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.
Kaua‘i
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.
O‘ahu
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.
Maui
Catch the sunset
- Grab a chair in the sand and order a cocktail at the Barefoot Bar at Hula Grill on Ka‘anapali Beach, as the sun sets over the neighboring island of Lana‘i. 808.667.6636
- Overlook all of Wailea Resort with views of Molokini and Kaho’olawe (and Lana‘i on a clear day) while dining at Capische at Diamond Resort. 808.879.2224
Remote (romantic) hike
- Haleakala Crater, whether you opt for the 3a.m. pickup for a sunrise hike, or just take one of the many trails, there is plenty of room on this 10,023-foot high dormant volcano to find a scenic path for two.
- Just past Hana. It takes awhile to get to the 7 Pools trailhead from the west side of the island, so leave early. Besides freshwater pools, the trail passes through bamboo forests and a remote black sand beach.
- Not an outdoor hike, but a romantic notion for a stroll…docent-led art tours at the Four Seasons show off the new museum-quality art collection with over 280 original works.
Romantic dinner
- Consistently rated one of the best restaurants in Maui, the Hailemaile General Store is a bit of a drive from most hotels, but the scenery is gorgeous and well worth the effort.
- Chez Paul in Olowalu enjoyed recent publicity when chef Patrick Callarec shared his culinary talents with the “Romance Me Maui” campaign. 808-283-9044.
- Duo at the Four Seasons — dine by the pool waterfall overlooking Wailea Beach.
- Mama’s Fish House in Kuau Cove on Maui’s North Shore While some say this longtime standby is too pricy and hyped, nobody seems to be listening….be sure to make reservations.
- Sushi for two? Locals and returning visitors flock to Sansei for its award-winning dishes. Two locations on Maui; Kapalua 808.669.6286 and Kihei 808.879.0004.
- Lunch or dinner at Ka’uiki Restaurant at Hotel Hana-Maui will be a meal to remember. 800.321.4262
Pack a picnic
- Aim for getting to Makena Beach around 11:30, before the crowds hit the Taco Truck. Located just where the road turns toward the beach, this white truck is popular among locals, who line up for the fish tacos and fish burritos. Once you’ve got your lunch, head over to the Cove at Secret Beach.
- On the way to Cove Park at Kihei Beach, stop off at Da Kitchen (808.875.7782, da.kitchen.com) in the Rainbow Mall in Kihei. After sharing a box lunch of Korean chicken, take a surf lesson offered on site.
Moloka‘i
Catch the sunset
- A rocking chair on the lanai of any room at the Lodge—they all face west.
- While wading in the tidepools off Kaupoa Beach at the Beach Village, search for medeka (minnows) and opihi shells.
Remote (romantic) hike
- Waikolu Valley. Depending on your fitness level, trek (or park near) the look-over to the forest reserve. Locals call it a truly untouched otherworldly valley.
- The most popular trail on the island (four people a day) is Halawa Valley. This daylong hike will take you through a waterfall spilling into a large bubbly (think champagne) pool. With soaring cliffs as the backdrop, the trail ends at Halawa Bay where it’s said the first Polynesians set foot on Moloka‘i.
Romantic dinner
- Reserve the intimate greenhouse on the grounds of the Lodge, for a private dinner created by chef Erwin Kudoba.
- Wiggle your toes in the sand, at your own table with private service a the Beach Village. Casual to formal, depends on your own style.
Pack a picnic
- Pick up a prepared lunch at the Lodge or the general store in Mauna Loa and head to Mile Marker 19: a remote white sand beach protected by a coral reef.
Lana‘i
Catch the sunset
- Veranda of Four Seasons Resort Lana`i, the Lodge at Koele. Overlooks the stables, and the ocean in the distance below.
- For a bit of the surreal, head to the Garden of the Gods, and watch the ancient red rock formations change color with the setting sun.
Remote (romantic) hike
- Plan for an early morning or late afternoon moderate hike along the Koloiki Ridge, which offers expansive views of the island and the ocean and neighboring isles.
Romantic dinner
- In-room romantic dinner at Manele Bay. Served at the dining table or most often on the private lanai. Candles, flowers, white cloth service.
Pack a picnic
- Both Manele Bay and the Lodge pack picnics for hikes, Jeep excursions or the beach.
Hawai‘i
Catch the sunset
- Huggo’s on the Rocks: Casual setting serves up cocktails, Hawaiian pupus and music right next to the iconic Huggos Restaurant on the south end of Kona’s downtown. 808.329.1493
- Any hammock-for-two on the Kohala Coast.
- Watch the sun set as fishing boats return to Keauhou Bay and the coastline of Kailua-Kona lights up while at Crystal Blue, an indoor/outdoor cocktail lounge at Sheraton Keauhou Bay Resort and Spa.
Remote (romantic) hike
- Meet up with the ancient Ala Kahakai trail at the public access parking lot behind the new Waikoloa Beach Marriot Resort and Spa and head south. Wear sturdy shoes and hats and bring sunscreen; this is a long and potentially hot trek over lava to freshwater lagoons and a black sand beach.
- Get existential about the meaning of life as you hike through the trails at Hawai‘i Volcanoes National Park. nps.gov/havo
Pack a picnic
- Waterfalls, lonely black sand beaches and wild ginger are just a few sights to behold when hiking the famed Waipi‘o Valley. Stop at the Waipi‘o Valley Artworks for a takeout deli sandwich along the way.
Romantic dinner
- Pahui‘a at the Four Seasons Resort Hualalai has been earning awards and accolades since opening. Aim for sunset when you make reservations. Desserts include a daily soufflé and the pièce de résistance; their warm dark chocolate lava cake. 888.340.5662.
Winter Weekend Getaways
O‘ahu
Kahala Love Song
One three-course romantic dinner for two at Hoku’s, the resort’s award-winning signature restaurant (alcoholic beverage not included), CD of Hawaiian love songs and champagne and chocolate-covered strawberries. Package rates start at $410 per night for courtyard rooms. Minimum four-night stay. Package inclusions are valued at $320. 888.261.0068, kahalaresort.com
Royal Hawaiian (Pink Palace of the Pacific)
“A Hui Hou – Until We Meet Again” at the Royal Hawaiian. The hotel will begin restoration on a new era of redefined luxury around June 1, 2008. Hence from March through May 2008 guests will receive complimentary daily breakfast for two, an elegant memento gift and a special room night gift certificate for a return to the Royal Hawaiian in 2009. Rates start at $299 a night with a minimum
of four nights’ stay. 808.923.7311, royal-hawaiian.com
The 5000 Kahala Package
Accommodations in either the presidential or governor suite. $400 daily activity credit for use at the spa suites or Dolphin Quest and private limousine airport transfers or luxury Hertz rental car. Daily buffet breakfast for two at Plumeria Beach House. Package is priced at $5,000 for two per night. 888.261.0068, kahalaresort.com
Maui
Hotel Hana-Maui
Three nights, luxury accommodations. Daily full American breakfast for two in Ka‘uiki. Welcome bottle of champagne on arrival. One three-course dinner for two in Ka‘uiki, the recent winner of a Wine Spectator Award of Excellence. 60-minute massage for two (one per guest) in a couples’ suite in Honua Spa. Rates start from $606 per night to $1173. This package is available through December 23, 2008, and does not include taxes and gratuities. hotelhanamaui.com, 800.321.4262
Sheraton Maui Resort
“Romance in a Box add-on Package” add $500 to the nightly rate for a romance package including; a category room upgrade, breakfast in bed, a romantic dinner, champagne and strawberries on arrival, embroidered robes and house slippers, bottled water, Aveda bath products, happily married/just married door hangers, a keepsake wooden box, a sunset sail for two, and a cabana on the beach. Rates start at $470. Sheraton-maui.com, 808.661.0031
The Ritz-Carlton, Kapalua
The Ritz-Carlton, Kapalua’s Pilialoha (Romance) Package includes champagne and chocolate truffles on the night of arrival, daily breakfast buffet for two in the Terrace Restaurant, a three-course dinner at the signature Banyan Tree Restaurant (once per stay), and the daily resort fee with a three-night minimum. This package is available thru December 19, 2008, starting at $699 per night. 888.669.6200, ritzcarlton.com
Moloka‘i
The Lodge at Moloka‘i Ranch
Romance package includes a massage or horseback riding for two, a private campfire, a private dinner and a compact car. While you’re having dinner, your room will be adorned with candles and flower petals and a bath will be drawn with Moloka‘i coconut salts. Three-night minimum $498 per night in a Lodge Luxury room or $448 in a beachfront “tentalow” at the Beach Village. 808.660.2824, molokairanch.com
Hawai‘i
Four Seasons Haulalai
Couples looking for a romantic epicurean escape can arrange for a romantic dinner on the beach. Return to a room scattered with orchid petals, flickering candles, and a drawn bath. Room rates start at $735 per night. Romantic Dinner on the Beach packages start at $550 for two. Call 888.340.5662 or visit fourseasons.com/hualalai.
Waikoloa Beach Marriot Resort & Spa
Spa For Two Escape! Head to this newly renovated oceanfront property on the Kohala Coast and check out the new Mandara Spa. Luxurious accommodations starting from $489 with a two 50-minute treatments per day. Rate is per room, per night, exclusive of applicable taxes and fees. Valid through February 29, 2008. 877.359.3696, waikoloamarriott.com
Kona Village
Bed, Breakfast & Beyond includes breakfast and the many Kona Village amenities but gives guests the option of whether or not to include lunch and dinner. Rates for BB&B begin at $512 per night for two. Rates with all meals and the usual array of resort amenities begin at $660 for two per night. 800.367.5290,
konavillage.com