San Juan Cruise Departures
Cruises that depart from Caribbean: Puerto Rico: San Juan
Cruises that visit San Juan
7 Night - Southern Caribbean Cruise
Starting in San Juan, Puerto Rico, Charlotte Amalie, St Thomas, Philipsburg, St Maarten, St Croix, US Virgin Islands, Fort-De-France, Martinique, Bridgetown, Barbados, San Juan, Puerto Rico
2026 Sails: Jan 17, More...
7 Night - St. Kitts, Barbados, Martinique & More
Starting in San Juan, Puerto Rico, Basseterre, Saint Kitts and Nevis, Bridgetown, Barbados, Fort-De-France, Martinique, St Johns AG, Antigua and Barbuda, Philipsburg, Sint Maarten, San Juan, Puerto Rico
2026 Sails: Jan 17, More...
14 Night - Southern Caribbean Adventurer
Starting in San Juan, Puerto Rico, St Thomas, US Virgin Islands, St Maarten, Antigua, Dominica, Barbados, San Juan, Puerto Rico, St Thomas, US Virgin Islands, St Maarten, Antigua, Guadeloupe (Pointe-a-Pitre), Barbados, San Juan, Puerto Rico
2026 Sails: Jan 18, More...7 Night - Southern Caribbean with Barbados and Antigua
Starting in San Juan, Puerto Rico, St Thomas, US Virgin Islands, St Maarten, Antigua, Dominica, Barbados, San Juan, Puerto Rico
2026 Sails: Jan 18, More...
7 Night - San Juan / San Juan
Starting in San Juan, Bridgetown, Les Anses-dArlet, Falmouth Harbour, Antigua, Virgin Gorda, Gustavia, San Juan
2026 Sails: Jan 18, Feb 15, More...
7 Night - Southern Caribbean Cruise
Starting in San Juan, Puerto Rico, Tortola, St Johns AG, Antigua, St Georges, Grenada, Kingstown, St Vincent, Roseau, Dominica, San Juan, Puerto Rico
2026 Sails: Jan 18, More...
7 Night - A Journey from San Juan to Miami
Starting in San Juan, Gustavia, Tortola / Road Town, St Johns AG, Antigua, Road Bay, Miami
2026 Sails: Jan 21, More...15 Night - An Extended Journey of Caribbean Inspiration and Island Beauty
Starting in San Juan, Gustavia, Tortola / Road Town, St Johns AG, Antigua, Road Bay, Miami, Charlotte Amalie (Saint Thomas), Terre-De-Haut, Bridgetown, Fort-de-France, Martinique, Basseterre, San Juan
2026 Sails: Jan 21, More...7 Night - Southern Caribbean Cruise
Starting in San Juan, Puerto Rico, Charlotte Amalie, St Thomas, Philipsburg, St Maarten, St Croix, US Virgin Islands, Roseau, Dominica, Bridgetown, Barbados, San Juan, Puerto Rico
2026 Sails: Jan 24, Jan 31, Feb 7, Feb 14, Feb 21, Feb 28, Mar 7, Mar 14, Mar 21, Mar 28, Apr 4, Apr 11, More...7 Night - Barbados, Antigua, Bvi & More
Starting in San Juan, Puerto Rico, Road Town, Tortola, British Virgin Islands, Bridgetown, Barbados, Fort-De-France, Martinique, St Johns AG, Antigua and Barbuda, Philipsburg, Sint Maarten, San Juan, Puerto Rico
2026 Sails: Jan 24, 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™.
7 Night - Southern Caribbean CruiseStarting in San Juan, Puerto Rico, Charlotte Amalie, St Thomas, Philipsburg, St Maarten, St Croix, US Virgin Islands, Fort-De-France, Martinique, Bridgetown, Barbados, San Juan, Puerto Rico
2026 Sails: Jan 17, More...
7 Night - St. Kitts, Barbados, Martinique & MoreStarting in San Juan, Puerto Rico, Basseterre, Saint Kitts and Nevis, Bridgetown, Barbados, Fort-De-France, Martinique, St Johns AG, Antigua and Barbuda, Philipsburg, Sint Maarten, San Juan, Puerto Rico
2026 Sails: Jan 17, More...
14 Night - Southern Caribbean AdventurerStarting in San Juan, Puerto Rico, St Thomas, US Virgin Islands, St Maarten, Antigua, Dominica, Barbados, San Juan, Puerto Rico, St Thomas, US Virgin Islands, St Maarten, Antigua, Guadeloupe (Pointe-a-Pitre), Barbados, San Juan, Puerto Rico
2026 Sails: Jan 18, More...
7 Night - Southern Caribbean with Barbados and AntiguaStarting in San Juan, Puerto Rico, St Thomas, US Virgin Islands, St Maarten, Antigua, Dominica, Barbados, San Juan, Puerto Rico
2026 Sails: Jan 18, More...
7 Night - San Juan / San JuanStarting in San Juan, Bridgetown, Les Anses-dArlet, Falmouth Harbour, Antigua, Virgin Gorda, Gustavia, San Juan
2026 Sails: Jan 18, Feb 15, More...
7 Night - Southern Caribbean CruiseStarting in San Juan, Puerto Rico, Tortola, St Johns AG, Antigua, St Georges, Grenada, Kingstown, St Vincent, Roseau, Dominica, San Juan, Puerto Rico
2026 Sails: Jan 18, More...
Deal link -> Special
7 Night - A Journey from San Juan to MiamiStarting in San Juan, Gustavia, Tortola / Road Town, St Johns AG, Antigua, Road Bay, Miami
2026 Sails: Jan 21, More...
15 Night - An Extended Journey of Caribbean Inspiration and Island BeautyStarting in San Juan, Gustavia, Tortola / Road Town, St Johns AG, Antigua, Road Bay, Miami, Charlotte Amalie (Saint Thomas), Terre-De-Haut, Bridgetown, Fort-de-France, Martinique, Basseterre, San Juan
2026 Sails: Jan 21, More...
7 Night - Southern Caribbean CruiseStarting in San Juan, Puerto Rico, Charlotte Amalie, St Thomas, Philipsburg, St Maarten, St Croix, US Virgin Islands, Roseau, Dominica, Bridgetown, Barbados, San Juan, Puerto Rico
2026 Sails: Jan 24, Jan 31, Feb 7, Feb 14, Feb 21, Feb 28, Mar 7, Mar 14, Mar 21, Mar 28, Apr 4, Apr 11, More...
7 Night - Barbados, Antigua, Bvi & MoreStarting in San Juan, Puerto Rico, Road Town, Tortola, British Virgin Islands, Bridgetown, Barbados, Fort-De-France, Martinique, St Johns AG, Antigua and Barbuda, Philipsburg, Sint Maarten, San Juan, Puerto Rico
2026 Sails: Jan 24, More...
