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4 Perfect Caribbean Island Itineraries

While a chill still has its grip on the country, a spring trip is oh so tempting. And where better to go for a guaranteed sun-drenched getaway than the Caribbean? Spring is the best time to head south to work on your tan, considering you’re dodging high season prices and crowds.

Of course, not all Caribbean islands are created equally—although most have got the basics of swaying palms, sublime beaches, and gorgeous weather down pat. Some islands are better suited for families, for unplugged escapists, or for outdoorsy adventurers. So we put together four prime itineraries for four types of travelers.

For the Family: Turks & Caicos


Thanks to Grace Bay beach, a stretch of sugary-white sand and turquoise waters, Turks & Caicos easily woos families. The beach is a national marine reserve, so it’s protected (i.e. no roaring jet skis or booze cruises) and not overcrowded, thanks to the lack of huge hotels and all-inclusive resorts. It’s the perfect, unspoiled playground for young and old alike, with kayaking, kite surfing, and just plain ol’ splashing around. Start at one of the best spots on the beach: Bight, where fish abound for snorkelers. There’s also a children’s park with swings and a jungle gym.

Spend a day at Taylor Bay, which has nearly 300 yards of shallow water for young ones to play in. Likewise, make time for horseback riding on the beach with Caicos Corrals—they offer small private group tours and welcome new riders and young kids.

Book at the Regent Palms, a 72-room, 12-acre property known for embracing little ones, thanks to its Conch Kritters Club. There’s no charge for children under 12 in guest rooms, and ample beach toys are provided for the infinity pool and sea. Regent Palms also offers day-trips to nearby sandbars for picnic adventures.

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Insider’s Tip: Low season in Turks & Caicos starts mid-April, so there’s no better time to find great rates.

For an Escape: Nevis


The sister island of St. Kitts may not have the chops of most Caribbean islands (casinos, miles of beaches, all-inclusive resorts) but that’s what makes Nevis so charming. It’s as old-school as it can get. There are no traffic lights, no retail chains and, best of all, no hordes of tourists. In fact, it’s one of the two islands where monkeys still freely roam, whether on the streets or in the rainforest. The entire island is eco-friendly, too, with a wind turbine that can produce up to 25 percent of the island’s power. Peel yourself off beach for a gorgeous (and intense) hike up to Nevis Peak. Or rent a bike for the day, take windsurfing lessons, or swim under waterfalls.

Most of the hotels (many only have a couple dozen rooms or less) have been transformed from 200-year-old plantation homes and estates. The inns are scattered around the island, some deep in the rainforest so you will hear monkeys, often on your rooftop. There’s plenty of monkey business at Golden Rock Plantation Inn, owned by American painter Brice Marden and his wife. Nisbet Plantation Beach Club is a favorite for repeat visitors with its 32 cottages spread on a perfectly manicured lawn. It’s home to a terrific beach frequented by friendly locals. And of course, for the ultimate splurge-y escape, there is the Four Seasons Nevis, which offers the perfect itinerary of beach-spa-food-nap-repeat with a little golf thrown in.

Insider’s Tip: The Four Seasons Nevis Spa uses local Nevisian volcanic sand in their massage, should you want to be rubbed down in a traditional treatment.

For Adventure: Curacao


One of the most popular islands in the Caribbean, Curacao is unique and wonderful with heaps of outdoor thrills. Adrenalin junkies make a beeline here: the island is bursting with adventures both in and out of water.

The underworld is the island’s claim to fame, touted as being one of the best dive sites in the world. Shore diving and Macro Diving give it street (er, ocean) cred, and divers easily spend an entire afternoon exploring, especially Mushroom Forest. Ocean Encounters offer the best experiences. While you’ll undoubtedly have run-ins with marine life, booking with Dolphin Academy ensures interactions with bottle-nose dolphins. Feel like staying dry? Hop on board a twin-turbo yacht for some deep-sea fishing with Bounty Adventures, and take home wahoo, tuna, and marlin.

On land, endless activities sprawl the landscape, from hiking the rugged north coast to exploring the Salinas where large colonies of flamingos are still found. Rock climbing and rappelling is offered in the San Pedro plains, where most participants are first-timers. Or, take a horse along unspoiled trails with Ashari’s Ranch for a slower pace.

For a touch of Curacao history combined with great food and an easy walk to downtown Willemstad, book at Hotel Kura Hulanda, a 100-room village concept-meets-hotel that spans 8 blocks. Mixing old-world charm with new-world amenities, Avila Hotel is the top choice for many travelers yearning for infinity pools and hot tubs outside, and flat screen TVs within.

Insider’s Tip: Curacao (along with neighbors Aruba and Bonaire) sit outside the hurricane belt, making it a safe choice in hurricane season.

For Nightlife: St. Maarten


While St. Maarten may hold the throne for Duty-Free shopping and a different restaurant for every day of the year, the island also knows how to unfurl a lively nighttime atmosphere.

On the Dutch side, Maho is the bustling tourist epicenter with popular nightclub Tantra. If your concierge can get you in, check out the club’s Opium Room on top of the main dance floor. It’s a VIP Lounge with rare spirits, vintage wines, and wild shenanigans. Nearby, the outdoor Sunset Beach Bar is more relaxed, and visitors congregate here for a nightcap and to watch oncoming planes descend dangerously close on the notorious runway.

On the French side, L’Escargot is dive-y, but it’s also a historic, 150-year-old Creole cottage. The French fare is fantastic but it’s the cabaret several times a week that’s the showstopper.

Nightlife isn’t limited to boozy watering holes. Head to Philipsburg, the capital of the Dutch side, where you’ll find tons of shops that stay open late and invite a bit of meandering and people watching Stop by Guavaberry Emporium, where you can sample the traditional, national guava berry used for liquors.

Book at La Samanna, the only hotel on Long Bay Beach that has 83 ocean-front rooms, two dining facilities, and a beach bar where you’re likely to bump into one of the celebrity guests that stay here.

Insider’s Tip: Wake up early one day and take a catamaran day trip to Prickly Pear Anguilla for fantastic snorkeling. (You can take a disco nap before going back out.)

Still looking for more sun, sand, and fun? Check out our perfect Hawaiian islands itineraries, too.

Jimmy Im is a freelance travel writer based in LA. He’s hosted programs on the Travel Channel and LOGO, and makes regular appearances on morning news shows as a “travel expert.” He teaches travel writing courses and is also cofounder of Follow him on Twitter: @dieselmad.

Photo credits: Turks & Caicos via Shutterstock; Nevis via Shutterstock; Diving in Curacao via Shutterstock; St Maarten via Shutterstock

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