Philadelphia Cruise Guide > Cruises > Caribbean
Many Caribbean cruises are available out of Philadelphia. It is the classic famous cruise destination. See the full list of departures below.
Caribbean islands on cruise itineraries include the Virgin Islands, Puerto Rico and the Dominican Republic. Most of the cruises are in the winter.
November 28, 2026: 10-day cruise to the Caribbean on Norwegian Cruise Line. Round-trip from Philadelphia to Tortola (British Virgin Islands), St Thomas (US Virgin Islands), San Juan (Puerto Rico) and Puerto Plata (Dominican Republic).
December 8, 2026: 10-day cruise to the Caribbean on Norwegian Cruise Line. Round-trip from Philadelphia to Tortola (British Virgin Islands), St Thomas (US Virgin Islands), San Juan (Puerto Rico) and Puerto Plata (Dominican Republic).
December 23, 2026: 11-day cruise to the Caribbean on Norwegian Cruise Line. Round-trip from Philadelphia to Philipsburg (St Maarten), St Thomas (US Virgin Islands), Tortola (British Virgin Islands), San Juan (Puerto Rico) and Puerto Plata (Dominican Republic).
January 3, 2027: 10-day cruise to the Caribbean on Norwegian Cruise Line. Round-trip from Philadelphia to Tortola (British Virgin Islands), St Thomas (US Virgin Islands), San Juan (Puerto Rico) and Puerto Plata (Dominican Republic).
January 13, 2027: 10-day cruise to the Caribbean on Norwegian Cruise Line. Round-trip from Philadelphia to Tortola (British Virgin Islands), St Thomas (US Virgin Islands), San Juan (Puerto Rico) and Puerto Plata (Dominican Republic).
January 23, 2027: 10-day cruise to the Caribbean on Norwegian Cruise Line. Round-trip from Philadelphia to Tortola (British Virgin Islands), St Thomas (US Virgin Islands), San Juan (Puerto Rico) and Puerto Plata (Dominican Republic).
February 2, 2027: 10-day cruise to the Caribbean on Norwegian Cruise Line. Round-trip from Philadelphia to Tortola (British Virgin Islands), St Thomas (US Virgin Islands), San Juan (Puerto Rico) and Puerto Plata (Dominican Republic).
February 20, 2027: 10-day cruise to the Caribbean on Norwegian Cruise Line. Round-trip from Philadelphia to Tortola (British Virgin Islands), St Thomas (US Virgin Islands), San Juan (Puerto Rico) and Puerto Plata (Dominican Republic).
March 2, 2027: 10-day cruise to the Caribbean on Norwegian Cruise Line. Round-trip from Philadelphia to Tortola (British Virgin Islands), St Thomas (US Virgin Islands), San Juan (Puerto Rico) and Puerto Plata (Dominican Republic).
March 28, 2027: 11-day cruise to the Caribbean on Norwegian Cruise Line. Round-trip from Philadelphia to Royal Naval Dockyard (Bermuda)(overnight), Tortola (British Virgin Islands), St Thomas (US Virgin Islands), San Juan (Puerto Rico) and Puerto Plata (Dominican Republic).
November 27, 2027: 11-day cruise to the Caribbean on Norwegian Cruise Line. Round-trip from Philadelphia to Puerto Plata (Dominican Republic), San Juan (Puerto Rico), St John's Antigua), Castries (St Lucia) and Philipsburg (St Maarten).
December 13, 2027: 10-day cruise to the Caribbean on Norwegian Cruise Line. Round-trip from Philadelphia to Puerto Plata (Dominican Republic), San Juan (Puerto Rico), St John's (Antigua) and Philipsburg (St Maarten).
December 23, 2027: 11-day cruise to the Caribbean on Norwegian Cruise Line. Round-trip from Philadelphia to Basseterre (St Kitts), Castries (St Lucia), St John's (Antigua), San Juan (Puerto Rico) and Puerto Plata (Dominican Republic). The ship is scheduled to be at sea on Christmas Day.