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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)



Windstar, Wind Star
Wind Star18 Night - Star Collector : Reefs & Rainforests : the Caribbean, Colombia, Panama & Costa Rica via the Panama Canal
Starting in Bridgetown, Bequia, St Georges, Kralendijk, Willemstad AN, Oranjestad, Cartagena CO, San Blas, Panama, Colon, Panama Canal, Balboa / Fuerte Amador, Isla Partida, Golfo Dulce (Puerto Jimenez), Quepos, Puerto Caldera
2026 Sails: Nov 24, More...
Costa Cruise Lines, Costa Favolosa
Costa Favolosa8 Night - Western Caribbean from Fort De France
Starting in Martinique (Antilles), Guadeloupe (Antilles), St Kitts (Antilles), Antigua (Antilles), Tortola, British Virgin Islands, Santo Domingo, Dominican Republic, Guadeloupe (Antilles), Martinique (Antilles)
2026 Sails: Nov 25, 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 25, More...
Costa Cruise Lines, Costa Favolosa
Costa Favolosa6 Night - Western Caribbean from Pointe a Pitre
Starting in Guadeloupe (Antilles), St Kitts (Antilles), Antigua (Antilles), Tortola, British Virgin Islands, Santo Domingo, Dominican Republic, Guadeloupe (Antilles)
2026 Sails: Nov 26, More...
Crystal Cruises, Crystal Serenity
Crystal Serenity5 Night - The Americas & Caribbean
Starting in San Juan, Jost Van Dyke, British Virgin Islands, Oranjestad, Aruba, Cartagena CO
2026 Sails: Nov 27, More...
Ritz-Carlton, Ilma
Ilma3 Night - San Juan / San Juan
Starting in San Juan, Gustavia, Virgin Gorda, San Juan
2026 Sails: Nov 27, 2027: Jan 19, More...
Windstar, Star Legend
Star Legend15 Night - Star Collector : Captivating Caribbean
Starting in Bridgetown, Anse Mitan, Rodney Bay, Castries, The Pitons, Mayreau, St Georges, Bequia, Bridgetown, Rodney Bay, The Pitons, Scarborough, Tobago, Bequia, Mayreau, St Georges, Willemstad AN, Oranjestad
2026 Sails: Nov 27, More...
Windstar, Star Legend
Star Legend7 Night - Jewels of the Windward Islands
Starting in Bridgetown, Anse Mitan, Rodney Bay, Castries, The Pitons, Mayreau, St Georges, Bequia, Bridgetown
2026 Sails: Nov 27, More...
Azamara Cruises, Azamara Journey
Azamara Journey7 Night - Eastern Caribbean Cruise : Saint Kitts, Nevis & Saint Barthelemy
Starting in Bridgetown, Castries, Roseau, Basseterre, St Kitts, Charlestown, Nevis, Philipsburg, Gustavia, San Juan
2026 Sails: Nov 28, More...
Azamara Cruises, Azamara Journey
Azamara Journey14 Night - Caribbean Cruise : Barbados, St. Lucia & St. Maarten
Starting in Bridgetown, Castries, Roseau, Basseterre, St Kitts, Charlestown, Nevis, Philipsburg, Gustavia, San Juan, Virgin Gorda, St Johns AG, Saint-Pierre, Port Elizabeth VC, Bequia, Saint Georges, Grenada, Scarborough, Tobago, Bridgetown
2026 Sails: Nov 28, More...

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Caribbean Cruise Departures