We're delighted to welcome home Phillip Chiesa to Island Sotheby's International Realty, where he continues to bring dedication to every client relationship. For Phillip, real estate is about understanding each client's goals, solving complex challenges, and helping people make confident decisions during one of life's biggest milestones. When he's not working with clients, you'll likely find him exploring Maui's incredible landscapes, climbing at the local rock gym, or enjoying the peaceful beauty of ʻĪao Valley.

Get to know Phillip as he shares more about his journey, what he loves most about Maui, and the philosophy that guides his approach to real estate.

What led you to where you are today?

I started my real estate career at 24 with,

Photo: Musician, Sunny Kalama

South Maui has always had a rhythm of its own. Maybe it’s 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 you’re 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,

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 island’s political power and extending

South Maui is often experienced through its beaches, sunshine, and easygoing coastal lifestyle…but there’s another side to being here that’s just as meaningful. Across Kihei and Wailea, there are countless ways to connect more deeply with the island through mālama, caring for the land, the ocean, and the community that makes this place home.

For residents and visitors alike, giving back isn’t separate from the Maui experience; it’s part of it. Whether you’re here for a week or a lifetime, there are meaningful ways to step in, connect, and contribute. Below are a few ways to get involved across Kihei and Wailea, with exactly how to start.

Aloha Backpack Buddies (Maui Food Bank)

Supporting local families often begins with something simple:

Courtesy: Curtis Wilson Cost Studio Gallery

Spring on Maui does not arrive all at once. It moves gently — through quiet roads, into historic storefronts, across neighborhoods, and out over rolling pastures. The mornings feel a little brighter. The air shifts. Something about the season invites a second look at the spaces we live in.

Life at home follows its own rhythm. We are drawn to space, to light, to the views outside our windows and the details within our walls. Spring is when many homeowners begin to shift their spaces. Windows stay open longer. Outdoor living areas are refreshed. And inside, rooms are reimagined with small but meaningful changes. One of the most powerful and personal ways to refresh a home this season is through art.

While much of the country is layering up, Maui’s version of the season is defined by golden light, gentle trade winds, and days that naturally unfold outdoors. Morning coffee on the lanai. Afternoons by the pool. Evenings that end with a sunset and the soft sound of the ocean. Homes designed around infinity edge pools embody that rhythm. They frame the horizon, extend the living space outward, and create a feeling that blends comfort with resort style ease.

These three exceptional properties offer distinct interpretations of that lifestyle, each capturing a unique expression of island living. Different settings, unique architecture, but all connected by a shared experience: elevated indoor outdoor living anchored by views, privacy, and a pool that

In West Maui, food has always carried meaning beyond what is on the plate. It is how stories are told without needing to be written down. How generations stay connected. How neighbors check in on one another. A shared table here is rarely rushed and almost never just about eating.

In Lahaina especially, food has long been one of the town’s quiet anchors. Restaurants are places where locals mark milestones, where fishermen drop off the day’s catch, where chefs know their farmers by name, and where visitors are welcomed into something that feels personal rather than polished. To dine in Lahaina is to experience the town’s rhythm, its warmth, and its generosity.

This February, the Lahaina Food and Wine Festival returns from February 18 through 22,

There are few places on Maui where the island’s resort lifestyle, natural beauty, and easy everyday rhythm blend as seamlessly as they do along the Kā‘anapali Beachwalk. Stretching across the golden shoreline and connecting world class dining, shopping, snorkeling, and recreation, this oceanside path is more than a scenic walkway. It is a way of life. Mornings begin with soft sunlight over the ocean, afternoons drift between beach and pool, and evenings invite sunset strolls framed by the silhouettes of Lāna‘i and Moloka‘i.

Along this celebrated coastline sits Honua Kai Resort & Spa, one of West Maui’s most coveted beachfront communities. With a prime location directly on the beachwalk, Honua Kai offers residents the ability to step from their

South Maui is often introduced through its sparkling beaches, sunset dinners, and resort pools, yet there is a deeper story woven into this coast. Ancient fishpond walls still catch the light at low tide. Lava flows remember the island’s most recent eruptions. Whales, turtles, and native birds return season after season, following paths that have existed long before any shoreline condos or beach paths.

This guide highlights some of South Maui’s lesser known cultural and natural landmarks, along with insight into why this coastline continues to captivate those seeking serenity and scenery.

Makena Landing and Turtle Town

Today, Makena Landing is known as a launch point for kayakers, snorkelers, and divers who head toward Nahuna Point and

Christmas on Maui feels a little extra magical. Cooler Upcountry mornings, oceanfront trees twinkling with lights, and the joyful spirit of giving filling every small town. Across the island, local makers are busy creating treasures that tell real stories. When you shop local here, you give a gift that means more. You support a neighbor. You uplift a family business. You help this resilient community thrive.

We have curated a list of Maui made businesses that are perfect for gifting this season. From handcrafted jewelry and cozy bakery treats to sustainable skincare and thoughtful apparel, every item is created with aloha and rooted in the beauty of our island home. Whether you are browsing from just down the road or from across the ocean, you can