As much of North America experiences cold temps, many 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 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.
| Caribbean Island | Best For | Superlative | Average Cost (3-Night Vacation, Including Airfare) |
|---|---|---|---|
| Dominican Republic | Budget Vacations, Adventure | Cheapest Flights from US | $1,500 – $2,500 |
| St. Lucia | Honeymoons, Couples, Adventure | Clearest Water, Most Picturesque | $1,750 – $3,250 |
| Jamaica | Couples, Adventure | $1,500 – $3,000 | |
| Cuba | History Buffs, Foodies, Affordability | $1,250 – $2,000 | |
| Aruba | Honeymoons, Couples, LGBTQ+ | Clearest Water, No Hurricanes | $2,000 – $3,500 |
| Puerto Rico | Non-Passport Carriers, Culture, Families | $1,250 – $2,250 | |
| Turks and Caicos Islands | Adventure, Couples, Luxury | Underrated | $2,500 – $4,500 |
| St. Martin/Sint Maarten | Adventure, Beaches | Picturesque | $1,750 – $3,000 |
| Barbados | Culture, Adventure | $1,750 – $3,000 | |
| Trinidad and Tobago | Culture, Foodies, Affordability | No Hurricanes | $1,250 – $2,000 |
| Anguilla | Foodies, Adventure, Luxury | Friendliest | $2,500 – $4,000 |
| Bahamas | Cruises, Culture | Clear Water | $1,500 – $3,000 |
| Curacao | Weather, Adventurers, Beaches | Most Picturesque | $1,750 – $3,000 |
| Cayman Islands | Adventure, Beaches, Luxury | Clearest Water | $2,750 – $4,750 |
| British Virgin Islands | Boating, Beaches, Luxury | Clearest Water, Friendliest | $2,500 – $4,000 |
| U.S. Virgin Islands | Cruises, Partying, Non-passport Carriers, Affordability | $1,500 – $2,500 | |
| Grenada | Beaches, Hiking | Underrated | $1,750 – $3,000 |
| Guadeloupe | Hiking, Remote Beaches | $1,500 – $2,750 | |
| Martinique | Beaches, Music, Fashion | Most Picturesque | $2,000 – $3,500 |
| St. Barts | Beaches, Shopping, Celebrity Spotting, Luxury | Most Picturesque | $3,000 – $6,000 |
| St. Kitts and Nevis | Friendly Locals, Honeymoons, Couples, Affordability | Underrated | $1,750 – $3,000 |
| Antigua | Beaches, Adventure, Culture | Friendliest | $1,750 – $3,000 |
Dominican Republic
Best For: Budget Vacations, Adventure
Superlative: Cheapest Flights from US
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
Best For: Honeymoons, Couples, Adventure
Superlative: Clearest Water, Most Picturesque
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
Best For: Couples, Adventure
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
Cuba
Best For: History Buffs, Foodies, Affordability
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
Related: The Ultimate Guide to Aruba
Best For: Honeymoons, Couples, LGBTQ+
Superlative: Clearest Water, No Hurricanes
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
Best For: Non-Passport Carriers, Culture
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
Best For: Adventure, Couples, Luxury
Superlative: Underrated
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
Best For: Adventure, Beaches
Superlative: Picturesque
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
Related: How to Choose a Group Tour That You Won’t Hate
Barbados
Best For: Culture, Adventure
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
Best For: Culture, Foodies, Affordability
Superlative: No Hurricanes
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
Best For: Foodies, Adventure, Luxury
Superlative: Friendliest
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
Bahamas
Best For: Cruises, Culture
Superlative: Clear Water
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
Related: The 9 Bang-for-Your-Buck All-Inclusives in the Caribbean
Curacao
Best For: Weather, Adventurers, Beaches
Superlative: Most Picturesque
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
Best For: Adventure, Beaches, Luxury
Superlative: Clearest Water
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
Best For: Boating, Beaches, Luxury
Superlative: Clearest Water, Friendliest
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.
Our Top Pick for a British Virgin Islands Hotel: Fort Recovery Beachfront Villa & Suites Hotel
Best For: Cruises, Partying, Non-passport Carriers, Affordability
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
Related: The 11 Best Caribbean Resorts with Private Plunge Pools
Grenada
Best For: Beaches, Hiking
Superlative: Underrated
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
Guadeloupe
Best For: Hiking, Remote Beaches
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
Martinique
Best For: Beaches, Music, Fashion
Superlative: Most Picturesque
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.
St. Barts
Best For: Beaches, Shopping, Celebrity Spotting, Luxury
Superlative: Most Picturesque
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.
Our Top Pick for a St. Barts Hotel: Manapany
Related: The Best Cruises for Solo Travelers
St. Kitts and Nevis
Best For: Friendly Locals, Honeymoons, Couples, Affordability
Superlative: Underrated
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.
Our Top Pick for a St. Kitts and Nevis Hotel: Four Seasons Resort Nevis, West Indies
Best For: Beaches, Adventure, Culture
Superlative: Friendliest
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
Caribbean FAQ’s
When is the cheapest time to go to the Caribbean?
Typically, the cheapest time is September through November, when the summer is over but hurricanes are still possible. You’ll find the best deals, but take a risk since hurricane season is still raging. Booking anytime from June 1 – November 30 (hurricane season) always poses a risk that your trip may be impacted by weather. September and October are the rainiest months to travel to the Caribbean.
When is the most expensive month to go to the Caribbean?
December is typically the most expensive month for Caribbean vacations, thanks to the ending of hurricane season and holiday vacations.
How far in advance should I book my Caribbean vacation?
With any vacation, you want to book as far in advance as possible to guarantee your accommodations. If you have a hotel you know you want to stay in, your best bet is to book 6-12 months in advance. However, you should wait 1-2 months in advance to book your flight. You may also be able to find a great deal three, two or even one month in advance, so keep an eye on the trends of when prices tend to drop before booking.
How many days should my Caribbean vacation be?
The length of your stay depends on many factors: your budget, how many days of vacation you have, and what you want to do. Three days is the shortest length of time you should plan on for a Caribbean vacation, but you can stay up to fourteen days if you have the time and money. If you hope to see and do a lot, and you’re not looking for a vacation simply sitting on the beach sipping a cocktail, you should plan on at least a week-long stay.
Additional reporting by Megan Johnson.
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