How to Hawaii Hop for the Ultimate Island Honeymoon

Say 'aloha' to allll of Hawaii

Updated 09/07/17

Getty Image

Looking for magic on your honeymoon? Let’s be honest, who isn’t? When it comes to sure things, Hawaii is the call to make. There’s no shortage of dreaminess to be had on these jewels of the Pacific, where there’s plenty of opportunity to indulge in the classic Hawaiian hallmarks—luau and ukulele lessons, anyone?—along with brilliant and less common experiences across the islands.

With daily flights from the mainland U.S. to several of the eight major islands, it could be tempting to fly in and plop down in the first infinity pool–adjacent lounge chair you see for 10 days. But that wouldn’t be doing justice to the diverse archipelago, which has so much to offer. An alternate plan: Hitting two to three of the stunners for an island-hopping adventure that is sure to serve up more beauty than imagined.

There are so many ways to go about piecing together your once-in-a-lifetime trip, but one way is by figuring out what you want. Is it a mix of a cosmopolitan city with picturesque beaches, views of Diamond Head, and maybe surfing one of the world’s most epic waves? Definitely get to Oahu. Are plush resorts with scene-y pools and incredible dining—and maybe some kitesurfing for a dose of adrenaline—your priority? Hit Maui. For total immersion in nature at its best with a strong sense of seclusion, there’s the Big Island, or Kauai, with its hippie vibe, verdant jungles, and plentiful opportunities to commune with Mother Earth on trails and cliffs.

Lanai, meanwhile, is more off the beaten path—almost literally, it has just one paved road on the whole island—yet boasts one of the world’s most fabulous resorts.

Once you have your priorities straight, it’s just a matter of fitting them all together, with short inter-island flights or even boats. You can hop an hour-long ferry from Maui to Lanai, and vice versa, for example, or another to Molokai, to get truly off the radar—Lanai is separated by the two islands by a wide channel, affording jaw-dropping views packed with fast-moving azure water, and jagged mountains and cliffs nine miles in the distance.

One idyllic itinerary might begin like this: Land in Honolulu and head west—away from overrun Waikiki—to the Four Seasons Resort Oahu at Ko Olina (new last year) where the sunset views are flawless and the adults-only pool and cabanas perfect for lazing a day away. Book a heavenly couples’ treatment (you can’t go wrong with a lomilomi massage preceded by a local passion fruit and Maui sugar cane scrub) in one of the Muliwai Healing Hales where, with one wall open to nature, you'll truly be living the Hawaiian dream.

Feast on the freshest fish prepared in a multitude of forms (tacos, grilled, poke) alongside mango-drizzled piña coladas and then mouthwatering Mediterranean-Italian fare at Noe, outfitted with vibrant artwork. Hike to a secluded waterfall, tour a local organic farm, snorkel with sea turtles, make haku lei flower crowns, stargaze with a powerful telescope, learn about ancient Polynesian voyaging, and practice the art of lauhala weaving.

When you’re ready to venture out, those in specialty suites (booked at published rates) can grab a Tesla Model S or X for a day trip, say up to the quaint North Shore to see the Banzai Pipeline surf reef break, or hike to WWII pillboxes, or to Waikiki or Honolulu for shopping and a day at the iconic beach. Make like the #couplegoals Obamas and grab a bite at Mahina and Sun’s restaurant. From there, those seeking more relaxation could head to the Fairmont Kea Lani on Maui, while couples who want to turn up the activity level may choose the Big Island, where Volcanoes National Park shouldn’t be missed—you can even trek near active red lava flow.

Hiking enthusiasts can get their fill all across the island on some of the most picturesque trails known to man.

But it’s not only hiking. Exploratory types can seek out black- and even green-sand beaches, which must be one of the world’s rarest sand colors. Base yourselves in Kona, where the beer and coffee are world-class, at a rental house on the beach or at the Four Seasons Hualalai, adjacent to Kekaha Kai State Park. There are also local wineries, as well as biking, golfing, and sunrise summits to make.

For any itinerary, Lanai makes the ideal finale. The tiny former pineapple plantation island—where Four Seasons Lanai is the place for luxury like you’ve never seen—offers some adventure, but also lots of ways to decompress together. The resort puts a premium on intimacy and privacy—as opposed to militaristic rows and rows of lounge chairs beside the pool, these free-form stunners are surrounded by lush gardens with hideaways and hammocks that allow couples to feel like they’re in their own gorgeous world.

Of course, staff can still find you to deliver fresh, fruity cocktails and light, colorful fare from Malibu Farms.

Because of the manageable size of the island, there’s no pressure on Lanai to do too much—a welcome feeling after the stress of a wedding. After opening the blackout curtain in your seductive room and spotting the alluring big blue ocean from your bed through floor-to-ceiling windows, you might be inclined to spend a lazy morning snorkeling alongside tropical fish and spinner dolphins just below the resort, and you’ll feel like you really accomplished something. Ditto if you rent a white Jeep Wrangler and venture out to the amazing red Mars-like landscape at Garden of the Gods, take a trail ride on horseback, or go to town for poke at the Ohana Poke Market stand and a movie at the small but world-class theater.

Stress-melting volcanic stone massages are also a good call, before a long drawn-out dinner under the blanket of stars at Nobu (don’t miss the tempura whitefish, only on Lanai’s menu), or the best surf and turf of your life at One Forty. While the property is filled with gorgeous, authentic reminders of where you are (like a giant wooden outrigger canoe), the most charming part may be the exotic birds who will likely bid you “aloha.”

Related Stories