Puerto Rico Cruise Departures
Cruises that depart from Caribbean: Puerto Rico
Cruises that visit Puerto Rico
Related areas: San Juan
6 Night - Southern Caribbean Cruise
Starting in San Juan, Puerto Rico, Tortola, British Virgin Islands, St Johns AG, Antigua and Barbuda, Castries, Saint Lucia, Basseterre, Saint Kitts and Nevis, San Juan, Puerto Rico
2026 Sails: Nov 14, More...
7 Night - A Journey of Blissful Escapes & Island Splendour
Starting in San Juan, Road Bay, St Johns AG, Antigua, Frederiksted, Saint Croix, Isla Catalina, Puerto Plata, Dominican Republic, Miami
2026 Sails: Nov 15, More...14 Night - An Extended Journey of Tropical Harmony & Natural Wonders
Starting in San Juan, Road Bay, St Johns AG, Antigua, Frederiksted, Saint Croix, Isla Catalina, Puerto Plata, Dominican Republic, Miami, St John VI (Cruz Bay), US Virgin Islands, St Johns AG, Antigua, Terre-De-Haut, St Maarten / Philipsburg, San Juan
2026 Sails: Nov 15, More...
7 Night - Southern Caribbean - San Juan
Starting in San Juan, Pr, Tortola, British Virgin Islands, St Johns AG, Antigua, Bridgetown, Barbados, Basseterre, Saint Kitts / Nevis, Philipsburg, St Maarten, Netherland Antilles, St Thomas, Vi, San Juan, Pr
2026 Sails: Nov 15, More...
7 Night - San Juan & the Virgin Islands
Starting in 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 15, 2027: Jan 10, Nov 1, Nov 15, 2028: Mar 20, More...14 Night - Star Collector : Lovely Leewards
Starting in 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, St Georges, Bequia, Mayreau, Les Saintes, Marigot, St Martin, San Juan
2026 Sails: Nov 15, 2027: Nov 1, Nov 15, 2028: Mar 20, More...
11 Night - Southern Caribbean Intensive
Starting in San Juan, Puerto Rico, Tortola, St Johns AG, Antigua, Castries, St Lucia, St Georges, Grenada, Bridgetown, Barbados, Kingstown, St Vincent, Fort-De-France, Martinique, Roseau, Dominica, San Juan, Puerto Rico
2026 Sails: Nov 17, More...8 Night - Southern Caribbean Cruise
Starting in San Juan, Puerto Rico, Charlotte Amalie, St Thomas, Willemstad AN, Curacao, Oranjestad, Aruba, Basseterre, Saint Kitts and Nevis, Philipsburg, Sint Maarten, San Juan, Puerto Rico
2026 Sails: Nov 20, More...
7 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...14 Night - Caribbean Combination 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...
Cruises that depart from Caribbean: Puerto Rico
Cruises that visit Puerto Rico
Click on a cruise ship itinerary sailing from Puerto Rico (below) and select a sail date to receive competing cruise quotes. To search all cruise itineraries (not just Puerto Rico), please visit: Cruise Search or try our Virtual Cruise Advisor™.
Related areas: San Juan
6 Night - Southern Caribbean CruiseStarting in San Juan, Puerto Rico, Tortola, British Virgin Islands, St Johns AG, Antigua and Barbuda, Castries, Saint Lucia, Basseterre, Saint Kitts and Nevis, San Juan, Puerto Rico
2026 Sails: Nov 14, More...
Deal link -> Special
7 Night - A Journey of Blissful Escapes & Island SplendourStarting in San Juan, Road Bay, St Johns AG, Antigua, Frederiksted, Saint Croix, Isla Catalina, Puerto Plata, Dominican Republic, Miami
2026 Sails: Nov 15, More...
Deal link -> Special
14 Night - An Extended Journey of Tropical Harmony & Natural WondersStarting in San Juan, Road Bay, St Johns AG, Antigua, Frederiksted, Saint Croix, Isla Catalina, Puerto Plata, Dominican Republic, Miami, St John VI (Cruz Bay), US Virgin Islands, St Johns AG, Antigua, Terre-De-Haut, St Maarten / Philipsburg, San Juan
2026 Sails: Nov 15, More...
7 Night - Southern Caribbean - San JuanStarting in San Juan, Pr, Tortola, British Virgin Islands, St Johns AG, Antigua, Bridgetown, Barbados, Basseterre, Saint Kitts / Nevis, Philipsburg, St Maarten, Netherland Antilles, St Thomas, Vi, San Juan, Pr
2026 Sails: Nov 15, More...
7 Night - San Juan & the Virgin IslandsStarting in 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 15, 2027: Jan 10, Nov 1, Nov 15, 2028: Mar 20, More...
14 Night - Star Collector : Lovely LeewardsStarting in 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, St Georges, Bequia, Mayreau, Les Saintes, Marigot, St Martin, San Juan
2026 Sails: Nov 15, 2027: Nov 1, Nov 15, 2028: Mar 20, More...
11 Night - Southern Caribbean IntensiveStarting in San Juan, Puerto Rico, Tortola, St Johns AG, Antigua, Castries, St Lucia, St Georges, Grenada, Bridgetown, Barbados, Kingstown, St Vincent, Fort-De-France, Martinique, Roseau, Dominica, San Juan, Puerto Rico
2026 Sails: Nov 17, More...
8 Night - Southern Caribbean CruiseStarting in San Juan, Puerto Rico, Charlotte Amalie, St Thomas, Willemstad AN, Curacao, Oranjestad, Aruba, Basseterre, Saint Kitts and Nevis, Philipsburg, Sint Maarten, San Juan, Puerto Rico
2026 Sails: Nov 20, More...
Deal link -> Special
7 Night - Southern Caribbean Cruise : Bequia, Grenada & TobagoStarting 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...
14 Night - Caribbean Combination Cruise : San Juan, Antigua & BarbadosStarting 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...
