Eastern Caribbean Cruises
Cruises that visit the Eastern Caribbean
Cruises by region
7 Night - Eastern Caribbean & Perfect Day
Starting in Orlando (Port Canaveral), Fl, Perfect Day Cococay, Bahamas, Charlotte Amalie, St Thomas, Philipsburg, St Maarten, Orlando (Port Canaveral), Fl
2026 Sails: Nov 29, Dec 13, Dec 27, 2027: Jan 10, Jan 24, Feb 7, Feb 21, Mar 7, Mar 21, Apr 4, Apr 18, 2028: Apr 23, More...
7 Night - A Tall Ship's Dream Destination
Starting in Philipsburg, St Johns AG, Antigua, Gustavia, North Sound / Virgin Gorda, Sail Through the Sir Francis Drake Channel, White Bay, Jost Van Dyke, Great Harbour / Jost Van Dyke, The Bight Bay / Norman Island, Philipsburg
2026 Sails: Nov 29, More...
5 Night - Bahamas
Starting in Port Canaveral (Orlando), Fl, Celebration Key, the Bahamas, Nassau, Bahamas, Relaxaway, Half Moon Cay, Port Canaveral (Orlando), Fl
2026 Sails: Nov 30, Dec 14, Dec 28, 2027: Jan 11, Jan 16, Jan 25, Feb 8, Feb 22, Mar 22, Apr 5, Apr 19, May 3, More...
4 Night - Very Merrytime Bahamian Cruise from Fort Lauderdale
Starting in Port Everglades, Disney Lookout Cay, Castaway Cay, Port Everglades
2026 Sails: Nov 30, More...
7 Night - Caribbean Escapade
Starting in Miami, Florida, Nassau, Bahamas, Emerald Bay, Exumas, Bahamas, San Salvador Island, Bahamas, Gordons Beach, Long Island, Bahamas, Grand Turk, Turks and Caicos Islands, San Juan, Puerto Rico
2026 Sails: Nov 30, More...
13 Night - Discover the Vibes of the Caribbean
Starting in Miami, Florida, Nassau, Bahamas, Emerald Bay, Exumas, Bahamas, San Salvador Island, Bahamas, Gordons Beach, Long Island, Bahamas, Grand Turk, Turks and Caicos Islands, San Juan, Puerto Rico, St John VI (Cruz Bay), US Virgin Islands, Nevis, Saint Kitts and Nevis, Falmouth Harbour, Antigua and Barbuda, Gustavia, Saint Barthelemy, Jost van Dyke, British Virgin Islands, Saint Thomas, US Virgin Islands
2026 Sails: Nov 30, More...
4 Night - Bahamas Duo
Starting in Port of Palm Beach, Nassau, Bahamas, Freeport, Grand Bahama, Port of Palm Beach
2026 Sails: Nov 30, Dec 24, Dec 28, 2027: Jan 4, Mar 15, Apr 26, Jun 21, Jul 5, Aug 2, Sep 6, Oct 18, More...
5 Night - Bahamas - Short
Starting in Jacksonville, Florida, Grand Bahama Island, Bahamas, Great Stirrup Cay, Bahamas, Key West, FL, Jacksonville, Florida
2026 Sails: Nov 30, More...
4 Night - Bahamas - Short
Starting in Orlando Beaches / Port Canaveral, Fl, Nassau, Bahamas, Great Stirrup Cay, Bahamas, Orlando Beaches / Port Canaveral, Fl
2026 Sails: Nov 30, 2027: Jan 11, Feb 8, Feb 22, More...
4 Night - Bahamas - Short
Starting in Miami, Fl, Great Stirrup Cay, Bahamas, Nassau, Bahamas, Miami, Fl
2026 Sails: Nov 30, Dec 14, 2027: Feb 8, Mar 8, Mar 22, Mar 29, Apr 5, 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™.
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7 Night - Eastern Caribbean & Perfect DayStarting in Orlando (Port Canaveral), Fl, Perfect Day Cococay, Bahamas, Charlotte Amalie, St Thomas, Philipsburg, St Maarten, Orlando (Port Canaveral), Fl
2026 Sails: Nov 29, Dec 13, Dec 27, 2027: Jan 10, Jan 24, Feb 7, Feb 21, Mar 7, Mar 21, Apr 4, Apr 18, 2028: Apr 23, More...
7 Night - A Tall Ship's Dream DestinationStarting in Philipsburg, St Johns AG, Antigua, Gustavia, North Sound / Virgin Gorda, Sail Through the Sir Francis Drake Channel, White Bay, Jost Van Dyke, Great Harbour / Jost Van Dyke, The Bight Bay / Norman Island, Philipsburg
2026 Sails: Nov 29, More...
5 Night - BahamasStarting in Port Canaveral (Orlando), Fl, Celebration Key, the Bahamas, Nassau, Bahamas, Relaxaway, Half Moon Cay, Port Canaveral (Orlando), Fl
2026 Sails: Nov 30, Dec 14, Dec 28, 2027: Jan 11, Jan 16, Jan 25, Feb 8, Feb 22, Mar 22, Apr 5, Apr 19, May 3, More...
4 Night - Very Merrytime Bahamian Cruise from Fort LauderdaleStarting in Port Everglades, Disney Lookout Cay, Castaway Cay, Port Everglades
2026 Sails: Nov 30, More...
7 Night - Caribbean EscapadeStarting in Miami, Florida, Nassau, Bahamas, Emerald Bay, Exumas, Bahamas, San Salvador Island, Bahamas, Gordons Beach, Long Island, Bahamas, Grand Turk, Turks and Caicos Islands, San Juan, Puerto Rico
2026 Sails: Nov 30, More...
13 Night - Discover the Vibes of the CaribbeanStarting in Miami, Florida, Nassau, Bahamas, Emerald Bay, Exumas, Bahamas, San Salvador Island, Bahamas, Gordons Beach, Long Island, Bahamas, Grand Turk, Turks and Caicos Islands, San Juan, Puerto Rico, St John VI (Cruz Bay), US Virgin Islands, Nevis, Saint Kitts and Nevis, Falmouth Harbour, Antigua and Barbuda, Gustavia, Saint Barthelemy, Jost van Dyke, British Virgin Islands, Saint Thomas, US Virgin Islands
2026 Sails: Nov 30, More...
4 Night - Bahamas DuoStarting in Port of Palm Beach, Nassau, Bahamas, Freeport, Grand Bahama, Port of Palm Beach
2026 Sails: Nov 30, Dec 24, Dec 28, 2027: Jan 4, Mar 15, Apr 26, Jun 21, Jul 5, Aug 2, Sep 6, Oct 18, More...
5 Night - Bahamas - ShortStarting in Jacksonville, Florida, Grand Bahama Island, Bahamas, Great Stirrup Cay, Bahamas, Key West, FL, Jacksonville, Florida
2026 Sails: Nov 30, More...
4 Night - Bahamas - ShortStarting in Orlando Beaches / Port Canaveral, Fl, Nassau, Bahamas, Great Stirrup Cay, Bahamas, Orlando Beaches / Port Canaveral, Fl
2026 Sails: Nov 30, 2027: Jan 11, Feb 8, Feb 22, More...
4 Night - Bahamas - ShortStarting in Miami, Fl, Great Stirrup Cay, Bahamas, Nassau, Bahamas, Miami, Fl
2026 Sails: Nov 30, Dec 14, 2027: Feb 8, Mar 8, Mar 22, Mar 29, Apr 5, More...