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Caribbean Cruise Departures

Cruises that depart from Caribbean

Cruises that visit Caribbean

Click on a cruise ship itinerary sailing from Caribbean (below) and select a sail date to receive competing cruise quotes. To search all cruise itineraries (not just Caribbean), please visit: Cruise Search or try our Virtual Cruise Advisor™.

Related areas: Antigua / Barbuda : Aruba : Bahamas : Barbados : Dominican Republic : Grenada : Guadeloupe : Martinique : Netherlands Antilles : Puerto Rico : Saint Lucia : Saint Martin : Virgin Islands (US)



PONANT, Le Bellot
Le Bellot12 Night - Panama, Colombia & Caribbean Islands
Starting in Fort-de-France, Les Saintes, Pigeon Island Beach, Soufriere, Port Elizabeth VC, Bequia Island, Mayreau Island, Bonaire, Santa Marta, Cartagena, San Blas Islands, Portobelo, Colon
2026 Sails: Oct 26, More...
Windstar, Star Pride
Star Pride11 Night - Masterpieces at Sea : Gems of the Leeward Islands
Starting in San Juan, St John VI (Cruz Bay), US Virgin Islands, Gustavia, Basseterre, Falmouth Harbour, Les Saintes, Rodney Bay, St Georges, Jost Van Dyke, Great Harbour, Virgin Gorda / Prickly Pear, British Virgin Islands, San Juan
2026 Sails: Oct 28, More...
Star Clippers, Royal Clipper
Royal Clipper14 Night - Barbados to Panama
Starting in Bridgetown, Barbados, Soufriere, St Lucia, Tobago Cays, Grenadines, St Georges, Grenada, Kralendijk, Bonaire, Willemstad AN, Curacao, Oranjestad, Aruba, Santa Marta, Colombia, Cartagena De Indias, Colombia, San Blas Archipelago, Panama, Panama Canal Transit, Balboa (Isla Flamenco), Panama
2026 Sails: Oct 31, More...
Virgin Voyages, Valiant Lady
Valiant Lady7 Night - Southern Caribbean Halloween Cruise
Starting in San Juan, Puerto Rico, Willemstad AN, Curacao, Oranjestad, Aruba, Fort-De-France, Martinique, Basseterre, Saint Kitts and Nevis, San Juan, Puerto Rico
2026 Sails: Oct 31, More...
Explora Journeys, EXPLORA III
EXPLORA III7 Night - A Journey Into Caribbean Exploration & Island Delights
Starting in San Juan, Tortola / Road Town, Basseterre, Gustavia, Road Bay, Miami
2026 Sails: Nov 1, More...
Explora Journeys, EXPLORA III
EXPLORA III14 Night - An Extended Journey Into Island Delights, Hidden Coves & Chic Coastlines
Starting in San Juan, Tortola / Road Town, Basseterre, Gustavia, Road Bay, Miami, Providenciales, Puerto Plata, Dominican Republic, La Romana, Jost Van Dyke, Gustavia, San Juan
2026 Sails: Nov 1, More...
Royal Caribbean, Vision of the Seas
Vision of the Seas7 Night - Southern Caribbean Cruise
Starting in San Juan, Puerto Rico, Charlotte Amalie, St Thomas, St Johns AG, Antigua, Philipsburg, St Maarten, St Croix, US Virgin Islands, Basseterre, St Kitts and Nevis, San Juan, Puerto Rico
2026 Sails: Nov 1, Nov 15, 2027: Mar 28, More...
Crystal Cruises, Crystal Symphony
Crystal Symphony7 Night - The Americas & Caribbean
Starting in San Juan, Jost Van Dyke, British Virgin Islands, St Johns, Gustavia, St Barthelemy, St Thomas, Fort Lauderdale
2026 Sails: Nov 4, More...
Viking Ocean, Viking Sea
Viking Sea10 Night - West Indies Explorer
Starting in San Juan, St Thomas (Charlotte Amalie), St Kitts (Basseterre), Castries, Bridgetown, Roseau, St Johns AG, Antigua, Philipsburg, St Croix (Frederiksted), San Juan
2026 Sails: Nov 5, Nov 15, Dec 5, 2027: Jan 15, Jan 25, Feb 4, Feb 14, Feb 24, Nov 27, Dec 7, Dec 17, Dec 27, 2028: Jan 27, Feb 6, Feb 16, More...
Azamara Cruises, Azamara Journey
Azamara Journey7 Night - Southern Caribbean Cruise : Antigua, Martinique & Grenada
Starting in San Juan, Virgin Gorda, St Johns AG, Saint-Pierre, Port Elizabeth VC, Bequia, Saint Georges, Grenada, Scarborough, Tobago, Bridgetown
2026 Sails: Nov 7, Dec 5, More...

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Caribbean Cruise Departures