Cruises to the Caribbean, 2024, 2025 and 2026 Caribbean Cruises | The Cruise Web

Caribbean Cruises

Relaxation comes standard when you choose a Caribbean cruise. You can sail away from your everyday life and find tropical bliss in the islands.

Whether you choose the Eastern, Western or Southern region, there’s so much to do and see during your cruise vacation. Sink your toes in white-sand beaches, or traverse lush mountainscapes. Barter in local island markets for one-of-a-kind treasures, or visit historic attractions that give insight on the roots of the intriguing native cultures. Go tubing down a river, dive headfirst into refreshing waters or zip-line through a rainforest.

All this, and even more when you choose to cruise the Caribbean.


Eastern Caribbean beach

Eastern Caribbean

Picture soft white sand, perfectly clear water and warm trade winds swaying your hammock, you’d be picturing the Eastern islands. The Eastern region is great for cruising year round, and may include stops in the Virgin Islands, Puerto Rico and the nations of Hispanola.

[Learn more about Eastern Caribbean Cruises]


Sea turtle in the Southern Caribbean

Southern Caribbean

Cruise to the Southern region's island paradises which are filled with beautiful beaches, waterfalls, butterfly farms and some of world's best spots for watersports like windsurfing, snorkeling and more. and concerns and replace them with sandy beaches, sunny days and clear, soothing waters.

[Learn more about Southern Caribbean Cruises]


Western Caribbean ruins

Western Caribbean

The Western islands' warm temperatures and colorful sea dwellers make this a great place to relax on the beach, or cool off in the turquoise water. You'll find exotic rainforests, colorful reefs and ancient ruins sharing tons of history from the Aztec and Mayan cultures.

[Learn more about Western Caribbean Cruises]


Caribbean cruises to Costa Rica

Costa Rica

Costa Rica is a nature lover’s paradise. With miles and miles of protected nature reserves, Costa Rica is full of fascinating animals, towering volcanoes and roaring waterfalls. Plus, the lively culture and history are just as inviting as the landscapes and scenery.

[Learn more about cruises to Costa Rica]



Things to Do on a Cruise to the Caribbean


Made up of more than 700 islands, the Caribbean is a top vacation destination for travelers the world over. This destination is divided into three regions: Eastern, Western and Southern. While each region has their own distinctions, they all offer wonderful weather, pristine beaches and stunningly clear water that sparkles in the sunlight.


Caribbean beach with straw umbrellas
  • Soak in the sun. One of the main reasons this destination is so sought after is its year round warm weather. Don’t miss a chance to lay out on one of the beaches and feel the warmth of the tropical sun.
  • Go shopping, islands like St. Thomas and St. Martin are known for having some of the most posh boutiques and shops; not to mention the duty free goods that make such great gifts.
Caribbean rainforest waterfall
  • Tour a rum distillery. Barbados is home to Mount Gay Rum, the oldest rum distillery in the world. However nearly every island produces their own brand rum, each with its own character.
  • Explore the amazing jungles. Many of the islands are covered with both rainforests and cloud forests where you can tour, hike or even swing from the trees via a zipline.
Snorkeling in the Caribbean
  • See what’s living in the beautiful blue waters by diving or snorkeling. Check out the fantastic reef off the coast of Cozumel, Mexico.
  • Try the local delicacies, fresh fish abounds and spices make for exciting flavor combinations. Try jerk chicken in Jamaica and Mofongo in Puerto Rico.

Map of the Caribbean:

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Caribbean: Cruise Lines

The Caribbean is the most cruised to destination in the world, and who can blame it. These islands are like fine crystals embellished on a cashmere sweater. Nothing beats a day in the sun with a view of the calm sea and tropical rainforests. Nearly every cruise line, luxury and popular, offer Caribbean itineraries.

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Caribbean: Departure Ports

There’s no beating the warmth of the sun in the Caribbean, and you don’t have to miss out as there are always cruises to the laid back, divine islands.  Florida’s ports like Miami and Fort Lauderdale are the start of many of the cruises. For a longer experience you can cruise from the north like New York, and Boston. You can even fly into ports like San Juan, which is a very popular point of embarkation for Southern itineraries.  But it doesn’t stop there because you can cruise to the Caribbean from South America, Europe, Africa, nearly anywhere. 

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