7,668 Caribbean cruises under $500/Night

Miami → Key West → Bimini → Nassau → Miami

Port Canaveral → Half Moon Cay → San Juan → Amber Cove → Grand Turk → Port Canaveral

New York → Puerto Plata → San Juan → Philipsburg → Basse-Terre → Tortola → St. Thomas → New York

Fort Lauderdale → CocoCay → Key West → Fort Lauderdale

Fort Lauderdale → Lookout Cay → San Juan → St. Thomas → Castaway Cay → Fort Lauderdale

Jacksonville → Great Stirrup Cay → Nassau → Freeport → Jacksonville

Bridgetown → Fort-de-France → Pointe-a-Pitre → Tortola → La Romana → Isla Catalina → Virgin Gorda → Philipsburg → Fort-de-France → St. John's, Antigua → La Romana → Isla Catalina → Bridgetown

Bridgetown → Fort-de-France → Pointe-a-Pitre → Tortola → La Romana → Isla Catalina → Virgin Gorda → Philipsburg → Fort-de-France → St. John's, Antigua → La Romana → Isla Catalina → Bridgetown

Fort Lauderdale → Grand Turk → Amber Cove → Celebration Key → Fort Lauderdale → Roatan → Belize City → Cozumel → Fort Lauderdale

San Juan → St. Thomas → Philipsburg → Roseau → Castries → Bridgetown

Fort Lauderdale → Nassau → Lookout Cay → Castaway Cay → Fort Lauderdale

Fort Lauderdale → Nassau → Lookout Cay → Fort Lauderdale

Miami → CocoCay → Samana → Puerto Plata → Labadee → Miami

Port Canaveral → Great Stirrup Cay → Falmouth, Jamaica → Georgetown → Cozumel → Port Canaveral

Miami → Roatan → Costa Maya → Cozumel → Ocean Cay → Miami → Puerto Plata → San Juan → Ocean Cay → Miami