movie circuit that touches all three islands. Bring snacks, a blanket or low-back chairs, and settle in under the stars — these screenings are designed as a simple, free way for neighborhoods to gather, no ticket or RSVP needed. Titles havent been announced yet, but the county typically adds them to its movie titles and updates page closer to each date, so its worth a check back before you head out. ProArts Playhouse July Concert Series Throughout July ProArts Playhouse, Kihei John Cruz — Jul 1, 15 & 29 Streetlight Cadence — Jul 3 Magic in Paradise (David Kuraya) — Jul 5, 12, 19 & 26 Jazz Organ Summit — Jul 10 Kalani Peʻa: Eia Lā 10-Year Anniversary Concert — Jul 11 R.E. Metoyer Blues, Rock & Soul Revue — Jul 14 Brock Ambrose — Jul 17 Tempa & Naor — Jul 18 Amy Hānaialiʻi: One Voice, One Guitar — Jul 26 South Mauis intimate 110-seat listening room stays busy all month, anchored by Nā Hōkū Hanohano winner John Cruzs recurring Island Style Series and David Kurayas weekend sleight-of-hand show, Magic in Paradise. The months two marquee nights both lean Hawaiian: four-time Grammy winner Kalani Peʻas Eia Lā concert on July 11 marks a decade since his first recording, and six-time Grammy nominee Amy Hānaialiʻi closes things out on July 26 with just her voice and guitar, the same year shes being honored in the Women Songwriters Hall of Fame in Washington, D.C. Beyond those two, the lineup ranges from organ jazz to R&B newcomer Brock Ambrose to the blues-rock-soul revue of R.E. Metoyer, keeping a steady pulse of live music going without ever leaving Kihei — the full July lineup and tickets are posted on their site. 4th of July Makawao Stampede Bull Bash Fri, Jul 3 (gates 3pm) · Championship Rodeo Sun, Jul 5 (doors 11am) Oskie Rice Event Center, Makawao Mauis paniolo heritage takes center stage upcountry this weekend, with nearly 250 competitors from across the Pacific battling for the buckle in bull riding, barrel racing, and team roping. The Friday night Bull Bash brings a preshow concert and fan field fun, while Sundays championship performance crowns the seasons All Around Cowboy and Cowgirl. This year also marks 110 years of Kaonoulu Ranch, the family operation thats kept this tradition alive for generations — full details and tickets are at Maui-Rodeo.com. Paddle Imua Sun, Jul 12, 2026 · race starts 1pm, ʻOhana Festival 1:305pm Maliko Gulch to Kanahā Beach Park, Kahului The legendary Maliko Downwinder draws paddlers of every discipline — SUP, OC1, OC2, OC6, surf ski, foil, and wing — down Mauis north shore for a cause close to home. Every entry supports Camp Imua, a recreational camp for Maui County keiki with special needs, and the day wraps with an ʻOhana Festival at the finish line where racers are greeted by the campers themselves. Its open to the public, with music, food vendors, and relay races for the whole family — race details and registration are up now. Young Artmakers 2026 Sessions run Jul 1417 and Jul 2124, 2026 Schaefer International Gallery, MACC, Kahului The MACCs summer visual arts program returns with five hands-on sessions for keiki ages 5 to 18, led by teaching artists in collagraph printing, mask making, papermaking, and copperplate etching. Each four-day session includes a guided tour of the gallerys summer exhibit, Through the Lens. Space is limited and sessions tend to fill quickly, so check session details sooner rather than later. Lahaina Homecoming Jul 1719, 2026 — Palengke Night Fri 510pm, Paʻūpili & Hoʻolauleʻa Sat 10am10pm, Homecoming Celebration Sun 510pm Front Street, Lahaina (Prison St to Dickenson St) Front Street welcomes the community home for a three-day gathering built on healing, storytelling, and reconnection, nearly three years after the 2023 wildfire. Cultural performances, vendor markets, and resource sharing run across the weekend, with Hawaiian Airlines sponsoring flights home for members of the Lahaina diaspora through a companion program. Mayor Richard Bissen has called it an important milestone in the towns recovery, and the full schedule is online now. Rebel Souljahz: Back 2 My Roots Tour Sat, Jul 18, 2026, 7pm (gates 6pm) Alexander & Baldwin Amphitheater, MACC, Kahului Island reggae powerhouse Rebel Souljahz returns to the MACC stage after a two-year touring hiatus, bringing the soulful, roots-deep sound thats made them staples of the genre since their start in Waipahu. The general admission show is named for their latest single, and patrons are asked to bring a non-perishable item for the Maui Food Bank as part of the MACCs ongoing wildfire recovery support. Get there early for the lawn, and find tickets and details before the amphitheater fills in. Deep Wisdom: A Film Journey Underwater with the Humpback Whales Thu, Jul 23, 2026, 7:30pm ProArts Playhouse, Kihei Whale Wise Productions, a Maui-based crew of ocean lovers and naturalists, premieres this 30-minute underwater film right where so many of these whales pass each winter. Its a quieter, more contemplative kind of summer night out, built for anyone whos ever watched a humpback breach from shore and wanted to know more. A filmmaker Q&A typically follows screenings like this one, and tickets are available now. Ali Wong Live ThuFri, Jul 3031, 2026, 7pm Castle Theater, MACC, Kahului Emmy and Golden Globe winner Ali Wong brings her stand-up back to the Castle Theater for two nights, fresh off directing credits and her acclaimed turn in Beef. Known for unflinching, hilarious specials like Baby Cobra and Hard Knock Wife, shes promised mature subject matter and a no-holds-barred set. Food and drinks are available in the Yokouchi Pavilion starting at 5pm before each show, and tickets and showtimes are on sale now. From rodeo dust to a long-awaited blessing on Front Street, July gives plenty of reasons to leave the beach chair behind for an evening. Aloha, and see you out there. ]]> Wed, 24 Jun 2026 14:25:00 -1000 https://www.islandsothebysrealty.com/blog/built-to-last-why-todays-luxury-buyers-are-choosing-homes-for-the-long-game.html https://www.islandsothebysrealty.com/blog/built-to-last-why-todays-luxury-buyers-are-choosing-homes-for-the-long-game.html leads@islandsothebysrealty.com (Island Sotheby's International Realty) Theres a shift happening in the way people think about their next home — and its not about square footage or finishes. Its about time. Not how long the escrow takes. How long they plan to stay. How well a home will serve them not just this season, but a decade from now, and the decade after that. The luxury buyer of 2026 isnt just acquiring property. Theyre making a decision about how they want to live — and for how long. Sothebys International Realtys 2026 Mid-Year Luxury Outlook, released this month, puts a name to what weve been watching unfold here on Maui: longevity is the new luxury. Wellness infrastructure, health-centered design, and the ability to age gracefully in a place you love are now primary drivers for high-net-worth buyers. Nearly 38 of real estate professionals working in the $10 million-and-above segment report that aging in place has become a growing factor in buyer decisions. Wellness real estate has more than doubled in the last five years and is projected to surpass $1.1 trillion by 2029. What does that look like, in practice? It looks a lot like Maui. The island that already got it right Long before longevity living became a trend report headline, Maui had built an environment around it without trying. Trade winds that move through an open home like a natural air filtration system. Ocean views shown by science to lower cortisol. Walking paths to beaches and restaurants that make a car optional. A pace of life that isnt aspirational — its structural. The properties that embody this the most completely tend to cluster in two places: Kapalua on the West Side, and Wailea-Makena in the South. Kapalua: a resort community built for the long haul Kapalua was designed as a complete world. Thats not marketing language — its architecture. The resort encompasses world-class golf, the Montage Kapalua Bay, coastal walking paths, protected beaches, and a community fabric that holds together whether youre visiting for two weeks or settled in for two decades. 52 Ironwood Lane — $5,950,000 Beautifully renovated and positioned directly on the bluff above Honolua Bay, this three-bedroom residence at the Ironwoods captures sweeping Pacific views alongside the ease of single-level, resort-amenity living — the kind where maintenance is managed, the grounds are pristine, and the day is yours. For buyers who want to simplify without sacrificing, this is what that looks like. Ocean view · Single-level · Resort amenities · Gated community · Coastal walking paths · Golf access 1 Bay Drive, Residence 1103 — $6,995,000 First-floor, single-level, over 2,900 square feet — with Kapalua Bay at your doorstep and year-round sunsets framed in every west-facing window. Its a home designed to be inhabited deeply, daily, without effort. Direct oceanfront · Single-level · First-floor access · Year-round sunsets · Beach access · Golf access 1008 Sunset Place — $5,195,000 A refined four-bedroom residence at the top of the ridge puts the full drama of the Pacific in view — gentle trade winds, glowing late afternoons, the kind of daily beauty that research increasingly connects to psychological wellbeing and quality of life. These arent coincidences of real estate. Theyre features of a life well-designed. Ocean view · Year-round sunsets · Trade wind ventilation · Gated community · Golf access · Walking paths   Wailea-Makena: where the south shore delivers Wailea has long attracted buyers who arrive for the sun and stay for the lifestyle. What the best properties here offer is a specific combination that longevity-minded buyers are prioritizing: low-maintenance luxury, walkable resort amenities, and the particular calm that comes from living at the edge of the sea. 17 Maluaka Place, Lot 5 — $9,950,000 A rare ¾-acre homesite within the gated Maluaka enclave in Makena — the opportunity to build exactly what you need, from the ground up, in one of Mauis most revered coastal neighborhoods. For buyers who know how they want to live at this stage and want a home engineered around that vision, land like this is the starting point. Ocean view · Build to suit · Gated enclave · Coastal setting · Near beach access · Sunset exposure 137 Holomoana Way, 4A — $2,900,000 A fully furnished, turnkey ocean-view residence with contemporary finishes and indoor-outdoor flow that makes every room an extension of the island itself. This is the home you move into and exhale. Contemporary design, thoughtfully curated, ready to grow into every chapter that follows. Ocean view · Fully furnished · Indoor-outdoor flow · Turnkey ready · Walkable to beach · Resort pool access 24 Kai Malu 3-A — $2,550,000 For those drawn to whats newest in the South Maui corridor, Laʻi Loa at Wailea Hills delivers it. Purchased new in 2024 and offered fully furnished, this two-bedroom ocean-view residence sits within one of South Mauis most recently completed luxury communities — modern design, seamless indoor-outdoor living, and the kind of low-friction lifestyle that lets you focus on what actually matters. Ocean view · Fully furnished · Newly built (2024) · Indoor-outdoor flow · Turnkey ready · Walkable to amenities The question worth asking Every luxury buyer eventually arrives at a version of the same question: not just where do I want to be, but how do I want to be — and for how long? The longevity lens reframes that question in a useful way. It asks: does this home support the life Im moving toward, not just the one I have right now? Is it designed for ease as well as beauty? Does it connect me to things that genuinely restore me — ocean, nature, community, movement, quiet? On Maui, the answer is almost always yes. This island has an extraordinary habit of meeting people where they are and growing with them. The buyers who figure that out tend to arrive and decide, often with some surprise, that theyre not leaving. Thats intention meeting place. Its longevity planning at its finest. ]]> Mon, 15 Jun 2026 09:02:00 -1000 https://www.islandsothebysrealty.com/blog/what-mauis-new-tax-rates-mean-for-property-owners-in-2026-2027.html https://www.islandsothebysrealty.com/blog/what-mauis-new-tax-rates-mean-for-property-owners-in-2026-2027.html leads@islandsothebysrealty.com (Island Sotheby's International Realty) The County of Maui adopted new real property tax rates effective July 1, 2026. Whether you own a primary home, an investment property, or a vacation rental, heres what changed from the prior year — and what it means for your bottom line. The Big Picture The FY202627 rate schedule reflects some meaningful adjustments across several categories, with tier breakpoints shifting alongside the rates in key classifications. The Countys direction is consistent: reward long-term housing and owner-occupancy, apply greater pressure on investment properties and short-term rentals at the upper end. Rate Changes by Category Rates are per $1,000 of net taxable assessed value. FY202526 rates were effective July 1, 2025 (Resolution No. 25-88); FY202627 rates are effective July 1, 2026 (Resolution No. 26-69). Classification FY202526(eff. July 1, 2025) FY202627(eff. July 1, 2026) Change Owner-Occupied (FY2627 breakpoints: up to $1.5M | $1.5M$4.5M | over $4.5M) Tier 1 $1.65 (up to $1.3M) $1.65 (up to $1.5M) — Same rate, wider tier Tier 2 $1.80 ($1.3M$4.5M) $1.80 ($1.5M$4.5M) — No change Tier 3 $5.75 (over $4.5M) $5.00 (over $4.5M) ▼ Lower Non-Owner-Occupied (FY2627 breakpoints: up to $1M | $1M$2.5M | over $2.5M) Tier 1 $5.87 (up to $1M) $6.25 (up to $1M) ▲ Higher Tier 2 $8.60 ($1M$3M) $9.00 ($1M$2.5M) ▲ Higher Tier 3 $17.00 (over $3M) $17.00 (over $2.5M) ▲ Same rate, lower threshold TVR / Short-Term Rental Home (STRH) (FY2627 breakpoints: up to $900K | $900K$3M | over $3M) Tier 1 $12.50 (up to $1M) $13.00 (up to $900K) ▲ Higher Tier 2 $14.00 ($1M$3M) $15.00 ($900K$3M) ▲ Higher Tier 3 $15.55 (over $3M) $17.00 (over $3M) ▲ Higher Long-Term Rental (FY2627 breakpoints: up to $1.5M | $1.5M$3M | over $3M) Tier 1 $2.95 (up to $1.3M) $2.90 (up to $1.5M) ▼ Lower rate, wider tier Tier 2 $5.00 ($1.3M$3M) $5.00 ($1.5M$3M) — No change Tier 3 $8.50 (over $3M) $8.50 (over $3M) — No change Commercialized Residential (FY2627 breakpoints: up to $1.5M | $1.5M$3M | over $3M) Tier 1 $2.00 (up to $1M) $2.25 (up to $1.5M) ▲ Higher rate, wider tier Tier 2 $3.00 ($1M$3M) $3.50 ($1.5M$3M) ▲ Higher Tier 3 $10.00 (over $3M) $10.00 (over $3M) — No change Non-Tiered Categories Apartment $3.50 $3.50 — No change Hotel & Resort $11.80 $11.80 — No change Time Share $14.70 $14.90 ▲ Higher Agricultural $5.74 $5.74 — No change Conservation $6.43 $6.43 — No change Commercial $6.05 $6.05 — No change Industrial $7.05 $7.05 — No change Sources: Maui County Resolution No. 26-69, FD2 (FY202627) and Resolution No. 25-88, FD2 (FY202526). Rates per $1,000 of net taxable assessed value. Five Things Property Owners Should Know 1. Owner-occupied luxury properties get a rate reduction The owner-occupied Tier 3 rate actually dropped this year, from $5.75 to $5.00 per $1,000. The Tier 1 breakpoint also widened from $1.3M to $1.5M, meaning more homeowners qualify for the lowest rate. For mid-range primary homeowners, rates hold steady — this is one of the more taxpayer-friendly categories in the new schedule. 2. Non-owner-occupied properties are being taxed harder across all tiers Every tier of the non-owner-occupied classification saw either a rate increase or a tightened threshold. Tier 1 rose from $5.87 to $6.25; Tier 2 increased from $8.60 to $9.00. Notably, the Tier 3 threshold dropped from $3M to $2.5M — meaning properties that previously fell in Tier 2 may now be taxed at the $17.00 rate. Investment and second-home owners should verify where their assessed value falls relative to the new breakpoints. 3. Short-term rentals face increases across every tier TVR-STRH rates climbed in all three tiers — from $12.50/$14.00/$15.55 to $13.00/$15.00/$17.00. The Tier 1 threshold also tightened from $1M to $900K, pushing more properties into higher brackets. If you operate a permitted vacation rental on Maui, your tax liability is going up regardless of assessed value. 4. Long-term rentals continue to be the most favorable non-owner-occupied classification The long-term rental category saw a small Tier 1 rate decrease (from $2.95 to $2.90) and a wider Tier 1 threshold (up to $1.5M vs. $1.3M). Upper tiers hold steady. This continues the Countys clear policy signal: landlords who commit to 12-month-plus leases for local residents are rewarded with significantly lower tax rates than those who rent short-term. 5. Tier breakpoints matter as much as the rates themselves Nearly every tiered category saw adjusted breakpoints this year — not just rate changes. A property sitting near a threshold could move into a different tier even with no change in assessed value, meaningfully shifting the tax bill. Its worth checking your current assessed value at mauipropertytax.com against the new thresholds before your next bill arrives. A note on assessed value: These rates apply to net taxable assessed value — not purchase price or current market value. Your home exemption, if active, reduces the portion of your assessed value that is taxed. If you occupy your property as a principal residence and havent filed for a home exemption, the difference in rate between owner-occupied and non-owner-occupied is substantial — its worth doing. Frequently Asked Questions When do the new rates take effect? The new rates are effective July 1, 2026, the start of Maui Countys fiscal year 202627. Tax bills issued for FY202627 will reflect these updated rates. How do I know which classification my property falls under? Classification is based on the propertys highest and best use, with specific exceptions for home exemptions, long-term rental exemptions, and permitted vacation rentals. You can look up your current classification at mauipropertytax.com or by contacting the Maui Real Property Assessment Division at 808-270-7297. What is the home exemption and do I qualify? The home exemption reduces the assessed value on which youre taxed and qualifies your property for the owner-occupied rate — substantially lower than non-owner-occupied. Its available to owners who use the property as their principal residence. You must file for it; it is not applied automatically. My condo is in a resort area — does that automatically make it TVR-STRH? Not necessarily. Classification depends on how the property is actually used and permitted, not just its location. If your condo is rented short-term without a home exemption or qualifying long-term rental exemption, it will typically fall into TVR-STRH or non-owner-occupied. If you have an active home exemption and a permitted STRH, it may qualify as commercialized residential — a very different rate. What qualifies as a long-term rental for tax purposes? A long-term rental is a dwelling unit rented to the same tenant for 12 consecutive months or more, and the property must have been granted a long-term rental exemption by the County. You cant simply claim the lower rate — the exemption must be applied for and approved. How do I calculate what Ill owe? The formula: (net taxable assessed value ÷ 1,000) × applicable rate. Net taxable value is your assessed value minus any exemptions. For tiered categories, each portion of value is taxed at its tiers rate — not the full value at the highest tier. The Countys How to Calculate Real Property Taxes guide walks through examples. Can I appeal my assessed value? Yes. Property owners can appeal to the Board of Review, typically within 30 days of receiving your assessment notice. If you believe your property has been overvalued or misclassified, consult with a real estate professional or tax advisor familiar with Mauis assessment process. Where can I get more information or verify my current tax status? Search your property at mauipropertytax.com, call the Real Property Assessment Division at 808-270-7297, or visit the Department of Finance at 200 S. High St., Wailuku. Office hours are Monday through Friday, 7:45 AM to 4:30 PM. This post is for informational purposes only and does not constitute tax or legal advice. Rate information sourced from official Maui County resolutions. For questions about how these changes may affect your specific property, contact a licensed real estate professional or tax advisor. Have questions about buying or selling real estate on Maui? Contact Island Sothebys International Realty — our agents know this market inside and out. ]]> Fri, 12 Jun 2026 08:55:00 -1000 https://www.islandsothebysrealty.com/blog/island-sothebys-international-realty-agents-earn-2026-realtrends-verified-recognition.html https://www.islandsothebysrealty.com/blog/island-sothebys-international-realty-agents-earn-2026-realtrends-verified-recognition.html leads@islandsothebysrealty.com (Island Sotheby's International Realty) This year, eight Island Sothebys International Realty agents were independently recognized in the 2026 RealTrends Verified rankings, one of the real estate industrys most rigorous and respected performance benchmarks. Each ranking is earned through audited MLS transaction data, which means there is no self-nomination, no subjective panel, and no shortcut. You either did the work, or you didnt. Our agents did the work. What makes this recognition meaningful goes beyond the numbers. The agents recognized this year serve buyers and sellers across West Maui, Upcountry, and South Maui, working in markets as varied as the island itself, and sharing one thing in common: a genuine commitment to the people and places they serve. Leading the group is Courtney M. Brown, whose nearly $69 million in verified closed sales volume reflects years of trust built in the West Maui luxury market. Courtney is joined by fellow West Maui agents Shaun Pederson and Heidi E. Dollinger, whose combined work in Lahaina and the surrounding resort communities speaks to the enduring demand and deep expertise that defines this stretch of coastline. Together, their presence in the rankings underscores just how much buyers and sellers across West Maui rely on Island Sothebys International Realty when it matters most. In South Maui, Ryan MacLaughlin closed $31 million in verified sales volume, serving buyers and sellers across the Kihei corridor with steady, knowledgeable guidance. Truman T. Taoka added $21.37 million across 17.2 transaction sides, a volume of activity that reflects an agent in constant, trusted motion across price points and property types in one of Hawaiis most resilient real estate markets. Upcountry Maui tells its own story through Mino McLean, Renona Barrozo, and Debra Merle, three agents whose work reflects the singular character of the communities they serve. Based across Makawao, they collectively bring decades of experience to a market defined by ranchland estates, pastoral retreats, flower farms, and the unhurried rhythm of life above the clouds. Upcountry is not a market you can navigate from a distance. It rewards those who are genuinely rooted in it, and these three agents are exactly that. Taken together, this group closed well over $150 million in verified sales volume, a figure that reflects the culture of a brokerage that attracts and supports agents who are serious about their craft. Island Sothebys International Realty was also recognized as a RealTrends Verified Best Brokerage in 2026, with $354.82 million in total brokerage sales volume and 235 transaction sides at the national level. That recognition belongs to every corner of this team: agents, support staff, and most importantly, the clients who placed their trust in us and made every one of these transactions possible. To each of you, mahalo. Your confidence in our agents is not something we take lightly, and it is the foundation everything else is built on. We are proud of each of these agents, and deeply grateful to the communities that make this work possible. Maui is far more than a place we do business. It is home, and we take seriously the privilege of helping people find their place within it. Frequently Asked Questions What is RealTrends Verified? RealTrends Verified is one of the most respected independent ranking programs in the American real estate industry. It evaluates agent and brokerage performance based on audited MLS transaction data, meaning every ranking is confirmed through third-party verification rather than self-reported figures. Only agents who meet a minimum production threshold and submit verifiable transaction records are eligible for inclusion. How are RealTrends Verified rankings determined? Rankings are calculated using closed sales volume and transaction sides from a defined performance period. Agents submit their MLS data, which is then independently audited before any ranking is assigned. The process is designed to ensure that every agent listed has genuinely earned their place based on documented production. What does it mean for a brokerage to earn RealTrends Verified Best Brokerage recognition? A RealTrends Verified Best Brokerage designation is awarded to brokerages that meet verified volume and transaction thresholds at the national level. It reflects the collective production of the brokerages agent team and is considered one of the most credible indicators of a brokerages overall market performance and professional depth. ]]> Thu, 11 Jun 2026 16:53:00 -1000 https://www.islandsothebysrealty.com/blog/rooted-here-a-guide-to-upcountry-mauis-nurseries-and-gardens.html https://www.islandsothebysrealty.com/blog/rooted-here-a-guide-to-upcountry-mauis-nurseries-and-gardens.html leads@islandsothebysrealty.com (Island Sotheby's International Realty) Theres a particular kind of magic that happens when you drive up into Upcountry Maui. The air shifts — cooler, cleaner, laced with something green. The light softens. And suddenly youre in a place where things grow that have no business thriving at sea level: lavender, protea, ʻōhiʻa lehua, naupaka, fruit trees heavy with durian and jaboticaba. For those who live here, that relationship with the land is woven into daily life. For those considering a move Upcountry, its one of the quiet revelations that comes early — this is a place where you can actually grow things. Heres a guide to the nurseries and gardens that make it all possible, organized roughly from the north shore up to Kula. NatureWorks Nursery — Haiku NatureWorks is a family-owned fruit tree nursery, landscape and orchard care business, and educational resource center in Haiku — operating as a kind of living genetic seed bank for tropical fruit and nut trees, ornamental shrubs, and herbaceous perennials. Its founder, Jayanti, spent 15 years living and farming in Kīpahulu before bringing that deep knowledge to the north shore. Community members consistently describe it as the place to consult before planting anything — particularly on old pineapple soil — for varieties proven to produce in this specific environment. The specialty list alone is worth the drive: avocado, mango, citrus, durian, breadfruit, jaboticaba, surinam cherry, soursop, and more. They also carry one of Mauis most diverse hibiscus selections — rare collector varieties and unusual color forms not commonly found in big-box stores. Grafting classes and on-site land consultations are available by appointment. 70 West Kuiaha Rd, Haiku · Tue, Thu & Sat 10am4pm · natureworksnursery.com Haiku Nursery — Haiku The practical complement to NatureWorks — and conveniently right next door. Haiku Nursery is a full landscape nursery with a large inventory of palms, groundcover, and shrubs at competitive prices, with landscape advice and contract growing for landscapers. Where NatureWorks focuses on fruit trees and food plants, Haiku Nursery covers the full landscape spectrum — making the two together a natural one-stop for anyone building out a property. Call ahead to confirm hours before visiting. West Kuiaha Rd, Haiku · (808) 298-0477 · haikunursery.com PC: Forest & Kim Starr Hoʻolawa Farms — Haiku One of Mauis oldest native plant nurseries, rooted in a philosophy as much as a place. Hoʻolawa Farms began growing native plants in the late 1980s, primarily for landscaping. As interest in conservation grew, founder Anna Palomino became more deeply involved in propagation for restoration projects — drawn to the plants that most truly belong here, and that are, paradoxically, the rarest and most endangered. The name itself says it all: hoʻolawa means to supply. Today the farm produces over 100 different native species and offers workshops and tours for school groups and the general public. For anyone wanting to plant a garden that connects to the deeper history of this ʻāina — koa, ʻōhiʻa, pili grass, indigenous ferns — this is the place to start. Call ahead; hours are limited. 3 Kahiapo Pl, Haiku · (808) 575-5099 · hoolawafarms.com PC: Forest & Kim Starr Sacred Garden of Maliko — Makawao Unlike anything else on this list. The Sacred Garden of Maliko is simultaneously a vibrant botanical garden, a working nursery, a peace sanctuary, a retreat center, and a temple — housed within a 10,000-square-foot greenhouse, with orchids, tropical plants, succulents, water plants, palms, and anthuriums among its collection. Two walking labyrinths thread through the grounds; koi ponds and garden statuary tuck into the greenery. Admission is free, with complimentary tea and hot chocolate available, and picnic areas throughout. Run by the nonprofit Divine Nature Alliance, the Sacred Garden operates on a donation model — every plant purchase helps keep this extraordinary place open to the community. Whether you leave with a pot of succulents or simply an hour of stillness, it earns a stop. 460 Kaluanui Rd, Makawao · Daily 10am5pm · Free admission · sacredgardenmaui.com Kula True Value Hardware & Nursery — Kula Dont let hardware store undersell it. Kula Hardwares nursery earns consistent praise from neighbors — the most wonderful selection of plants, an excellent nursery for avid hobby gardeners and farmers eager to grow all the things. The selection deliberately goes beyond what national chains carry, with a better variety of trees, shrubs, and seeds suited to Upcountry conditions — ʻōhiʻa lehua, olive trees, vegetable starts, fruit trees, ornamental shrubs, and seasonal flowers. Its also a retail outlet for Maui Native Nurserys native Hawaiian plants, which means you can often pick up locally propagated koa, ʻōhiʻa, and other indigenous species without a wholesale appointment. For Upcountry residents, this is the anchor — the place you stop on a Saturday morning, talk story with people who know the land, and leave with your trunk full. 3100 Lower Kula Rd, Kula · MonFri 7am6pm, Sat 8am5pm · (808) 878-2551 · truevalue.com/find-a-store Kula Botanical Garden — Kula Established in 1968 by Warren and Helen McCord as a display for their landscape architecture business, Kula Botanical Garden has grown into a family-owned destination home to nearly 2,000 species of indigenous Hawaiian flora and fauna — with the showy protea as its crown jewel. Nine acres of paths connect collections ranging from bromeliads and alocasias to staghorn ferns and beyond. Every plant is labeled with its botanical name, common name, and country of origin. Its less a shopping nursery and more an education — a place to understand what Upcountrys elevation and soil can actually hold. Walk it slowly before you plant anything. Youll leave with a wish list and a much clearer sense of what thrives here. 638 Kekaulike Ave, Kula · Open daily 9am3:15pm · (808) 878-1715 · kbgmaui.com Aliʻi Kula Lavender — Kula Created by Agricultural Artist and Horticultural Master Aliʻi Chang, this 13.5-acre farm sits at roughly 4,000 feet on the slopes of Haleakalā — home to multiple varieties of lavender alongside olive trees, hydrangea, protea, succulents, and a wide variety of other plants, all thriving in Kulas Mediterranean-like climate. Several varieties bloom year-round, making it a garden that rewards a visit in any season. The farm offers guided walking tours, a gift shop stocked with lavender-infused products and baked goods, and sweeping views across both coastlines. For Upcountry residents, its a reminder of the microclimate gift youre living in — a place where lavender not only survives but flourishes, year after year, at the edge of a volcano. 1100 Waipoli Rd, Kula · aliikulalavender.com · (808) 878-3004 A Note on Growing Upcountry Elevations between 1,500 and 4,000 feet mean cooler nights, reliable rainfall, and a growing range that simply doesnt exist near the shore. Fruit trees bear heavily. Flowers bloom longer. Native plants find their footing. The nurseries and gardens listed here are staffed by people who understand this land intimately — and who are generous with that knowledge. Whether youre a longtime Upcountry resident expanding your garden or someone imagining what life might look like where lavender grows in the front yard and protea nods in the morning fog — this corner of Maui has room for roots.   Frequently Asked Questions Do I need an appointment to visit these nurseries? Most are open during their listed hours without one — but NatureWorks, Hoʻolawa Farms, and Sacred Garden of Maliko all benefit from a call before you make the drive. NatureWorks offers land consultations and grafting classes by appointment, and Hoʻolawas hours are limited. Sacred Garden is open daily, but availability for guided experiences can vary. Can I bring plants purchased Upcountry back to the mainland? It depends on the plant. Hawaii has strict agricultural export regulations, and the mainland has its own restrictions on importing tropical plants. Many nursery plants — particularly fruit trees, soil-rooted specimens, and certain tropicals — are not permitted for transport out of state. Check with the USDAs APHIS guidelines before you buy with travel in mind, and the nursery staff can usually advise you as well. Are there resources for gardening with native Hawaiian plants specifically? Yes — two places on this list are particularly strong starting points. Hoʻolawa Farms in Haiku propagates over 100 native species and offers workshops and tours. Kula True Value also serves as a retail outlet for Maui Native Nursery, so you can often pick up locally propagated koa and ʻōhiʻa without a wholesale appointment. Kula Botanical Garden, while not a plant-sale nursery, is an extraordinary educational resource — every specimen is labeled, and a slow walk through its nine acres will give you a clear picture of what this land can hold. ]]> Tue, 09 Jun 2026 13:59:00 -1000 https://www.islandsothebysrealty.com/blog/june-on-maui-parades-taiko-slack-key-and-nights-under-the-stars.html https://www.islandsothebysrealty.com/blog/june-on-maui-parades-taiko-slack-key-and-nights-under-the-stars.html leads@islandsothebysrealty.com (Island Sotheby's International Realty) June on Maui is a sweet spot — the island is lush from spring rains, the ocean has settled into its clearest summer blue, and the trade winds keep things comfortable well into the evening. It is also one of the busiest months on the cultural calendar, with free outdoor films, a royal parade, world-class concerts, and festivals that have been drawing locals and visitors alike for decades. Whatever brings you to the Valley Isle this month, there is something worth showing up for.     Starry Night Cinema: Zootopia 2 & Lilo and Stitch Fri June 5 & Sat June 6, 2026 · Gates 6:00 pm, Film 7:30 pm each night A&B Amphitheater Lawn / Castle Theater, MACC, Kahului The MACCs Starry Night Cinema series kicks off the month with two back-to-back free film nights the whole ʻohana will love. On Friday, Zootopia 2 brings Judy Hopps and Nick Wilde back for a new mystery — and on Saturday, the Hawaiʻi-set live-action Lilo & Stitch hits the lawn in a setting that feels almost too perfect: an open-air amphitheater on the very island where the story unfolds. Both evenings feature preshow music by Sunny Kalama, keiki activities before the film, and local food trucks to keep everyone fed. Pack a low-back beach chair or blanket, leave the cooler at home, and check out the full Starry Night Cinema series at the MACC for everything you need to know before you go.     Alice in Wonderland Ballet Alexander Academy of Performing Arts Saturday, June 6 (2:00 pm & 6:00 pm) & Sunday, June 7 (12:00 pm & 4:00 pm), 2026 Seabury Hall Aʻaliʻikuhonua Creative Arts Center, Makawao Upcountrys performance community shines this weekend as the Alexander Academy of Performing Arts brings Lewis Carrolls classic tale to life in full ballet form. Under the artistic direction of Amelia Nelson, the production is a whimsical, imaginative journey through Wonderland, with vivid costumes lovingly crafted by Jennifer Oberg and The Sewing Hui. Four performances over two days mean there is plenty of opportunity to catch this family-friendly celebration of dance, dedication, and community spirit. Read more about the Alice in Wonderland ballet by Alexander Academy and plan your afternoon in Makawao around it.     Maui Pops Chamber Players: Four Masters One Afternoon Sunday, June 7, 2026 · 2:004:00 pm Saint Anthonys Church, 1618 Lower Main Street, Wailuku If Friday and Saturday nights are for the movies, Sunday afternoon belongs to the music. The Maui Pops Chamber Orchestra takes over the beautiful Saint Anthonys Church in Wailuku for an intimate two-hour concert built around four of the repertoires most beloved works: Bachs Orchestral Suite No. 1, Shostakovichs Jazz Suite No. 1, Barbers Adagio for Strings, and Mozarts Horn Concerto No. 1, featuring soloist Mars Gelfo. It is the kind of afternoon that reminds you what live classical music can do in a room — not a concert hall, not a stadium, just musicians and an audience close enough to feel every note. Tickets are $30 for adults and $15 for students 18 and under; find details and purchase at Maui Pops Chamber Players.     ʻAha Niu: Maui Nui Coconut Celebration Festival Saturday, June 13, 2026 · 9:00 am3:00 pm Maui Nui Botanical Gardens, 150 Kanaloa Ave, Wailuku Niu — coconut — is one of the great Hawaiian canoe plants, carried across the Pacific by the ancestors who first settled these islands, and this free festival is a full day devoted to honoring everything it provides. At the Maui Nui Botanical Gardens, cultural practitioners, farmers, educators, and chefs will gather to offer hands-on workshops in weaving pāpale lau niu, making kaula niu cordage, cooking with coconut, and planting niu — alongside moʻolelo, food and craft vendors, and a free sprout giveaway while supplies last. Few events make the living culture of this ʻāina so tangible — come ready to get your hands into it. Space is limited, so complete your ʻAha Niu Coconut Festival registration before heading out.     Earth, Wind & Fire Sunday, June 14, 2026 · 7:00 pm (Gates 5:00 pm) Alexander & Baldwin Amphitheater, Maui Arts & Cultural Center, Kahului There are concerts, and then there are moments — and Earth, Wind & Fire at the MACC amphitheater under a Maui night sky is firmly the latter. The nine-time Grammy Awardwinning legends, whose catalog stretches from September to Shining Star and beyond, bring their full electrifying live show to Kahului for one night only, fresh off their Honolulu date the evening before. Get your tickets and details at Earth, Wind & Fire at the MACC before this one sells out.     Wailuku Film Festival WednesdaySunday, June 1721, 2026 · Closing screenings June 21, 3:009:30 pm at the MACC ʻĪao Theater & Naylor Theater, Wailuku; MACC Castle Theater, Kahului Wailukus historic downtown gets its moment in the spotlight this June as the inaugural Wailuku Film Festival brings five days of independent cinema, community conversation, and celebration of place to the Valley Isle. The festival spotlights four categories — Hawaiʻi, Indigenous Voices, Watersports, and Student Shorts — and pairs screenings with industry panels, workshops, and the late-night Fuzz Flix Fringe Fest for those who like their cinema a little more adventurous. The week culminates on June 21 at the MACC Castle Theater with audience-choice encore screenings of the Best of Hawaiʻi (3 pm) and Best Watersports (6 pm) films. Regular screening blocks are $15; closing night screenings are $20 — find the full schedule and tickets at the Wailuku Film Festival website.     Maui Songwriters Festival Summer Series: Grace Tyler June 19, 2026 · 6:009:00 PM Alaloa Lounge, The Ritz-Carlton Maui, Kapalua Rising country artist Grace Tyler brings her soulful songwriting and modern country sound to West Maui for an intimate evening at one of the islands most beautiful resort settings. Known for her viral hit My Mistake and debut EP Everything I Didnt Say, Tyler blends classic country roots with contemporary storytelling — the kind of performance that hits differently with the Kapalua coastline as your backdrop. The Maui Songwriters Festival Summer Series is first-come, first-served with a $10 entertainment fee per person — waived for hotel guests. Complimentary valet parking.     Nā Kamehameha Commemorative Pāʻū Parade & Hoʻolauleʻa Saturday, June 20, 2026 · Hoʻolauleʻa 9:00 am; Parade 9:45 am Parade: Maui Lani Parkway along Kaʻahumanu Avenue to Kahului Beach Road; Hoʻolauleʻa: Queen Kaʻahumanu Center Every June, Maui pauses to honor the legacy of Kamehameha I with one of the most moving community celebrations on the island. The Pāʻū parade — wahine on horseback draped in flowing island-color gowns, floral floats, and marching bands rolling down Kaʻahumanu Avenue — carries a dignity and beauty that never grows old, no matter how many times you have lined the route to watch. This years Hawaiʻi-wide theme, E Kū, E Hoʻololi — stand upright and change unpleasant conditions — feels as resonant as ever for a Maui community still finding its footing. After the parade, the hoʻolauleʻa continues at Queen Kaʻahumanu Center; read the full details and route information for the Nā Kamehameha Commemorative Pāʻū Parade on Maui Now, and plan to arrive early — Kaʻahumanu Avenue closes at 8:30 am.     Zenshin Daikos 27th Annual Taiko Festival Saturday, June 20, 2026 · 7:00 pm MACC Castle Theater, Kahului After the parade wraps up, the energy of June 20 keeps rolling right into the evening with Zenshin Daikos 27th Annual Taiko Festival at the Castle Theater. Since forming in 1999, this Maui-rooted nonprofit has shared the thundering, communal art of taiko with over 1,200 events across the islands and beyond, and this annual concert is always a highlight. Joining them this year are the prestigious Stanford Taiko — one of North Americas leading collegiate taiko groups — and the Naʻ Aliʻi Big Band, making for a lineup that is equal parts power and heart. Tickets are $20 for keiki and $38 for adults; pick yours up at the Zenshin Daiko Taiko Festival at the MACC before the show fills up.     45th Annual Kapalua Wine & Food Festival ThursdaySunday, June 2528, 2026 The Ritz-Carlton Maui, Kapalua Forty-five years in, the Kapalua Wine & Food Festival remains the gold standard of culinary celebrations in Hawaiʻi — and arguably in the entire country, as one of the oldest wine and food festivals in the United States. This milestone edition brings Food Network stars Maneet Chauhan, Antonia Lofaso, and the Voltaggio Brothers to the cliffs of Kapalua alongside world-class winemakers, intimate tasting seminars, and the grand tasting gala under the Maui sky. Whether you are a dedicated oenophile or simply someone who loves exceptional food paired with an exceptional view, the four-day experience is worth planning your June around. The full 45th Kapalua Wine & Food Festival lineup has all the details on individual events and multi-day passes.     35th Annual Kī Hōʻalu Guitar Festival Sunday, June 28, 2026 · 2:00 pm (Gates 1:30 pm) Alexander & Baldwin Amphitheater, Maui Arts & Cultural Center, Kahului June closes out the way it should — with slack key guitar, warm sun, and the whole community gathered on the MACC lawn for one of Mauis most beloved free events. The 35th Annual Kī Hōʻalu Guitar Festival brings together some of Hawaiʻis finest players, including Jeff Peterson, Bobby Moderow, Kevin Brown, Piilani Arias, and many more, for an afternoon of melodious Hawaiian music rooted in the paniolo campfire tradition that gave this art form its soul. Arts and crafts vendors and food trucks open at 1:30 pm, so come early, find your spot, and let the afternoon unfold at island pace. For those off-island, the 35th Annual Kī Hōʻalu Guitar Festival at the MACC will be livestreamed on the MACCs Facebook and YouTube channels.     June on Maui is always something special — but this months lineup feels particularly rich, layered with culture, community, and the kind of moments you carry home long after the summer ends. Get out there, bring your ʻohana, and soak it all in. A hui hou.     ]]> Wed, 27 May 2026 07:12:00 -1000 https://www.islandsothebysrealty.com/blog/history-you-can-feel-5-west-maui-places-with-more-to-say.html https://www.islandsothebysrealty.com/blog/history-you-can-feel-5-west-maui-places-with-more-to-say.html mapuanamarie@gmail.com (Mapuana Andrade) West Maui has a way of pulling your attention with a single glance. The ocean, the light, the ridgelines of the Pali, the stretch of coastline from Olowalu to Honolua. It is the kind of place where most people are thinking about where to swim, where to eat, or where to catch the sunset. Look past the scenery for a moment, and something else comes into focus. A lot of what you are seeing is not just beautiful, it is layered with history that goes back nearly a thousand years. For example, this coastline was first settled between roughly 600 and 1100 AD. By the 15th century, all of Nā Hono a Piʻilani, the six bays of West Maui, were under the rule of Chief Piʻilani. He unified East and West Maui, strengthening the islands political power and extending influence across Kahoʻolawe, Molokai, and Lānaʻi. These bays were not just geographic landmarks, they were part of a living system of governance, travel, fishing, and community life. And the interesting part is, you can still stand in these places today without realizing what you are standing on. Here are five West Maui places where that history is still very much present. 1. Olowalu: More Than a Scenic Stop on the Drive If you have ever driven the West Maui coastline, you know Olowalu as that stretch where the ocean suddenly opens up, the cliffs glow red in the sunlight, and everything feels a little quieter. What most people do not realize is that Olowalu was once a thriving Hawaiian village with farms, a fishpond, a heiau, and a chiefess. It was governed by Kalola, daughter of the Maui ruler Kekaulike and grandmother of Keopuolani, one of the most sacred chiefesses in Hawaiian history. The land was known for dry-land taro and breadfruit groves fed by Olowalu Stream. By 1831, when a census was taken, 831 Hawaiians were recorded living here.  Olowalu was also considered a puʻuhonua — a place of refuge. Anyone who had broken kapu, even aliʻi, could come here and be protected. Violating that sanctuary was punishable by death. That alone tells you how deeply respected this place was. The valley was connected to an ancient trail linking West Maui to Wailuku — a treacherous mountain pass high above that could shave days off a journey made by sea. It was not an easy route, but it was a known one, used by chiefs, guides, and travelers for centuries. The same pass is where Kalanikupule is said to have fled in 1790 after his defeat to Kamehameha in the Battle of Kepaniwai, and where missionary parties were still crossing in the 1820s with the help of Hawaiian guides trained as bird-catchers, navigating ridges barely wide enough for a foothold. After the route fell into disuse in the 1840s, several climbers attempted the crossover but few succeeded. In that same year of 1790, Olowalu was also the site of one of the most devastating early encounters between Hawaiians and Western visitors. An American sea captain named Simon Metcalf opened fire on Hawaiian canoes after a small boat was stolen from his ship, killing more than 100 people and wounding many more. Metcalf then sailed on — but the violence set off a chain reaction. Back on the Big Island, a chief seized the next Western ship to arrive — the Fair American — killing the entire crew save one: Isaac Davis, a Welsh sailor who was taken in by Kamehameha. Metcalf sailed on to China, never knowing his actions had indirectly caused his own sons death.  Just inland from all of this history, you will find Puʻu Kilea, part of the Olowalu Cultural Reserve, with over 70 petroglyphs carved into the basalt cliffs at the mouth of the valley. Ancient Hawaiians called them kiʻi pohaku — images in stone. The carvings depict people, children, animals, and sailing canoes — left by the community that lived and farmed here, and by travelers who stopped to rest at the base of these same cliffs on their way through the pass. It is easy to miss from the road, but it is one of those reminders that this coastline has been lived in and used with intention for a very long time. Even the ocean here carries that weight. The reef system is not just beautiful for snorkeling; it sits in a place that was once both a sanctuary and a significant historical crossroads. 2. Lahaina: A Place of History Beneath Your Feet Lahaina has always been more than a place to pass through. Before the wildfires we had Front Street, the banyan tree, the harbor, the restaurants. It was easy to experience it as a lively coastal town and not think much beyond that. But Lahaina, once known as Lele, was the capital of the Hawaiian Kingdom from 1837 to 1845. It was a center of governance, decision-making, and cultural change during a critical period in Hawaiian history. Right beneath what many people would never notice lies Mokuʻula, once a sacred island and royal residence of King Kamehameha III. It was considered a piko, a spiritual center, and played a key role in the formation of Hawaiʻis early constitution and land division system. Over time, the site was buried and forgotten as the landscape changed. Sugar plantations diverted the water that fed the fishpond, and in 1914 the pond and island were filled in with coral rubble to make way for a ballpark. It became known as the forgotten island, hidden under what most people knew only as a county park on Front Street. The effort to bring it back started in 1990, when a group of cultural practitioners and hotel employees founded the Friends of Mokuʻula. A 1993 archaeological excavation confirmed what they believed — royal structures, a wooden pier used by aliʻi, significant cultural remnants just feet below the surface. The site was added to the National Register of Historic Places, and the ballpark was quietly closed in 1999 once it was confirmed the field sat directly on top of it. A federal grant followed. A developer tried to build a shopping center on part of the land and was stopped. And then, for nearly two decades, the momentum stalled. It took the 2023 wildfire to change that. In August 2024, one year after the fire, the state transferred the land to Maui County specifically for cultural and ecological restoration. The plans are still taking shape, but the direction is clear — Mokuʻula belongs to Lahaina, and Lahaina intends to bring it back. 3. Kāʻanapali: Black Rock  Kāʻanapali is one of Mauis most well known beach areas, with resorts, walkways, and sunset views that draw people in every day. But at the north end of the beach sits Puʻu Kekaʻa, better known as Black Rock, and it has a meaning most visitors do not expect. In Hawaiian tradition, this was ka leina a ka ʻuhane, the “leap of the soul,” a place where spirits would transition from this world to the next. It was also a site associated with leadership and ceremony. Chief Kahekili, the last independent ruler of Maui, was known for lele kawa, or cliff diving, here. It was a physical demonstration of strength and status, but also tied to cultural identity and belief. Today, people still climb the rock and jump into the water below.  4. Kapalua: Makaluapuna Point  At first glance, Makaluapuna Point in Kapalua looks like something out of a fantasy landscape. The lava rock formations known as Dragons Teeth rise sharply from the coast, shaped by ancient flows meeting the ocean. But this is also a wahi pana, a sacred and storied place. Nearby is the Honokahua Burial Site, where over a thousand iwi kūpuna, ancestral remains, are believed to rest. This gives the entire area a cultural significance that goes far beyond its visual appeal. The Kapalua Coastal Trail passes through this landscape, connecting beaches and coves along the shoreline. It is a beautiful walk, but it is also one where respect matters deeply. You are moving through a place that holds ancestral memory. It is one of those spots where nature and culture are not separate things. They are completely intertwined. 5. Honolua: A Bay Still Holds Its Story Honolua Bay is one of the most striking places on the West Maui coastline. Calm, protected waters. Dense reef systems. Steep green cliffs. It is also one of the most culturally significant. This area was part of Nā Hono a Piʻilani and was settled as early as 600 to 1100 AD. Under Piʻilanis rule, it became part of a network of six bays that supported fishing, agriculture, travel, and community life. Honolua has long been associated with surfing in its earliest Hawaiian forms, and later became a place of agricultural and ranching use over time. Even with those changes, its deeper identity as a cultural and ecological refuge has remained. It is also known as the 1976 launch site of Hōkūleʻa, a pioneering canoe voyage of 15-17 individuals who completed the maiden voyage from Hawaiʻi to Tahiti without modern instruments. Today, Honolua is both a marine preserve and a gathering place for people who come to experience its beauty, often without realizing how much history is sitting beneath the surface of the water. Overall, it is easy to experience West Maui as a series of beautiful stops along the coast. A beach here, a viewpoint there, a sunset somewhere in between. But when you know even a little of what came before, the experience shifts. There are places that have been lived in, governed, protected, traveled through, and cared for over generations. And the most interesting part is that none of that history is hidden. It is still right there in the land, the water, and the coastline you are already enjoying. ]]> Thu, 07 May 2026 10:22:00 -1000 https://www.islandsothebysrealty.com/blog/lei-day-to-mayhem-whats-happening-on-maui-this-may.html https://www.islandsothebysrealty.com/blog/lei-day-to-mayhem-whats-happening-on-maui-this-may.html leads@islandsothebysrealty.com (Island Sotheby's International Realty) May on Maui belongs to the kamaāina — the humpbacks have headed back to Alaska, the visitor crowds are still thin, and the island fills its calendar with the kind of events that remind you exactly why you live here. From Lei Day celebrations to surf contests, craft fairs to cultural performances, theres something worth showing up for almost every day, and some weekends youll have to choose.     Lei Day on Maui May 1, 2026 Hale Hōʻikeʻike at the Bailey House, Wailuku May Day is Lei Day in Hawaiʻi, and one of the most beloved celebrations on the island happens right in the heart of historic Wailuku. The Maui Historical Societys Lei Day Heritage Festival transforms the peaceful grounds of the Bailey House into a living celebration of Hawaiian culture — mele Hawaiʻi, hula, hands-on lei making, and cultural demonstrations, all free and open to the whole ʻohana. Its unpretentious, deeply rooted, and the kind of community event that reminds you exactly why you live here. Make a day of it — Maui does Lei Day like nowhere else.     Gary Owen: No Hard Feelings Tour May 1, 2026 · 7:30 PM Maui Arts & Cultural Center, Kahului Cap off Lei Day with a night of laughter on the MACC stage. Gary Owen is one of Americas most consistently funny touring comedians — sharp, high-energy, and genuinely hilarious — and this is the kind of show that reminds you how good it feels to just sit back and laugh with a room full of strangers. Grab tickets before theyre gone.     HHSAA State High School Surfing Championship May 12, 2026 Hookipa Beach Park, North Shore This one is history in the making. For the first time ever, surfing is an official interscholastic state championship sport in Hawaiʻi — and Mauis own Hoʻokipa Beach Park is hosting the inaugural event. Watch the next generation of Hawaiian surfers compete across shortboard, longboard, and bodyboard divisions, carrying forward a tradition that runs as deep as the ocean itself. Free to attend — check the details at hhsaa.org and make the drive to the North Shore.     CIRCA Humans 2.0 May 3, 2026 · 7:30 PM Maui Arts & Cultural Center, Kahului Australias extraordinary CIRCA company returns to Maui with Humans 2.0 — a breathtaking physical theater experience that uses acrobatics to ask what it really means to be human. Expect gasps, silence, and a standing ovation. This is the kind of live performance that stays with you for weeks, the sort that reminds you why leaving the couch is always, always worth it.     Cinco de Mayo at Lahaina Cannery May 5, 2026 Lahaina Cannery, West Maui This one carries extra meaning this year. For the first time since the Lahaina fires, the Cinco de Mayo festivities at Lahaina Cannery are bringing joy, culture, and celebration back to the Front Street area — a neighborhood that has worked so hard to reclaim its spirit. A great excuse to head to West Maui and celebrate.   Boots, Buckles & Big Dreams on Maui May 7-10, 2026 Oskie Rice Arena, Makawao The Hawaii High School Rodeo Association Junior High State Championships are coming to Upcountry Maui, May 7-10 at the iconic Oskie Rice Arena in Makawao. Come cheer on the next generation of Hawaiis paniolo tradition as young competitors from across the state vie for top honors. A true only-on-Maui experience you wont want to miss.     Starry Night Cinema: The Little Mermaid May 8, 2026 · 7:30 PM Maui Arts & Cultural Center, Kahului There is something especially right about watching The Little Mermaid outdoors on an island surrounded by the Pacific. MACCs Starry Night Cinema series brings movies under the open sky, and this one is perfect for families, date nights, or anyone who wants to sing along with the trade winds blowing through. Bring a blanket, arrive early for a good spot, and enjoy one of those simple, perfect Maui evenings.     Seabury Hall Craft Fair May 9, 2026 · 9:00 AM4:00 PM Seabury Hall, 480 Olinda Rd, Makawao, Upcountry Maui Fifty years in and still one of the best days on the Upcountry calendar. The Seabury Hall Craft Fair brings together Mauis finest artisans, jewelers, crafters, and floral designers for a vibrant open-air marketplace on the schools beautiful Makawao campus. Proceeds support financial aid programs, so every purchase does double duty — and with live music, local food, and a silent auction, its an easy way to spend a beautiful May morning. Admission is $10 for adults; keiki under 12 get in free.       Maui Brewers Festival — 15th Anniversary May 16, 2026 · 2:00 PM Maui Arts & Cultural Center, Kahului Fifteen years of great beer, great company, and one of the best afternoons on Mauis event calendar. The Maui Brewers Festival brings together local and national craft breweries for a day of tasting and live music on the MACC grounds. The 15th anniversary edition promises to be the best yet — raise a glass to a decade and a half of this beloved island tradition.     Ian Walsh Menehune Mayhem May 1617, 2026 Hookipa Beach Park, North Shore Hoʻokipa hosts another beloved community event — the Ian Walsh Menehune Mayhem youth surf contest, now in its 21st year. This free two-day event is pure Maui: keiki charging waves, families cheering from the sand, and a community rallying around the next generation of surfers. Come for the surfing, stay for the spirit of the whole thing.     Maui Matsuri Japanese Festival May 23, 2026 · 10:00 AM9:00 PM University of Hawaii Maui College, Kahului One of Mauis most festive annual cultural celebrations, the Maui Matsuri Japanese Festival fills the UHMC campus with free entertainment, keiki crafts, food booths, eating contests, and traditional Bon dancing as evening falls. Its a joyful, multigenerational event that reflects the deep Japanese cultural roots woven into the fabric of this island — and the food alone is worth showing up for.     Lei Kaulana May 31, 2026 · 2:00 PM Maui Arts & Cultural Center, Kahului Close out the month with something quietly beautiful. Lei Kaulana is a celebration of Hawaiian culture through the sacred art of lei — performance, tradition, and community woven together on the MACC stage. Its a fitting way to end a month that began with Lei Day: a reminder that in Hawaiʻi, the lei is never just a flower. Its a greeting, a farewell, an expression of love, and a thread that connects us all.   ]]> Tue, 28 Apr 2026 10:29:00 -1000