7,663 Caribbean cruises under $500/Night

Miami → Philipsburg → St. John's, Antigua → St. Thomas → Nassau → Miami → Grand Turk → Ocean Cay → Nassau → Miami

San Juan → Willemstad → Oranjestad → Kralendijk → Fort Lauderdale

Port Canaveral → Half Moon Cay → Celebration Key → Port Canaveral

Cartagena, Colombia → Willemstad → Kralendijk → Oranjestad → Colon → Cartagena, Colombia

Port Canaveral → Puerto Plata → St. Thomas → Tortola → Great Stirrup Cay → Port Canaveral

Galveston → Amber Cove → San Juan → Basseterre → Castries → St. George's, Grenada → Montego Bay → Galveston

Jacksonville → Half Moon Cay → Celebration Key → Jacksonville

Port Canaveral → Cozumel → Georgetown → Falmouth, Jamaica → Castaway Cay → Port Canaveral

Miami → Nassau → San Juan → Basseterre → St. John's, Antigua → Philipsburg → St. Thomas → Puerto Plata → Miami

San Juan → St. Thomas → Philipsburg → Roseau → Castries → Bridgetown → San Juan → Tortola → Basseterre → Fort-de-France → St. George's, Grenada → Bridgetown → San Juan

Fort Lauderdale → Grand Turk → San Juan → St. Thomas → Half Moon Cay → Fort Lauderdale

Port Canaveral → Ocean Cay → Grand Turk → Puerto Plata → Nassau → Port Canaveral

Port Canaveral → Tortola → St. Thomas → Castaway Cay → Port Canaveral

Miami → CocoCay → Nassau → Miami

Pointe-a-Pitre → Basseterre → Tortola → La Romana → Isla Catalina → Samana → Amber Cove → Grand Turk → Cabo Rojo → La Romana → Kingstown → Bridgetown → Pointe-a-Pitre