Maui Adventures for Singles

Once the province of family vacations and honeymoons, Maui has become increasingly renowned as the "it" place for singles. And is it any wonder? With its ‘Grammable landscapes, award-winning dining scene, and abundance of activities, it’s the perfect place to find yourself—or your next S.O. (even if it’s just a holiday romance). Here are the leading things to do for independent travelers:

Dine in Style

The Mill House has garnered a reputation as one of the hottest and most unique eateries on the island. Situated at the base of the West Maui Mountains—lush, vertiginous peaks that are often draped in mist—the restaurant has it all: Stellar views, a charming setting that showcases Maui’s plantation past, excellent cocktails, and, of course, dynamite, farm-to-table fare. On select weekend nights, The Mill House’s top talent steps outside of their usual kitchen to present Maui’s Chef’s Table—a feast that tells the chefs’ stories through the freshest seasonal ingredients. Deemed an interactive dining experience, the multicourse meal encourages conversation with the chefs while the beauty of Maui Tropical Plantation beckons. Given that the inspired food is served at communal tables, you’ll no doubt strike up connections with other diners. Bon appétit—or, as we say in Hawaii, e ‘ai kaua.

Mill House

Snorkel with Kindred Spirits

Whether you’re an avid diver or have never dipped a toe in the Pacific, Maui—with its luminous water (and everything from calm breaks to enormous waves)—has got you covered. One of the best ways to explore its magnificent ocean is with the crew at Redline Rafting. Based in beachy Kihei, the lively, eco-conscious company takes small groups out on their customized, 35-foot rafts (read: fun, fun, fun). Aboard their Molokini snorkeling tours, you’ll hit up a volcanic caldera to see remarkable marine life before backtracking to the scene of Maui’s last lava flow. The views at Molokini Crater are astonishing—grottos, caves, the blue beyond, even the possibility of spinner dolphins. The experience is intimate in the best possible way: You’ll have a ball with the other guests but without the crowds of larger charters.

Molokini Crater

Hit Up the Barmuda Triangle

For years, Maui and nightlife were seldom featured in the same sentence. But in the last decade, the island’s after-dark scene has gone from nonexistent to chill to outright wild, completely depending on your preferences. If you’re looking for a sedate experience—say, enjoying a handcrafted cocktail while listening to mellow Hawaiian music—stick to the resort areas, where places such as the Four Seasons Resort Maui at Wailea offer precisely this vibe in their lobbies. But if you’re after a raucous night, by all means, take an Uber to Kihei’s Triangle. Here, eight watering holes offer an array of distinct experiences but all, really, have one point in mind: To part-ay. Start off with a pint of boutique beer at What Ales You before traipsing next door to the Dog & Duck Irish Pub for a round of darts. Then, belt out a karaoke song or two at Haui’s Life’s a Beach before waltzing into the South Shore Tiki Lounge to dance. (And that’s just our getting started.) It can be crazy-entertaining, but be sure to call it a night before the bars officially close: Like the real Bermuda Triangle, this place can get sketchy.

Kihei Triangle

Redefine the Contemporary Luau

Luaus have long struck visitors as the embodiment of a tropical holiday. The leis, the hula dancing, the drums, the fruity umbrella drinks—the Hawaii vacation staple is as enticing as it seems. But when traveling solo, you might not be keen on dining by your lonesome for every meal; at the same time, the vast crowds at many luaus may seem overwhelming. Your solution? Maui’s newest luau, The Feast at Mokapu. Presented by the Andaz Maui Wailea Resort, the luxe but cozy event (a maximum of 150 guests) takes place on one of the island’s most splendid beaches. Fourteen plated courses are served as the sun descends beyond the horizon—and the night lights up with the melodies and movements of Polynesian musicians and dancers. With the meals served ‘ohana style, and tables that are set to stimulate connection, chances are you’ll meet someone special—or get gleefully reacquainted with yourself.


                                                                                      The Feast at Mokapu

HopAboard a Booze Cruise

While the Kai Kanani—to our delight—is more about cruising then boozing, their Adventure Sunset Sail will remind you why you’re traveling solo: There’s something exquisite about cavorting with others while still savoring dazzling scenery entirely unfettered. Almost entirely, that is: The deluxe catamaran accommodates a relatively intimate number of guests as it departs from Maluaka (a must-see beach in Makena) and heads towards the horizon. Along the way, you’ll hear the dreamy notes of Maui-made musician Brother Dwight, dig into ahi and charcuterie, relish the golden hour that concludes Maui days, partake in a champagne toast—and, perhaps, flirt with a fellow traveler. Salute indeed.

Kai Kanani Sunset Sail

Hang Ten

There are few things more empowering than learning a new sport—and bonus points if said sport happens to be conducted on one of Earth’s most luminous bodies of water. Maui claims a wealth of incredible options, from kitesurfing to stand-up paddling to outrigger canoeing. Classes abound across the island, but we have an affinity for Maui Surfing Lessons. Group courses guarantee that your time on the water is as instructive as it is pleasurable—and it’d be no surprise if you found someone to hit pau hana with after.

Maui Surfing Lessons

Sail Down One of the World’s Largest Dormant Volcanoes

Haleakala—the colossal volcano that comprises three quarters of the island of Maui—is impossible to disregard. Towering 10,023 feet into the sky, it possesses one of the more stunning landscapes most will ever see (and this isn’t hyperbole either). Its sunrises are so epic that they require advance registration with the National Park Service—and joining a crew to see it before biking down the mountain’s slopes will render it unforgettable. Bike Maui is just the outfit to go with for this experience. The high-spirited crew makes you feel loved and welcomed, and Cruiser Phil’s Guided Sunrise Tour includes not only dawn at Haleakala’s summit but also a staggeringly gorgeous journey to Kula Marketplace (where you’ll find eats and art in equal measure) and an hour in the enclave of Paia. It’s the perfect option for outdoorsy types who want to be around other intrepid travelers.

                                                                      Biking down the Haleakala Volcano road

Venture into The Wild

The 52-mile stretch of coastline that comprises the Road to Hana has been hailed as many things, from one of the World’s Best Travel Journeys (FlightNetwork) to “one of the world’s best drives” (Travel & Leisure). Serpentine, lush, and so picturesque it’ll leave you breathless, the rainforest-laden route is as phenomenal as its accolades suggest. Rather than heading out on the three-hour drive by yourself, book a Road to Hana tour with Valley Isle Excursions. Why? Other than why not—a vacation is a chance to spoil yourself, after all, and making the drive alone may become tedious. This venerable company will help you make the most of your experience. Their plush vans have a maximum capacity of 12 guests; they also boast elevated seats and extra-large windows, which will allow you to soak up the eye candy. Trust us, it’s profuse, from the spectacular Wailua Valley to the tiered waterfalls at Oheo. Along the way, you’ll find pockets of silence so rich you’ll hear your own heartbeat—and be reminded that traveling solo is a profoundly rewarding experience.

Exploring the Road to Hana

Soar Above the Treetops

Zip lining in Hawaii is a bucket list activity—how else can you see unspoiled landscapes while getting one of the greater thrills of your life? Well, a helicopter ride, you might argue, but zip lining kind of epitomizes singlehood, doesn’t it? While Maui boasts several superb lines, Skyline Hawai’i’s Ka’anapali tour is one for the record books. Voted the #1 zip lining tour in Hawaii by readers of Hawai’i Magazine, this 8-line adventure tour will take you from the site of ancient petroglyphs to a waterfront oasis. Plus, you’ll be doing good while having a grand time: Skyline is the first zip line operator in the world to join 1% For The Planet—a cadre of businesses that contributes at least one percent of sales to environmental preservation.

  Ka'anapali Tour zipline