Wailea Luxury Guide for families: Where to Stay, What to Eat, and Best Things to Do while visiting Maui.
Hawai'i is truly a destination unlike any other. With its warm and welcoming people, breathtaking beaches and diverse landscapes, it offers something for every traveler. Maui holds a special place in my heart as the first island I visited. Embark on an adventure and drive the winding road to Hana, where hidden beaches and waterfalls await discovery. Dive into the crystal-clear waters and snorkel at Molokini Crater, just off the coast. Experience the awe-inspiring sunrise or sunset from the island's highest point, the majestic volcano Haleakalā. Located on the southwestern coast, Wailea beckons with luxurious resorts and world-class cuisine, serving as the perfect starting point for your Maui adventure.
Pick Wailea if you want:
· Luxury
· Gorgeous walkable trail perfect for sunrise or sunset views.
· Outstanding Fine Dining
· High End Shopping & Art
· Relaxation
This guide is for travelers who want Wailea’s best luxury resorts without overplanning. I design Maui vacations for couples, families, and gay dads traveling with kids who want the island to feel effortless. If you want help matching the right resort and building a smooth itinerary, I’ve got you.
Where to Stay
Four Seasons Resort Maui at Wailea – Luxury perfected. Expect a warm greeting each morning you arrive at the decadent breakfast (complimentary when booking with me). Retreat to your own private poolside chairs where you can relax while ordering delicious food delivered poolside. The turkey club does not disappoint. Embrace all that Hawaii has to offer from one of my favorite hotels in the world. All Four Seasons Preferred Partner Benefits included.
Andaz Maui at Wailea – Another great option in Wailea, you’ll fall in love with the gorgeous infinity pools that offer endless sunset views during your stay. They host a fantastic luau on site as well that you have to experience. All Virtuoso Perks included.
Grand Wailea Maui – Hands down the best pool on Maui. There’s slides, obstacles, rapids, and even a mini-wading pool beach for littles. The grounds are massive and impeccably maintained. They’ve spent a lot of time doing refurbishments over the last few years and it shows. This hotel is such a comfort for me as I visited when I was a child. Your family will love it too. All Virtuoso Perks included.
Fairmont Kea Lani – An all suite hotel? If you like a bit more room, this place is perfect for you. It offers a bit more privacy as it’s tucked away toward the end of Wailea. Fantastic restaurants and a great pool, you will get lost in this little slice of paradise. All Virtuoso Perks included.
Montage Kapalua Bay – Montage doesn’t get enough attention and these villages on the North West side of the Island will not disappoint. Luxurious. Spacious. Perfect for your next family getaway. All Virtuoso Perks included.
Where to Eat
· Humuhumunukunukuapua'a: This staple at the Grand Wailea recently went through a refresh and menu update. Highlighting outstanding seafood from the area with a dining area design to make you feel like you are eating on your own little island. Make a reservation near sunset and prepare to be treated to one of my favorite views on the island.
· Duo Steak & Seafood: Whether you are stopping in for their one-of-a-kind breakfast buffet or booking a reservation for dinner, Duo is an outstanding offering located at the Four Seasons hotel. If you visit more than once, then the friendly staff will certainly remember your name. It’s a wonderful restaurant offering steak and seafood fare that you’d expect from the name with truly incredible service.
· Ferraro's: Another offering by the Four Seasons, this one offering lunch and dinner with an Italian/Mediterranean inspired menu. This establishment has also recently got a few lovely upgrades and dinners are sure to appreciate a prime view of the ocean while dining under the newly installed shade.
· Hotel Wailea Restaurant: The Hotel Wailea is an adults only resort - but the restaurant welcomes diners of all ages. Try the chef’s course for an excellent meal with a great elevated view of the Wailea coast. The scallops, if available, are extraordinary.
· Lineage: A local Asian fusion restaurant - it’s got great flavors and is located in the Shops at Wailea. I’d recommend making a reservation for here as well as the wait can be quite long at prime time.
· Mama’s Fish House - This isn’t in Wailea - but who cares? This is the best restaurant in Hawai'i, and possibly the world if you ask me. The fish is fresh and caught daily by a local fisherman. The ambience, the food and the service are all quintessential Hawai'i. This place books up quickly, you will likely need to plan months, if not a year in advance, if you want to secure a reservation - but to say its worth it is an understatement.
· Lappert’s Ice Cream - There’s usually a line here, and that’s because its an iconic Hawai'ian ice cream chain. Anything with macadamia nut is my favorite, but there are plenty of uniquely Hawai'ian and classic flavors here. I’d recommend getting a cone and grabbing a seat in the nearby remodeled plaza.
Honolulu Cookie Company - This is a great place to grab a souvenir for friends and family back home. These classic shortbread cookies come in a variety of flavors such as lilikoi or go for a classic macadamia nut.
What to do
· Whale Watching - Likely the most WHALE-known activity - grab your binoculars or even just take a peek from the view of your resort balcony. Humpback whales fill the waters outside of Maui from mid-December through the end of April. Take a boat tour to see and hear these magnificent creatures up close!
· Snorkel Molokini - Molokini Crater is just a few minutes sailing from the shores of Wailea. Hop aboard a sailing yacht and be prepared to experience some of the best snorkeling the world has to offer. You’ll likely see lots of exotic fish and my personal favorite - sea turtles!
· Road to Hana - The road to Hana is a full day trip experience in my opinion. Rent a car and head up the coast and along the winding road. Download an audio guide that shares the history of the island and points out unique and interesting stops along the way. From hidden food stands to gorgeous waterfalls this is a journey you won’t want to miss.
· ʻĪao Valley State Monument - Want to see gorgeous mountains and lush jungle? Then go no further than the ʻĪao Valley State Monument. Check out the visitor’s center and learn about the history of King Kamehameha. The park now requires out-of-state visitors to make a reservation - but it is well worth it!
· Beaches - Grab your sunscreen, pull up a beach chair and plop open that umbrella! There’s no shortage of beaches in Wailea including Wailea beach adjacent to both the Four Seasons and the Grand Wailea. These beaches are kept in wonderful condition and are perfect for families. There’s plenty of room and it affords the opportunity to relax and watch a beautiful sunset in the evening.
· Wailea Walking Path - Along almost the entirety of Wailea is a walking path that connects the major resorts and shopping while offering breathtaking views of the ocean. This is a perfect trail for a morning or afternoon stroll (and I highly recommend going for a walk at least once a day!).
· Shopping & Art - The Shops at Wailea offer a variety of restaurants, high-end shopping and of course it wouldn’t be a trip to Hawai'i without an ABC convenience store. There are also many fine art dealers highlighting beautiful pieces by local and international artists. Don’t forget to stock up on some snacks at the Island Gourmet Market (or even stop by for breakfast and lunch!).
Sample 5 Day Wailea Rhythm (Easy, Luxury, Family Friendly)
DAY 1Arrive in Maui, check into your Wailea resort, and ease into island time. After a swim and a sunset stroll, head to Duo Steak & Seafood at the Four Seasons for a relaxed first-night dinner. Excellent steak and seafood, and a perfect welcome to Wailea.
DAY 2Start the day with a Molokini snorkel cruise. Hop aboard a catamaran and spend the morning in crystal-clear water with tropical fish and sea turtles. Afterward, head back to the resort for a slow afternoon by the pool. Finish with dinner at Humuhumunukunukuapua‘a at the Grand Wailea, ideally around sunset.
DAY 3Rent a car and take on the classic Road to Hāna. Download an audio guide so you can enjoy the drive without stressing about stops. Waterfalls, overlooks, little fruit stands, and yes, do not skip the banana bread. On the way back, end the day with dinner at Mama’s Fish House in Paia. Reservations are a must, and it is the perfect reward after a full day.
DAY 4Keep the morning intentionally light. Indulge in a spa treatment or a quiet beach day and embrace full relaxation. In the evening, attend one of Maui’s wonderful luaus for a classic cultural experience with great food, music, and performances.
DAY 5If you’re visiting in whale season, head to the marina for a whale watching cruise and see humpbacks up close. Spend your final afternoon at the beach or pool, then close out the trip with the three-course chef’s menu at Hotel Wailea Restaurant. The view at sunset is unbeatable and a lovely finale to Wailea.
Want this tailored to your dates and travel style?
I plan Maui vacations for families and gay dads who want luxury without over planning. If you’d like me to match the right resort and build a smooth itinerary, start here.
More travel guides coming soon, including Paris & London.
