Hawaii: Finding the Right Slice of Paradise for Your Personality
No matter who you are, your next (or maybe first) Hawaiian sojourn will come with certain givens: You’ll continually test the bounds of flip-flop appropriateness; your social accounts will start auto-populating the words #sunset_madness within, oh, a day; and you’ll devise at least one perfectly reasonable-seeming plot to move there.
Beyond these basics, however, things start to differ dramatically. Each island has its own distinct personality—and at least one pairs perfectly with yours. Use this cheat sheet to find your match, then go. Soon. Autumn travel brings not only cheaper flights and fewer crowds, but also a sweet deal at any of Hawaii's 12 Hilton hotels: a free fourth, fifth, sixth or seventh night, depending on the property.
For nature lovers: Island of Hawaii
Five volcanoes have helped form Hawaii’s youngest and largest island, and one in particular has helped keep it in the news: Kilauea continues to erupt, and while the display is breathtaking, the lava flow affects less than one percent of the island's 4,028 (and counting!) square miles—nowhere near the resorts. In other words, you’re good to go.
Catch Madame Pele in action
The local goddess of fire and volcanoes, Pele’s been notoriously busy at Kilauea, where you can check out her telltale red rivers from an amazing perspective—and a safe distance—on an aerial tour with the Blue Hawaiian Helicopters.
Night-snorkel with manta rays
On the Kona coast, plankton drawn to floodlit waters lure hungry mantas, who in turn lure curious humans. As the winged wonders—each up to 12 feet across—glide and somersault beneath, you’ll snorkel in a state of perpetual disbelief.
Meet a menagerie
For amazing animal encounters back on terra firma, head to Kona’s Three Ring Ranch Exotic Animal Sanctuary, home to rehabbing creatures from Polynesia and abroad. Schedule a private tour, and you may get meet-and-greets with Hawaiian owls, petrels and hawks, among other intriguing locals.
Be starstruck
The most dazzling show on the Big Island is Mauna Kea’s night sky. The visitor center at 9,200 feet above sea level offers ranger talks, telescopes and star shows. Tour companies will shuttle you from your hotel to the 14,000-foot summit if you want to see the sunset before stargazing at the visitor center.
Where to stay: Hilton Waikoloa Village on the west side of the island, where two golf courses, a tennis court, spa and the Legends of Hawaii Luau with hula and fire dancers round out lagoon-based activities; Grand Naniloa Hotel Hilo—a DoubleTree by Hilton, 2 miles from the Hilo International Airport on the island's east side, where the pool and 9-hole golf overlook Hilo Bay.
How to take advantage of your free night: Relax at Hilton Waikoloa Village’s 4-acre saltwater lagoon, where you’ll spy tropical fish and sea turtles while you snorkel, stand-up paddleboard or kayak.
For die-hard romantics: Maui
Vista-blessed vineyards, miles of gorgeous beaches and one of the most staggering sunrises on earth make Maui ridiculously romantic.
Toast to your love
In a 19th-century tasting room born as a cottage for King Kalākaua—the penultimate Hawaiian monarch—sip pineapple wine and other varietals from local favorite MauiWine. To ratchet up the romance even more, schedule a private tour of the company’s drop-dead gorgeous Ulupalakua Vineyard.
Share a couples massage
The ultimate tandem treatment? Hawaiian Lomi-Lomi Massage for two at the largest spa (and one of the most award-winning) in the state: the Spa Grande at the Grand Wailea Resort, where gifted therapists use their forearms (in addition to hands, fingers and the occasional elbow) to pamper you into happy oblivion.
Drive the Road to Hana
A rhapsody in waterfalls, bridges and curves, the rain forested Hana Highway routinely ranks among the most romantic road trips on earth—with guaranteed hand-grabbing ops as you snake along the coastal cliffs' hairpin turns. Though this drive isn't technically long (somewhere between 52 and 64 miles, depending on whose stats you trust), you do want to allot all day for it. You'll be going slowly to begin with (see: hairpin turns on coastal cliffs), and you'll want to stop early and often (see: waterfalls).
Take a bucket-list bike ride
Watch one of the planet’s most iconic sunrises from the crater of a dormant volcano— Haleakalā—10,023 feet above sea level, where cuddling is mandatory: Predawn temperatures in the 40s aren’t at all unusual. Once the sun’s up and you’ve regained your composure after the surreal gorgeousness you’ve just witnessed, jump on your bikes and coast through more than 20 whoop-de-doo switchbacks. If you want to plot something, ahem, particularly romantic at the top, make sure the ring is well secured in your bike shorts and reach out to the concierge at Grand Wailea, a Waldorf Astoria Resort. In fact, the concierge will happily arrange for any kind of romantic outing.
Where to stay: Grand Wailea, A Waldorf Astoria Resort, where romance might mean hand-crafted cocktails in the Grotto Bar, a swim in the adults-only Hibiscus Pool or sunset dining with a personalized menu in a private cabana.
How to take advantage of your free night: Celebrate your final sunset (or hey, every sunset) in style on a Trilogy Deluxe Sunset Sail, with—among other things—chef-plated appetizers, craft cocktails (try the Moloka'i Mule) and local lager to accompany the orange orb’s descent into the Pacific.
For adventurers: Kauai
Carpeted in rain forests, laced with waterfalls, cleaved by a canyon and edged in crenellated cliffs, the oldest of the Hawaiian islands invites you to take a walk on the wild side.
Zip along the Na Pali Coast
If this 17-mile stretch of towering, accordion-pleated coastline strikes you as prehistoric-looking, you’re having the same reaction as the "Jurassic Park" location scouts, who wound up setting one of the movie’s most stunning scenes here. Get up close and personal with this primordial beauty on a zodiac cruise—under waterfalls, through sea caves and alongside dolphins.
Paddle the Wailua River
One of the few navigable Hawaiian rivers, the Wailua is the ultimate jungle gym. Its tranquil waters are perfect for stand-up paddling or kayaking through this ridiculously lush landscape, where you’ll also find a fern-filled grotto, a 120-foot waterfall and a divine swimming hole. Join a guided tour with Outfitters Kauai or strike out on your own.
Explore Ni’ihau
Sail to this roadless, off-the-grid outpost, a storied little world so unto itself, it’s still known as the Forbidden Island in certain circles. Beyond the fascinating local history—whose cast of characters includes Kiwi sugar barons, Japanese fighter pilots and native artisans—the local nature is worth exploring, not least, the snorkel-able submerged caldera.
Ride horses to a waterfall
Saddle up at Princeville Ranch, where—between the local fields and the Makaleha Mountains—every shade of emerald will compete for your attention while you ride. Tie up Trigger and trek through the fern-filled jungle to a private 80-foot waterfall for a swim and picnic; your hike back takes you over streams and up a 10-foot rock wall.
Where to stay: Hilton Garden Inn Kauai Wailua Bay, on the beach where the Wailua River meets the ocean. Though you’ll be loath to leave the ocean-view pool, do walk to Lydgate Beach Park next door to swim or snorkel in two protected lagoons.
How to take advantage of your free night: Given all of the above adventures, you may want to use your bonus day to chillax. Tour and taste your way through Lihue’s Koloa Rum factory, where the liquor is distilled from locally sourced coffee, coconut, pineapple and sugar. Mai-tais, anyone?
For the eclectic soul: Oahu
Home to 75% of Hawaii’s population, iconic Waikiki Beach, and the state capital of Honolulu, Oahu balances big-city pleasures with plenty of surfing, snorkeling and sunbathing ops.
Tour a Ukulele factory
Learn about this uniquely Hawaiian instrument—including how to play a few notes—at the famed Koaloha factory. If you turn out to be a super-fan, the full immersion tour lets you customize your own uke.
Buy ‘em, Danno
For aloha-style additions to your closet and home, check out Waikiki Beach Walk’s boutiques, adjacent to Embassy Suites by Hilton Waikiki Beach Walk, or International Market Place, across the street from Hilton Garden Inn Waikiki Beach. Or browse the Hilton Hawaiian Village’s 90 specialty stores for all things local, from Moana Quilts to "Hawaii Five-O" official merchandise.
Go nuts at Tropical Farms
Guides in traditional Hawaiian garb lead hourlong tours twice a day to idyllic orchards that grow not only macadamia nuts but also avocados, starfruit and guava. The grand finale? A fire-twirling show and coconut-opening tutorial. Needless to say, you won't want to leave without some of the farms namesake loot, whether you prefer pure, unadulterated macadamias, or flavors that range from caramel to Kona coffee.
Swim with sea turtles
Take a North Shore Hawaii Turtle Tour to snorkel with Hawaiian green sea turtles, some of whom weigh in at 250 pounds. During the guided bus trip from Waikiki, you’ll take in the fabled vistas from Diamond Head Lookout, Makapu’u Point Lookout and Hālona Blowhole.
Where to stay: You'll find several Hilton hotels in the heart of Honolulu, but the most prominent is the oceanfront Hilton Hawaiian Village, which sits on 22 acres of Waikiki Beach and claims the island’s largest pool, 20 restaurants and bars and Friday night fireworks. If you’re looking for a quieter side of Oahu (and guaranteed spacious digs), book at the Embassy Suites by Hilton Oahu Kapolei, where you'll have easy access to Ko Olina Beach, Pearl Harbor and the secluded beaches of Kaena Point State Park, the westernmost point in Oahu.
How to take advantage of your free night: After painting the town red, indulge your late-night cravings by taking on the same beast Adam Richman did on the Travel Channel's "Man v. Food": the famed triple stack of 14-inch M.A.C. Daddy Pancakes at M.A.C. 24/7 at Hilton Waikiki Beach. If—like few others before you—you manage to down the trio in 90 minutes, the meal is free, and you'll get a photo on the Wall of Fame, plus a tee (which may or may not fit after you finish).