You will have to try very hard to be bored at Four Seasons Resort Maui at Wailea. Despite that rather hackneyed claim by most every resort in the world, it is actually true that here, there’s something for everyone.
Consider this: Near-perfect year-round weather; pristine beaches (pick golden or black sand!); districts packed with art galleries and boutiques or the sleepiest of towns, blissfully free of distraction; a good dose of history; haute cuisine and kitschy food trucks (both delicious); and most importantly for families, a resort that knows precisely how to create bespoke travel experiences for your time alone, together…or en masse.
If your experience in Hawaii has been limited to massive resort developments such as Waikiki in Oahu, you’ll be surprised by the spacious feel of this southern part of Maui. Wailea is known for its resorts, but this district of pricey homes, championship golf courses and incredible crescent-shaped beaches is spread across an area three times that of Waikiki. Between the high-end retail of The Shops at Wailea and nearby surfing beaches, this is where the blingiest of beach babes effortlessly coexist with leathery, full-time surfers. Farther afield, the road to Hana offers a day (or more) of breathtaking driving; fertile farms welcome visitors; and history awaits in a 19th century village.
*Scenic drives. Maui is full of dramatic drives, historic towns, waterfalls and pristine beaches. Even the most remote corner is only 53 miles away.
*“We Time/Me Time.” The resort’s new program expands on what the concierges do beautifully: create custom experiences so families can enjoy time together and separately. Think: a couple’s massage in a thatch-roofed hale while your kids go on gecko hunts, make leis and learn Hawaiian bowling.
*Kids’ gear. Down to Pack ‘n Plays in poolside cabanas so families with infants can enjoy the pool, Four Seasons makes sure you can pack light. The resort also furnishes car seats for transfers, baby monitors, singing baby swings, bathroom step stools and pop-up tents. Staff will even baby proof the balcony for you. Room service has kids’ meals, and kids five and under eat free at DUO and Ferraro’s when accompanied by dining parents.
*The quintessential luau. One of the best is nearby in Lahaina. Though most are buffets, with the requisite Kalua pig, poi, lomi salmon and haupia (coconut custard), The Feast at Lele elevates the experience with gourmet courses that correspond with the storytelling and dancing—from Hawaii, New Zealand, Tahiti and Samoa.
*Two family-friendly swimming pools for excited kids, surrounded by shaded cabanas, just steps away from the beach. Attendants pass out goodies such as fruit pops all day long and towel huts are stocked with lots of sunscreen.
*Shell leis. Our four-year-old Emily adored these.
*A custom book. The resort has commissioned its own online comic book, Howie Goes to Maui, written by Danny Zuker, executive producer of the TV comedy “Modern Family.” A fun story written from the point of view of young Howie, he tells his parents about all the great features the resort has to offer—and how “We Time/Me Time” can make the whole family’s vacation fun and stress-free.
*Games. A lower lobby games room has Ping-Pong, pool, video games, iPods and Kindles on loan, a big-screen TV and board games. Just ask, and the resort will set up a beach volleyball net for your big game. Tennis courts, a putting green and daily fitness classes are all included.
* Waterfall Pool. Little kids will love this one with a mini slide just long enough for a tiny tot to get a thrill, and a separate shallow pool for the tiniest water babies.
*Adventures. Horseback riding, helicopters, eco tours, zip-lining through the jungle, tours of incredible Haleakala volcano. (Ask the concierge to arrange.)
*Custom itinerary: Choose the times you want to spend with your partner and together with the kids, and the concierge will create an entire vacation around your wishes!
*A couples’ massage oceanside. With the sound of waves lapping, have a rhythmic and fragrant lomi lomi Hawaiian massage. Romantic and tranquil. Spa therapists can teach you how to melt your partner’s tension away with a lesson you can share.
*Romantic strolls. There are few vistas that can surpass this beach walk, with the island of Kaho’olawe and the Molokini Atoll in the distance. (In winter you’ll almost certainly see humpback whales playing offshore.)
*Snorkeling around Wailea Beach, protected by black lava points at its crescent-shaped tips. Four Seasons has complimentary snorkeling gear. Not SCUBA certified? Test out that waters with complimentary introductory scuba lessons in the pool, or certify with Maui Under Sea Adventures.
*Unforgettable Events: this year’s one-of-a-kind experiences include the Aloha Windsurfing Clinic, led by legendary windsurfers Matt Pritchard and Shawna Cropas; Wailea Tennis Fantasy Camp taught by famous players (past instructors include Lindsay Davenport and Tracy Austin); a performance by virtuoso violinist Elizabeth Pitcairn playing the legendary 1720 “Red Mendelssohn” Stradivarious, which inspired the film “The Red Violin” along with an Opus One-paired dinner; and an incredible cycling camp taught by Tour de France veteran and Canadian Olympian Ryder Hesjedal.
*Serenity pool. You’d hardly know this tranquil pool is on property, separated as it is from the action by a set of stairs. Book yourself into one of the Missoni Home-decorated cabanas; perks include a bottle of bubbly, a fruit plate and TV. While we were there, an attendant delivered luscious gelato cones (don’t turn down the Kahlua flavor).
*Stylish shopping. Think all hotel boutiques are created equal? Visit the resort’s 22 Knots and revise your opinion: Carefully curated pieces from Stella McCartney, Lanvin, Jimmy Choo and Missoni stock the shelves. Also, every day from 8 am to 1:30 pm, local artisans display— and sell—their paintings, sculpture and jewelry all through the open-air lobby.
Traditional outrigger canoes. The resort’s champion paddling team takes guests out four times daily around the reefs of Wailea Bay—a simultaneous history lesson and workout.
Dine In—Breakfast is a major event at DUO Steak and Seafood, which has one of the best buffets we’ve ever seen. It stretches from bread and pastry stations; to chefs making Belgian waffles, omelettes and anything else you can think of on demand; to dim sum. Don’t miss the daily smoothies, served in cute little beakers to every table.
The restaurant completely transforms at night. Steak and seafood are elevated by careful preparation of beautiful local ingredients from the fertile Maui soil. Try the simple-but-elegant Haiku tomatoes three ways: with saffron, parsley and tomato aioli, and pickled Maui onions. The restaurant caters to kids: extra points for the server who asked my permission before bringing Emily the complimentary post-dinner cotton candy.
Have at least one night alone at Four Seasons’ Ferraro’s Bar e Ristorante, and ask for a table overlooking the ocean. Simple Italian preparations tapping local ingredients are superlative: neon-red and orange local tomatoes came with a silky burrata, and the chicken involtini, with goat cheese, basil and tomato confit over creamy polenta, had us wanting to lick the plate.
(Note: children under five and under eat free at both resort restaurants (above) when accompanied by a paying adult.)
Wofgang Puck’s Spago is a fun combo of the Asian-inspired Spago you know from his flagship and Hawaiian dishes. A delicious choice—with a nod to retro Hawaiian cuisine: the grilled Mahi Mahi with pineapple, ginger barbecue and sweet Maui onions.
Dine out—Roadside dining is fun all over the island. Kids will love the shrimp trucks, like Geste Shrimp in Kahului, where you can order a dozen shrimp (try Hawaiian Scampi or Spice Pineapple) right from the truck. We sampled at least a half dozen loaves of homemade banana bread sold roadside (extra points for macadamia nut topping!).
It may be a chain now, but the original five locations of Maui Tacos still serve the best grilled fish tacos around. There’s a location just minutes away from Four Seasons in Kihei.
About a 14-mile drive north from Wailea Beach, you’ll find some of Maui’s most authentic eats between Wailuku and Kahului. Stop in at Sam Sato’s, a noodle palace serving saimin, chow fun and other specialties here since 1933.
Ma’alaea Waterfront Restaurant, a 20-minute drive northwest of Four Seasons on Ma’alaea Road, is classic continental—made with wonderful local ingredients. Look for fish like Monchong, Ono, Opah, Ahi and Onaga. Try the Opakapaka En Bastille and a delicious cioppino (made from local fish, of course), all with an unparalleled view of the lapping waves where south and west Maui meet.
1. Scenic drive. Motor along the spectacular, curving, 53-mile Road to Hana, looking for its waterfalls, hiking spots and vistas. Stop at the Wai’anapanapa Black Sand Beach at mile marker 32. Kids will love Coconut Glen’s, a little outdoor shack around mile marker 27 that serves incredible ice cream made with coconut milk and served in coconut bowls—with coconut spoons!
Young historians will be entranced by the hard-to-find entrance to the resting place of aviator Charles Lindbergh, at mile 41 in Kipahulu, on a windswept cliff overlooking the ocean, with a little chapel that’s sometimes open for visitors.
2. Milk goats. Show the kids where some of the creamy goat cheese they’ve been eating at Four Seasons comes from. Surfing Goat Dairy, on the slopes of Haleakala Crater in lower Kula, gives tours of its goat farm and lets you milk a goat. Order one of the amazing goat cheese truffles at the dairy.
3. Lahaina. Stroll down lively Front Street in Lahaina, a historic 19th century whaling town, that’s now teeming with art galleries, restaurants and eclectic shops. History buffs will love the U.S. Seamen’s Hospital, Lahaina Prison, the Pioneer Inn and the Lahaina Historic Trail. Banyan Tree Park is filled with amazing and huge trees, dating back to the 1870s, when they were imported from India.
4. Culture. Music festivals, Japanese culture shows, pop fashion and even beer festivals (for parents) are on tap at the Maui Arts & Cultural Center, which always has something going on within its two indoor theaters, outdoor amphitheater and art gallery.
5. Beach day. One of the best beaches in America is just a short drive from Four Seasons. Every night at sunset at Kaanapali Beach in western Maui, a cliff diver lights torches along the beaches northernmost cliffs and dives off Black Rock, a dramatic ceremony that reenacts a feat by revered 18th century King Kahekili.
*Babies: Ask the concierge for their preferred nanny from The Nanny Connection, a nanny agency that’s been on Maui for 20 years. Our nanny, Audrey, showed up with a bathing suit and fun things to do, and Emily was in love before we’d even left the room. We kept in text contact during the day, and they had the time of their lives swimming, eating pizza at Ferraro’s and beachcombing. Easily the best babysitting experience we’ve ever had. Prices are around $19 per hour, with $3 additional per child—a bargain for multiple kids!
*Toddlers: Kids under five can go to the complimentary Kids for All Seasons (KFAS)* kids’ club—(it’s a state law that they can’t be left alone under five). But accompany them, and you might just have the time of your life. Our four-year-old learned to dance the “Hukilau”—complete with grass skirt, coconut bikini and lei. (Your nanny may also accompany your child to the KFAS club.) Everyone will love the live hula dancing that happens in the lobby at sunset, as well as the man who goes around the property with a torch, lighting the torches and blowing his conch shell to welcome the evening.
*Kids 5-10: Let kids go crazy all day long at the complimentary Kids for All Seasons (KFAS)* kids’ club program (ages five to 12). The clubhouse, with an outdoor patio and climbing wall, checks kids in and out all day, and posts a roster of the day’s events, including games, sports, music, treasure hunts, arts and crafts, movies, sandcastle building and visits with Ricky and Lucy, the house parrots. During peak seasons (for a nominal fee), the club even holds night events: an “amazing race,” pirate night, crab hunts…
*Tweens & teens: Action-oriented programs include the resort’s incredibly popular “Under the Water-On the Water-On the Beach” program, where teens can snorkel, scuba dive, kayak and take stand-up paddleboarding lessons—and of course, hang out at the Waterfall and Fountain pools. They’ll love getting time all to themselves in the tricked out game room. And they can check out footballs, Frisbees, iPods, beach volleyballs, boogie boards and tons of other gear that will keep them blissfully independent of pesky parental units.
*Kids For All Seasons (KFAS) is a Four Seasons complimentary recreational and educational program for children of resort guests. Most KFAS clubs are designed for youth four to 12 years old, and open daily from 9 to 5. (Younger children can often join KFAS with a nanny or parent, or resorts can arrange for babysitting.) But details vary from property to property, so check the resort’s website for more information.
Kids can go all day or just for an hour or two. Activities inside and out include games, sports, music, treasure hunts, swimming, arts and crafts, cultural education, environmental preservation work and yoga. Not your average camp, the VIP offerings are pretty extraordinary—for example, at Four Seasons Resort Costa Rica at Peninsula Papagayo, there’s a Dive-In Movie Night where kids watch a film from inflatable seats floating in the pool with the screen suspended between two palm trees. The fun roster includes Spanish lessons, mini golf, pizza making with the chef and—on special occasions—traditional Costa Rican nights with live Merengue and Salsa, stiltwalkers, traditional garb, acrobats and drumming.
Read more about Maui in Four Seasons Magazine.
Read our “Concierge Recommendations” for Maui in Four Seasons Magazine.
Andrea Bennett is a contributing editor for Travel + Leisure whose work you can also find in T:The New York Times style magazine, Town & Country, and The New York Post. Andrea has also written for The Wall Street Journal (for whom she wrote the weekly "Takeoffs and Landings" column, Money, Fortune, Men’s Journal, Islands, Departures, Town & Country Travel, Business Traveler, and Southern Living. She currently consults with hotel companies and is a partner in Bespoke Content Studio. After years in New York City, South Carolina and Kuwait, she and three-year-old Emily (who has worked a passport since six months of age) now call Las Vegas home.
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