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Looking for an in-depth Caribbean travel guide?

Then you’re in the right place!

The islands of the Caribbean are high on any traveler’s list for their gorgeous beaches, rich culture, and laid-back vibes. This region is truly the perfect place for a relaxing vacation for those who want to get away from it all.

Of course, the Caribbean is much more than its beaches. In fact, there’s a Caribbean destination for every kind of traveler out there.

Whether you’re an action-oriented traveler looking to hike the world or want to explore as many cultures as you can, you’ll find something exciting in the Caribbean.

On this page, you’ll find complete travel guides for several Caribbean destinations, including Antigua, The Bahamas, the Cayman Islands, Puerto Rico, and more.

We’ve compiled some of the best things to do in each location as well as tips on hotels, activities, and food.

Plus, we’ve answered some of your most burning questions about budgets, safety, planning, and other travel considerations for the region.

Keep reading for some serious travel inspiration and to dive into resources that will help you with planning a trip to the Caribbean islands.

Note that this travel guide to the Caribbean contains affiliate links to trusted partners!

Caribbean Map

Use this Caribbean travel map to begin planning your trip!

Caribbean map

Click here for an interactive version of the above map.

Antigua Travel Guides

Antigua is home to some of the best places to travel in the Caribbean, a few of which are highlighted here.

Bahamas Travel Guides

Traveling to the Caribbean? Don’t miss these incredible Bahamas travel experiences!

Cayman Islands Travel Guides

No Caribbean tourism experience would be complete without visiting the Cayman Islands. Here’s why.

Things To Do In The Dominican Republic

Visit the Caribbean — specificially the Domincan Republic — for an amazing vacation. Here’s how.

Things To Do In Guadeloupe

If you’re planning a vacation to the Caribbean islands you’ll want to put Guadeloupe on your itinerary.

Things To Do In Puerto Rico

Want to travel in the Caribbean? Puerto Rico has so much to offer, like…

Things To Do In St. Lucia

Looking for Caribbean travel tips? Here’s one: Don’t miss visiting St. Lucia and having the following incredible experiences.

Trinidad & Tobago Travel Guides

Trinidad and Tobago is home to some top Caribbean points of interest, and these guides can help you explore them.

Caribbean Tours

Book an experience with a Caribbean tour guide and get to know the culture through a local.

Click here for a full list of Caribbean travel tours!

Caribbean Hotels

Click here to browse hotels in the Caribbean!

Prefer self-contained stays? 

Click here to check out unique local Airbnbs! 

You can also use this map to search for local stays and experiences:

Caribbean Travel Insurance

It doesn’t matter if you’re traveling solo or with a group on a Caribbean tour. When visiting the Caribbean — or any other country in the world — make sure to get travel insurance to protect your health and safety.

In my opinion, the best travel medical insurance for travelers is SafetyWing as they’ve got a large network and offer both short-term and long-term coverage — including coverage if you’re traveling for months as well as limited coverage in your home country).

Additionally, SafetyWing is budget-friendly and offers $250,000 worth of coverage with just one low overall deductible of $250.

With coverage, you’ll have peace of mind as you embark on your Caribbean itinerary.

Click my referral link here to price out travel insurance for your trip in just a few clicks.

Renting A Car In The Caribbean

Renting a car in the Caribbean?

Use Discover Cars to quickly compare your car rental options.

Their comparison tool does the homework for you, so there’s no need to have up 10+ tabs trying to figure out which company is the most affordable. Actually, you can save up to 70% using their tool!

Caribbean Travel Guide FAQ

Below, find answers to frequently asked questions about traveling to the Caribbean

Q: What are the Caribbean travel destinations?

There are 29 different island nations and destinations you can visit in the Caribbean. These include:

  • Aruba
  • Anguilla
  • Antigua and Barbuda
  • The Bahamas
  • Barbados
  • Bonaire
  • British Virgin Islands (including Tortola, Virgin Gorda, Anegada and Jost Van Dyke)
  • Cayman Islands
  • Cuba (note: U.S. citizens can only travel to Cuba with an organized and licensed tour group)
  • Curacao
  • Dominica
  • Dominican Republic
  • Grenada
  • Guadeloupe
  • Haiti
  • Jamaica
  • Martinique
  • Montserrat
  • Puerto Rico
  • Saba
  • Saint Barthelemy (aka St. Barts)
  • Saint Kitts and Nevis
  • Saint Lucia
  • Saint Martin/Sint Maarten
  • Saint Vincent and the Grenadines
  • Sint Eustatius
  • Trinidad and Tobago
  • Turks and Caicos
  • U.S. Virgin Islands (including St. Croix, St. John, and St. Thomas)

Q: How many islands are in the Caribbean?

The Caribbean region contains 700 islands organized into 28 different island nations. Not all of these islands are inhabited or accessible but that still leaves a lot to explore in this beautiful area!

Q: How do you travel between Caribbean islands?

One of the best ways to travel between Caribbean islands is by ferry or boat. Several companies offer ferries between Caribbean islands, particularly those that are closest in distance to each other. For example, there are several weekly ferries between Puerto Rico and the Dominican Republic as well as daily service between the US Virgin Islands and the British Virgin Islands.

If you’re planning on spending a few days in each destination and want to plan your own itinerary, ferries are the way to go. Another great way to island-hop is via cruise ship. Though you won’t have much control over your itinerary, cruises are a great way to visit several Caribbean islands in a short amount of time, particularly those not easily accessible by ferry.

Direct flights between Caribbean islands can be hard to come by but are available. You’ll have the most luck finding flights for a Western Caribbean island-hopping adventure between islands like St. Martin and Guadeloupe.

Q: What is the best month to go to the Caribbean?

Winter and early spring are considered the best times to go to the Caribbean. The dry season makes for beautiful warm weather without the humidity and threat of hurricanes that the summer season brings.

Winter is also peak tourist season in most Caribbean destinations, so places tend to be more crowded and prices can be higher.

If you’re looking for the best prices — and the quietest beaches — you may want to hold off until May once Spring Break season and the Easter holidays have passed.

Q: What are the most dangerous Caribbean islands?

Though beautiful and culturally rich, Jamaica has a reputation for being one of the most dangerous Caribbean islands. The country has a high homicide rate compared to the global average and crime is common in certain areas. As such, a trip to Jamaica may require a higher level of vigilance than other destinations.

The Dominican Republic and Trinidad and Tobago have similar reputations for crime. Most state departments recommend exercising increased caution in these countries.

Q: Which Caribbean islands are the cheapest to visit?

While the Caribbean is known for its lavish beach resorts, you can find some great deals when traveling to certain islands. Your money will go farthest at up-and-coming destinations in the Southern Caribbean like Martinique, Curacao, Trinidad, and Tobago, and Grenada. Here, you can enjoy free beach access, delicious street food, and reduced hotel rates as well as each island’s unique cultural offerings.

Puerto Rico is also a less expensive option in the Caribbean for American travelers, as many low-cost American airlines offer regular flights to the island.

Q: What is the cheapest month to go to the Caribbean?

The least expensive months to travel to the Caribbean are June through November, during the heart of hurricane season. Though while you’ll find some great deals on hotels and flights during this time, you’ll need to contend with the humidity and the risk of severe storms.

The best way to avoid any bad weather during this time is to visit islands outside of the hurricane belt such as the ABC islands of Aruba, Bonaire, and Curacao.

Q: What are some top Caribbean points of interest?

The top points of interest for any Caribbean island are usually its beautiful beaches! You’ll find some of the most gorgeous beaches throughout the Caribbean, with soft white sand and clear waters perfect for snorkeling and swimming. Relaxing on the beach is the number one activity in the Caribbean for a reason.

Beyond the beach, many Caribbean islands have other natural wonders to explore, like towering volcanoes and lush rainforests. You’ll find some great hiking throughout the region, so make sure to get out and explore!

Q: What is the rainy season in the Caribbean?

The rainy season in the Caribbean takes place through summer and fall, from June 1st to November 30th.

Q: What are the West Indies islands?

The West Indies islands are comprised of three major groups of islands: the Greater Antilles (Cuba, Jamaica, Haiti, Dominican Republic, and Puerto Rico); the Lesser Antilles (the Virgin Islands, Anguilla, Saint Kitts and Nevis, Antigua and Barbuda, Montserrat, Guadeloupe, Dominica, Martinique, Saint Lucia, Saint Vincent and the Grenadines, Barbados, and Grenada); and the North American and South American continental shelves (The Bahamas and Turks and Caicos to the North, Trinidad and Tobago, Aruba, Bonaire, and Curacao to the South).

What would you add to this Caribbean travel guide?