Courtesy of Hotel Wailea. Photo by Travis Rowan.
If you’re looking for the ultimate in comfort, privacy and beauty, Wailea, Maui, is the place for luxury travel. Choose from Maui’s top luxury resorts, condominiums or private homes for your stay—just a mile from award-winning golf courses, world-renowned restaurants and spas, and some of the island’s most beautiful spots to snorkel, swim and hike. Wailea, with its stunning coastal views, is the restorative getaway you and your loved one have been looking for.
5-Night Luxury Travel Itinerary
Day 1: Arrive and settle into your suite.
Unwind from your flight in your luxury suite, complete with a kitchen, living room, lanai and oversized bathtub. Order a snack from room service, pop a bottle of champagne—maybe even treat yourself to a nap.
Hotel Wailea (3 nights)
Courtesy of Hotel Wailea. Photo by Travis Rowan.
Hotel Wailea is a Relais & Châteaux property and adults-only luxury hotel in the high-end resort community of Wailea, Maui.
From $799/night
Koast
Kampachi collar from Koast Maui. Photo by Sarah Burchard.
Koast is Top Chef Masters winner and James Beard Award-nominated chef Chris Cosentino’s first Hawaiʻi venture, right here in Wailea. Enjoy Mediterranean fare expertly crafted with local ingredients in a breezy resort-like atmosphere.
$25-$100 per person
Day 2: Beach day and shopping spree.
Today you’ll relax on the beach with a gourmet picnic and complete the day with shopping and dinner at Wailea’s high-end retail destination just down the road.
Luxe Beach Picnic
Photo courtesy of Hotel Wailea.
Enjoy a luxe beach picnic with snacks prepared by Spoon & Key Market on the Wailea beach of your choice. Just put on your swimsuit, Hotel Wailea does the rest.
From $300
The Shops at Wailea
Photo from Shutterstock.
Maui’s premier retail destination, The Shops at Wailea, features more than 70 luxury and lifestyle retail stores, including Gucci, Louis Vuitton and Prada.
Aurum Maui
Seared Kanpachi with cauliflower puree, market vegetables and yuzu-kosho dashi emulsion at Aurum Maui. Photo by Sebastian Sayegh/Sayegh Visuals.
Coming July 2025 to The Shops at Wailea, Maui chef Taylor Ponte’s new restaurant, Aurum Maui, offers refined yet approachable dining, blending New American cuisine with Hawaiʻi’s freshest, locally-sourced ingredients. Guests can expect à la carte service, with a strong focus on delivering value through exceptional food, hospitality and an upscale, yet relaxed experience.
$25-$100 per person
Day 3: Hit the green, relax by the pool and dine with the chef.
Today you’ll play a round of golf at an award-winning golf course, unwind in your own spacious pool cabana and enjoy an exclusive bespoke dinner.
Wailea Golf Club
Courtesy of Wailea Golf Club. Photo by Angela Treimer.
Play a round of golf at the premier golf course on Maui: Wailea Golf Club. Choose from three award-winning courses. Courses are located mauka (toward the mountain) of the shoreline on the foothills of Mount Haleakala; at that elevation, golfers can enjoy an abundance of ocean and island vistas. Virtually every hole offers gorgeous ocean views.
From $175 per person
- Wailea Blue Course 18-hole round – $255
- Wailea Emerald or Gold Course – $285
- Wailea Package includes three days of unlimited play on any or all three Wailea courses plus discounted rental club rates (potential savings of $250 or more)
- Afternoon rates – $175 per round on the Wailea Blue or $200 per round on the Wailea Emerald or Gold.
- All prices are per person and subject to applicable Hawaii GET.
Hotel Wailea Pool Cabana
Courtesy of Hotel Wailea.
Enjoy some cabana downtime by the pool. Your reservation ensures a server will check on you regularly with full food and beverage service, fresh towels, plenty of cushy places to lounge and a ceiling fan to keep you cool.
$250
The Chef’s Table at Hotel Wailea
Courtesy of Hotel Wailea
Join chef Ryan Cruz and his team in The Restaurant by Hotel Wailea’s kitchen for an exclusive Chef’s Table experience. You’ll get a front-row seat to the action and special attention from the culinary team as they prepare a curated five-course menu just for you and a guest. Add the wine pairing to enhance your meal. The wine list here is one of the largest on Maui.
From $550 per person
Day 4: Hello Grand Wailea!
Today you will check out of Hotel Wailea and into the Grand Wailea for award-winning spa treatments and dinner at the world-famous Nobu.
Grand Wailea (2 nights)
Courtesy of Grand Wailea, A Waldorf Astoria Resort.
The Grand Wailea, a Waldorf Astoria Resort, is located on 40 acres of tropical beachfront property. It is home to Maui’s largest private art collection, the award-winning Kilolani Spa, Maui’s first Nobu restaurant and your choice of 58 inclusive suites, as well as 50 nearby luxury villas that provide guests with access to all of the Grand Wailea amenities.
From $995 per night
Kilolani Spa
Courtesy of Grand Wailea Maui
No luxury travel vacation is complete without spa treatments. Rejuvenate at Grand Wailea’s Kilolani Spa, voted one of Vogue Magazine’s 2025 best 100 spas in the world.
From $245
Nobu Grand Wailea
Courtesy of Grand Wailea. Photo by Parker Burr.
Enjoy world-renowned chef Nobu Matsuhisa’s signature dishes, such as Black Cod with Miso and Yellowtail Jalapeño at Nobu Grand Wailea – a spectacular 13,000 foot indoor/outdoor restaurant featuring elevated service and cuisine, exquisite artwork and panoramic ocean views.
$100-$200 per person
Day 5: Ocean adventure and upcountry excursion.
Start your morning on the water paddling out to an underwater world of coral reefs and tropical fish to discover. Then hit the road with some sight seeing in paniolo town and dinner at one of Maui’s most acclaimed pizzarias.
Outrigger Canoe Paddle & Snorkeling
Courtesy of Grand Wailea. Photo by Parker Burr.
Start your morning with a paddle out to Grand Wailea’s favorite snorkeling spot in a Hawaiian outrigger canoe, hosted by Maui Pacific Tours. Your guide will point out various tropical fish as you float above brightly colored coral reefs.
$159 per person
Upcountry
Makawao, courtesy of Hawaii Tourism Authority. Photo by Tor Johnson.
Leave the coast for the afternoon to explore Upcountry – a rural region of Maui on the slopes of the Haleakala volcano.
Visit Makawao, a small town known for its paniolo culture, shopping boutiques and art galleries.
Then head to Kula, home to the majority of Maui’s farms and cattle ranches. Schedule a farm tour at Kula Country Farms, known for its strawberries, blueberries and fall pumpkin patch. Or visit Ali’i Kula Lavender for a walk through the lavender fields. Ocean Organic Vodka also hosts tours of its distillery with guided tastings.
Marlow
Courtesy of Marlow.
Before leaving Upcountry, visit the town of Pukalani for a dinner at Marlow. Chef and co-owner Jeff Scheer – Maui No Ka Oi Magazine’s ‘Aipono ‘Chef of The Year’ in 2015 and James Beard Foundation Semi-Finalist for Best Chef in the Pacific / North West in 2024 – creates elevated, seasonal local fare specializing in artisan Neapolitan sourdough pizza.
$25-$50 per person
Then, enjoy a nightcap back at the hotel. Tomorrow you pack and get ready to head home, rested and reeling from your luxury travel experience on Maui.
