San Juan Cruise Departures
Cruises that depart from Caribbean: Puerto Rico: San Juan
Cruises that visit San Juan
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, 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, 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 - Thanksgiving : St. Isles, Aruba & CuraaAo
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...
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 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...
7 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...7 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...
Cruises that depart from Caribbean: Puerto Rico: San Juan
Cruises that visit San Juan
Click on a cruise ship itinerary sailing from San Juan (below) and select a sail date to receive competing cruise quotes. To search all cruise itineraries (not just San Juan), please visit: Cruise Search or try our Virtual Cruise Advisor™.
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...
Deal link -> Special
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, 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, 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 - Thanksgiving : St. Isles, Aruba & CuraaAoStarting 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...
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 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...
7 Night - Caribbean EscapadeStarting 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...
Deal link -> Special
7 Night - Southern Caribbean - San JuanStarting 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...
