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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)



Azamara Cruises, Azamara Journey
Azamara Journey14 Night - Caribbean Cruise : San Juan, St. Lucia & St. Kitts
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, Road Town, Tortola, San Juan
2026 Sails: Nov 7, More...
Virgin Voyages, Valiant Lady
Valiant Lady7 Night - Southern Caribbean Cruise
Starting in San Juan, Puerto Rico, Philipsburg, Sint Maarten, Bridgetown, Barbados, Castries, Saint Lucia, Fort-De-France, Martinique, Basseterre, Saint Kitts and Nevis, San Juan, Puerto Rico
2026 Sails: Nov 7, Dec 12, 2027: Jan 16, 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 Croix, US Virgin Islands, Philipsburg, St Maarten, St Johns AG, Antigua, Roseau, Dominica, San Juan, Puerto Rico
2026 Sails: Nov 8, Nov 29, Dec 13, 2027: Jan 10, Jan 24, Feb 7, Feb 21, Mar 7, Mar 21, More...
Windstar, Star Pride
Star Pride7 Night - Windward Islands Surf & Sunsets
Starting in San Juan, St Georges, Bequia, Mayreau, Les Saintes, Marigot, St Martin, San Juan
2026 Sails: Nov 8, Nov 22, 2027: Nov 8, Nov 22, 2028: Mar 13, Mar 27, 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, Basseterre, Gustavia, Philipsburg, St Maarten, Jost Van Dyke, Great Harbour, Virgin Gorda / Prickly Pear, British Virgin Islands, San Juan
2026 Sails: Nov 8, 2027: Nov 8, 2028: Mar 13, More...
Ritz-Carlton, Evrima
Evrima7 Night - San Juan / Panama City
Starting in San Juan, Casa de Campo, Cartagena CO, San Blas Islands (Marina Day), Transit Panama Canal, Panama City
2026 Sails: Nov 12, More...
Azamara Cruises, Azamara Journey
Azamara Journey14 Night - Caribbean Cruise : Barbados, St. Lucia & St. Kitts
Starting in Bridgetown, Castries, Roseau, Basseterre, St Kitts, Charlestown, Nevis, Philipsburg, Road Town, Tortola, San Juan, Virgin Gorda, St Johns AG, Saint-Pierre, Port Elizabeth VC, Bequia, Saint Georges, Grenada, Scarborough, Tobago, Bridgetown
2026 Sails: Nov 14, More...
Azamara Cruises, Azamara Journey
Azamara Journey7 Night - Eastern Caribbean Cruise : Barbados, Saint Lucia & British Virgin Islands
Starting in Bridgetown, Castries, Roseau, Basseterre, St Kitts, Charlestown, Nevis, Philipsburg, Road Town, Tortola, San Juan
2026 Sails: Nov 14, More...
Royal Caribbean, Rhapsody of the Seas
Rhapsody of the Seas7 Night - Southern Caribbean Cruise
Starting in San Juan, Puerto Rico, Philipsburg, St Maarten, St Johns AG, Antigua, Roseau, Dominica, Basseterre, St Kitts and Nevis, St Croix, US Virgin Islands, San Juan, Puerto Rico
2026 Sails: Nov 14, More...
SeaDream Yacht Club, SeaDream I
SeaDream I7 Night - British & French Islands Discovery Cruise
Starting in Philipsburg, Sopers Hole, Tortola, Norman Island, Spanish Town, Virgin Gorda, Leverick Bay, Virgin Gorda, Gustavia, Terre De Haut, Iles des Saintes, Mayreau, Bridgetown, Barbados
2026 Sails: Nov 14, More...

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Caribbean Cruise Departures