May on Maui belongs to the kama'āina — 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, there's something worth showing up for almost every day, and some weekends you'll 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 Society's Lei Day Heritage Festival transforms the peaceful grounds of the Bailey House into a living celebration

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Island Sotheby’s International Realty is excited to welcome Mark Janes RS-86830 to our team! A seasoned professional whose unique blend of Silicon Valley business acumen, hands-on homebuilding experience, and passion for Maui living sets him apart in the luxury real estate market. With over 30 years in real estate and development, Mark brings a detail-driven, strategic approach to helping clients create and discover their own piece of paradise. We sat down with him to learn more about his journey, his love for Maui, and what makes his approach truly one-of-a-kind.

What led you to where you are today?

I spent over a decade in Silicon Valley building startups and honing skills in design, project execution, and strategic thinking. Now, with more

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Island Sotheby’s International Realty is proud to announce that nine of our outstanding agents have been recognized in the 2025 RealTrends Verified. This annual list honors the highest-performing residential real estate professionals, based on their 2024 sales volume.

Their remarkable performance is a reflection of the market expertise, client dedication, and elevated service that define our team.

“This recognition is a testament to the heart and hustle our agents bring to every relationship,” said Ryan McLaughlin. “We are incredibly proud of the professionals who represent our brokerage at the highest level—not just in sales volume, but in the way they serve with aloha, integrity, and purpose. Their success is a reflection of the deep trust

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March on Maui is packed with exciting events, from live concerts and theater performances to fundraisers and outdoor activities. Whether you’re a local or visiting the island, there’s something for everyone. Here’s your guide to the top events happening this month.

Art Affair 2025 – Vintage Poolside: A Retro Sunset Soirée

March 1, 2025

Hui No‘eau Visual Arts Center, 2841 Baldwin Avenue, Makawao, HI 96768

Dive into an evening of elegance and nostalgia at the Art Affair 2025 – Vintage Poolside: A Retro Sunset Soirée, the signature fundraising event for Hui No‘eau Visual Arts Center. Set against the backdrop of the historic Kaluanui Estate's iconic reflection pool, this soirée promises a blend of gourmet cuisine, live music, dancing, and

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Photo: Dante Parducci

Island Sotheby's International Realty's Ryan MacLaughlin, R(B) and Alex Cortez, R(B) represented the buyers in the significant sale of 4585 Makena Road, Kihei Hawai'i.

Sold for $25,000,000, this 7 bedroom, 8.5 bathroom Makena Estate offers sophisticated, contemporary flair and over two acres of manicured tropical landscaping, making it both an ideal private retreat and a home for those who love to entertain. 

Photo: Dante Parducci

This significant sale finalized in late May marks the highest on Maui in the last five years. Nothing surprising for our seasoned realtors as both Ryan and Alex also represented the sellers of the previous highest sale in the last five years, 4508 Makena Road, which sold for $24,600,000 in

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The County of Maui Department of Finance’s Real Property Assessment Division announced today that a new long-term rental classification and exemption have been established as part of the Maui County Code.

Effective Jan. 1, 2022, real property occupied as a long-term rental, with a signed contract to lease for 12 consecutive months or longer to the same tenant, may qualify an owner for an exemption of up to $200,000.

Real property rented on a long-term basis (12 consecutive months or longer) without a home exemption, will be eligible for the $200,000 long-term rental exemption and will be classified as Long-term Rental. Real property with a home exemption that also qualifies for the long-term rental exemption will be eligible for an additional

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Deb Schonewill puts the A in aloha with her passionate admiration for the island of Maui and everything she does for her clients. Having always felt a magnetic pull to Maui, Deb moved to the island with good wishes from the most influential mentors in her life. She sees the culture, natural beauty, and the rich community as an incredible place to live one’s life. She is joining the Island Sotheby’s International Realty ohana because she believes realty is founded on making genuine relationships. 

“Island Sotheby's Realty has the authentic aloha and family culture paired with shining exceptional service.”

Honesty and sincere respect are at the foundation of Deb’s relationships with her clients. To her, real estate is about making those

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1. Kamaole Beach Park 1

When the water is glistening and the sun is shining, grab a snorkel and some flippers and bask in the aquarium like abundance of tropical fish and crystal waters. Out on the shore, walk the white sandy beach at sunrise or sunset to take in the beautiful view of pinks, oranges, and reds reflecting off the water. This beach is perfect for kids who want to play in the soft, smooth sand or for the families who enjoy boogie boarding along the shoreline. Find good food and great shops only minutes from the beach including an ABC store stocked with the best beach snacks. Set up next to the barbecues on the grassy area or dive into a game of volleyball with the net set up on the grass. We like to call this beach the crown pleaser

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Island Sotheby’s International Realty’s Candy Mulcoy R(S) sells another extraordinary residence on Maui’s west side shores, Kahua Kai Pl, located in the coveted gated community of Kaanapali Golf Estates.

This 3,800 Sq Ft residence features a spacious 3 bedrooms and 4 baths with an ocean view office that makes any work from home job a dream. The 1,000 Sq Ft of covered lanai offers the ultimate entertaining space or outdoor oasis. A gorgeous pool and relaxing spa and sauna are just a few of the many amenities offered.

Located in this residence you will find that the custom interior design blends some of the most exotic arrays of wood and Italian marble imported from Italy. The professionally designed kitchen is decorated with the finest

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  Imagine. Maui. This exceptional vintage garden view one bedroom two bath townhome with a spacious loft is ideally located in the historic district of Lahaina. Pumana 8-1 listed by Lori Powers, R(S) and Anita White, R(B), offers a unique community that is a quiet oasis of 30 oceanfront acres of tropical gardens and swaying palm trees. Your day begins with the morning beverage of choice on your private lanai. Your residence has views of the West Maui Mountains, where the sun rises, and at sunset enjoy the neighborhood gathering place in front of the Puamana Clubhouse where homeowners and guests mingle and watch the spectacular sunsets. For those interested in exploring the Lahaina real estate market and available opportunities, visit our West Maui…