Dine on Fresh Seafood, Explore the Island’s Beauty and Stay at One of the Best Resorts on Maui

When Maui calls, you must answer. And here’s the best answer: Take 72 hours to soak up the sun, explore hidden coves and indulge in pure luxury at the iconic Grand Wailea, A Waldorf Astoria Resort. Forget your everyday worries; this is your ticket to a tropical escape crafted for maximum relaxation and adventure. By way of land and sea, Maui will greet you with waterfalls and gardens, fresh seafood and private charters—and, of course, a grand lu’au. Ready to trade your to-do list for a mai tai? Let’s dive into a three-day itinerary that will leave you dreaming of Maui long after you’ve returned home.

 

STAY

Grand Wailea, a Waldorf Astoria Resort

The hospitable spirit of the island can be felt throughout the entirety of Grand Wailea—with the stunning blue of Wailea Beach in front of you and 40 acres of tropical greenery all around you. “E komo kai,” or welcome in Hawaiian, is more than just a phrase at this luxury destination. Whether you’re here to revel in the sun and scenery or seek adventure throughout your days, Grand Wailea offers endless amenities that will maximize your long weekend.

Wake up in a new Wellness Room, where details are designed to optimize wellbeing, such as the Theragun massage gun, premium eucalyptus bedding, an air purifier and more. Then, stroll to the Kilolani Spa Hydrotherapy Gardens for a contrast bathing circuit that will stimulate your entire body, including a Hawaiian inspired Hammam, saltwater vitality pool, cold plunge, saunas, and waterfall showers. Next, you’ll want to indulge in a slow and casual breakfast buffet with gorgeous ocean views at ‘Ikena before heading out on a cultural tour of the island. All this before noon—unless somehow the adults-only Hibiscus Pool and sandy beach demands total relaxation. And if three days isn’t enough, you can Stay Longer In Paradise—imagine five or more days at this island oasis—and enjoy the benefits of 20% savings.

Location: Wailea

 

DINING DESTINATIONS

Humuhumunukunukuāpuaʻa

When the sun starts to set, head to Humuhumunukunukuāpuaʻa, to experience the refresh of this signature seafood and steakhouse restaurant set amid a beachfront lagoon. The thatched-roof dining area features a circular bar with a glass aquarium, which allows sight of fish swimming beneath you and looks out onto stunning views of the Pacific. Start with a tiki-style craft cocktail, share some Ahi tuna ceviche served in a fresh coconut and go for the 60-ounce porterhouse steak. If you plan ahead, you can also book unique dining experiences like the sunset Seaside Toast or a romantic Waterfall Private Dining option.

Location: Wailea 

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Olivine

It’s not uncommon to crave Italian food when you’re on a seaside vacay, and that’s where Olivine fits into your Grand Wailea respite. Named after one of Maui’s primary minerals, Olivine tricks your senses into thinking you’re on the Mediterranean, with an alfresco setting and all the handmade pasta you could ask for. Kick off lunch with some bubbly or settle into dinner with a Smoke Over Pompei—an appropriately titled aperitif made with bourbon, green walnut liqueur and two types of amaro. If you’re at the resort on a Friday, don’t miss the Vino Flights & Bites Series during happy hour. Space is limited, so take advantage of their virtual concierge before you arrive!

Location: Wailea 

 

‘Ikena Sunday Seafood and Rosé Brunch

One might think that a daily brunch buffet with views of sea and sky at every turn couldn’t get any better. And while there’s plenty of food to choose from every day of the week, you’ll want to take it up a notch on Sundays from 11 a.m. to 1 p.m. with ‘Ikena’s Seafood and Rosé Brunch. Settle into the day with live music and a glass of rosé, then choose from a sumptuous seafood buffet that includes a ceviche bar, crab claws, shrimp cocktail and more. Be certain to reserve your spot—this is the prime way to start any vacation at Grand Wailea.

Location: Wailea

 

Botero Lounge

Named after renowned artist Fernando Botero, Botero Lounge resides in the open-air lobby of Grand Wailea amid nine larger-than-life sculptures made by the late Botero himself. This lounge is where you’ll start a late afternoon and finish off a late night, with craft cocktails designed for every palate (even those desiring zero proof). Fresh sushi is on offer—made with fish and seafood straight from nearby waters. And this is the place to satisfy your craving for liliko’i, which is featured in their creme brulee. There’s live music from 6-9 p.m. nightly, too.

Location: Wailea   

 

Tin Roof Maui

When you’re ready to step out from the resort, we recommend dropping by Tin Roof Maui for some reimagined mom-and-pop takeout. Grab a poke bowl to go, then post up at a nearby beach for a picnic before joining a game of volleyball or flying a kite with the kiddos. Check out the daily menu and even order online. This shop was designed to rejoice in rain on a tin roof, which is a reminder to those who call Hilo home. Honest ono food is what you’ll find here, made by a renowned local chef who knows the true value of community.

Location: Kahalui

 

Spoon & Key Market

There’s something about bubbly and a board of bites that make a meal romantic, and Spoon & Key Market is the Wailea spot to assemble the best. Head into the market to build your own, or schedule ahead if it’s a double date. You can also roll in for breakfast all day for a wrap or a panini, and lunch is available with creative sandwich compositions. But the ultimate date night is on Fridays and Saturdays when Spoon & Key delivers a farm-to-table tasting menu by reservation only.

Location: Wailea   

 

Loulu

A laid-back café-market inspired by Hawaii’s own native loulu palm, this artisanal spot perfectly embodies the island’s spirit of sustainability and wellness with a curated selection of local goods, imported specialties and organic gourmet items. Whether you’re craving made-to-order meals or need something quick from the grab-and-go, Loulu at Grand Wailea has you covered. Here, guests can nourish their bodies with fresh, handcrafted bites, including exclusive items from Erewhon, LA’s iconic organic grocer. It’s Hawaii’s only spot to feature Erewhon products, making Loulu a go-to place for elevated, feel-good eats.

Location: Wailea

 

ON-LAND ACTIVITIES

Kilolani Spa

Designed to help you seek balance within, Kilolani Spa at Grand Wailea embodies the wisdom of Hawaiian culture, offering a space for healing, rejuvenation and restoration. The spa’s programming is inspired by the “kaulana mahina,” the Hawaiian moon calendar, and features treatments and practices that are enhanced by modern wellness innovations. Step into the Hydrotherapy Gardens (book a 2-hour pass here) to stimulate the circulatory system and strengthen immunity with a selection of water therapies, including a co-ed Hammam. Check out the fitness facilities for an ongoing selection of classes, such as Beach Yoga and Sound Healings. And stay on top of your nutrition with wellness-focused menu items at the Wellness Cafe. This is where you’ll want to be to celebrate the next full moon!

Location: Wailea

 

Cultural Tour at Grand Wailea

Grand Wailea takes pride in its Green Pledge, integrating environmental sustainability into everything they do—from the bedding it chooses to the adventures it curates. Guests can immerse themselves in local culture by joining Hawaiian Cultural Ambassador Kalei ‘Uwē ko’olani for a weekly Culture Tour of the property. You will learn about Hawaiian history through the eyes of a local, touching on traditions, medicine and culture. This event happens every Wednesday and requires reservations.

Location: Wailea

 

Blue Hawaiian Helicopter Tours

For those who want to take to the sky, check out Blue Hawaiian Helicopter Tours for an opportunity to witness some of the most remote and beautiful places on the island. Led by expert pilots, these beautiful blue helos promise the tour of a lifetime, showing you an aerial view of the untouched coastline. Our pick near the resort: Waterfalls of West Maui and Molokai. This tour will have you chasing waterfalls in style. 

Location: Kahului

 

Garden of Eden Arboretum & Botanical Garden

Located on the drive to Hana, Garden of Eden is an arboretum and botanical garden that features the island’s spectacular flora. Meander through 26 acres of nature trails to witness rare trees and unique flowers—basically all the tropical blossoms you can imagine. This is where the opening sequence to Jurassic Park was filmed, which adds some unexpected kitsch to an already otherworldly experience. From the Banana Patch to the Enchanted Forest, you’ll make your way from land to sea, arriving at overlooks that promise breathtaking ocean views. 

Location: Haiku

 

Road to Hana

Located on the far east side of the island, Hana is a lush rainforest with many majestic waterfalls and pools. This is a day trip taken by many travelers and requires a 3-hour drive in and out. But instead of rushing through the scenery, locals recommend a slower pace, regardless if you drive yourself or take a tour. Start here for some pointers on how best to enjoy Hana, and then consider one of these top-five tours of the area. Whether you take the waterfall and beach loop or the skyline route, Hana will live on in your memory for a lifetime.

Location: Hana

 

AT-SEA ACTIVITIES

Outrigger Tours

Wailea means “waters of Lea” in Hawaiian—in fact, Wailea is the goddess of canoe builders. It makes sense then that joining an Outrigger Tour would be at the top of your list during a stay at Grand Wailea. Climb into a traditional outrigger canoe and take a guided paddling journey along the golden coast. Plan ahead and book a spot—limited seating is available each morning—then arrive at 7 a.m. for two hours of snorkeling or one hour of turtle watching. And if you’re lucky to be there from December to April, you might spot a whale or two!

Location: Wailea

 

Snorkel with Turtles

Now, more about those turtles! This family-friendly Maui activity lets you get up close and personal with Maui’s famous sea turtles. The guides are so confident that you’ll see the turtles that they offer a money-back guarantee if you don’t. This specialized outrigger tour paddles along Maui’s South shores and provides snorkel gear for the experience. These friendly creatures, called “honu” in Hawaiian, are ready to say hello. These semi-private tours start at 7 a.m. daily and run for one hour.

Location: Wailea

 

UFO Parasailing

When adventure beckons in Hawaii, UFO Parasailing is there to lead the way. With over 39 years of safe chuting, this outfit will take you up, up and away on a one-hour parasailing trip. Check out a first-person view of what it’s like to be strapped in and floating high above the water. Tours start at 8 a.m. daily, with the last one embarking at 4:30 p.m.. But take note of those trade winds, and try to book an earlier time for smooth sailing. For those who want to stay on the boat, UFO Parasailing also offers private charters for fishing and seasonal whale watching.

Location: Lahaina

 

Waterfall Swim at Twin Falls

When you make your way to Hana, be sure to stop by Twin Falls for a dip before you continue the journey. These falls and pools are the first easily accessible water features on the drive to Hana. And rumor has it that the parking lot features one of the best snack stands on this road. Take note that this 1.8-mile out-and-back trail is popular—so popular that sometimes tourists get turned away. But don’t let that deter you since any journey on Maui is really the destination. Non-Hawaii residents will be charged $10 to park and enter. Also, keep in mind that the first Saturday of every month is reserved for Maui residents.

Location: Haiku 

 

UNIQUE EXPERIENCES

Grand Lūʻau

Can you call it a trip to Hawaii if you don’t hula dance at least once? Joining a Grand Lūʻau at Grand Wailea is a must-do experience while on the island. You’ll witness performances that showcase the myths and legends of Maui, all while seated from the comfort of a table overlooking the beach. Interactive entertainment aside, this luau is the most elevated one around, promising unforgettable sights, sounds and flavors. The menu features traditional fare, such as pounded taro, dressed breadfruit, mahi-mahi and roast pig. There are plenty of sweets that highlight the local bounty, too—don’t say no to the fresh Maui Gold pineapple!

Location: Wailea

 

Day Trip to Historic Paia Town + Watch Surfers at Jaws

Four miles into your drive to Hana resides a tiny town known for one very big thing: windsurfing. Once a booming plantation town for the sugar cane industry, Paia is now considered the windsurfing capital of the world. Post up near Ho’okipa Beach in the winter months to watch pro windsurfers and kite surfers dominate giant waves. Make certain to catch sight of the famous Jaws Surf Break—legendary for a reason! Even if you don’t get wet, you’ll work up an appetite. We recommend a fish burger at the popular Pāʻia Fish Market before window shopping your way through this rustic town.

Location: Paia

 

Sound Bath Healing Classes at Grand Wailea

When you’re back at the resort and ready to chill, there’s no better way to improve your overall wellbeing than taking part in a sound bath. Surround yourself with this primal meditative experience with the sounds of chimes, the vibrations of crystal bowls and the resonance of a water drum. These sensations combined are designed to promote inner peace through sound therapy. Classes take place every Saturday at 4:30 p.m. in the Movement Studio. You’ll want to book a space in advance.

Location: Wailea