Top Caribbean Sea Tours & Vacations 2024/2025 [reviews &...

Caribbean Sea Tours & Travel Packages 2024/2025

22 Caribbean Sea trips. Compare tour itineraries from 9 tour companies. 0 reviews.

Small Group Caribbean Sea Tours

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Top Caribbean Sea Attractions

  • Visiting North America’s oldest colonial city, Santo Domingo in the Dominican Republic, where a number of “firsts” can still be toured.
  • Walking around Old Havana, Cuba, to view former Hemingway haunts and 1950s-era American cars, still running. 
  • Beachcombing on some of the world’s finest sands throughout the Caribbean.
  • Riding a cable car across rhe treetops on the lush island of Dominca. 
  • Swimming with rays in the Cayman Islands.
  • Cruising through the gorgeous Virgin Islands -- both U.S. and British -- on a warm, sunny day. 
  • Touring a rum distillery on Grenada.
  • Windsurfing off the northern (Atlantic) coast of the Dominican Republic, where the breezes are just right. 
  • Strolling through Old San Juan, Puerto Rico, with its colonial architecture, imposing fortresses, and lively ambience. 
  • Marveling at the Dutch architecture and brightly painted houses on Curacao.

Caribbean Sea Tours & Travel Guide

Caribbean Sea Attractions & Landmarks Guide

The Caribbean -- also commonly called the  West Indies because Columbus thought he had sailed to India -- is truly a polyglot, with each island having its own particular qualities and charms.

Besides the Spanish heritage of Puerto Rico and the Dominican Republic, Cuba -- currently the most talked about (and controversial) Caribbean destination after some loosening of travel restrictions by the U.S. -- you’ll find French islands such Martinique and Guadeloupe, which are actually overseas departments of France.

French-speaking Haiti shares Hispaniola with the Dominican Republic, while French territory St. Martin shares its island with Dutch Sint Maarten. Other Dutch islands include Aruba, Bonaire, and Curacao (the “ABC” islands).

British, American, Danish and African Heritages

For a taste of British heritage, head for the British Virgin Islands, The Bahamas, Cayman Islands, Turks and Caicos, Anguilla, Jamaica, St. Kitts and Nevis, Grenada, St. Vincent and the Grenadines, Dominica, St. Lucia, and Trinidad and Tobago among others. (Technically, Turks and Caicos and The Bahamas are in the Atlantic Ocean, but are traditionally included among the Caribbean islands because of cultural and other similarities; Bermuda, well to the north, is not.) 

The U.S. Virgin Islands still reveal some Danish heritage, especially in its early architecture and place names. .

And of course, African heritage -- dating back to slaving days -- pervades the Caribbean, influencing language, music, cuisine, dance, art, and many other aspects of the culture. Amerindian culture, which was native to the Caribbean, lives on only in a few places since the arrival of Europeans destroyed them rapidly through disease, violence, and overwork. 

The Basics of Caribbean Geography

For cruise ship purposes, the Caribbean is usually divided into the Western Caribbean (such as Mexico's Cozumel island, Jamaica, and Grand Cayman); the Eastern Caribbean (such as St. Martin/Sint Maarten, Dominican Republic, Puerto Rico), and the Southern Caribbean (such as Barbados, Grenada, St. Vincent and the Grenadines, Curacao, St. Lucia, Martinique). 

But in geographical terms, the northernmost islands -- including Cuba, Puerto Rico, Jamaica, and Hispaniola -- are called the Greater Antilles, while the eastern and southern islands are known as the Lesser Antilles. The latter, in turn, are divided into the Windward Islands (facing the wind: Grenada, St. Lucia, Martinique, St. Vincent) and the Leeward Islands (away from the wind: Dominica, Guadeloupe, St. Kitts, the Virgin Islands, Anguilla).

Some of the countries bordering the Caribbean -- both in Central America and northern South America -- are sometimes also grouped as part of the Caribbean.

Choices Abound

Are you looking for lush, green rainforests? Head to Grenada or Dominica.

Is a dry, desert-like island more your style? Barbados or Curacao would fill the bill.

History and culture? Try the Dominican Republic, Cuba, or Puerto Rico. 

Great music? Trinidad and Jamaica have the beat.  

Scuba diving and snorkeling? Bonaire, the Cayman Islands, and Cozumel are tops.

Beautiful beaches? They're nearly everywhere, but you can't go wrong with Anguilla or Aruba. 

To find the tour that's right for your Caribbean adventures, turn to Stride for guidance -- we'll help you narrow down your choices, though you'll probably want to come again and again to sample as many of these diverse and delightful islands as possible. 

Traveling to Caribbean Sea, an FAQ

1. Does Travelstride have all the tour operators?

Travelstride has the widest selection of tours and tour companies. All the largest companies are on the site and most smaller local operators though we are adding new operators daily. Unlike other websites and agencies, we show you all the options, regardless of whether or not we are paid by the company.

2. How does the Member Savings program save me money?

Travelstride membership is absolutely free. You receive special benefits including saving up to $700 on select tours with top tour operators. The main requirement is to write a review after your trip to access the savings.

3. Can I trust the tour operator and trip reviews on Travelstride?

Yes. Travelstride has both expert reviews, written by Travelstride staff and local experts as well as traveler reviews written by people like you who have used the company and traveled to that destination.

4. What does ‘Stride Preferred’ mean?

Stride Preferred and Stride Premier are status categories to help you sort quickly through known and reliable travel companies. Since there are thousands of tour operators around the globe, Preferred or Premier badges are awarded to companies that Travelstride has determined meet the highest standards of professionalism, customer satisfaction, and quality.