Hawaiian Island Honeymoon Destinations: Maui & Kauai

The pool at the St. Regis Princeville, Kauai.

The idea of a honeymoon in Hawaii conjures up the images we’ve all seen before—the fancy hotel, the welcome leis, the colorful luaus. And while those rituals will more than likely be part of your Hawaiian getaway (and with good reason!), the truth is that our 50th state holds so much more: breathtaking landscapes, cuisine you won’t soon forget, and the unending chance for adventure. The truth is, it’s nothing short of magic.

By choosing the particular islands you visit and the type of hotels you stay in, you have the opportunity to design your dream getaway. And for the perfect blend of relaxation and adventure, we’ve found just the itinerary: your first days spent lounging, recharging and exploring on the smaller island of Kauai, nestled in the luxurious St. Regis Princeville on the North Shore, followed by an energized stay at the Four Seasons Maui at Wailea, on the southern side of the island, where there’s no shortage of surfing, whale-watching, snorkeling and sailing, to ensure that every single minute is a blast until, as they say, the honeymoon is over.

The Four Seasons Maui at Wailea

BY DAY: That sought-after relaxation will hit you hard on the St. Regis beach, where you’ll finally take that months-overdue nap to the sound of the Hawaiian breeze in the palm trees. Should you feel like wandering from your lounger, there are several ways to explore Kauai’s Na Pali Coast. Two popular ones: Hike Hanakapi’ai—there’s an eight-mile route to a waterfall or four miles to the beach—or hop aboard a Sunshine Helicopter tour (spring for the front row for the best view) to see natural waterfalls up close.

The Serenity Pool at the Four Seasons Maui

In Maui, sign up for a surf lesson with Maui Wave Riders early in your trip, so that when you fall in love with it you still have time for another. Talk to the concierge about which Trilogy-run tour suits you best: the half-day snorkeling jaunt to Molokini, or the full-day catamaran sail to Lana’i, where you’ll whale-watch before disembarking for a tour of the island—a former pineapple plantation—and a crew-cooked lunch by the water. Back at the Four Seasons, indulge in an outdoor spa treatment: Book a couple’s massage in one of the thatched huts near the ocean, or inform your pool attendant that you’d love a pool-side therapist to swing by for a mini massage, during which you needn’t even move your chair out of the sun.

Take in the amazing view from the Terrace at the St. Regis Princeville

BY NIGHT: In Kauai, spend a few evenings wandering through the neighboring town of Hanalei, where seafood restaurants and surf shops line the quiet main drag. A more bustling version of this can be found in Lahaina in Maui; plan on hanging here a bit after your Trilogy tour docks for the night. Perhaps your most memorable nighttime activity, though, will be watching the sunrise on Haleakala: The tour guide picks you up at 3 a.m., and by near-morning, you’re standing at the summit of the 10,000-foot volcano.

WHAT TO EAT: You’ll have your first “I’m on my honeymoon” moment when you sit down for breakfast at Makana Terrace at the St. Regis, which overlooks miles of ocean and mountains. They serve a lovely dinner there, too—but in Hanalei, you’ll want to sample sushi at the Dolphin and tapas at Bar Acuda. And your poolside must-order: Hawaiian “nachos”—ahi poke and avocado tossed over a bed of Maui onion chips. At the Four Seasons, hit up each restaurant at the resort, from Ferraro’s (fish tacos and poke bowls during the day and sophisticated Italian at night) to DUO Steak & Seafood (do not skip the Tuesday raw bar). Set aside other nights to check out nearby Monkeypod, Ka’ana Kitchen at the neighboring Andaz resort, and Mama’s Fish House in Paia, where you’ll have one of your most special, delicious meals yet.

Scallops from Kauai Grill at the St. Regis Princeville

WHERE TO STAY: It’s worth the upgrade to one of the St. Regis suites just for the view (of Hanalei Bay) and morning coffee service (a life-saving blend of Kona brought by your personal butler), but any of the resort’s 251 guest rooms and suites will set your trip (and marriage) off on the right foot. And if not for the siren song of all that Maui holds, you’d hesitate to ever leave the Four Seasons. Every inch of it reminds you that you’re on the vacation of a lifetime, from the crescent-shaped crook of Wailea beach it sits on to the lush grounds and immaculate service.

WHAT TO PACK: Loads of sun gear: hats, bathing suits, sandals and easy dresses, not to mention gobs of sunscreen (plus sneakers and the like for more rigorous activities)—but you’ll want to bring several resort-chic outfits, too.

The Lokelani Suite at the Four Seasons Maui

BEST TIMES TO GO: Generally, crowds and rates in Hawaii are at their highest from December through March, when weather is lousy elsewhere. On Kauai, the weather is especially lovely from April to June. It’s much the same in Maui, though if you’re looking to surf, conditions are best in winter.

NEWLYWED NEWS: Before you go, check out the St. Regis’s online honeymoon registry that allows gift-givers to treat you to meals and activities throughout your stay. At the Four Seasons, look into the new “Unforgettable Experiences,” which include visiting the Serenity Pool after it’s closed at night to enjoy a couple’s massage in a cabana, followed by a gourmet meal.

HOW TO GET THERE: Direct flights run from New York to Honolulu, but otherwise you’ll need to make at least one stop. From Philly, a layover in Phoenix divides the trip nicely into nearly equal legs. Check with your hotel about airport transportation while booking; in several cases, you’ll need to hop your own taxi.

For more on honeymoons—advice, tips and destinations—go here. 

Like PW on Facebook | Follow PW on Twitter | Sign up for the PW newsletter