Southern Caribbean Cruises
Cruises that visit the Southern Caribbean
Cruises by region
7 Night - Windward Ways & Tobago Cays
Starting in Oranjestad, Kralendijk, Kingstown, The Pitons, Bequia, Mayreau, Scarborough, Tobago, Bridgetown
2026 Sails: Mar 15, More...
6 Night - Jewels of the Windward Islands
Starting in Bridgetown, Tobago Cays, Pigeon Island, Castries, The Pitons, Mayreau, Bequia, Bridgetown
2026 Sails: Mar 15, More...
11 Night - Panama Canal & Southern Caribbean
Starting in Fort Lauderdale, Florida, Cartagena CO, Panama Canal (Cruising), Colon, Panama, Oranjestad, Aruba, Willemstad AN, Curacao, Kralendijk, Bonaire, Fort Lauderdale, Florida
2026 Sails: Mar 16, More...
12 Night - Southern Caribbean with Panama
Starting in Fort Lauderdale, Florida, Aruba, Curacao, Cartagena CO, Colon, Panama, Limon, Costa Rica, Grand Cayman, Cayman Islands, Fort Lauderdale, Florida
2026 Sails: Mar 17, More...
15 Night - An Extended Journey to Abc Island Heritage and Flavour
Starting in Miami, Charlotte Amalie (Saint Thomas), Terre-De-Haut, Bridgetown, Fort-de-France, Martinique, Basseterre, San Juan, Kralendijk, Willemstad AN, Oranjestad, St Maarten / Philipsburg, San Juan
2026 Sails: Mar 18, More...
8 Night - San Juan / San Juan
Starting in San Juan, Canouan, Bridgetown, Les Anses-dArlet, Terre-De-Haut (Marina Day), St Johns AG, Virgin Gorda, San Juan
2026 Sails: Mar 20, More...
8 Night - Southern Caribbean
Starting in Port Canaveral (Orlando), Fl, Curacao, Aruba, Celebration Key, the Bahamas, Port Canaveral (Orlando), Fl
2026 Sails: Mar 21, May 16, Jun 13, Oct 3, Oct 31, Nov 28, Dec 26, 2027: Jan 23, Feb 20, Apr 17, More...
7 Night - History and Culture Visiting Caribbean Jewels
Starting in Philipsburg, Prickley Pear Cays, Gustavia, Charlestown, Nevis, Falmouth Bay, Barbuda, Les Saintes, Pointe-a-Pitre
2026 Sails: Mar 21, More...
12 Night - Southern Caribbean Cruise
Starting in Baltimore, Maryland, St Croix, US Virgin Islands, Basseterre, St Kitts and Nevis, Fort-De-France, Martinique, Roseau, Dominica, Philipsburg, St Maarten, Baltimore, Maryland
2026 Sails: Mar 21, Apr 18, More...
7 Night - Southern Caribbean Cruise
Starting in San Juan, Puerto Rico, Road Town, Tortola, British Virgin Islands, Bridgetown, Barbados, Castries, Saint Lucia, St Johns AG, Antigua and Barbuda, Philipsburg, Sint Maarten, San Juan, Puerto Rico
2026 Sails: Mar 21, More...
Cruises that visit the Southern Caribbean
Cruises by region
Click on a cruise ship itinerary in the Southern Caribbean (below) and select a sail date to receive competing cruise quotes. To search all cruise itineraries (not just Southern Caribbean), please visit: Cruise Search or try our Virtual Cruise Advisor™.
7 Night - Windward Ways & Tobago CaysStarting in Oranjestad, Kralendijk, Kingstown, The Pitons, Bequia, Mayreau, Scarborough, Tobago, Bridgetown
2026 Sails: Mar 15, More...
6 Night - Jewels of the Windward IslandsStarting in Bridgetown, Tobago Cays, Pigeon Island, Castries, The Pitons, Mayreau, Bequia, Bridgetown
2026 Sails: Mar 15, More...
11 Night - Panama Canal & Southern CaribbeanStarting in Fort Lauderdale, Florida, Cartagena CO, Panama Canal (Cruising), Colon, Panama, Oranjestad, Aruba, Willemstad AN, Curacao, Kralendijk, Bonaire, Fort Lauderdale, Florida
2026 Sails: Mar 16, More...
12 Night - Southern Caribbean with PanamaStarting in Fort Lauderdale, Florida, Aruba, Curacao, Cartagena CO, Colon, Panama, Limon, Costa Rica, Grand Cayman, Cayman Islands, Fort Lauderdale, Florida
2026 Sails: Mar 17, More...
15 Night - An Extended Journey to Abc Island Heritage and FlavourStarting in Miami, Charlotte Amalie (Saint Thomas), Terre-De-Haut, Bridgetown, Fort-de-France, Martinique, Basseterre, San Juan, Kralendijk, Willemstad AN, Oranjestad, St Maarten / Philipsburg, San Juan
2026 Sails: Mar 18, More...
8 Night - San Juan / San JuanStarting in San Juan, Canouan, Bridgetown, Les Anses-dArlet, Terre-De-Haut (Marina Day), St Johns AG, Virgin Gorda, San Juan
2026 Sails: Mar 20, More...
8 Night - Southern CaribbeanStarting in Port Canaveral (Orlando), Fl, Curacao, Aruba, Celebration Key, the Bahamas, Port Canaveral (Orlando), Fl
2026 Sails: Mar 21, May 16, Jun 13, Oct 3, Oct 31, Nov 28, Dec 26, 2027: Jan 23, Feb 20, Apr 17, More...
7 Night - History and Culture Visiting Caribbean JewelsStarting in Philipsburg, Prickley Pear Cays, Gustavia, Charlestown, Nevis, Falmouth Bay, Barbuda, Les Saintes, Pointe-a-Pitre
2026 Sails: Mar 21, More...
12 Night - Southern Caribbean CruiseStarting in Baltimore, Maryland, St Croix, US Virgin Islands, Basseterre, St Kitts and Nevis, Fort-De-France, Martinique, Roseau, Dominica, Philipsburg, St Maarten, Baltimore, Maryland
2026 Sails: Mar 21, Apr 18, More...
7 Night - Southern Caribbean CruiseStarting in San Juan, Puerto Rico, Road Town, Tortola, British Virgin Islands, Bridgetown, Barbados, Castries, Saint Lucia, St Johns AG, Antigua and Barbuda, Philipsburg, Sint Maarten, San Juan, Puerto Rico
2026 Sails: Mar 21, More...
