Aerial view of Le Ponant white sailing ship with 3 masts cruising through turquoise sea on a sunny day in the Caribbean.

Caribbean Small Ship Cruises

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. 

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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.

Luxury Caribbean cruise ship with blue & white exterior sits offshore of a private island white-sand beach.

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 upscale Le Ponant. Revel in French-inspired opulence aboard modern expedition ship Le Champlain. 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 2026 & 2027

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.

2 women sit at water's edge on a sandy beach at sunset with their private Caribbean catamaran charter yacht in the distance.