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Plan your spring break: The Caribbean A to Z

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It’s time to get your spring break plans in order, and if you’re looking for some fun in the sun, the Caribbean is a prime destination. But with thousands of islands (although only a few dozen are inhabited) to choose from, that doesn’t narrow things down much. That’s why we at Oyster have created an A to Z (well, actually, an A to V) guide to the Caribbean, so choosing your island and resort will be a piece of cake. First stop: Anguilla.

Anacaona Boutique Hotel, Anguilla

The boutique Anacaona has two pools.
 

Anguilla is a tiny British territory that covers fewer than 40 square miles and is a popular spot for couples and celebs (Sofia Vergara went on a girls’ trip to the island) due to its small size and upscale vibe. Visitors must either fly to St. Martin and take a short ferry to the island, or fly in directly (by way of a small seaplane) from San Juan, Puerto Rico. Thus, getting to the island can be pricey. So once you’re there, we’d recommend staying at the boutique Anacaona in the island’s West End. Though its not quite as luxe as the CuisinArt or Viceroy, it offers access to the same gorgeous white-sand beach as the neighboring Viceroy – through an off-property path — as well as to the nearby Greg Norman’s golf course and a few restaurants, and it’s prices are considerably lower. With two small pools, a great restaurant serving Caribbean fare with a twist, and a massage hut on the beach, the hotel is a good pick for value.

Hyatt Regency Aruba Resort and Casino

The Hyatt boasts beautiful landscaping.
 

Aruba is often considered the top gaming destination in the Caribbean, so if you’re looking to gamble, it’s a great spot to visit. Even if you already have your spring break destination picked out, Aruba sits outside of the Caribbean hurricane belt, making it a nice spot to visit year-round.  One of the nicest resorts on the island, the Hyatt Regency not only boasts a large casino, but also has plenty to offer families and couples as well, with water sports, a playground, and a luxe spa.

Old Bahama Bay Resort & Yacht Harbor, Bahamas

Old Bahama Bay Resort sits on one of the nicest stretches of sand on the island.

An English-speaking archipelago that begins about 50 miles off the south coast of Florida, the Bahamas is a great spot for East Coasters looking for a quick getaway. With 29 islands, 661 cays, and a few thousand rocks, the Bahamas differ dramatically from one to the next — but, uniformly, you’ll find a pleasantly infectious culture focused on conch, beer, and slow-paced good times. Everyone’s heard of the family-friendly megaresort Atlantis, and the ultra-luxe One&Only Ocean Club (where scenes from the 2006 remake of Casino Royale were filmed), and we’d argue that Old Bahama Bay is the perfect mix of the two; it lacks the crowds of Atlantis and the exorbitant prices of the Ocean Club, but has the upscale vibe of the Club and a good number (although certainly not all) of the activities offered at Atlantis. Guests stay in big, beautiful suites, and have access to a marina, top-notch snorkeling excursions, free bicycle rentals, and one of the best hotel beaches on the island.

Sandy Lane, Barbados

Sandy Lane is the creme de la creme of Caribbean resorts.
 

At first glance, it might be easy to view the white and pink sand beaches and breathtaking coral reefs of Barbados as a clichéd Caribbean island experience, but there’s more to it than that. The friendly locals (known as Bajans) maintain a noticeable amount of British customs from their colonial past, such as afternoon tea time and driving on the left. And even the local cuisine is a hybrid: expect to see flying fish on every menu, and spicy Caribbean stews served next to starchy English staples such as potatoes. Barbados is also home to Sandy Lane, not only one of the very top resorts in the Caribbean, but in the entire world. Guest amenities run rampant; perhaps the most noteworthy is access to the super exclusive Green Monkey golf course. A Rolls Royce Phantom, top-notch spa, outstanding restaurants, and celebrity sightings are just a few aspects that set the elegant Palladian-style hotel apart from the rest.

Sivory Punta Cana, Dominican Republic

The Sivory has a tranquil vibe that many all-inclusives lack.
 

Almost everyone who visits the Dominican Republic stays at an all-inclusive resort. While “all-inclusive” often  brings to mind large crowds, bad food, and poor service, it doesn’t have to (as long as you’re willing to pay for the upgrade). The Sivory is one of a handful of boutique hotels in Punta Cana, and is part of an even smaller group as one of the rare crossbreeds of both a boutique hotel and an all-inclusive one. Everything is designed to promote relaxation — from the comfortable rooms to the spa to the reflecting pool attached to the lobby.

Moxons Beach Club, Jamaica

Decks stretching into the water allow for extra spots for lounging.
 

Beyond the nonstop all-inclusive, booze-fest — which can be a lot of fun — there’s a different Jamaica: brilliant reggae, jerk chicken, rugged cliffs, blue lagoons, and friendly locals. And with direct flights from many major U.S. cities, getting to Jamaica can be relatively easy and inexpensive. But if you’re looking to save as much cash as possible, we recommend smaller, lesser-known hotels, such as Moxons Beach Club. Authentic Jamaican food, great cocktails, a friendly staff, and a beautiful, intimate setting bring guests back to the remote, beachfront Moxons year after year. The beach area may be small, but its uncrowded and over-water decks provide plenty of lounge chairs.

W Retreat & Spa – Vieques Island, Puerto Rico

The W has a cool, modern vibe.


Once under Spanish rule and now a commonwealth of the U.S., Puerto Rico has features of both the Caribbean and the States. Huge malls, golf courses, and casinos meet tropical rainforests and beautiful white-sand beaches, while well-preserved 15th-century Spanish forts loom over charming towns with colorful colonial buildings. Though the mainland can be crowded, Vieques is a small, 20-mile-long island about eight miles off the mainland, with beautiful white-sand beaches and a bioluminescent bay. One of just a handful of resorts on the island, the W has the modern, funky feel of the W brand with a tropical twist — it’s right on two private beaches, the lobby and rooms feature bright colors and concrete floors, and the infinity pool overlooking the ocean has a pool bar serving up poolside drinks and meals.

Fond Doux Holiday Plantation, St. Lucia

Rooms are simple and quaint, and surrounded by lush greenery.

Unlike more developed Caribbean islands, such as Aruba and the Bahamas, the sparsely populated island-nation of Saint Lucia still maintains a sense of unspoiled, exotic beauty. Its landscapes of pristine beaches and mountainous terrain are among the most stunning you’ll find anywhere in the Caribbean. With just 10 freestanding cottages on 130 acres, the eco-minded Fond Doux is intensely lush, filled with coconut groves, fruit-bearing trees, and a working cocoa plantation. Though tour groups perusing the grounds can be distracting to some, the hotel offers quaint rooms, two excellent restaurants, a small spa, and best of all, a solid value.

Gansevoort Turks and Caicos, a Wymara Resort

The pool at the Gansevoort is sleek and sexy.
 

Generally speaking, Turks and Caicos is relatively pricey — but for a reason. This 37-mile chain of islands radiates a particular Caribbean-ness, with dreamy blue waters, golden beaches, excellent snorkeling, and bioluminescent glow worms lighting up the water at night. If you want to fit in with the classy vibe, we recommend the Gansevoort, without a doubt the sexiest resort on Grace Bay. Its stunning pool and breeze-filled lobby wow guests from the moment they set foot on the property. Equally enticing are the resort’s gourmet restaurant, poolside and beachside service, sleek rooms, and Exhale Spa.

Bitter End Yacht Club, Virgin Gorda

Cottages at Bitter End boast gorgeous views.


Virgin Gorda is one of the four main islands that make up the British Virgin Islands, clustered to the east of Puerto Rico. It’s a beautiful spot in the Caribbean and even Richard Branson owns a couple of islands in the area, which is known as a premiere sailing destination. The Bitter End Yacht Club, snuggled into a steep hill on the scenic North Sound, is a relaxed resort where families and couples come to recharge and reconnect (rooms are purposefully tech-free). Many feature stunning views from the balconies, and the sliding doors allows breezes to sweep through; some rooms do not have air-conditioning but most guests find they don’t miss it.

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