How to Spend 48 Hours in Wailea
This small stretch of breathtaking land on the island of Maui not only lives up to the hype—it goes beyond expectations.
In Wailea, Hawaii, it’s not uncommon to see sea turtles float by as you wade in crystal-clear water or catch humpback whales breaching while you’re sipping a sunset beverage on a balcony overlooking the ocean. Known for its five picturesque crescent-shaped beaches and incredible golf courses, Wailea is a luxurious resort community in south Maui that covers over 600 hectares of land and offers staggering views and world-class restaurants and hotels. Here are our top picks for a 48-hour jaunt to this little slice of paradise.
Stay
Fairmont Kea Lani
Nestled at the foot of Haleakalā—a 3,000-metre-high dormant volcano in a breathtaking national park—is the Fairmont Kea Lani. With its sweeping balconies, dome-topped spires, serene white exteriors and arched breezeways, the entire resort has a modern Mediterranean elegance. Opened in 1991 and recently renovated, the property was designed by architect José Luis Ezquerra, a specialist in Middle Eastern and Mediterranean styles. As Hawaii’s only all-suite and -villa oceanfront resort, Kea Lani offers guests an abundance of space and privacy, and the Fairmont brand has mastered the art of creating destinations that are both family-friendly and sophisticated enough for a romantic escape for two. The interiors have been fully refurbished and feature calming hues, wooden accents and island-modern pieces. The two- or three-bedroom villas are ideal for multi-generational travel—each has its own plunge pool, well-appointed kitchen and barbecue area—and all the suites have spacious rooms, bathrooms and balconies.
In the palatial lobby, the new Hale Kukuna (“House of Enlightenment”) serves as the resort’s immersive Hawaiian cultural centre with traditional clothing and tools on display. Guests can also participate in daily activities like ukulele playing, lei making and hula dancing. Just steps away from Hale Kukuna is Pilina, a stylish new bar and lounge offering panoramic views of the Pacific Ocean and local fare. Try the Mauka (“Toward the Mountains”), a specialty cocktail featuring lavender, FY Hawaii Wet Gin and hi‘a lehua honey as well as a delicate honeycomb design on its surface. Pilina also serves some of the island’s finest sushi and sashimi, so don’t miss one of its signature rolls.
Wailea Beach Resort
This seaside resort has everything you could need for a family vacation. The new beachfront villas offer one of the best views on the island and put you just steps from the water. Accommodations are spacious and contemporary with tasteful mahogany accents. Other recently added facilities include the Sundeck Garden Oasis rooms, which feature a private covered outdoor area with a deep bathtub and firepit.
The resort boasts Hawaii’s longest hotel water- slide—along with three others that range in length and age-appropriateness—which is almost 100 metres and will keep the kids (and those young at heart) entertained for hours. The nearby pool has large cabanas for shade and splash areas for smaller kids; there are also quieter swimming areas (including an adults-only oceanfront infinity pool) as well as another family pool, this one situated by the Kapa Bar & Grill for easy access to food and drinks. Kid favourite Luigi’s Andiamo Pizza Kitchen by Roy Yamaguchi is a quick takeout spot with outdoor seating. Next door, a retro arcade and games room (all free) will keep them busy while their pizza bakes in the open-flame brick oven. End the evening by sending the kids to the in-house movie theatre so the adults can enjoy a cocktail at Sunset’s Bar.
Eat + Drink
Ka’ana Kitchen, Andaz Maui at Wailea
Starting the day with a filling breakfast will help you make the most of your dream Hawaiian vacation. Ka’ana Kitchen is a well-known hot spot for dinner, but it has also been quietly turning out one of the best breakfast buffets around. There’s a fresh-juice station that includes healthy ginger shots, coconut water and green juice. Fruit is in abundance; the eggs, bacon and sausage are sourced with care; the omelettes are made to order; and crisp, warm waffles and doughnuts are lightly dusted with icing sugar. Don’t skip the banana bread—it’s an island specialty—and be sure to ask for some HI Spice, Maui’s handcrafted hot sauce, to take home as a tasty souvenir.
Aurum Maui, The Shops at Wailea
Aurum brings seriously comforting American-style bistro food to Maui using local purveyors. The restaurant truly reflects the community it inhabits in every aspect—think ingredients sourced from Maui farms and fishers and interiors decorated by local artists. Chef Taylor Ponte, who was born and raised in Maui, and general manager Natasha (who’s also Ponte’s wife) have created a family environment with thoughtful food and warm service. Try the catch of the day with cauliflower purée or the crowd-pleasing Paniolo Smash Burger, which features a patty that’s made with local pork and beef and topped with caramelized onions and bacon. Bonus: A kids menu is also available, which is not often the case at restaurants of this calibre.
Nobu, Grand Wailea
The celebrity-backed international restaurant group from chef Nobu Matsuhisa has arrived in Maui with a new 1,200-square-metre indoor-outdoor restaurant. Chef Matsuhisa’s Japanese-Peruvian-fusion cuisine fits perfectly with the pan-Asian and European food influences of Hawaii and allows Nobu to shine through what it does best: fresh seafood and bold flavours. All of the restaurant’s beloved classics are served here, including the famous Black Cod With Miso, but the view alone makes it worth a visit and is hands down the best one Nobu has to offer.
KŌ restaurant, Fairmont Kea Lani
One of the most beloved restaurants on the island, the newly refurbished Kō celebrates the many cultures that settled in Maui during the “sugar cane era,” highlighting Filipino, Portuguese, Korean, Japanese and Chinese flavours. Executive chef Matt Dela Cruz balances technical prowess with a comfort-food spirit and digs deep into his own family’s Hawaiian heritage.
Lobby Lounge, Four Seasons Resort Maui at Wailea
Wear your best outfit to grab a drink and people-watch at the Lobby Lounge at the Four Seasons—which just so happens to be the stand-in for the fictional resort in the first season of The White Lotus. There’s a nightly hula show here as well as torch lighting at sunset and live music throughout the evening.
Do
Kilolani Spa, Grand Wailea
A recent $55-million rebuild has turned the Kilolani Spa at Grand Wailea into one of the best spas in the world. Honouring the Kilolani, the stargazers of ancient Hawaii who looked to the skies to navigate the sea, the sprawling space pulls from the energy of Maui. The wellness ethos here is based on Hawaii’s lunar calendar. Every 10 days, the programming changes according to the lunar phase, and treatments are tailored to the accompanying themes: Anahulu Ho’Onui (new beginnings and self-discovery), Anahulu Poepoe (illumination and clarity) and Anahulu Ho Emi (surrender and reflection). Try a Holistic Hawaiian Beauty Facial with naturally derivedbotanicalsoraLomiP hakumassagewithhot lava rocks. A two-hour Hydrotherapy Gardens pass allows you to fully experience the Hawaiian-inspired hammam as well as the hot-and-cold-plunge bathing circuit, which is sure to combat any remaining jet lag.
Wailea Golf Club
This world-class club has three golf courses to play on, including “Gold,” which has been honoured multiple times as one of the 100 best resort courses in the United States by industry experts at publications including Golfweek, Golf Digest, Golf Advisor and Golf Magazine. In a verdant tropical setting, this green boasts unbeatable views, with the Pacific Ocean on one side and the spectacular Haleakalā volcanic peak on the other.
Wailea Beach Path
This whole area of Maui is connected by an approximately 2.4-kilo- metre-long paved path along the coastline—perfect for an early morning or evening (when the temperatures and crowds are at their lowest) run or walk. It allows you to access all of the resorts in the area, the shopping mall and the local grocery store as well as spy hidden coves and waves crashing on the dark volcanic rock. Be sure to take note of marked historical sites and informative signs about local flora and fauna along the way.
Skyline Hawaii
Skyline Hawaii started in 2002 as the first commercial zip-line operation in the U.S. and is now a Certified B Corporation that is committed to reforesting Maui with native plants. Since its inception, the company has planted over 20,000 trees, and its Rooted in Aloha initiative—run in collaboration with Fairmont Kea Lani—helps promote and raise funds for the reforestation efforts. For about $55, you can sponsor the planting and long-term care of a tree, but the more adventurous and hands-on types can head to Skyline’s Haleakalā location for a zip-line tour, during which guides will explain the program and give information about the native plants en route. You can even help plant some trees.
The Shops at Wailea
This open-air shopping complex is walking distance from most of the area’s hotels and resorts. Find everything from high-end designer brands like Gucci, Bottega Veneta and Tiffany & Co. to local businesses like KaiAloha Supply (apparel), Maui WaterWear, OluKai (footwear) and Mele Ukulele. Adjacent to the shops is Island Gourmet Markets, which has a fully stocked grocery store, prêt-à-manger foods—including lots of local specialties—and beach essentials.
