The Ultimate Cheat Sheet on Where to Go in the Caribbean

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As much of North America experiences cold temps, plenty of people consider ditching their jackets for a sunny Caribbean vacation. But then comes the question of where to visit -- each country in the region has its own unique atmosphere, and what could be the perfect destination for someone seeking a high-end resort with beachfront views might not work well for budget travelers who wish to immerse themselves in local culture. If you're thinking about heading to the Caribbean, but aren't quite sure where to go, here are a few suggestions.

Dominican Republic

Occupying the eastern half of the island of Hispaniola (which it shares with Haiti to the west), the Dominican Republic has long been a traveler favorite. It’s celebrated for its mix of history, culture (merengue and bachata, anyone?), and of course, gorgeous beaches. Even better, the Dominican Republic is both easy to get to and affordable, thanks to a wide range of reasonably priced all-inclusive resorts and six international airports around the country, almost all of which have direct daily flights to the U.S.

Our Top Pick for a Dominican Republic Hotel: Majestic Colonial Punta Cana

St. Lucia

If breathtaking scenery is what you’re after, St. Lucia will not disappoint, thanks to its mystical mountain terrain characterized by sharp mossy peaks jutting up from the Caribbean Sea. While the island nation doesn’t have much of a party or shopping scene, it’s great for both romantic holidays as well as for active vacations. Visitors will appreciate the excellent scuba diving, hiking, and windsurfing opportunities, plus the hot springs and delicious Creole cuisine.

Our Top Pick for a St. Lucia Hotel: Jade Mountain Resort


Jamaica is a great choice if you are interested in both local culture and white-sand beaches. While there are plenty of resorts where you can flop down on powdery sand for the entirety of your trip, the country’s large size, population, and geological diversity means that it’s easy to have a rewarding vacation here without setting foot on a beach. And although Jamaica’s best-known cultural export is its homegrown reggae and dancehall music, the island nation also offers plenty of historic old houses, gorgeous jungle waterfalls, and a wide variety of culinary specialties, from jerk chicken to the national dish of salt fish and ackee (a local fruit that’s cooked to the consistency of eggs).

Our Top Pick for a Jamaica Hotel: Secrets Wild Orchid Montego Bay


Formerly off-limits to Americans, Cuba is now open to U.S. travelers, though there are still some rules to follow. And while things are developing fast, the country is still often likened to a time capsule, with lots of gorgeous old colonial buildings painted in rich pastel hues, vintage cars, and historic forts. There’s also a strong musical tradition here, including a variety of popular styles influenced by African and Latin traditions, plus plenty of great scuba diving and beach resorts for those who like a little R&R with their culture.

Our Top Pick for a Cuba Hotel: Saratoga Hotel


One of the more popular year-round Caribbean destinations (it’s located outside the Caribbean hurricane belt, and therefore, has limited rainfall), Aruba attracts those willing to shell out a pretty penny for high-end shopping, golf at the famous Tierra del Sol course, excellent international cuisine, abundant casinos, and gorgeous stretches of white-sand beach. Although it has more of a tourist vibe than some of the larger island nations (namely, Jamaica, Cuba, and the Dominican Republic), it’s also one of the more welcoming places, thanks to a low crime rate and plenty of family-friendly resorts. Unlike other Caribbean destinations like Jamaica, the country also prides itself on its all-around gay-friendly population.

Our Top Pick for an Aruba Hotel: Hyatt Regency Aruba Resort and Casino

Puerto Rico

If you don’t have an up-to-date passport and want to get a quick fix of Caribbean sunshine, Puerto Rico might be your best bet. It’s a U.S. territory, so traveling here is like going to another state (you just need your driver’s license or state ID), the currency is the dollar, and your cell phone will work just like it would in the U.S. However, ease of travel isn’t the only reason to visit this culturally rich island. Puerto Rico offers a lot for visitors, including gorgeous beaches, excellent diving, snorkeling, and surfing opportunities, historic forts, great shopping (particularly for arts and handicrafts), wildlife-rich rainforests, and a world-famous bioluminescent bay. And in case you’re wondering, the destination is back in business following Hurricane Maria.

Our Top Pick for a Puerto Rico Hotel: La Concha Renaissance San Juan Resort

Turks and Caicos Islands

The Turks and Caicos Islands offer the type of scenery that postcard photographers dream of — long expanses of powdery, white-sand beaches, waters so vividly turquoise that you’ll never need to add filters to your photos, and not a single McDonald’s to spoil the views (all the shops here are local). The 37-mile-long island chain offers plenty to do, from snorkeling and diving amid one of the longest coral reefs on the planet to visiting conch farms and bird sanctuaries. You’ll also find plenty of lodging options, which range from all-inclusive resorts to charming local inns.

Our Top Pick for a Turks and Caicos Hotel: Beaches Turks & Caicos Resort Villages & Spa

St. Martin/Sint Maarten

Split between the French and the Dutch, but with no real boundary marks, St. Martin and Sint Maarten each have different governments, languages, cuisine, currencies, and attitudes in general. Although there isn’t a strict border, once you’ve crossed over into the other country’s land, you’ll soon know it. The Dutch Sint Maarten offers high-rise condos and timeshares that are popular with Americans. It’s a busy cruise port, and has long been a lively trade and tourism hub. On the other hand, St. Martin takes up the northern two-thirds of the island. The native language is French, and the island is subject to French law. Less developed than the Dutch side, St. Martin offers plenty of natural attractions, including the beautiful (and clothing-optional) Orient Beach. There are around 40 beaches across the island, many of which offer water sports like parasailing, windsurfing, and jet skiing. The island is also reputed to have some of the world’s best snorkeling. And while it did face major damage from Hurricane Irma, businesses and resorts are slowly making a comeback.

Our Top Pick for a St. Martin Hotel: Sonesta Ocean Point Resort


While many of the Caribbean islands are known for their white-sand beaches, Barbados mixes things up a bit by offering plenty of pink sand on its stretches of coastline. A former British colony, the island country maintains many cultural traits more often associated with Blighty (think afternoon tea) blended with strong Afro-Caribbean influences. Travelers to Barbados can anticipate gorgeous beaches, great snorkeling and wreck diving, a mix of hotels for all budgets, relatively decent nightlife in the capital city of Bridgetown, and plenty of inland hiking opportunities. Plus, as the island is outside of the Caribbean’s hurricane belt, you won’t need to worry too much about what time of year you visit.

Our Top Pick for a Barbados Hotel: Sandals Barbados

Trinidad and Tobago

The birthplace of calypso music, Trinidad and Tobago is a small, two-island country in the Caribbean, just off the coast of Venezuela. Each island offers its own vibe — Trinidad is the larger, more industrialized island (and also home to a significant amount of crime), Tobago is the smaller “resort” island. Unlike some of the other Caribbean destinations, where the focus is only on tourism, Trinidad and Tobago is home to a lot of other industries. In other words, it’s easy to go off-the-beaten-tourist-track and immerse yourself in local culture. The cuisine here is also top notch (as is the rum), and it’s a great place for snorkeling, diving, and bird-watching.

Our Top Pick for a Trinidad and Tobago Hotel: The Villas at Stonehaven


Anguilla, a small British territory in the Caribbean, spans fewer than 40 square miles. With no direct flights from the U.S. mainland, visitors must either fly to St. Martin and take a short ferry to Anguilla, or fly via seaplane from San Juan, Puerto Rico. Most choose to spend their days sipping on drinks beach-side and dining at one the island’s hotels. One of our favorite spots on the island is the CuisinArt Resort & Spa, which reopened following the devastating Hurricane Irma. The food is a real standout here, and most meals served on premises include ingredients from the resort’s hydroponic farm. Plus, the property’s white-sand beach is an absolute stunner.

Our Top Pick for an Anguilla Hotel: CuisinArt Golf Resort & Spa


An English-speaking archipelago that begins about 50 miles off the south coast of Florida, the 29 islands, 661 cays, and a few thousand rocks that make up the Bahamas differ dramatically from one to the next — from bustling, modern business centers in Nassau, to flashy casinos packed with thousands of docked cruise ship passengers, to Americanized shopping centers that house a McDonald’s, Dunkin Donuts, Tony Roma’s, and five-star outposts from Food Network denizens like Bobby Flay and Jean-Georges Vongerichten (all at Atlantis), to entirely isolated beaches far removed from an airport, bank, or grocery store. But, uniformly, you’ll find a pleasantly infectious culture focused on conch, beer, and slow-paced good times.

Our Top Pick for a Bahamas Hotel: Melia Nassau Beach – All Inclusive


Aruba’s lesser known (and less crowded) cousin, Curacao is an island in the Dutch Caribbean known for its year-round, near-perfect weather. Due to constant trade winds and warm waters, Curacao is a popular spot for windsurfing. The postcard-perfect beaches also make it a popular spot for scuba divers, while the capital, Willemstad, features photogenic colonial architecture, the floating Queen Emma Bridge, and other cultural attractions.

Our Top Pick for a Curacao Hotel: Baoase Luxury Resort

Cayman Islands

A British Overseas Territory, the Cayman Islands consist of three islands in the the Caribbean Sea, and include some seriously beautiful beaches. Grand Cayman’s Seven Mile Beach, for example, features white sand along beautiful clear waters and is often considered one of the best in the Caribbean. The Cayman Islands also boast some of the world’s best scuba diving, with notable spots like Bloody Bay Marine Park, and Keith Tibbetts shipwreck. Other attractions offer a lovely nature preserve, turtle farm, and forested hiking trail to the island’s undeveloped center. If you happen to be visiting Grand Cayman, be sure to eat lots of fresh seafood and make a visit to Stingray City, a series of shallow sandbars where visitors can pet and feed the sea creatures.

Our Top Pick for a Cayman Islands Hotel: Caribbean Club Luxury Boutique Hotel

British Virgin Islands

The British Virgin Islands (a.k.a. the B.V.I.) is the name given to an archipelago of more than 60 islands, some of which are uninhabitable. Visitors can expect to stumble upon protected national parks, white-sand beaches, turquoise waters, and rainforests during their stay. This is also a big boating destination where sailboats can make stops between the hubs of Tortola, a popular cruise ship port, and Virgin Gorda, where smaller boats can put down anchor and head for shops and restaurants in the village of Spanish Town. Although the British Virgin Islands were impacted by Hurricane Irma, many of the businesses and properties are open again.

Our Top Pick for a British Virgin Islands Hotel: Fort Recovery Beachfront Villa & Suites Hotel

U.S. Virgin Islands

The small collection of mostly arid islands that make up the U.S. Virgin Islands have long been a seafarers stomping ground — from the pirates of yore to today’s more abundant cruise ship hordes and the occasional yachtsman. And as they have for the past 400 years, people come to the islands mainly to drink, relax on the beach, and bargain shop — often, in just that order. Considered “insular areas” or “unincorporated territories” of the United States, traveling to the islands is in many ways analogous to traveling within the U.S. — citizens don’t need a passport, the U.S. dollar is the official currency, and English is the official language. The islands’ hotels are largely concentrated on the three main islands — St. Thomas, St. John, and St. Croix. These areas were also hit by the hurricanes, and while remnants can still be seen throughout, they’re reemerging newer and stronger.

Our Top Pick for a U.S. Virgin Islands Hotel: The Ritz-Carlton, St. Thomas


One of the Caribbean’s hidden gems, Grenada is often overlooked for other more popular destinations; we advise against this. Along with dozens of gorgeous beaches, it offers a mountainous landscape with hiking trails and spice plantations (it’s even dubbed the “Spice Isle”). Plus, the island’s nature preserve and rainforest allow for encounters with monkeys and tropical birds. And its capital, St. George’s, is home to colorful homes and Georgian buildings.

Our Top Pick for a Grenada Hotel: Sandals Grenada Resort & Spa


A French overseas territory, Guadeloupe is a group of five islands in the Lesser Antilles for outdoorsy Francophiles who seek authentic culture and natural beauty. The two largest islands, separated by a river and accessed by bridges, resemble a butterfly: On the easter side is Grande-Terre, where several uncrowded beach towns offer visitors long stretches of sand for relaxing and waters sports, while on the west is the more mountainous Basse-Terre, boasting the Guadeloupe National Park, where visitors can hit the two-hour trail to see a spectacular active volcano. Another day-trip: Ferry over to Les Saintes, recognized as one of the most beautiful bays in the world by UNESCO.

Our Top Pick for a Guadeloupe Hotel: La Toubana Hotel & Spa


The French territory of Martinique is somewhat of a secret gem, especially considering that it’s one of the Caribbean’s most cosmopolitan destinations for those who prioritize gourmet beach cuisine, live music, French fashions, and natural beauty in the way of white-sand beaches and tropical rain forests. To top it off, the destination boasts a live volcano that looks over the harbor town of St-Pierre. What’s more, visitors can choose between big luxury resorts, stylish small hotels, or private luxury villas here.

Our Top Pick for a Martinique Hotel: Le Cap Est Lagoon Resort & Spa

St. Barts

Nicknamed St. Barts, St. Barthelemy in the French West Indies has been a playground to the rich and the famous for several decades. Nowadays, the well-heeled venture out to St. Barts for its gourmet restaurants, high-end designer shops, secluded beaches, and exclusive location. French is spoken by many locals (although almost everyone on the island can speak some English) and much of the cuisine has a French flair. Seafood, including conch — an island speciality — is caught locally. St. Barts is home to 22 public beaches, 15 of which are good for swimming and other water activities. With this plethora of beaches, there seems to be a beach for everyone; the leeward side of the island is home to calmer waters, great for divers and families, while the windward side is a popular spot for wind-surfing and surfing. The hub of activity on the island can be found in St. Bart’s capital, Gustavia. Home to the main harbor, Gustavia has streets lined with high-end shops and restaurants and locals sell homemade wares such as hats and bags made from palm fronds along the streets as well. St. Barts was impacted by Hurricane Irma, though much of the island is back open for business.

Our Top Pick for a St. Barts Hotel: Manapany

St. Kitts and Nevis


St. Kitts and Nevis are two islands located west of Puerto Rico. Nevis, the smaller of the two islands, is an unspoiled paradise with a lot to offer. Friendly people, pristine beaches like Pinney’s, and lush tropical rain forests make this island a spectacular choice for a romantic getaway. Those who enjoy hiking should check out the 3,232-foot Nevis Peak, a dormant volcano that erupted roughly 100,000 years ago. St. Kitts also features lush mountains and beaches with white and black sand. While here, don’t miss the historic Brimstone Hill Fortress National Park, a UNESCO World Heritage site. It’s worth noting that St. Kitts and Nevis were also impacted by the hurricane, though most hotels are open and welcoming visitors.

Our Top Pick for a St. Kitts and Nevis Hotel: Four Seasons Resort Nevis, West Indies


Home to some of the bluest water in the Caribbean, Antigua is situated just north of Guadeloupe. Here, travelers fill their time by relaxing on the sandy beaches, snorkeling, or sailing on a catamaran. But there’s plenty of culture and history to soak up as well; don’t miss landmarks like Fort James and St. John’s Cathedral, an Anglican church. Free-spirit adults can head to Hawksbill Beach, a remote and calm area on the west side of the island where clothing is optional.

Our Top Pick for an Antigua Hotel: Galley Bay Resort & Spa

What to Bring: Summersalt Swimwear

Ranging from sizes 2-24, Summersalt has something for everyone. Be sure to pack a few for your next Caribbean trip.

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