Caribbean
13 Trips And 2 Offers Available
Panama & Colombia: Exploring The Caribbean CoastNext Trip
8 Days Cruise Caribbean
Trips, Tours & Cruises

Why Choose a Caribbean Islands Trip

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7 Cruises
6 Land Tours
2 Offers

The Caribbean is a melting pot of religions, languages and cultures. Trips through this vibrant region can be very meaningful. On our Caribbean trips, experience “the place on the way to everywhere” through idyllic bays, secluded beaches, historic ports and remote resorts.

Choose Caribbean travel with AdventureSmith for sunny locales coupled with impressive accommodations. Sail the tradewinds from Barbados, experience over 360 islands of Guna Yala, access the best Caribbean beaches of Bocas del Toro and venture into the interior jungles of Belize and Guatemala where Maya ruins and the temples of Tikal are waiting.

Our longstanding relationships with reputable companies offering Caribbean vacations by land and sea translate into Caribbean trip savings. Our Adventure Specialists know the best Caribbean island trips, where to go in the Caribbean and how to explore the fabled region.

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8 Day Cruise
Sailing the Caribbean Aboard Sea Cloud

Sail round-trip from Barbados aboard the historic 58-guest Sea Cloud. Swim and snorkel in pristine tropical waters, explore remote cays and beaches, and experience historic forts and natural wonders.

Special Offer
From $9658USD
Jan Feb
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8 Day Cruise
History & Culture: Visiting Caribbean Jewels

Come aboard 32-guest Le Ponant to sail among dancing waves and explore little-known places and long beaches lined with palm trees over 8 unforgettable days.

From $7850USD
Jan Feb Mar Apr Dec
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8-13 Day Cruise
Pearls of the Caribbean Cruise

Explore enchanting islands including Tobago, Grenada and more, on this luxury Caribbean cruise aboard a 184-guest luxury French ship. Enjoy a mix of Creole culture, UNESCO World Heritage sites, white-sand beaches, snorkeling and optional diving.

From $4540USD
Jan Feb Mar Nov Dec
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Caribbean Trips

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Caribbean trips with AdventureSmith Explorations pair tropical adventure with unique history and a variety of cultures. Ensure the best Caribbean travel featuring rainforest, waterfalls and beaches among the more than 700 uninhabited islets. Caribbean vacations reveal stunning waterfalls, lush rain forest, dayglo underwater species, foods filled with tantalizing spices and ancient Mayan ruins ready to reveal secrets of the past.

Expertly guided Caribbean trips bring to life the region’s unique geography and physical makeup. Discover a cultural mosaic of French, Dutch, English and Spanish influence, as well as a regional history of Maya ruins, temples and culture. Discover your ideal Caribbean islands trip and book with confidence through AdventureSmith.

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Caribbean Trips
with AdventureSmith

Small group Caribbean trips ensure that your Caribbean travel is off the beaten path, away from crowds. Think secluded beaches, local interactions, insightful guides and pristine environment.
Why book your Caribbean travel with AdventureSmith? 

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Active

Our Caribbean trips offer snorkeling, diving, paddling, fishing, biking, hiking, zip-lining & more.

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Wilderness

Explore lavish jungle, unspoiled bays & small communities on our Caribbean vacations. 

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Personalized

Work with one Adventure Specialist to find, book & prepare for your Caribbean travel.

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Value

Our relationships with reputable companies translates into deals on Caribbean vacations.

Group of family travelers jump off the back of a private catamaran into calm turquoise waters during a Caribbean family vacation.

Top Caribbean Family Vacations

Small group and charter Caribbean trips make ideal Caribbean family vacations. Our Caribbean trips offer active, educational, cultural and engaging opportunities for travelers of all ages. Transit the Panama Canal, meet indigenous communities of Panama’s Darien Jungle, walk though Mayan ruins or explore the world’s second largest reef—the Belize Barrier Reef. View all of our Caribbean vacations and then contact us to help you find and book your optimal Caribbean family vacation.

Learn More About Family Travel With AdventureSmith

Luxury Caribbean Vacations

Luxury Caribbean vacations mean different things to our travelers, and we’re here to help you find that sweet spot with your Caribbean travel. Want to travel with your own private group on a customized itinerary? Consider our Belize Catamaran Charter Cruise. Craving the onboard experience of a 5-star hotel? Look to our Pearls of the Caribbean or The Caribbean Under Sail Aboard Le Ponant. Yearning for a private beachside suite or deluxe treetop hideout? Experience both on our Belize Sacred Caves & Coast itinerary. Our Caribbean experts are ready to match you with the best luxury Caribbean vacations.

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Small wooden dinghy sits anchored in calm turquoise waters by a deserted beach backed by lush jungle on a sunny day during a luxury Caribbean vacation.

“Ensure that your Caribbean travel is off the beaten path, away from crowds.”

Climate

Caribbean Trips

Temperature & Rainfall

Month Jan Feb Mar Apr May Jun Jul Aug Sep Oct Nov Dec
Avg. High (F) 80 81 83 84 85 87 86 87 88 86 82 81
Avg. Low (F) 72 73 74 76 78 79 79 79 78 77 74 73
Avg. Water Temp (F) 80 80 81 82 84 85 84 85 85 84 83 81
Avg. Rainfall (Inches) 3.5 2.3 1.8 1.4 2.9 4.6 5.2 4.7 5.3 6.1 5.4 4.4

Year-Round Caribbean Travel

Our Caribbean vacations are offered all year, however some itineraries operate during North America’s winter, when there are dependable Caribbean tradewinds. Consider your desired activities—for diving, North America’s summer months are ideal. Note that the climate data referenced above is for Placencia, Belize, with even warmer temps encountered farther south on small cruise ships in the Caribbean.

When Should You Plan Your Caribbean Travel?

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Caribbean Trips

Learn what life is like on board an exclusive sailing yacht in Belize and how it differs from a motor yacht or small cruise ship.
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Caribbean Trips

Exploring Panama for the first time with my wife and young sons, age six and nine, we crafted a custom 8-day trip to Panama City, Bocas del Toro and Gamboa.
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Caribbean Trips

A review of the inaugural Costa Rica, Panama and Colombia Cruise aboard the 72-guest Variety Voyager written by AdventureSmith Explorations' founder.
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Book with the confidence that comes from experience.

100+ combined years of experience, 7 continents explored, decades of expedition cruising around the world & here to help you find & book your dream trip.

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Accommodations

Hand-Picked Caribbean Accommodations

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Our Caribbean resorts, seaside lodges and ships provide travelers with personalized experiences. With the Caribbean’s hundreds of animal and bird species, crystal-clear waters rich with spectacular coral reefs and gorgeous vistas that unfold onto deserted shores, accommodations here provide a basecamp in paradise.

We offer only the best Caribbean land and sea accommodations, providing privileged access to remote areas as well as the highest level of safety and comfort. From classic and classy to modern and high tech, our large variety of Caribbean accommodations are ready to make any traveler feel at home, with expert naturalist guides on site.

Expert Reviews

Caribbean Travel Reviews

Our Caribbean travel reviews reveal insights into traveling on Caribbean trips. Read these detailed trip reviews and journals written by travelers and our staff to learn about their experiences adventuring among the Caribbean Islands and other warm-weather destinations. What are the locals like? What are the top historical points of interest? These fun and personal stories can not only help you learn more about what it’s like but also help you find the best Caribbean cruise or land adventure.

Special Offers

Caribbean Trip Deals

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For special offers on Caribbean trips and travel to other warm-climate destinations, contact the AdventureSmith experts. Our longstanding relationships with reputable companies enable our talented team to find you the latest discounts, explain the ins-and-outs of the landscape and help you secure your top choice to this amazing place at the best rate. Our team can help you narrow down your choices and identify which Caribbean land or sea adventure is the best fit for you.

Our Expertise

Our Experts Are Your Fastest Way To See The Caribbean The Way You Want

Receive Personalized Recommendations

Need assistance narrowing down all the Caribbean travel options? Our experts are just a phone call or email away, ready to provide a personalized-to-you recommendation on the Caribbean vacation for your travel style, budget and timing needs. Still want to research yourself? Filter through all the cruse and land-tour options on our Caribbean Trip Finder.

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