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The Caribbean Tours & Travel Packages 2025/2026
27 The Caribbean trips. Compare tour itineraries from 18 tour companies. 71 reviews. 4.7/5 avg rating.
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Top The Caribbean Attractions
- Touring the Caribbean’s three most historic cities: Havana, Cuba; Santo Domingo, Dominican Republic; and San Juan, Puerto Rico
- Taking a windjammer cruise that docks in a French island one day, a Dutch island the next, and a British island on the third
- Enjoying the tropical flavor of Costa Rica’s Caribbean coast
- Soaking in hot springs on the beautiful lush island of Dominica
- Watching uniformed school kids dance to the infectious beat of steel drum bands on St. Lucia or Trinidad
- Sailing on a five-masted tall ship through the gorgeous British Virgin Islands
- Exploring indigenous villages in the rainforests of northern Panama
The Caribbean Tours & Travel Guide
The Caribbean Attractions & Landmarks Guide
The Caribbean conjures up images of tropical breezes, lush islands, turquoise waters, sandy beaches, steel drum bands, and rum cocktails. They’re all there, to be sure – but there’s much more to this highly diverse region of multiple nations, languages, cultures, and landscapes. Whether you’re looking to snorkel with manta rays, explore history, climb volcanoes or anchor off isolated coves, you’ll find tours or small-ship cruises to suit every taste in the Caribbean.
While the Caribbean’s main geographic features are the Caribbean Sea and its islands, the region also includes the northern shorelines of a number of mainland countries in Central and South America. Most of the Caribbean is located southeast of the United States mainland (the easternmost point of the U.S. is situated on St. Croix in the U.S. Virgin Islands).
The Caribbean’s 45,000,000 residents are a diverse group, with a variety of often mixed ethnicities, religions – Roman Catholic to Rastafarian -- and languages. English, Spanish, French, and Dutch are all spoken in various regions of the Caribbean, as are various Creole dialects. These often incorporate words that emanated from West Africa during the centuries of the slave trade, when Africans were brought to the Caribbean to work the blistering hot cane fields for the production of sugar and rum.
Caribbean History: First Came the Spanish
The Spanish – represented by the Italian explorer Christopher Columbus and his crews – were the first Europeans to arrive in the late 1400s, promptly wiping out most of the native populations via imported disease, weaponry, and slave labor. (The Amerindian Carib people, who gave their name to the region, have been reduced to about 3,000 descendants on the island of Dominica.)
Cuba, the Dominican Republic, and Puerto Rico are all products of Spanish culture, and history and architecture buffs can enjoy the centuries-old atmospheres of Havana, Santo Domingo, and San Juan. Santo Domingo holds the record for the most “firsts” in North America – hospital, paved street, school, etc. – while Havana and San Juan battle it out for the most beautiful colonial-era cities with their Spanish-style plazas, forts, and churches.
Much – though not all -- of the Caribbean regions of Central and South America are also culturally Spanish.
The Next Waves of Europeans to the Caribbean
The British, French, Dutch, and to a lesser extent the Danes and Germans all followed in the wake of the Spanish. The British were very active in the slave and rum trades, forming a kind of devil’s triangle between West Africa, the Caribbean, and the American colonies. Rum remains important to the economies of a number of islands, and you can visit historic distilleries on Grenada, Trinidad, Jamaica, St. Kitts, and other onetime British colonial islands.
The French and British fought a number of 19th century battles over St. Lucia and Dominica -- two of the most naturally beautiful Caribbean islands. The Brits eventually prevailed there, while Martinique and Guadeloupe (now integral parts of France) were settled by the French.
France also divided up the island of St. Martin with the Dutch and the island of Hispaniola with the Spanish, though, on the latter, Haiti gained its independence following an early 19fth-century slave revolt.
Pirates, Palm Trees, Beach Bars and Baseball in the Caribbean
Jamaica, the British Virgin Islands, and Puerto Rico were among the Caribbean islands most affected by waves of piracy in the 18th and 19th centuries, spearheaded by Blackbeard and other notorious brigands. You can visit pirate lairs in Port Royal, Jamaica, and Norman Island in the British Virgins (one of the candidates for the model of Stevenson’s “Treasure Island”), among others. Treasure hunting is optional.
While we definitely recommend getting beyond the beach in the Caribbean to soak up some culture as well as sun, there’s nothing wrong with sampling a palm-fringed stretch of sand or a fine island rum (every island has its own style). You can even make a compelling case for an educational tour of offbeat beach bars, where local characters hang out (“lime”) or, in some cases, run the joints themselves.
Trust us, you’ll learn a lot about the Caribbean over a cold island brew or cutthroat game of dominoes. The latter -- along with soccer, baseball, and cricket -- are the region’s four most popular sports. And yes, the way folks of all ages play dominoes in the Caribbean – with fervor – it does legitimately qualify as a sport.
While swimming and snorkeling above coral reefs and amid manta rays and dolphins (an environmentally questionable practice) are tourist favorites, don’t pass up an opportunity to attend a baseball game in the Dominican Republic, which is now furnishing the Major Leagues with dozens of top players. It’s a truly wild experience – in some ways as fascinating as climbing a volcano in Central America, only much, much louder. If the volcano happens to be erupting, it might be a draw.
The Caribbean Reviews & Ratings
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Berchules, Sierra Nevada, Spain
Another great holiday thanks to Exodus! This was my 13th walking holiday with Exodus and one of the best, thanks to the varied walks, excellent leader, great scene...
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Spain
This is a wonderful combination of walking in the lovely Sierra Nevada mountains and then staying in Granada, although we extended our trip to give us 3 days in Gr...
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Top Autumn Walking
There is a lot of enjoyable walking to be had on this trip, varied routes and tantalising views of big ridges and high peaks. There is also wildlife a plenty but ...
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Loved it!
Our first Exodus holiday and it will certainly not be the last. Everything ran smoothly even though we had to have a replacement guide due to illness. Dan, our gui...
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Great time
Stars aligned for this trip, Outstanding Lead, Landscape, hosts and crew. Our guide Dan, had a bit of style and swagger. instilled confidence in all the group makin...
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