Caribbean Small Ship Cruises

7 Cruises
2 Offers
Cruise among more than 700 Caribbean islands, visiting secluded bays only accessible to small ships, catamarans and yachts. Talk to our experts about the options in this incomparable region to sail. 
Trips, Tours & Cruises

Why Choose a Caribbean Small Ship Cruise

View All Caribbean Cruises
7 Cruises
2 Offers

The Caribbean features uninhabited islets populated by hundreds of animal and bird species, crystal-clear waters rich with spectacular coral reefs and gorgeous vistas that unfold onto deserted shores. Aboard small cruise ships in the Caribbean, come face to face with rich biodiversity while swimming in tropical waters and learn about the enchanting ruins and history of the region.

Selecting a Caribbean cruise vacation with AdventureSmith safeguards your adventure as it’s backed by a fully insured, U.S.-based company. We also gain you access to remote, off-the-beaten path islands, away from tourist crowds. Relish the sense of seclusion only a small ship can bestow. The expert guides traveling alongside you are often from the region, ensuring each unspoiled stop is both special and fascinating.

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Caribbean Small Ship Cruises
with AdventureSmith

Small cruise lines in the Caribbean offer up-close, off-ship exploration of vibrant barrier reef, peaceful beaches, wildlife-filled jungles, mythical ruins and welcoming communities. Why book your Caribbean cruise vacation with AdventureSmith? 

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More Exploration

Enjoy an active cruise with snorkeling, diving, swimming, paddling, hiking & more.

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Tropical Wilderness

On your small Caribbean cruise, explore lush jungle, idyllic bays & private islands. 

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Large Selection

Choose from a wide variety of itineraries, locales & small cruise ships in the Caribbean under 200 guests.

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Added Value

We focus on premier experiences at the best value & discounts when available. Never pay more with us.

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Find Your Small Caribbean Cruise

Our luxury Caribbean cruise options offer top-notch guides and five-star onboard service. Consider one of our Caribbean tall ship sailing cruises aboard the historic Sea Cloud. Revel in French-inspired opulence aboard modern expedition ship Le Dumont D’Urville. Enjoy the luxury-meets-active feel of Le Ponant motorsailer. Or opt for the luxury of an exclusive Caribbean catamaran charter aboard a private Belize charter yacht or any of our small ships. Our experts are ready to help you find the best luxury Caribbean cruise based on your timeline and interests.

Year-Round Cruises to the Caribbean in 2024 & 2025

Our Caribbean sailing vacations are offered year-round. Some itineraries focus on the North American winter, when the weather is ideal and there are dependable tradewinds. Conversely, the North American summer months offer the best diving. Search by month, or ask our experts to help narrow down the options, from Barbados to the Belize Barrier Reef.

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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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