Direct flights out of San Francisco International Airport make long weekends on the islands not only doable, but fairly seamless. Just hop on a flight and within five to six hours you can be lounging poolside beneath a canopy of palm trees at your resort or taking in the rugged natural beauty of the island from a blanket on the beach.
Nicknamed the Valley Isle, Maui is flanked by two large volcanoes, Haleakalā and the West Maui Mountains. What lies in between is an expanse of luxury hotels, white sand beaches, and feral landscapes overrun by greenery.
So how should you spend your days while visiting? We are so glad you asked.
Where to Stay on Maui’s Sunniest Coast
The Grand Wailea Maui was recently renovated.
(Courtesy of @grandwailea)
On the island’s south shore, which was once a rugged desert, temperatures tend to be highest, promising more sunny days than the island’s other regions. Wailea is home to eight luxury resorts, many of which are on Wailea Beach, a roughly quarter-mile stretch of golden sand. The luxury coast is home to the Four Seasons Resort Maui (3900 Wailea Alanui Dr.) at Wailea, where the premiere season of White Lotus was filmed; the recently renovated Grand Wailea Maui (3850 Wailea Alanui Dr.); the Fairmont Kea Lani Maui (4100 Wailea Alanui Dr.), which has day passes available to non-resort guests through resortpass.com; and the Andaz Maui at Wailea Resort (3550 Wailea Alanui Dr.), which has an impressive set of cascading infinity pools.
At the Grand Wailea, guests can check into ocean-view rooms and spend days exploring the multi-tiered pool system boasting slides, rope swings, and a hidden sports bar in the 21 and over grotto. There’s also an adults-only pool deck if you want to escape the chaos, with a pool, two hot tubs, and private loungers and cabanas. Rooms booked with Napua Lounge access include drinks and snacks, an open bar, and a private lounge area with additional amenities throughout the day. Kids will love the ability to grab ice cream on demand.
The Four Seasons Resort is the epitome of extravagance, featuring private cabanas with butlers and more tailored service (and extra perks) on the property’s exclusive eighth floor, where staff-to-visitor ratios are extremely low. You won’t want to leave without experiencing the spa and its menu of culture-driven services like The Queen’s Garden Fern Ritual, an invigorating massage and aromatherapy treatment featuring fern oil sourced from the islands.
Where to Dine on Fresh Local Fare
The lilikoi foam-topped mai tai at Monkeypod Kitchen
(Courtesy of Hawaii Media Collective)
Any trip to Maui is incomplete without sampling the island’s best cuisine. Sure, you can score a bowl of fresh pineapple just about anywhere and the famous Honolulu Cookie Company sells their treats at the airport, but that’s just scratching the surface.
For an authentic Hawaiian plate lunch, we recommend Tin Roof (360 Papa Pl. Ste. 116, Kahului), a counter-serve, to-go establishment. It typically has a line but the food—from garlic noodles and fresh shrimp to white rice and pork belly with cabbage—is worth it. The casual eatery is near the airport for a convenient first or last meal.
Monkeypod Kitchen (multiple locations) has quite the following, and while all of the food is notable, it’s the lilikoi foam-topped mai tai that even locals rave about. Mama’s Fish House (799 Poho Pl.) is a local landmark in Paia at the mouth of the road to Hana on Maui’s North Shore.
If you’re looking for a high-end and atmospheric dining destination, book yourself into the new Nobu at the Grand Wailea. The sushi and seafood restaurant has a gorgeous dining room overlooking the ocean with a picturesque balcony that’s ideal for sunset. Much of the menu is caught local and the waitstaff is happy to share recommendations. For a post-dinner drink, saunter down to Humahumanukunukuapua’a, the island’s only “fish bar”—yes, there’s a live aquarium floating underneath your martini glass.
Instead of leaning into local catches, The Four Seasons’ newest establishment, Komo, brings all of its ingredients in from Japan for a menu in which everything from the sauces to the preparations feel distinctly of that country’s cuisine. The taiyaki with ube ice cream is a fun and flavorful dessert that will bring out the inner child in you. Just across the lobby, Wolfgang Puck’s Spago has set up shop with a menu that leans heavily into local Hawaiian specials without losing the Spago sparkle. Another gorgeous indoor-outdoor space, guests can dine on fresh and local hamachi, thick sushi rolls, and Japanese A-5 Wagyu served with Hawaiian pineapple and seared in an immaculate presentation.
If you’re a fan of beer, the island is home to quite a few tasting rooms, from the well-distributed Maui Brew Co. (605 Lipoa Pkwy, Kihei), which has a full kitchen boasting flavorful pizzas, wings, and other elevated bar food, to little secrets like Lahaina Brewing Company (112 Wailea Ike Dr., Wailea), Waikiki Brew Co. (3750 Wailea Alanui Dr. B-25, Wailea-Makena), and Koa Brewing Company (2511 S. Kihei Rd. A, Kihei).
Where to Book a Luau
The Myths of Maui luau
(Courtesy of @mythsofmauiluau)
Sunset luaus are one of the best ways to sample local fare. Most include cultural dance performances, music, and a buffet brimming with staples such as kalua pork, taro rolls, and poi.
The island isn’t short on luau opportunities, with some held at local resorts and others on their own established grounds. Myths of Maui at the Royal Lahaina Resort & Bungalows (2780 Kekaa Drive, Lahaina) is one of the longest-running luaus on the island, featuring ancient dances and authentic dress. There is also the Wailele Luau at The Westin Maui Resort & Spa in Lahaina (2365 Kaanapali Pkwy).
The Grand Wailea has its own luau on select nights called Te Au Moana. Instead of a buffet, waitstaff here bring out each course to diners at private tables, with VIP tables set in the front. Other activities include lawn games and temporary tattoos.
Where to Find Your Ideal Adventure on the Water
(Courtesy of Wailea Resort Association)
Beach hopping may be enough to satiate your appetite for the water and the south shore is home to a few ultra-sunny spots including Wailea Beach, Ulua Beach, Polo Beach, and Mokapu Beach. Each is ideal for paddleboarding out into the warm ocean or snorkeling with the sea turtles. Remember: The water is calmest in the morning.
If you’re looking for something more organized, the protected reef at the Molokini Crater is one of the island’s best destinations for snorkeling. Locals, however, will tell you, you can see most of the same fish without the crater experience at La Perouse Bay.
A more leisurely tour with just the right dose of culture includes an outrigger canoe ride off the shores of Wailea Beach. Book a tour and learn how to row like the locals do (outrigger rowing is a common sport for kids and adults on the islands with huge competitions throughout the year). Some guides even serenade their crews with ukuleles and local tunes. If you stay at the Four Seasons, your ride is complimentary. You can also rent paddleboards and other aquatic equipment from local outfitters near the sand.
Where Else to Explore on the Island
(Courtesy of nlang06/Pixabay)
While most people make their Maui homebase in Wailea or Kaanapali, don’t miss the island’s other regions. Paia is a hot bed of restaurants and shopping with a touch of nightlife (although most places still close on the early side). Makawao is just a 10- to 15-minute drive further and is more of an artist’s village. From there you can drive into the less touristy upcountry, where the climate is rainier and cooler and you’ll find cowboy culture and plenty of farm tours.
The Road to Hana is one of the busiest attractions on the island, a 64-mile scenic drive through a natural playground with swimming holes, waterfalls, and hiking trails. The Road to Hana website breaks down the sites mile-to-mile, making it easy to create a full-day’s itinerary with an blend of hidden spots and tourist favorites.
