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Weekend Wanderings

Romantic Getaways in the 50th State

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The holidays are fun, but the hectic pace gets me fantasizing about remote tropical islands. Take Moloka‘i, for example, the least populated of the Hawaiian island chain—sparse, white-sand beaches as far as the eye can see, plus historical sites like the monument commemorating Father Damien in the remote village of Kalaupapa. Besides being a remote getaway, the island now has luxury accommodations—which is also part of my fantasy. On the other end of the spectrum, there’s Waikiki: easy to get to, same warm, gentle Pacific and tons of shopping and world-class restaurants, all within walking distance. And then there’s my favorite hammock at the Big Island’s Kona Village Resort, overlooking Kahuwai Bay and its resident pod of honu, or green sea turtles. I can hear the tide rolling in and feel the warm trade winds pass over me as my husband I and swing back and forth in front of our private beach hale. To help fend off this year’s winter blahs, I asked a few kamaaina friends to give me some inspiration, in the form of tips on what they consider to be the most romantic spots on all the islands.


Catch the sunset


  • Positioned perfectly to catch the nightly show of pinks, oranges and possibly a flash of green. The Point at Sheraton Kaua‘i has been serving up island-inspired cocktails and pupus to swooning couples for decades.


  • Hop aboard a late afternoon boat tour to experience unnamed shades of green and gold as the sun sets on the majestic Na Pali Coast.
  • Walk the beach at Hanalei on the north shore and if you’re lucky you might see the infamous green flash.
  • Watch the sun ease into the Pacific from the most western point in the United States – Polihale Beach, which is also considered a Hawaiian-style-Sahara with dazzling white sand dunes, some rising 100 feet.

Remote (romantic) hike


  • The Kalalau Trail along the Na Pali Coast.Leave early (as in 6 a.m.) to avoid the hot sun and crowds. Head to the secluded Hanakapi‘ai beach about 2.5 miles from the trailhead, have a snack and then it’s another 2 miles to Hanakapi‘ai falls.

Romantic dinner



  • Ask for a window seat at the Bali Hai restaurant located in the Hanalei Bay Resort, 808.826.6522


  • Reserve a table for two on the terrace of Café Hanalei at the Princeville Resort, 808.826.9644
  • The Beach House in Poipu is an ideal spot to watch surfers take the last wave of the day as you enjoy a sampling of island cuisine and a glass or bottle of wine. 808.742.1424
  • Cozy into a beach-facing gazebo, order a mango martini, and share fresh sashimi as Hawaiian musicians serenade the sunset at the Aupaka Terrace sushi bar at the Kaua`i Marriott Resort & Beach Club. Or plan ahead and ask executive chef Guy Higa to prepare a customized meal for two in a private seaside cabana with a view of Kalapaki Beach. 808.245.5050

Pack a picnic


  • Paddle your own kayak up the Wailua River to a romantic waterfall grotto. Most kayak tours include a picnic lunch.


  • Grab lunch at the Shrimp Station in Waimea, before heading to a lookout in the picturesque Waimea Canyon.

Catch the sunset


  • For expansive views of Waikiki and beyond, check out the Diamond Head Lookout. From the parking lot at Diamond Head State Park, there is a short hike to the top.


  • Celebrate literary history at the Sunset Lana‘i Bar at the New Otani Kaimana Beach Hotel. Word has it, Robert Louis Stevenson wrote poems here to the Princess Kaiulani, under the shade of the hau tree fronting the property. 808.923.1555
  • Perched to catch the very last rays, the Hau Terrace at the venerable Outrigger Canoe Club has been a locals’ choice for sunset dining for decades. Located on the southern end of Waikiki, this social club has reciprocity with most yacht club memberships. 808.923.1585
  • The Kane‘ohe Yacht Club defines island casual; flip-flops and T-shirts (only if there’s a breeze). It’s hard to beat the cement patio and fold-out chairs for a front-row view of the sun setting behind the jagged ridge of the Ko‘olau range. Toast the day with a chilled Bud Light. Any mainland yacht club membership is reciprocal. 808.247.4121

Romantic dinner


  • Reserve a private dining gazebo right on the water at Hoku’s restaurant in the Kahala Resort on O‘ahu. 808.739.8888


  • For the past century visitors and locals alike have enjoyed the sunset and Diamond Head views and award-winning island-inspired cuisine at Halekulani’s House Without a Key 808.923-2311
  • Reserve a table at sunset at Jameson’s by the Sea in Haleiwa, a casual indoor/outdoor setting. 808.637.6272
  • For an oceanfront dining experience, Ola at the Turtle Bay Resort recently opened to rave reviews. 808.293.6000

Remote (romantic) hike


  • Old Pali Trail is short and steep (coming back). The first part is not remote, but once you head off the main trail, Likelike Trail is a lush, uncrowded, narrow path that passes through waterfalls. Go at sunrise or sunset for the best views of the Ko‘olau Range and the windward coast; trailhead starts at the Pali lookout.


  • The Makapu’u Lighthouse hike is not remote, since the trailhead is right off Highway 72, but once you crest the hill after a mile-long easy ascent, it’s just pounding surf and miles of blue sky.

Pack a picnic


  • Pick up a veggie sandwich or tuna melt at Kalapawai Market in Kailua, then head to Kailua Beach State Park, consistently rated a “Best Beach in the World” by coastal expert Dr. Stephen Leatherman.


  • O‘ahu’s North Shore is famous for big surf and laid-back vibe, but it’s also a great place to spend the day. Grab a grilled sandwich to go at Ku Aina in Haleiwa, bring a towel and beach mat and head to the scenic Waimea Bay. Even if the surf isn’t pounding, there will be plenty of people-watching.
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