Eastern Caribbean Cruises
Cruises that visit the Eastern Caribbean
Cruises by region
7 Night - Caribbean and Antilles
Starting in Miami, Florida, Puerto Plata, Dominican Republic, San Juan, Puerto Rico, Ocean Cay Msc Marine Reserve, Bahamas, Miami, Florida
2026 Sails: Nov 28, Dec 12, Dec 26, 2027: Jan 9, Jan 23, Feb 6, Feb 20, Mar 6, Mar 20, More...
12 Night - Eastern Caribbean - Tampa
Starting in Tampa, Fl, San Juan, Pr, Tortola, British Virgin Islands, Basseterre, Saint Kitts / Nevis, Philipsburg, St Maarten, Netherland Antilles, St Thomas, Vi, Falmouth, Jamaica, George Town, Cayman Islands, Tampa, Fl
2026 Sails: Nov 28, More...
10 Night - Caribbean-Philadelphia
Starting in Philadelphia, Pa, Tortola, British Virgin Islands, St Thomas, Vi, San Juan, Pr, Puerto Plata, Dominican Republic, Philadelphia, Pa
2026 Sails: Nov 28, 2027: Jan 23, Feb 20, More...
7 Night - Eastern Caribbean with Celebration Key
Starting in Fort Lauderdale, Florida, Grand Turk, Turks and Caicos, Amber Cove, Dominican Republic, Celebration Key, Bahamas, Fort Lauderdale, Florida
2026 Sails: Nov 28, Dec 26, 2027: Feb 6, Mar 6, More...
13 Night - Lisbon to Miami
Starting in Lisbon, Gibraltar, Royal Naval Dockyard, Bermuda, Miami, Fl
2026 Sails: Nov 28, More...
7 Night - Treasure Islands
Starting in Philipsburg, St Maarten, Road Bay, Anguilla, White Bay, Jost Van Dyke, Sopers Hole, Tortola, Sailing Sir Francis Drake Channel, The Bight / Norman Island, British Virgin Islands, Spanish Town, Virgin Gorda, Beach, Captains Best, British Virgin Islands, Basseterre, St Kitts (Morning), South Friars Bay, St Kitts, Gustavia, St Barts, Philipsburg, St Maarten
2026 Sails: Nov 28, Dec 12, 2027: Jan 9, 2028: Jan 22, More...
5 Night - Mexico & Bimini Beach Club
Starting in Miami, Florida, Costa Maya, Mexico, The Beach Club at Bimini, Bahamas, Miami, Florida
2026 Sails: Nov 28, 2027: Jan 4, More...
7 Night - Bahamas
Starting in Baltimore, MD, Nassau, Bahamas, Relaxaway, Half Moon Cay, Celebration Key, the Bahamas, Baltimore, MD
2026 Sails: Nov 29, 2028: Jan 2, Feb 6, Feb 20, Mar 5, Mar 19, Apr 2, Apr 16, More...
7 Night - Key West & Bahamas Cruise
Starting in Tampa, Florida, Key West, Florida, Bimini, Bahamas, Nassau, Bahamas, Tampa, Florida
2026 Sails: Nov 29, More...
5 Night - Bahamian Cruise from Port Canaveral
Starting in Port Canaveral, Castaway Cay, Disney Lookout Cay, Nassau, Port Canaveral
2026 Sails: Nov 29, Dec 13, 2027: Jan 10, Feb 12, Feb 21, Feb 26, Mar 7, Mar 12, Mar 21, Apr 4, Apr 9, May 7, Sep 19, Oct 3, Oct 17, Oct 31, More...
Cruises that visit the Eastern Caribbean
Cruises by region
Click on a cruise ship itinerary in the Eastern Caribbean (below) and select a sail date to receive competing cruise quotes. To search all cruise itineraries (not just Eastern Caribbean), please visit: Cruise Search or try our Virtual Cruise Advisor™.
7 Night - Caribbean and AntillesStarting in Miami, Florida, Puerto Plata, Dominican Republic, San Juan, Puerto Rico, Ocean Cay Msc Marine Reserve, Bahamas, Miami, Florida
2026 Sails: Nov 28, Dec 12, Dec 26, 2027: Jan 9, Jan 23, Feb 6, Feb 20, Mar 6, Mar 20, More...
12 Night - Eastern Caribbean - TampaStarting in Tampa, Fl, San Juan, Pr, Tortola, British Virgin Islands, Basseterre, Saint Kitts / Nevis, Philipsburg, St Maarten, Netherland Antilles, St Thomas, Vi, Falmouth, Jamaica, George Town, Cayman Islands, Tampa, Fl
2026 Sails: Nov 28, More...
10 Night - Caribbean-PhiladelphiaStarting in Philadelphia, Pa, Tortola, British Virgin Islands, St Thomas, Vi, San Juan, Pr, Puerto Plata, Dominican Republic, Philadelphia, Pa
2026 Sails: Nov 28, 2027: Jan 23, Feb 20, More...
7 Night - Eastern Caribbean with Celebration KeyStarting in Fort Lauderdale, Florida, Grand Turk, Turks and Caicos, Amber Cove, Dominican Republic, Celebration Key, Bahamas, Fort Lauderdale, Florida
2026 Sails: Nov 28, Dec 26, 2027: Feb 6, Mar 6, More...
13 Night - Lisbon to MiamiStarting in Lisbon, Gibraltar, Royal Naval Dockyard, Bermuda, Miami, Fl
2026 Sails: Nov 28, More...
7 Night - Treasure IslandsStarting in Philipsburg, St Maarten, Road Bay, Anguilla, White Bay, Jost Van Dyke, Sopers Hole, Tortola, Sailing Sir Francis Drake Channel, The Bight / Norman Island, British Virgin Islands, Spanish Town, Virgin Gorda, Beach, Captains Best, British Virgin Islands, Basseterre, St Kitts (Morning), South Friars Bay, St Kitts, Gustavia, St Barts, Philipsburg, St Maarten
2026 Sails: Nov 28, Dec 12, 2027: Jan 9, 2028: Jan 22, More...
5 Night - Mexico & Bimini Beach ClubStarting in Miami, Florida, Costa Maya, Mexico, The Beach Club at Bimini, Bahamas, Miami, Florida
2026 Sails: Nov 28, 2027: Jan 4, More...
7 Night - BahamasStarting in Baltimore, MD, Nassau, Bahamas, Relaxaway, Half Moon Cay, Celebration Key, the Bahamas, Baltimore, MD
2026 Sails: Nov 29, 2028: Jan 2, Feb 6, Feb 20, Mar 5, Mar 19, Apr 2, Apr 16, More...
7 Night - Key West & Bahamas CruiseStarting in Tampa, Florida, Key West, Florida, Bimini, Bahamas, Nassau, Bahamas, Tampa, Florida
2026 Sails: Nov 29, More...
5 Night - Bahamian Cruise from Port CanaveralStarting in Port Canaveral, Castaway Cay, Disney Lookout Cay, Nassau, Port Canaveral
2026 Sails: Nov 29, Dec 13, 2027: Jan 10, Feb 12, Feb 21, Feb 26, Mar 7, Mar 12, Mar 21, Apr 4, Apr 9, May 7, Sep 19, Oct 3, Oct 17, Oct 31, More...