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Caribbean tours

Soft gold sands, burnt-orange sunsets, and kaleidoscopic culture all typify the Caribbean—but so do Indigenous history, European colonization, and the interplay between the two. See the full spectrum on our Caribbean tours, from Old Havana’s famous blue buildings to El Yunque’s lush forest greenery.

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What to know before you go

POPULATION
Roughly 44.5 million people live across the Caribbean’s 13 countries and 12 territories. Distribution varies wildly from island to island, though: Haiti’s population, the highest in the region, sits at nearly 12 million, while Saint Kitts and Nevis—the Caribbean’s smallest sovereign nation—counts fewer than 47,000 residents.

MAJOR CITIES
Santo Domingo, Havana, and San Juan—three of the biggest cities in the region—share more than a language: As former Spanish territories, they’re replete with colonial architecture, hulking fortresses, and more. (We also visit each on our guided tours of the Caribbean.)

CULTURAL QUICK TAKE
As old-world powers fought for influence in—and spirited African slaves to—the Caribbean, they attempted to assert their dominance over other cultures. But their attempts at erasure led to the creation of new customs and beliefs. Take Santeria as an example: When forced to attend Mass, African slaves began equating Roman Catholic saints to traditional Yoruba deities, laying the foundation for a uniquely Cuban religion.

WHAT TO GO FOR
History buffs can lose themselves in Santo Domingo’s UNESCO-listed Colonial Zone, while nature lovers won’t want to get out of the life-filled waters off Belize’s Ambergris Caye. And whatever your travel style, no Caribbean vacation package would be complete without some time on the beach, listening to the rumble of the sea from the shade of a swaying palm tree.

UNIQUE EXPERIENCES ON TOUR
Dance from mural to colorful mural in San Juan’s Santurce neighborhood, try your hand at whipping up Dominican dishes during a cooking class in Jarabacoa, sip guarapo (sugar cane juice) as you walk between industrial machinery at a Cuban sugar-mill-turned-museum, and more.

Dive into something new

Beyond the beaches (and there’ll be plenty of opportunity to indulge), our Caribbean cultural tours highlight the people and places that make the region shine. These two itineraries introduce new-to-us destinations—and all the wonders they hold within.

Plan your Caribbean tour with help from the experts (that’s us!)

So you’ve booked a guided tour of the Caribbean. Now, build it out with free-time suggestions and more, courtesy of our team.

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Belize Travel Guide: the best things to do, see, and eat

Mayan ruins. Belikin beer. You’ll find all the basics (and some insider tips) in this comprehensive article.

16 incredible islands to visit all around the world

A destination we visit on one of our Caribbean group tours cracked the top five—but to see which, and where, you’ll have to click below.

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Signature experiences for your memory vault. Why don’t you...

Swim and float over La Parguera’s reefs

Plunge into crystal-clear waters for a morning of snorkeling. Try it on our Highlights of Puerto Rico: Bioluminescent Bay, Beaches & El Yunque tour.

Learn how to make a mean mangu

Follow along as local instructors teach you the tricks behind traditional meals. Try it on our Dominican Republic: Santo Domingo, Jarabacoa & North Coast Beaches tour.

Ride the current through a mystifying cave network

Hop atop an inner tube and coast through Jaguar Paw, where ancient Mayans sourced sacred water. Try it on our A Week in Belize: Ruins, Reefs & Rainforests tour.

Sample the spirit of San Juan’s districts

Pair the murals of the Santurce neighborhood with a rum tasting in Old San Juan. Try it on our Highlights of Puerto Rico: Bioluminescent Bay, Beaches & El Yunque tour.

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Experiential travel made easy

You dream it. We’ll take care of every last detail.

Pick your perfect trip

We offer 200+ immersive, guided tours around the world. Wherever you choose to go, you’ll enjoy lots of advantages that make traveling with us different.

Put just $99 down

That’s all it takes to secure a spot on one of our group tours when you sign up for AutoPay. Plus, you can pay in interest-free,
monthly installments.

Prep your packing list

While you’re deciding what to take, we’ll be busy arranging your hotels, meals, tickets, and more tour essentials. That’s what going guided is all about.

Go far (and get rewarded)

Take off on your big adventure— but why stop there? Every trip you book with us earns rewards that you can use to keep expanding your horizons.

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What travelers are saying about Caribbean tours

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5 out of 5 stars

Cuba calls….

3rd-time traveler Nicoa

This was the best trip that anyone could ask to go on. It had multiple levels of excitement. We experienced the world of art, music, dancing and our taste buds met flavors of...

5 out of 5 stars

Un-belize-able

2nd-time traveler Carly

The tour was amazing! Hotels were great, food was delicious, bus driver and tour director knowledgeable and focused on safety and fun for all travelers. Would highly recommend...

5 out of 5 stars

Awesome tour! Great Cultural Experience!

4th-time traveler Anonymous

This was my 6th GoAhead tour and one of my favorites. The tour was rich with culture, history, food, and unique experiences. I found all of it so enriching and way more than just...

5 out of 5 stars

Cuba--People and Culture

2nd-time traveler William

Had a truly terrific trip to Cuba! Local guide Jorge, tour director Gustavo, and bus driver Yunior made it unforgettable. We dove deeply in Havana's history, monuments, art...

5 out of 5 stars

Havana

2nd-time traveler Melinda

What a fantastic tour. Our guides Yaz and Louis were very impressive with their extensive knowledge base. Our days were packed with personally picked opportunities to share the...

5 out of 5 stars

Outstanding!

1st-time traveler Lori

Our tour guide Ezy (Efrain) was amazing. He was well organized, took great care of the group and made the trip exciting and enjoyable. I highly recommend doing this tour. The...

5 out of 5 stars

Visit Cuba!

2nd-time traveler Sarah

With only a budget and travel dates, my daughter chose Cuba for our summer travel. I had never thought of Cuba as must-see destination, but now I would encourage everybody to go....

5 out of 5 stars

Great Tour

4th-time traveler Connie

The Cuba tour was excellent. So many great things were included. Our Tour Director and Guide were both fabulous. My only complaint was the heat. We had AC in hotels but not at...

5 out of 5 stars

Wonderful Experience

2nd-time traveler Lillian

Cuba is a wonderful country full of vibrant people, culture, and environment. This tour is a great combination of meeting local Cubans and learning about the community projects...

5 out of 5 stars

Fantastic

8th-time traveler Debra

Great fun with our tour group and our guide, Herbert. Herbie is well organized and great fun. He went above and beyond his role to make sure we were all well cared for and to...

5 out of 5 stars

Excellent

6th-time traveler Thea

Had a fantastic time on this tour! Herbie was an excellent guide and while some things were not available (wrong growing season for oranges) we still learned quite a bit about...

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There’s even more on the mainland

World-famous coffees, standard-setting conservation, and epic terrain wherever you look? Mix Caribbean flair with Pacific grandeur on these tours to Costa Rica, Panama, and Mexico.

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Travel tips for Caribbean trips