Eastern Caribbean Cruises
Cruises that visit the Eastern Caribbean
Cruises by region
14 Night - Eastern Caribbean : Bahamas & San Juan Holiday
Starting in Miami, Florida, Amber Cove, Dominican Republic, Grand Turk, Turks and Caicos, RelaxAway, Half Moon Cay, Bahamas, Key West, Florida, Miami, Florida, Grand Turk, Turks and Caicos, San Juan, Puerto Rico, St Thomas, US Virgin Islands, RelaxAway, Half Moon Cay, Bahamas, Miami, Florida
2026 Sails: Dec 19, More...
14 Night - Caribbean and Antilles
Starting in Miami, Florida, Philipsburg, St Maarten, Basseterre, St Kitts and Nevis, Charlotte Amalie (St Thomas) Virgin Islands, Amber Cove, Dominican Republic, Miami, Florida, Grand Turk Island, Turks and Caicos, Ocean Cay Msc Marine Reserve, Bahamas, Nassau, Bahamas, Miami, Florida
2026 Sails: Dec 19, 2027: Jan 2, Mar 27, More...
5 Night - Bahamas - Short
Starting in Jacksonville, Florida, Great Stirrup Cay, Bahamas, Nassau, Bahamas, Grand Bahama Island, Bahamas, Jacksonville, Florida
2026 Sails: Dec 19, More...
7 Night - Reverie Under Sail in the Heart of the Lesser Antilles
Starting in Marigot, Sandy Island, Anguilla, Virgin Gorda, Cooper Island, Norman Island, Jost Van Dyke, Beef Island, Dog Island, Anguilla, Marigot
2026 Sails: Dec 19, 2027: Feb 13, Mar 13, Dec 13, 2028: Jan 31, Feb 28, Mar 27, More...
7 Night - Eastern Caribbean with Puerto Rico Holiday
Starting in Fort Lauderdale, Florida, Relaxaway, Half Moon Cay, San Juan, Puerto Rico, St Maarten, Fort Lauderdale, Florida
2026 Sails: Dec 19, More...
14 Night - Eastern / Western Caribbean Withcelebration Key Holiday
Starting in Fort Lauderdale, Florida, Cozumel, Mexico, Belize City, Belize, Roatan (Isla Tropicale), Honduras, Fort Lauderdale, Florida, Grand Turk, Turks and Caicos, Amber Cove, Dominican Republic, Celebration Key, Bahamas, Fort Lauderdale, Florida
2026 Sails: Dec 19, More...
10 Night - Lesser Antilles Journey
Starting in Miami, Cruising the Atlantic Ocean, Charlotte Amalie, Roseau, St Johns, Basseterre, Tortola, Cruising the Atlantic Ocean, Miami
2026 Sails: Dec 19, More...
4 Night - Bahamas & Perfect Day Cruise
Starting in Orlando (Port Canaveral), Fl, Perfect Day Cococay, Bahamas, Nassau, Bahamas, Orlando (Port Canaveral), Fl
2026 Sails: Dec 19, More...
8 Night - Caribbean Celebration I Cruise
Starting in Charlotte Amalie, St Thomas, St John VI (Cruz Bay), US Virgin Islands, Norman Island, Leverick Bay, Virgin Gorda, White Bay, Jost van Dyke, Spanish Town, Virgin Gorda, Trellis Bay, Beef Island, Marigot, Sandy Ground, Gustavia, Charlotte Amalie, St Thomas
2026 Sails: Dec 19, More...
8 Night - Caribbean Celebration Ii Cruise
Starting in San Juan, Gustavia, Sandy Ground, Spanish Town, Virgin Gorda, Trellis Bay, Beef Island, Leverick Bay, Virgin Gorda, Cane Garden Bay, Tortola, Norman Island, White Bay, Jost van Dyke, San Juan
2026 Sails: Dec 19, 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™.
14 Night - Eastern Caribbean : Bahamas & San Juan HolidayStarting in Miami, Florida, Amber Cove, Dominican Republic, Grand Turk, Turks and Caicos, RelaxAway, Half Moon Cay, Bahamas, Key West, Florida, Miami, Florida, Grand Turk, Turks and Caicos, San Juan, Puerto Rico, St Thomas, US Virgin Islands, RelaxAway, Half Moon Cay, Bahamas, Miami, Florida
2026 Sails: Dec 19, More...
14 Night - Caribbean and AntillesStarting in Miami, Florida, Philipsburg, St Maarten, Basseterre, St Kitts and Nevis, Charlotte Amalie (St Thomas) Virgin Islands, Amber Cove, Dominican Republic, Miami, Florida, Grand Turk Island, Turks and Caicos, Ocean Cay Msc Marine Reserve, Bahamas, Nassau, Bahamas, Miami, Florida
2026 Sails: Dec 19, 2027: Jan 2, Mar 27, More...
5 Night - Bahamas - ShortStarting in Jacksonville, Florida, Great Stirrup Cay, Bahamas, Nassau, Bahamas, Grand Bahama Island, Bahamas, Jacksonville, Florida
2026 Sails: Dec 19, More...
7 Night - Reverie Under Sail in the Heart of the Lesser AntillesStarting in Marigot, Sandy Island, Anguilla, Virgin Gorda, Cooper Island, Norman Island, Jost Van Dyke, Beef Island, Dog Island, Anguilla, Marigot
2026 Sails: Dec 19, 2027: Feb 13, Mar 13, Dec 13, 2028: Jan 31, Feb 28, Mar 27, More...
7 Night - Eastern Caribbean with Puerto Rico HolidayStarting in Fort Lauderdale, Florida, Relaxaway, Half Moon Cay, San Juan, Puerto Rico, St Maarten, Fort Lauderdale, Florida
2026 Sails: Dec 19, More...
14 Night - Eastern / Western Caribbean Withcelebration Key HolidayStarting in Fort Lauderdale, Florida, Cozumel, Mexico, Belize City, Belize, Roatan (Isla Tropicale), Honduras, Fort Lauderdale, Florida, Grand Turk, Turks and Caicos, Amber Cove, Dominican Republic, Celebration Key, Bahamas, Fort Lauderdale, Florida
2026 Sails: Dec 19, More...
10 Night - Lesser Antilles JourneyStarting in Miami, Cruising the Atlantic Ocean, Charlotte Amalie, Roseau, St Johns, Basseterre, Tortola, Cruising the Atlantic Ocean, Miami
2026 Sails: Dec 19, More...
4 Night - Bahamas & Perfect Day CruiseStarting in Orlando (Port Canaveral), Fl, Perfect Day Cococay, Bahamas, Nassau, Bahamas, Orlando (Port Canaveral), Fl
2026 Sails: Dec 19, More...
8 Night - Caribbean Celebration I CruiseStarting in Charlotte Amalie, St Thomas, St John VI (Cruz Bay), US Virgin Islands, Norman Island, Leverick Bay, Virgin Gorda, White Bay, Jost van Dyke, Spanish Town, Virgin Gorda, Trellis Bay, Beef Island, Marigot, Sandy Ground, Gustavia, Charlotte Amalie, St Thomas
2026 Sails: Dec 19, More...
8 Night - Caribbean Celebration Ii CruiseStarting in San Juan, Gustavia, Sandy Ground, Spanish Town, Virgin Gorda, Trellis Bay, Beef Island, Leverick Bay, Virgin Gorda, Cane Garden Bay, Tortola, Norman Island, White Bay, Jost van Dyke, San Juan
2026 Sails: Dec 19, More...