Caribbean

Experience the idyllic beaches and turquoise waters of the Caribbean small ship cruise adventure, accessing charismatic ports that the large cruise ships can’t reach. Enjoy the romance as you sail on a tall ship or indulge in the luxuries of a mega yacht as you explore Barbados, Antigua, Dominica, Saint Lucia and Grenada. Take a step back in time while visiting the colonial cities of Cuba and marvel at the feat of engineering that is the Panama Canal or discover hidden coves in the picture-perfect Grenadines.  If you desiring a Caribbean cruise, do it right on a small ship cruise with Backwaters.

Top 5 Small Ships in Caribbean

Sea Cloud

Built by Wall Street businessman E. F. Hutton for his wife, the 58-passenger Sea Cloud exemplifies grace and elegance. She carries 30 sails which are raised by hand and has an “open bridge” policy...

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Sea Cloud II

Sister ship of the legendary Sea Cloud, the Sea Cloud II boasts the same high standards and elegance of this romantic tall ship with its own, unique character. It features four expansive decks...

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Variety Voyager

Built in line with the latest international safety regulations, the Variety Voyager is a state-of-the-art mega yacht with the capacity for just 72 guests. She’s designed with sleek lines and...

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Caribbean Cruise Deals

$200 off per person, first time booking with Backwaters.

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All Caribbean Small Ship Cruises

Costa Rica, Central America & Cuba: Colon - Cienfuegos

0
15 Days
Caribbean, Central America

Enjoy Central America and the Caribbean on this 15-day sailing adventure from Colon to Cienfuegos aboard your luxury sailing schooner the Sea Cloud II. Discover the unique range of flora and fauna in...

From

$8,755
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Costa Rica & Panama Canal: Curaçao to Panama

0
8 Days
Caribbean, Central America

Sail from Curaçao to Cartagena, Colombia, and disembark in Panama City, experiencing Caribbean summer winds and the Latin-American zest for life. Explore Aruba, Bonaire and Curaçao – the ABC...

From

$3,895
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Sights and Sounds of Cuba: Havana to Cienfuegos

0
8 Days
Caribbean

Imagine going back to other times - the culture, music, art, and people of Cuba await! Enjoy lively beats, picture-perfect beaches, and narrow city streets with colonial charm on this incredible 8-...

From

$3,299
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Sights and Sounds of Cuba: Cienfuegos to Havana

0
8 Days
Caribbean

Start your "bucket list" cruise in the enchanting and French-styled city of Cienfuegos, declared a UNESCO World Heritage site. Visit the graphic arts workshop and attend a local musical performance....

From

$3,299
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Ports of South Cuba: Santiago de Cuba to Cienfuegos

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8 Days
Caribbean

It has never been so easy to go back in time to a place rooted in culture and history, where the people are as warm and welcoming as the climate. Cruise through Cuba during 8 days aboard the Variety...

From

$3,299
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Caribbean: Barbados to Antigua via Grenada

0
10 Days
Caribbean

Enjoy the spectacular pastels of the Caribbean while sailing into the sun along famous pirate routes. When the Sea Cloud meets the Sea Cloud II against an exquisite Caribbean backdrop and they sail...

From

$5,915
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Caribbean and Cuba: Cienfuegos - Antigua

0
12 Days
Caribbean

Join the Sea Cloud on this fantastic 12-day cruise exploring Caribbean and Cuba hot spots. Visit the colorful small cities and the exceptional beaches this archipelago is famous for as you sit back...

From

$7,675
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Caribbean: Round-trip Bridgetown

0
12 Days
Caribbean

Experience the blue waters of the wonderful Caribbean on this 12-day round-trip cruise from Barbados. As you sail, visit the charming port cities and remote coves of Tobago Cays, Soufriere, Cabrits,...

From

$8,025
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Caribbean: Antigua - Bridgetown

0
16 Days
Caribbean

Enjoy the spectacular pastels of the Caribbean while sailing into the sun along famous pirate routes. When the Sea Cloud meets the Sea Cloud II against an exquisite Caribbean backdrop and they sail...

From

$10,375
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Caribbean: Santo Domingo - Bridgetown

0
16 Days
Caribbean

Experience the blue waters of the wonderful Caribbean on this 16-day cruise from Santo Domingo to Barbados. As you sail, visit the charming port cities and remote coves of Tobago Cays, Soufriere,...

From

$10,395
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Balearic Islands & Corsica

0
8 Days
Caribbean, Europe, Spain, France, Italy, Mediterranean

Starting at the delightful port of Malaga, this incredible sailing expedition takes you to some of the most important and historic towns of the Balearic Islands and the charming island of Corsica....

From

$1,880
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