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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)



Virgin Voyages, Valiant Lady
Valiant Lady8 Night - Southern Caribbean Cruise
Starting in San Juan, Puerto Rico, St Thomas, US Virgin Islands, Willemstad AN, Curacao, Oranjestad, Aruba, Basseterre, Saint Kitts and Nevis, Philipsburg, Sint Maarten, San Juan, Puerto Rico
2026 Sails: Nov 20, More...
Azamara Cruises, Azamara Journey
Azamara Journey7 Night - Southern Caribbean Cruise : Bequia, Grenada & Tobago
Starting in San Juan, Virgin Gorda, St Johns AG, Saint-Pierre, Port Elizabeth VC, Bequia, Saint Georges, Grenada, Scarborough, Tobago, Bridgetown
2026 Sails: Nov 21, More...
Azamara Cruises, Azamara Journey
Azamara Journey14 Night - Caribbean Cruise : San Juan, Antigua & Barbados
Starting in San Juan, Virgin Gorda, St Johns AG, Saint-Pierre, Port Elizabeth VC, Bequia, Saint Georges, Grenada, Scarborough, Tobago, Bridgetown, Castries, Roseau, Basseterre, St Kitts, Charlestown, Nevis, Philipsburg, Gustavia, San Juan
2026 Sails: Nov 21, More...
Emerald Cruises, Emerald Sakara
Emerald Sakara7 Night - Caribbean Escapade
Starting in San Juan, Puerto Rico, Grand Turk, Turks and Caicos Islands, Gordons Beach, Long Island, Bahamas, San Salvador Island, Bahamas, Emerald Bay, Exumas, Bahamas, Nassau, Bahamas, Miami, Florida
2026 Sails: Nov 21, More...
SeaDream Yacht Club, SeaDream I
SeaDream I7 Night - the Glorious Grenadines Cruise
Starting in Bridgetown, Barbados, Soufriere Bay, Kingstown, Port Elizabeth VC, Bequia, Tobago Cays, Mayreau, St Georges, Bridgetown, Barbados
2026 Sails: Nov 21, More...
Norwegian Prima7 Night - Southern Caribbean - San Juan
Starting in San Juan, Pr, Tortola, British Virgin Islands, Basseterre, Saint Kitts / Nevis, Bridgetown, Barbados, St Lucia, Saint Lucia, Philipsburg, St Maarten, Netherland Antilles, St Thomas, Vi, San Juan, Pr
2026 Sails: Nov 22, Nov 29, 2027: Jan 10, Jan 24, Feb 21, Dec 18, 2028: Jan 1, Jan 8, Feb 12, Feb 26, Mar 4, Mar 11, Mar 25, Apr 1, Apr 8, Apr 15, More...
Royal Caribbean, Vision of the Seas
Vision of the Seas7 Night - Southern Caribbean Cruise
Starting in San Juan, Puerto Rico, Tortola, St Johns AG, Antigua, Philipsburg, St Maarten, St Croix, US Virgin Islands, Basseterre, St Kitts and Nevis, San Juan, Puerto Rico
2026 Sails: Nov 22, Dec 6, 2027: Feb 14, More...
Windstar, Star Pride
Star Pride14 Night - Star Collector : Lovely Leewards
Starting in San Juan, St Georges, Bequia, Mayreau, Les Saintes, Marigot, St Martin, San Juan, St John VI (Cruz Bay), US Virgin Islands, Gustavia, Basseterre, Philipsburg, St Maarten, Jost Van Dyke, Great Harbour, Virgin Gorda / Prickly Pear, British Virgin Islands, San Juan
2026 Sails: Nov 22, More...
MSC Cruises, MSC Opera
MSC Opera7 Night - South Caribbean
Starting in La Romana, Dominican Republic, Samana Bay, Dominican Republic, Virgin Gorda, British Virgin Islands, Philipsburg, St Maarten, Basseterre, St Kitts and Nevis, Catalina Island, Dominican Republic, La Romana, Dominican Republic
2026 Sails: Nov 23, More...
Windstar, Wind Star
Wind Star11 Night - Colombian & Southern Caribbean Coastlines
Starting in Bridgetown, Bequia, St Georges, Kralendijk, Willemstad AN, Oranjestad, Cartagena CO, San Blas, Panama, Colon
2026 Sails: Nov 24, More...

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Caribbean Cruise Departures