Puerto Rico Cruise Departures
Cruises that depart from Caribbean: Puerto Rico
Cruises that visit Puerto Rico
Related areas: San Juan
7 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: May 30, Jun 13, Jun 27, Jul 11, Jul 25, Aug 8, Aug 22, Sep 5, Oct 3, Oct 31, Nov 7, Nov 21, Dec 5, Dec 19, 2027: Jan 2, Jan 16, Feb 27, More...7 Night - Southern Caribbean Cruise
Starting in San Juan, Puerto Rico, Tortola, Philipsburg, St Maarten, St Johns AG, Antigua, Basseterre, St Kitts and Nevis, St Croix, US Virgin Islands, San Juan, Puerto Rico
2026 Sails: Jun 6, Jun 20, Jul 4, Jul 18, Aug 15, Aug 29, Sep 12, Sep 26, Oct 10, Oct 24, Nov 28, Dec 12, 2027: Jan 23, Feb 6, Feb 20, More...7 Night - Southern Caribbean Cruise
Starting in San Juan, Puerto Rico, Tortola, Philipsburg, St Maarten, Basseterre, St Kitts and Nevis, St Johns AG, Antigua, St Croix, US Virgin Islands, San Juan, Puerto Rico
2026 Sails: Aug 1, More...
11 Night - The Americas & Caribbean
Starting in San Juan, Marigot, St Martin, Roseau, Bridgetown, Castries, St Lucia, St Johns, Jost Van Dyke, British Virgin Islands, Samana, Grand Turk, New York
2026 Sails: Sep 14, More...7 Night - Southern Caribbean Cruise
Starting in San Juan, Puerto Rico, Charlotte Amalie, St Thomas, Tortola, Philipsburg, St Maarten, St Johns AG, Antigua, Roseau, Dominica, San Juan, Puerto Rico
2026 Sails: Sep 19, Oct 17, More...
11 Night - Masterpieces at Sea : Gems of the Leeward Islands
Starting in San Juan, St John VI (Cruz Bay), US Virgin Islands, Gustavia, Basseterre, Falmouth Harbour, Les Saintes, Rodney Bay, St Georges, Jost Van Dyke, Great Harbour, Virgin Gorda / Prickly Pear, British Virgin Islands, San Juan
2026 Sails: Oct 28, More...
7 Night - Southern Caribbean Halloween Cruise
Starting in San Juan, Puerto Rico, Willemstad AN, Curacao, Oranjestad, Aruba, Fort-De-France, Martinique, Basseterre, Saint Kitts and Nevis, San Juan, Puerto Rico
2026 Sails: Oct 31, More...
7 Night - A Journey Into Caribbean Exploration & Island Delights
Starting in San Juan, Tortola / Road Town, Basseterre, Gustavia, Road Bay, Miami
2026 Sails: Nov 1, More...14 Night - An Extended Journey Into Island Delights, Hidden Coves & Chic Coastlines
Starting in San Juan, Tortola / Road Town, Basseterre, Gustavia, Road Bay, Miami, Providenciales, Puerto Plata, Dominican Republic, La Romana, Jost Van Dyke, Gustavia, San Juan
2026 Sails: Nov 1, More...
7 Night - Southern Caribbean Cruise
Starting in San Juan, Puerto Rico, Charlotte Amalie, St Thomas, St Johns AG, Antigua, Philipsburg, St Maarten, St Croix, US Virgin Islands, Basseterre, St Kitts and Nevis, San Juan, Puerto Rico
2026 Sails: Nov 1, Nov 15, 2027: Mar 28, 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
7 Night - Southern Caribbean CruiseStarting 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: May 30, Jun 13, Jun 27, Jul 11, Jul 25, Aug 8, Aug 22, Sep 5, Oct 3, Oct 31, Nov 7, Nov 21, Dec 5, Dec 19, 2027: Jan 2, Jan 16, Feb 27, More...
7 Night - Southern Caribbean CruiseStarting in San Juan, Puerto Rico, Tortola, Philipsburg, St Maarten, St Johns AG, Antigua, Basseterre, St Kitts and Nevis, St Croix, US Virgin Islands, San Juan, Puerto Rico
2026 Sails: Jun 6, Jun 20, Jul 4, Jul 18, Aug 15, Aug 29, Sep 12, Sep 26, Oct 10, Oct 24, Nov 28, Dec 12, 2027: Jan 23, Feb 6, Feb 20, More...
7 Night - Southern Caribbean CruiseStarting in San Juan, Puerto Rico, Tortola, Philipsburg, St Maarten, Basseterre, St Kitts and Nevis, St Johns AG, Antigua, St Croix, US Virgin Islands, San Juan, Puerto Rico
2026 Sails: Aug 1, More...
11 Night - The Americas & CaribbeanStarting in San Juan, Marigot, St Martin, Roseau, Bridgetown, Castries, St Lucia, St Johns, Jost Van Dyke, British Virgin Islands, Samana, Grand Turk, New York
2026 Sails: Sep 14, More...
7 Night - Southern Caribbean CruiseStarting in San Juan, Puerto Rico, Charlotte Amalie, St Thomas, Tortola, Philipsburg, St Maarten, St Johns AG, Antigua, Roseau, Dominica, San Juan, Puerto Rico
2026 Sails: Sep 19, Oct 17, More...
11 Night - Masterpieces at Sea : Gems of the Leeward IslandsStarting in San Juan, St John VI (Cruz Bay), US Virgin Islands, Gustavia, Basseterre, Falmouth Harbour, Les Saintes, Rodney Bay, St Georges, Jost Van Dyke, Great Harbour, Virgin Gorda / Prickly Pear, British Virgin Islands, San Juan
2026 Sails: Oct 28, More...
7 Night - Southern Caribbean Halloween CruiseStarting in San Juan, Puerto Rico, Willemstad AN, Curacao, Oranjestad, Aruba, Fort-De-France, Martinique, Basseterre, Saint Kitts and Nevis, San Juan, Puerto Rico
2026 Sails: Oct 31, More...
Deal link -> Special
7 Night - A Journey Into Caribbean Exploration & Island DelightsStarting in San Juan, Tortola / Road Town, Basseterre, Gustavia, Road Bay, Miami
2026 Sails: Nov 1, More...
Deal link -> Special
14 Night - An Extended Journey Into Island Delights, Hidden Coves & Chic CoastlinesStarting in San Juan, Tortola / Road Town, Basseterre, Gustavia, Road Bay, Miami, Providenciales, Puerto Plata, Dominican Republic, La Romana, Jost Van Dyke, Gustavia, San Juan
2026 Sails: Nov 1, More...
7 Night - Southern Caribbean CruiseStarting in San Juan, Puerto Rico, Charlotte Amalie, St Thomas, St Johns AG, Antigua, Philipsburg, St Maarten, St Croix, US Virgin Islands, Basseterre, St Kitts and Nevis, San Juan, Puerto Rico
2026 Sails: Nov 1, Nov 15, 2027: Mar 28, More...
