The Insider’s Guide to Maui

Ever wish you could text the most stylish people in the world for their lists of things to do in the places they know best? Here are insider travel tips for those who would never be caught dead in a tourist trap. Bon voyage!

Who

The island that once served as the capital of the Hawaiian Kingdom is a rural gem rich with jaw-dropping nature, eucalyptus-lined cowboy villages, world-class surfing and windsurfing, and deeply layered culture. Three Maui locals share their favorite places and tips for visiting: Naomi Acacia Newirth, the founder and designer of ACACIA Swimwear; Graham Ezzy, a former pro windsurfer who now teaches high-level windsurfing and works with his family company, the iconic Ezzy Sails; and six-time James Beard-nominated Sheldon Simeon, the chef and owner of Tin Roof and the beloved local institution Tiffany’s. Newirth and Ezzy both grew up on Maui and live in the North Shore town of Haiku. Simeon is from Hilo, Hawaii and has been on Maui for over 20 years. He’s based in Wailuku and will release a new cookbook, Ohana Style, at the end of March.

What

What to Bring

Like its neighboring islands, Maui is laid-back at heart. “You don’t need a lot,” says Ezzy. “When I showed up to college, my biggest shock was that people cared about what I wore because on Maui, nobody cares. There’s no dress code. You can go to lunch in a bathing suit or a cocktail dress, whatever makes you feel your best.”

In practice, you can get around with a few swimsuits, worn-in t-shirts, a couple pairs of shorts, and slides. That said, some choice items are advised. Newirth recommends reef-safe sunscreen, plus “a reusable water bottle, comfortable sandals, and light layers for mornings and evenings,” says the designer. “I always suggest swimsuits, sarongs, and simple pieces that move easily from day to night.”

More than anything, “pack patience,” Simeon says. “Then come with an open heart and understand that people live here. Some people think that the whole island is a resort, but to this day, the Hawaiians say, ‘You take care of the land and the land will take care of you.’ If you come with that respect and understanding, you’ll enjoy Maui.”

What to Leave Behind

This is not the place to go if you are craving a high-intensity social schedule, nightlife, and big -ity speed. “Leave behind the need to rush,” says Newirth. “Maui reveals itself at a slower pace.”

What to Keep in Mind

All of our insiders agree: “Be mindful that this is home for the people who live here,” says Ezzy. “Support the local community by shopping local, tipping well, and recognizing that you’re a guest in someone’s home.”

Another thing to keep in mind is the fact that the island is still recovering from the fires that ravaged Lahaina in 2022. “Supporting locally owned businesses and donating to verified organizations supporting Lahaina and surrounding communities makes a tangible difference,” says Newirth. “Move slowly. Be present. Visit respectfully. And if you have the time, take the drive to Hana, it’s truly special, as long as you’re comfortable with the winding road.”

Where

Where to Stay

The entire island is rural and slow-moving. You’ll get a different experience depending on what area you visit. “The North Shore offers a quieter, more nature-driven pace, while Wailea and Kaanapali lean more resort-oriented,” says Newirth. On the North Shore, you’ll find small towns full of independent shops and cafés linked by winding roads and pastures of horses grazing. Head to the south and west end and you’ll be met with luxury and total getaway vibes. Hana, on the eastern end of the island, is a lush rainforest region perfect for camping and long, quiet hikes. Haleakala National Park is named for the dormant volcano that makes up 75 percent of the island.

Newirth recommends Lumeria, a 24-room Upcountry guesthouse with farm-to-table dining and programs in horticulture, local culture, and immersive retreats,. A stay at this peaceful wellness-focused option may include open-air classes on Maui’s indigenous herbs and fruit-bearing trees, daily yoga and meditation, and a range of elevated spa offerings like their lomi lomi pokano (hot stone) massage to a sage cleansing palo santo energy massage.

Ezzy also loves the North Shore. “I recommend escaping the resort bubbles of Wailea and Kaanapali,” he says. “Haiku, Paia, and Makawao carry the country soul of Maui. Lumeria and the Banyan Bed and Breakfast are both hidden-gem hotels on the northern slopes of Haleakala.”

For those looking to be pampered, Grand Wailea, A Waldorf Astoria Resort, has an incredibly expansive spa and some of the most beautiful gardens on the island. Next door, you’ll find The Four Seasons, with all the impeccable service for which the group is known. Then there is the Fairmont Kea Lani, a palatial property with pools, three world-class golf courses plus full service tennis, and at least one restaurant with its menu almost entirely sourced locally.

Kaanapali is next to Lahaina. It’s full of resorts and is a beautiful location for whale watching and other ocean activities.

Where to Begin the Day

Ezzy suggests Clhei Cafe for high-quality coffee. Momona is his go-to for a pastry and a flat white.

On Wednesdays and Saturdays, a trip to the Upcountry Farmer’s Market is highly recommended. Grab a honey lavender latte at Crema Maui, then explore the stands overflowing with in-season mangos, lychee, apple bananas, and other local specialties. “We still have the best produce there is,” Simeon says with a grin. Over 40 farms sell their fruit, vegetables, and other goods at the market, many of which are indigenous to Hawaii and can only be found locally.

Where to Eat

Maui is known for its nutrient-rich soil and all of the incredible produce that stems from it. “The local ingredients are insanely high-quality,” explains Ezzy, echoing Simeon’s assertion. “The fish, of course. But the cows and deer graze on grass that grows in the rich volcanic soil that also nourishes the fruits and veg.”

The food culture brings together the many diverse communities that make up the island. “I’m happy to see local indigenous cuisine influencing resort hotels, food that speaks to our immigrants who came here to work on the plantations,” Simeon says. “For many years, [food on the island] catered to our visitors’ palette. But now you start to see flavors of my grandparents, you see Filipino flavors, you see Hawaiian and Japanese.”

Simeon recommends Velzyland Burger Co. in Wailuku. “They do such an awesome job,” says the chef. “They use a hundred percent local beef, and they make their own buns.”

The shaved ice placed next door is the perfect way to end the meal, he adds. “Grab-and-go shops are huge for me.” He gives Oki’s Seafood Corner a shout. His own restaurants, Tin Roof and Tiffany’s, are local institutions. “Tin Roof is a small take-out spot with a menu designed by one of Maui’s up-and-coming star chefs,” Ezzy says. “Everything’s good. The mochiko chicken or the poke bowl are my go-tos.”

Ezzy also likes Cafe Mambo. “It was recently bought by a group of young surfers who transformed the menu and modernized the vibe,” he says. “If I’m up in Kula, I go to Marlow. Maybe the best meatballs in the state? Their olive oil honey gelato? Life changing.”

“Nuka is our go-to for sushi and is just a short drive from home,” Newirth adds. “Paia Fish Market is another staple and never disappoints. For poke, we’ll stop at Tobi’s, where the fish is always fresh and never frozen, or pick some up from the uncle who occasionally sets up at Ho‘okipa. For beach days, Mana Foods is essential. The hot bar and salad bar are an easy option when we’re on the move.”

She also suggests Sale Pepe, an independent Italian spot from a Milanese chef and Brooklyn native who lost their home and restaurant in the Lahaina fire and managed to rebuild in 2023. The restaurant combines locally sourced ingredients with Italian-imported flour, fior di latte, and Bufala mozzarella with homemade pastas and artisanal pizzas.

Where to Shop

The island is filled with independent shops and bohemian, family-run boutiques. Walk through Makawao, the historic paniolo (Hawaiian cowboy) town at the base of Haleakala, and find local artist galleries, the traditional lei seller Haku Maui, and more than a few concept stores offering tie-dyed silk wraps, Kauai-designed bikinis, and aura-cleansing crystals. The town has a rustic, warmly eccentric charm.

If you drive down the volcano, you’ll find the sunbathed Paia, next to the iconic Ho’okipa. Wander through the shops lining the ocean. Here, you’ll find ACACIA, Newirth’s flagship. Her swimsuits are perhaps the only ones I’ve worn that comfortably withstand Hawaii’s powerful waves. They’re made for ocean sports but are beautifully refined, a rare combination. Alongside her own line, ACACIA stocks lightweight, natural-fiber dresses, minimal strappy sandals, and independent favorites, like the ’70s-inflected yoga shorts from Australian merino wool activewear brand Nagnata.

“Beyond our shop, CLHEI and Imrie, both in Paia, are longtime favorites run by close friends,” Newirth says. CLHEI is a Maui-local apparel and leather accessories line; Imrie is the perfect place to go for a just-right organic cotton t-shirt.

Simeon, meanwhile, recommends Native Intelligence in Wailuku. “They’re a Native Hawaiian-owned store that sells indigenous-driven art and inspired products,” he says. Think: classic aloha shirts, fresh double Maili leis, and Na lima hulu no’eau, handmade feather leis from the island of Kauai. The shop champions local artisans and works to preserve ancient Polynesian and Hawaiian craftsmanship.

For Bottega Veneta, Prada, and the like, head to Wailea.

Where to Swim and Surf

Maui is a legendary windsurfing destination, with year-round trade winds and dynamic conditions that bring in beginners and pros alike. It’s also a beautiful location for surfing, snorkeling, and other water sports. Black, red, and golden-sand beaches with clear turquoise waters are ideal for sunbathing and sunset picnics.

Ezzy introduces Maui’s most renowned break: “Ho’okipa is the Mecca of windsurfing, and I get out in the waves there every day I can. Even if you’re not a surfer, I recommend going to Ho’okipa in the afternoon to watch the best windsurfers in the world play in the waves. If you want to learn a wind sport (windsurfing, kiting, winging, foiling), Kanaha Beach Park is one of the best beaches in the world for learning. HST is Maui’s main wind sport school—tell them I sent you and they’ll take extra good care of you.”

For a beautiful, calm beach option, Chef Simeon recommends Kapalua Bay in Kaanapali. “It will always be our family favorite. Our kids learned to swim there,” says Simeon. Next door is Napili Bay, a gorgeous crescent-shaped bay ideal for swimming and snorkeling. Drive over and feel out which one is right for you.

Newirth prefers the North Shore most days. “Hamoa on the east side is another favorite; it’s stunning, with crystal-clear water and black sand,” she says.

Where to Hike

“The most life-changing hike on Maui is the hike into Haleakala crater. It feels like you’re on Mars,” says Ezzy. “Reportedly, it is the quietest place on earth. But make sure you bring plenty of water and a sweater (it can be shockingly cold!). The whole hike from Sliding Sands to the Switchbacks takes upwards of 10 hours, but you can walk into the crater and turn around whenever you want. Just remember that it’s much easier to walk downhill than uphill.”

For a breathtaking experience, wake up before sunrise and begin the hike as the day begins. It’s also possible to cycle down the crater—a very special experience particularly as the sun sets.

Beyond Haleakala, “there are countless beautiful places on the island,” Newirth says. “Twin Falls is a favorite, with trails that lead to a series of waterfalls, and Hosmer Grove offers a quieter hike. Each place gives a different experience of the island.”

Simeon’s favorite hike is The Cross Heights in Wailuku. “It's awesome,” he says. “It’s a pretty strenuous hike, but it’s short.”

Where to Unwind

The entire island is a reset. “Nature itself: the ocean, the mountains, quiet moments outdoors. Those are my grounding rituals,” says Newirth.

For those looking for a top spa treatment, Ezzy recommends Lumeria or Ho’omana Spa.

Where to Grab a Drink

Maui has a few special beverage offerings. “If you’re out in Wailea, the perfect two spots are right next to each other,” says Simeon. “Lahaina Brewing Company is building back up following the fires. Next door is Tikehau Lounge, a fun little rum-driven restaurant by some of the best bartenders and mixologists on island.”

Newirth likes Belle Surf. “Occasionally, we’ll also try for a bar seat at Mama’s Fish House which, is always worth it when it works out,” she adds. “Wailuku has some hidden gems.”

If you’re in Haiku, there is only one bar. “Colleen’s. A gathering spot for everyone in the neighborhood,” says Ezzy. “Wear your cowboy boots to fit into the country vibe.”

When

Maui is beautiful year-around. Simeon likes the tail end of summer. “It’s perfect weather. The sun doesn’t go down until almost seven, so it’s nice to be out at the beach till late,” he says.

Newirth recommends winter, when the wind softens. Ezzy prefers fall and spring. “They have the best wind and waves,” he explains. “Generally, in Haiku, the winter is wet and the summer is dry. But the big mountains block the rain from falling on Maui’s southern sides, so Wailea and Kaanapali are dry year-round. If you plan to spend time on the north shore, skip the winter if you don’t like rain.”

Why

“Maui has a way of recalibrating you,” shares Newirth. “The connection to nature, the sense of community, and the respect for the land are deeply grounding. Growing up here has shaped who I am, personally and creatively.”

The island has a centering effect. It’s also not as disconnected as one may imagine. “Maui is a center of the world.,” says Ezzy. “Even though Hawaii is the most isolated land mass—stuck in the middle of the Pacific—everyone comes through here. Don’t be surprised if you find yourself annoyed at Steven Tyler holding up the line at the checkout in Mana Foods, or bodysurfing next to the Obamas. Still, nowhere else I’ve been allows for such a simple, physical life. It’s a collective step outside the flow of culture—for better or worse.”