13 Trips And 2 Offers Available
Trips, Tours & Cruises

Why Choose a Caribbean Islands Trip

View All Caribbean Trips
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.

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

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

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

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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.

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.

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.”


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?

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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