Maui is one of the world’s favorite vacation destinations, having earned the title of Best U.S. Island from Condé Nast Traveler’s Readers Choice Awards for more than 20 years in a row. Inspirato’s accommodations in Wailea — located on Maui’s southwestern coast — are tucked inside three award-winning resorts. At the Fairmont Kea Lani, the club’s residences have private plunge pools just steps from secluded Polo Beach. Our striking contemporary villas at the Andaz Maui at Wailea Resort have lovely ocean views, while a stay at Ho’olei at Grand Wailea grants access to the many amenities of its namesake resort next door.

Each resort is its own unique oasis with plenty of ways to stay entertained on-site, but Inspirato Members love to explore all of the other incredible ways to experience Wailea and Maui. From water sports to spa treatments, a vacation to Maui can be equally action-packed and laid-back. Keep reading for our picks for the best things to do, places to see, dishes to try, and things to know about this beloved island.

We loved the Andaz Maui - great location and amenities. Our room had a beautiful view of the ocean and was very comfortable. The hotel staff couldn't have been more pleasant and accommodating. Our favorite memories were an incredible sunset one night and playing golf at the Wailea Emerald course with its incredible views of the ocean. A great trip!

Deborah OgburnInspirato Member

Things to Do

Helicopter Tour

Some of Maui’s best views aren’t visible by land. Blue Hawaiian Helicopters offers various tours, including the West Maui and Molokai 50-minute ride that takes you over gorgeous valleys, cascading waterfalls and striking sea cliffs.

Spa Treatment

Selected as a Top 10 U.S. spa by several prestigious travel publications, Spa Grande at Grand Wailea resort has 40 treatment rooms within its 50,000-square-foot facility, the largest in Hawaii. The stunning, award-winning spas at the Fairmont Kea Lani and Andaz are also ideal for a soothing treatment.

Sunset on Haleakala

Instead of waking at 2 a.m. to join hundreds of other visitors to catch the sunrise atop Maui’s famous volcano, Haleakala, we recommend a view just as stunning: the Haleakala sunset. On the drive to the top, make sure you appreciate the sweeping views of the island, then hang around to see the thousands of stars that seem to be at your fingertips.

Hang Ten

Don’t let Maui Surfer Girls‘ name mislead you. Both men and women participate in their surf classes, and their student-to-teacher ratio is hard to beat. Learn some basic Hawaiian language and board technique before hitting the waves.


Play three championship courses just minutes away from Inspirato’s accommodations at the Wailea Golf Club‘s Emerald, Gold, and Old Blue Courses. Top golf magazines have heaped praise upon these courses, two of which were designed by Robert Trent Jones, Jr. Inspirato’s on-site Destination Concierge team can help members determine the ideal course, depending on skill level and interests.


Rise and shine for superb snorkeling on Kai Kanani’s Molokini Crater Tour. With food, drinks, and snorkeling gear included, you’ll be ready for any encounter at snorkel spot Turtle Town.



Humuhumunukunukuapua’a – Named after the state fish of Hawaii, this unique restaurant at the Grand Wailea floats on a lagoon and features traditional Polynesian design. Prepare for a memorable dinner: Chef Mike Lofaro was named Maui’s top chef in 2016.

Fine Dining

Morimoto Maui – Helmed by James Beard Award-winning master chef Masaharu Morimoto, this showstopper is located within the stunning Andaz Maui at Wailea. Soak in the ocean views over sushi and appetizers, or indulge in the chef’s tasting menu: the nine-course omakase.


Kihei Caffe – Have breakfast at this local favorite. While it is cash-only, you won’t want to miss their enormous macadamia nut and banana pancakes alongside unique coffee beverages.


Grand Luau at Honua’ula – Experience a Hawaiian tradition. Located near the beach at Grand Wailea, you’ll dine on authentic Polynesian cuisine while taking in traditional island entertainment.

Travel Tips

Fly into Kahului Airport (OGG), which is located on Maui near Haleakala. You’ll generally connect through Honolulu to get there and many major airlines offer service.

Maui is six hours behind New York, three hours behind San Francisco and 11 hours behind London. This also means departure flights commonly occur late at night (on Maui time).

A rental car is the most convenient option for exploring the varied terrain of Maui, but Inspirato’s team is happy to arrange private transportation or members, as well.

Maui weather can be unpredictable. It might be raining in West Maui but sunny and dry everywhere else, so it’s a good idea to be flexible when planning outdoor activities. On the flip side, the changes in climate keep Maui fresh and interesting. Year-round highs linger in the 80s, while the lows rarely dip below a pleasant 63 degrees. Gentle trade winds maintain a comfortable beachfront breeze.

When you leave the beach, you’ll likely encounter one of Maui’s numerous microclimates. The island’s leeward (downwind) side is generally less humid, while on the windward (upwind) side of the island, you’ll find a wetter climate that’s home to earthly ecosystems that are uniquely Hawaiian.

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