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5 romantic date ideas in Hawai‘i

The Treehouse at Hotel Wailea. The Treehouse at Hotel Wailea on Maui is the perfect venue for a romantic gourmet dinner. | Photo by Aaron Scales

Hawai‘i is synonymous with romance. Kick off your shoes and walk arm in arm, barefooted, on scimitars of smooth sand. Admire sunset skies awash in orange, magenta, violet, and gold. Delight in rainbows and waterfalls, fragrant flowers and fern-draped mountains, starlight and moonlight over swaying palms.

You and your sweetheart will find many ways to write your love stories in the Islands. Here are 5 special date ideas.

1. Kaua‘i: Enjoy a massage

At Anara Spa, you and your sweetheart can enjoy a couple’s massage in a thatched-roof hale. | Photo courtesy Grand Hyatt Kaua‘i Resort and Spa

At Anara Spa, you and your sweetheart can enjoy a couple’s massage in a thatched-roof hale. | Photo courtesy Grand Hyatt Kaua‘i Resort and Spa

The word lomi means “to knead, to rub, to press.” Practitioners of lomilomi, the art of traditional Hawaiian massage, combine that healing touch with a blessing, positive intent, and a loving demeanor to promote harmony and balance of body, mind, and spirit.

As in ancient times, there is no one “correct” way to lomilomi; therapists have their own styles. In addition to their palms and fingers, some use their elbows, forearms, and even their knees and feet to produce fluid, rhythmic motions that gently yet deeply work their way into muscles, releasing tension and negative thoughts.

At Anara Spa, the perfect place to indulge in a couple’s lomilomi is an open-air, thatched roof hale (house) in a lush garden of plumeria, ti, ginger, bamboo, monstera, crotons, and laua‘e fern. A nearby waterfall cascades down lava rock, adding its soothing music to the lovely setting.

Enjoy additional treatments, such as a coconut scalp massage or a volcanic pumice foot massage, to enhance the experience. Consider aromatherapy or sound therapy, where the sounds of wind chimes, small gongs, singing bowls, and rain sticks coax you and your partner into complete relaxation … together.

Anara Spa, Grand Hyatt Kaua‘i Resort and Spa1571 Po‘ipū Road, Po‘ipū. (808) 742-1234. In your private garden hale, indulge in a side-by-side Lokahi Garden Couple’s Massage. 50 minutes for $195 per person; 100 minutes for $350 per person. Other treatments are available, including the signature wai, or freshwater, float-therapy treatment; prices vary. 

2. O‘ahu: Explore on horseback

gunstock ranch

Steal a kiss on horseback during the Private Sunset Dinner Ride. | Photo by Jayden Smith/Smitty Photography

Put on your jeans and boots and head to Gunstock Ranch in paniolo (cowboy) country for a romantic ride at a 900-acre working cattle ranch. Even greenhorns will feel comfortable in the saddle because this ride is done at a walk, and there are horses to suit every level of experience.

Your exclusive Private Sunset Dinner Ride begins in the subdued light of late afternoon. After an orientation that includes riding basics, you’ll mount up and head mauka (toward the mountains) on trails that go through forested areas and expansive pastureland where cattle graze.

High on a hill, you’ll pause to drink in an incredible view of Lāi‘e town, Lāi‘e Bay, Mālaekahana Bay, and the verdant Windward coast. With that panorama as a backdrop, lean over and give your beloved a kiss as your guide captures that sweet moment with your camera.

Soon you’ll be ready to dismount for a hearty supper that you’ve chosen in advance from seasonal specialties such as macadamia nut–crusted mahimahi, boneless short rib with kalbi sauce, or pan-seared free-range chicken with mirin ginger beurre blanc. Then snuggle by the campfire as you roast marshmallows or make s’mores before stretching your legs for the ride back to the barn.

Gunstock Ranch, 56-250 Kamehameha Highway, Kahuku. (808) 341-3995. The 2-hour Private Sunset Dinner Ride costs $199 per person (kama‘āina and military receive a 10 percent discount).

3. Maui: Whale watch in a kayak

whale watching tour

A private kayak tour offers you and your sweetie front-row seats to a possible whale encounter. | Photo courtesy Hawaiian Paddle Sports

Just after dawn, when the sea is calm and the air is cool and fresh, embark on Hawaiian Paddle Sports' private Whale Watching Kayak Tour with your special someone. The bonus this time of the year are the humpback whales, which migrate to Hawai‘i from Alaska to mate, give birth, and nurse their young.

You’ll have to be in sync as you paddle your sturdy, stable vessel while keeping your eyes peeled for those majestic creatures. Breach, fin slap, head lunge, fluke-up dive—there’s no guarantee what you’ll see, but being right on the water with a front-row seat, instead of on a crowded boat that emits engine noise and fumes, makes any encounter memorable.

Feel like snorkeling? Dive right in! Your guide has completed marine-naturalist training and can point out green sea turtles and a variety of tropical fish, including cornetfish; Achilles tang; porcupine puffers; milletseed butterflyfish; Commerson’s frogfish; and Hawai‘i’s state fish, the humuhumunukunukuāpua‘a (reef triggerfish). If you’re lucky, you might also see dolphins, manta rays, and eagle rays gliding by.

Your guide will snap pictures throughout the morning as a complimentary keepsake of your Maui adventure.

Hawaiian Paddle Sports. (808) 442-6436. The 3-hour Maui Whale Watching Kayak Tour is available December 1 through March 31. Cost for a private tour is $229 per person (kama‘āina receive a 20 percent discount). 

4. Hawai‘i Island: Stroll in a Japanese garden

Lili‘uokalani Gardens

Slip away for some relaxing time together in pretty, peaceful Lili‘uokalani Gardens. | Photo by Dan Corson

Lili‘uokalani Gardens beckons to lovers. This nearly 25-acre oasis was named for Queen Lili‘uokalani, Hawai‘i’s last reigning monarch, and is dedicated to the thousands of Japanese immigrants who came at the turn of the last century to work on Island sugar plantations. The queen reputedly donated the first 5 or so acres for the garden, and the territorial legislature designated 17 more. Groundbreaking was in November 1917, the month Lili‘uokalani died.

Stroll paths that meander past gazebos, bridges, stone lanterns, torii (Japanese gates), an ancient fishpond, a traditional Japanese teahouse, stands of bamboo, vivid patches of camellia and azalea, and monkeypod, palm, banyan, and black pine trees.

There are hundreds of Japanese gardens in North America, but Lili‘uokalani Gardens is notable for its age, size, and seaside location. Views encompass Hilo Bay, Hilo’s historic district, and Mokuola islet, which can be reached via a footbridge. The best times for a walk and picnic in the park are sunrise (visible from Mokuola) and late afternoon, before sunset’s spectacular show over Mauna Kea.

Lili‘uokalani Gardens49 Banyan Drive, Hilo. (808) 895-8130. Lili‘uokalani Gardens is open from dawn to dusk daily. Admission is free.

5. Maui: Dine in a treehouse

The Treehouse at Hotel Wailea

Savor a private, 7-course dinner in the treetops at Hotel Wailea. | Photo by Aaron Scales

An evening in The Treehouse at the Hotel Wailea, an intimate venue amid 30-foot avocado and mango trees, is a splurge that’s sure to win your Romeo or Juliet’s heart. It begins with a champagne toast at sunset as you gaze at a 180-degree view of the ocean, Lāna‘i, Kaho‘olawe, Molokini islet, the West Maui Mountains, and, possibly, breaching humpbacks (February is the peak month for whale watching). Below is the resort’s orchard, where mango, banana, starfruit, and papaya grow.

No other buildings on the property are in sight; neither can anyone see you. Dine by candlelight at a table adorned with fresh flowers, and savor each dish on your customized 7-course menu. For example, there might be watermelon poke; Kona kanpachi with miso, sea vegetables, and citrus; seared diver scallop with brioche and avocado; prawns with house-made pasta and Hawaiian chile peppers; mango-liliko‘i intermezzo; Wagyu rib eye cap with fingerling potatoes and squash; and coconut panna cotta with Kaffir lime and blueberries.

Hotel Wailea is an adults-only luxury resort with just 72 suites on 15 hilltop acres overlooking the Pacific. Secluded and quiet, landscaped with beautiful tropical gardens, it could be the Hawai‘i escape of your dreams.

The Treehouse, Hotel Wailea555 Kaukahi Street, Wailea. (808) 874-0500. The private Treehouse dinner costs $1,200 per couple. Optional live music starts at $350; wine pairings start at $95 per person.

Cheryl Chee Tsutsumi has fallen in love many times in—and with—Hawai‘i, her home. Her other stories for AAA Explorer include:

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AAA Travel Alert: Many travel destinations have implemented COVID-19–related restrictions. Before making travel plans, check to see if hotels, attractions, cruise lines, tour operators, restaurants, and local authorities have issued health and safety-related restrictions or entry requirements. The local tourism board is a good resource for updated information.

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