These five island getaways make for easy winter escapes from major U.S. hubs.

By Stirling Kelso
January 16, 2014
Kauai Visitors Bureau


Weekly Nonstop Flights From the U.S.: 27
U.S. Cities with Nonstop Flights:
Flight Time:
3 to 5 hours
Ongoing airport upgrades have made flying to this West Indies isle more efficient. Stay at the Galley Bay Resort & Spa (all-inclusive; $$$$), just 20 minutes from the airport, where thatched-roof cottages come with private plunge pools.

Providenciales, Turks, and Caicos

Weekly Nonstop Flights From the U.S.: ~60
U.S. Cities with Nonstop Flights:
Flight Time:
1 1/2 to 4 hours
Next month, Delta launches nonstops to Providenciales from JFK and Boston. The all-suite Regent Palms ($$$), on Grace Bay Beach, is our pick for families: kids under 12 stay for free.

Video: American Island Escapes


Weekly Nonstop Flights From the U.S.: 95
U.S. Cities with Nonstop Flights:
Flight Time:
2 1/2 to 4 1/2 hours
Set just off the coast of Venezuela, this island may seem far away, but it’s an easy jaunt—especially from the East. With two pools, a powdery beach, and a 24-hour casino, the 320-room Ritz-Carlton ($$$$) is the island’s new grande dame.

Sanibel Island, Fla.

Weekly Nonstop Flights From the U.S.: ~1,000
U.S. Cities with Nonstop Flights:
Flight Time:
1 to 3 1/2 hours
An increasing number of flights are heading to Fort Myers, 23 miles from this barrier island. Fresh off a redo, the 1895 Island Inn ($$) is full of Old Florida charm (shell-inlaid tables; screened porches).


Weekly Nonstop Flights From the U.S.: 15
U.S. Cities with Nonstop Flights:
Flight Time:
5 1/2 to 7 hours
Alaska Airlines’ new nonstop from San Diego means even more West Coasters can fly to Kauai and check in to the St. Regis Princeville Resort ($$$) by the afternoon. Hike the rugged coast or snorkel off the resort’s quiet beach.

Our Experts: For suggestions, we tapped several warm-weather specialists from our T+L A-List of top travel advisors: Julia P. Douglas, Jessica Griscavage, Margie Hand, and Kimberly Wilson Wetty.

Hotel Pricing Key
$ Less than $200
$$ $200 to $350
$$$ $350 to $500
$$$$ $500 to $1,000
$$$$$ More than $1,000

St. Regis Princeville Resort

Unveiled in September 2009 after its conversion from a Starwood Luxury Collection property, this resort on Kauai’s North Shore borders two of Hawaii’s most famous golf courses (the Makai Golf Club and the Prince Course, which were both designed by Robert Trent Jones, Jr.). In its new incarnation, however, the property now also offers enough amenities to tempt even the links-averse—including an 11,000-square-foot spa doling out taro-clay wraps and maile-oil massages; Kauai Grill, a Jean-Georges Vongerichten restaurant; a 5,000-square-foot infinity pool; and a sheltered beach good for snorkeling and for families. The 251 rooms—some of the largest on Kauai—are all gleamingly new and done up in pale blue and warm wood tones; Premium Ocean View rooms and suites overlook Hanalei Bay to Mt. Namolokama and, in the distance, Mt. Makana (famously depicted as Bali Hai in the South Pacific film).

Margie Hand

Hand has traveled to 15 islands in just the past few years, including Jamaica, Grand Cayman, Nassau, St. Martin. She takes particular interest in planning multigenerational vacations, like a recent trip for a family of 17 in Turks and Caicos. (The men went deep-sea fishing while the women spent a day at the spa.) Hand, an avid scuba diver who first fell in love with the Caribbean on her honeymoon two decades ago, is able to secure room upgrades, private sailing trips and yoga classes, spa credits, and other perks.

New favorite: The Malliouhana, an Auberge Resort, in Anguilla, reopened last November after a three-year renovation. Sitting on a hilltop with 360-degree water views, the 44-room resort now has an Auberge Spa, alfresco cliff-side dining, and a two-tiered infinity pool surrounded by private cabanas.

Specialties: The Caribbean, Destination weddings

Kimberly Wilson Wetty

The copresident of Valerie Wilson Travel has clients who have relied on her expertise for two decades. She logs their travel history, understands their goals, and keeps track of their interests so that she can make the right suggestion, whether it’s a relaxed Caribbean getaway, a culture-focused European trip, or an adventurous vacation in Australia.

Top tip: When traveling to the Mayan Riviera, book a half-day trip with Paradise Catamarans, which hosts sunset sails and half-day snorkeling trips. The service on the 46-foot vessel is top-notch, and safety is a prior- ity. As for family-friendly places to stay, Wetty recommends the Rosewood Mayakoba and Grand Velas Riviera Maya resorts.

Other specialty: Family travel, Cruises

Galley Bay Resort & Spa

Forty acres of verdant tropical gardens and a nearly mile-long sweep of white beach make Galley Bay—set on Antigua’s westerly Five Islands peninsula—feel like a true oasis. Most of the 98 airy units (outfitted with vaulted ceilings, tile floors, and gleaming acacia-wood furniture) are set along the waterfront, just steps from the sand. The common areas include three alfresco restaurants, three fabulous open-air cocktail bars, and a spa offering decadent treatments such as papaya–pineapple–crème fraîche body wraps.

Regent Palms Turks and Caicos

The elegant 72-suite Regent Palms sits on Grace Bay Beach and adjoins approximately a dozen acres of manicured gardens. The studio rooms; one, two, three bedroom suites; and penthouses feature classic Caribbean decor as well as modern perks like full kitchens with Viking appliances, washers and dryers, and king beds with hand-tufted linens. The family-friendly resort offers the Conch Critters activity club for children ages 4-12, while adults may choose from an extensive array of pampering spa services within 17-treatment rooms. On-site dining includes upscale Parallel23, which specializes in Caribbean fusion fare and features a display kitchen and a palm-lined terrace, as well as more casual Plunge, where guests can dine al fresco.

The Ritz-Carlton, Aruba

Breezy Aruba is home to one of the newest Ritz-Carlton resorts, located on the far, quiet end of burgeoning Palm Beach. Two pools, a 13-treatment-room spa (don’t miss the weightless Zoya hammock massage), and a flashy casino are some of the property’s highlights. All of the 320 rooms have private balconies, and bathrooms are equipped with Asprey amenities. Four Oranjestad restaurants offer everything from fiery Argentinean to classic Italian fare. For a more intimate experience, book a private dinner on the beach.