⚓ Cruises

Caribbean cruises from Bridgetown

146 itineraries with a bookable sailing ahead, 160 sailings, most popular first. Each card: how long, how many ports, when, from what price — and the bucket-list thing to do at every stop.

All cruises › Caribbean cruises from Bridgetown

Cruise line

MSC Cruises53 Princess29 Silversea27 Regent5 Windstar2 Seabourn21 Azamara8 Explora Journeys1

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Ranked by what people search for and where the cruise lines send the most ships.

Port of Kingstown

14-night Caribbean from Bridgetown

MSC Cruises · MSC World Europa

10 ports
Round trip
Sails Jan 12, 2027
From $3,225 pp
Contemporary

Port of Kingstown La Soufrière Volcano Summit Hike: St. Vincent's Crown
St. Georges Grenada Private Taxi Tour: Your Island, Your Way
Fort-de-France Mount Pelée & Saint-Pierre: Volcano, Ghost Town & Dark History

See the whole trip →

Port of Kingstown

14-night Caribbean from Bridgetown

MSC Cruises · MSC World Europa

10 ports
Round trip
Sails Jan 26, 2027
From $2,223 pp
Contemporary

Port of Kingstown La Soufrière Volcano Summit Hike: St. Vincent's Crown
St. Georges Grenada Private Taxi Tour: Your Island, Your Way
Fort-de-France Mount Pelée & Saint-Pierre: Volcano, Ghost Town & Dark History

See the whole trip →

Port of Kingstown

14-night Caribbean from Bridgetown

MSC Cruises · MSC World Europa

10 ports
Round trip
Sails Feb 9, 2027
From $1,760 pp
Contemporary

Port of Kingstown La Soufrière Volcano Summit Hike: St. Vincent's Crown
St. Georges Grenada Private Taxi Tour: Your Island, Your Way
Fort-de-France Mount Pelée & Saint-Pierre: Volcano, Ghost Town & Dark History

See the whole trip →

Port of Kingstown

14-night Caribbean from Bridgetown

MSC Cruises · MSC World Europa

10 ports
Round trip
Sails Feb 23, 2027
From $1,995 pp
Contemporary

Port of Kingstown La Soufrière Volcano Summit Hike: St. Vincent's Crown
St. Georges Grenada Private Taxi Tour: Your Island, Your Way
Fort-de-France Mount Pelée & Saint-Pierre: Volcano, Ghost Town & Dark History

See the whole trip →

Port of Kingstown

14-night Caribbean from Bridgetown

MSC Cruises · MSC World Europa

10 ports
Round trip
Sails Mar 9, 2027
From $1,661 pp
Contemporary

Port of Kingstown La Soufrière Volcano Summit Hike: St. Vincent's Crown
St. Georges Grenada Private Taxi Tour: Your Island, Your Way
Fort-de-France Mount Pelée & Saint-Pierre: Volcano, Ghost Town & Dark History

See the whole trip →

St. Georges

14-night Caribbean from Bridgetown

MSC Cruises · MSC World Europa

10 ports
Round trip
Sails Mar 23, 2027
From $1,994 pp
Contemporary

St. Georges Grenada Private Taxi Tour: Your Island, Your Way
Port of Kingstown La Soufrière Volcano Summit Hike: St. Vincent's Crown
Fort-de-France Mount Pelée & Saint-Pierre: Volcano, Ghost Town & Dark History

See the whole trip →

Port of Kingstown

14-night Caribbean from Bridgetown

MSC Cruises · MSC Meraviglia

10 ports
Round trip
Sails Nov 30, 2027
From $1,841 pp
Contemporary

Port of Kingstown La Soufrière Volcano Summit Hike: St. Vincent's Crown
St. Georges Grenada Private Taxi Tour: Your Island, Your Way
Fort-de-France Mount Pelée & Saint-Pierre: Volcano, Ghost Town & Dark History

See the whole trip →

Port of Kingstown

14-night Caribbean from Bridgetown

MSC Cruises · MSC World Asia

10 ports
Round trip
Sails Nov 30, 2027
From $1,908 pp
Contemporary

Port of Kingstown La Soufrière Volcano Summit Hike: St. Vincent's Crown
St. Georges Grenada Private Taxi Tour: Your Island, Your Way
Fort-de-France Mount Pelée & Saint-Pierre: Volcano, Ghost Town & Dark History

See the whole trip →

Port of Kingstown

14-night Caribbean from Bridgetown

MSC Cruises · MSC Meraviglia

10 ports
Round trip
Sails Jan 11, 2028
From $1,881 pp
Contemporary

Port of Kingstown La Soufrière Volcano Summit Hike: St. Vincent's Crown
St. Georges Grenada Private Taxi Tour: Your Island, Your Way
Fort-de-France Mount Pelée & Saint-Pierre: Volcano, Ghost Town & Dark History

See the whole trip →

Port of Kingstown

14-night Caribbean from Bridgetown

MSC Cruises · MSC Meraviglia

10 ports
Round trip
Sails Feb 8, 2028
From $2,461 pp
Contemporary

Port of Kingstown La Soufrière Volcano Summit Hike: St. Vincent's Crown
Castries Cosol Tours: All-Island Private Safari with 7 Stops
St. Georges Grenada Private Taxi Tour: Your Island, Your Way

See the whole trip →

Port of Kingstown

14-night Caribbean from Bridgetown

MSC Cruises · MSC World Asia

10 ports
Round trip
Sails Feb 8, 2028
From $2,308 pp
Contemporary

Port of Kingstown La Soufrière Volcano Summit Hike: St. Vincent's Crown
Castries Cosol Tours: All-Island Private Safari with 7 Stops
St. Georges Grenada Private Taxi Tour: Your Island, Your Way

See the whole trip →

Port of Kingstown

14-night Caribbean from Bridgetown

MSC Cruises · MSC Meraviglia

10 ports
Round trip
Sails Mar 7, 2028
From $2,181 pp
Contemporary

Port of Kingstown La Soufrière Volcano Summit Hike: St. Vincent's Crown
St. Georges Grenada Private Taxi Tour: Your Island, Your Way
Fort-de-France Mount Pelée & Saint-Pierre: Volcano, Ghost Town & Dark History

See the whole trip →

Port of Kingstown

14-night Caribbean from Bridgetown

MSC Cruises · MSC World Asia

10 ports
Round trip
Sails Mar 7, 2028
From $1,998 pp
Contemporary

Port of Kingstown La Soufrière Volcano Summit Hike: St. Vincent's Crown
Castries Cosol Tours: All-Island Private Safari with 7 Stops
St. Georges Grenada Private Taxi Tour: Your Island, Your Way

See the whole trip →

Port of Kingstown

14-night Caribbean from Bridgetown

MSC Cruises · MSC Meraviglia

10 ports
Round trip
Sails Mar 21, 2028
From $2,341 pp
Contemporary

Port of Kingstown La Soufrière Volcano Summit Hike: St. Vincent's Crown
St. Georges Grenada Private Taxi Tour: Your Island, Your Way
Fort-de-France Mount Pelée & Saint-Pierre: Volcano, Ghost Town & Dark History

See the whole trip →

Port of Kingstown

14-night Caribbean from Bridgetown

MSC Cruises · MSC Meraviglia

10 ports
Round trip
Sails Apr 4, 2028
From $2,341 pp
Contemporary

Port of Kingstown La Soufrière Volcano Summit Hike: St. Vincent's Crown
St. Georges Grenada Private Taxi Tour: Your Island, Your Way
Fort-de-France Mount Pelée & Saint-Pierre: Volcano, Ghost Town & Dark History

See the whole trip →

Fort-de-France

4-night Bridgetown to La Romana

MSC Cruises · MSC Opera

5 ports
One way
Sails Nov 11, 2027
From $996 pp
Contemporary

Fort-de-France Mount Pelée & Saint-Pierre: Volcano, Ghost Town & Dark History
Pointe-a-Pitre Death in Paradise Filming Locations & Botanical Garden
Road Town Norman Island: The Indians & Sea Caves Sailing & Snorkel

See the whole trip →

Fort-de-France

14-night Caribbean from Bridgetown

MSC Cruises · MSC Opera

9 ports
Round trip
Sails Jan 28, 2027
From $1,565 pp
Contemporary

Fort-de-France Mount Pelée & Saint-Pierre: Volcano, Ghost Town & Dark History
St. John's Private Half-Day Island Adventure & Trunk Bay Beach
Road Town Norman Island: The Indians & Sea Caves Sailing & Snorkel

See the whole trip →

Fort-de-France

14-night Caribbean from Bridgetown

MSC Cruises · MSC Opera

9 ports
Round trip
Sails Feb 25, 2027
From $1,778 pp
Contemporary

Fort-de-France Mount Pelée & Saint-Pierre: Volcano, Ghost Town & Dark History
St. John's Private Half-Day Island Adventure & Trunk Bay Beach
Road Town Norman Island: The Indians & Sea Caves Sailing & Snorkel

See the whole trip →

Port of Spain

14-night Caribbean from Bridgetown

MSC Cruises · MSC Meraviglia

10 ports
Round trip
Sails Dec 28, 2027
From $1,911 pp
Contemporary

Port of Spain Caroni Swamp: Scarlet Ibis Sunset Boat Safari
St. Georges Grenada Private Taxi Tour: Your Island, Your Way
Fort-de-France Mount Pelée & Saint-Pierre: Volcano, Ghost Town & Dark History

See the whole trip →

San Juan

7-night Caribbean from Bridgetown

Princess · Crown Princess

5 ports
Round trip
Sails Jan 15, 2027
From $1,549 pp
Premium

San Juan Walk El Morro & Old San Juan's City Walls
St. Maarten Maho Beach: Legendary Extreme Plane-Spotting Experience
St. Georges Grenada Private Taxi Tour: Your Island, Your Way

See the whole trip →

San Juan

7-night Caribbean from Bridgetown

Princess · Crown Princess

6 ports
Round trip
Sails Jan 8, 2027
From $2,679 pp
Premium

San Juan Walk El Morro & Old San Juan's City Walls
St. Thomas Private Catamaran Sail & Snorkel at Honeymoon Beach, Water Island
St. Maarten Maho Beach: Legendary Extreme Plane-Spotting Experience

See the whole trip →

San Juan

7-night Caribbean from Bridgetown

Princess · Crown Princess

6 ports
Round trip
Sails Jan 22, 2027
From $1,349 pp
Premium

San Juan Walk El Morro & Old San Juan's City Walls
St. Thomas Private Catamaran Sail & Snorkel at Honeymoon Beach, Water Island
St. Maarten Maho Beach: Legendary Extreme Plane-Spotting Experience

See the whole trip →

San Juan

7-night Caribbean from Bridgetown

Princess · Crown Princess

6 ports
Round trip
Sails Feb 19, 2027
From $1,109 pp
Premium

San Juan Walk El Morro & Old San Juan's City Walls
St. Thomas Private Catamaran Sail & Snorkel at Honeymoon Beach, Water Island
St. Maarten Maho Beach: Legendary Extreme Plane-Spotting Experience

See the whole trip →

San Juan

7-night Caribbean from Bridgetown

Princess · Crown Princess

6 ports
Round trip
Sails Mar 5, 2027
From $1,429 pp
Premium

San Juan Walk El Morro & Old San Juan's City Walls
St. Thomas Private Catamaran Sail & Snorkel at Honeymoon Beach, Water Island
St. Maarten Maho Beach: Legendary Extreme Plane-Spotting Experience

See the whole trip →

San Juan

7-night Caribbean from Bridgetown

Princess · Crown Princess

6 ports
Round trip
Sails Mar 19, 2027
From $1,309 pp
Premium

San Juan Walk El Morro & Old San Juan's City Walls
St. Thomas Private Catamaran Sail & Snorkel at Honeymoon Beach, Water Island
St. Maarten Maho Beach: Legendary Extreme Plane-Spotting Experience

See the whole trip →

San Juan

7-night Caribbean from Bridgetown

Princess · Emerald Princess

6 ports
Round trip
Sails Dec 3, 2027
From $1,920 pp
Premium

San Juan Walk El Morro & Old San Juan's City Walls
St. Thomas Private Catamaran Sail & Snorkel at Honeymoon Beach, Water Island
St. Maarten Maho Beach: Legendary Extreme Plane-Spotting Experience

See the whole trip →

San Juan

7-night Caribbean from Bridgetown

Princess · Emerald Princess

6 ports
Round trip
Sails Dec 17, 2027
From $1,544 pp
Premium

San Juan Walk El Morro & Old San Juan's City Walls
St. Thomas Private Catamaran Sail & Snorkel at Honeymoon Beach, Water Island
St. Maarten Maho Beach: Legendary Extreme Plane-Spotting Experience

See the whole trip →

San Juan

7-night Caribbean from Bridgetown

Princess · Emerald Princess

6 ports
Round trip
Sails Dec 31, 2027
From $1,979 pp
Premium

San Juan Walk El Morro & Old San Juan's City Walls
St. Thomas Private Catamaran Sail & Snorkel at Honeymoon Beach, Water Island
St. Maarten Maho Beach: Legendary Extreme Plane-Spotting Experience

See the whole trip →

San Juan

7-night Caribbean from Bridgetown

Princess · Emerald Princess

6 ports
Round trip
Sails Jan 28, 2028
From $1,624 pp
Premium

San Juan Walk El Morro & Old San Juan's City Walls
St. Thomas Private Catamaran Sail & Snorkel at Honeymoon Beach, Water Island
St. Maarten Maho Beach: Legendary Extreme Plane-Spotting Experience

See the whole trip →

San Juan

7-night Caribbean from Bridgetown

Princess · Emerald Princess

6 ports
Round trip
Sails Feb 11, 2028
From $1,544 pp
Premium

San Juan Walk El Morro & Old San Juan's City Walls
St. Thomas Private Catamaran Sail & Snorkel at Honeymoon Beach, Water Island
St. Maarten Maho Beach: Legendary Extreme Plane-Spotting Experience

See the whole trip →

San Juan

7-night Caribbean from Bridgetown

Princess · Emerald Princess

6 ports
Round trip
Sails Feb 25, 2028
From $1,854 pp
Premium

San Juan Walk El Morro & Old San Juan's City Walls
St. Thomas Private Catamaran Sail & Snorkel at Honeymoon Beach, Water Island
St. Maarten Maho Beach: Legendary Extreme Plane-Spotting Experience

See the whole trip →

San Juan

7-night Caribbean from Bridgetown

Princess · Emerald Princess

6 ports
Round trip
Sails Mar 10, 2028
From $2,054 pp
Premium

San Juan Walk El Morro & Old San Juan's City Walls
St. Thomas Private Catamaran Sail & Snorkel at Honeymoon Beach, Water Island
St. Maarten Maho Beach: Legendary Extreme Plane-Spotting Experience

See the whole trip →

San Juan

7-night Caribbean from Bridgetown

Princess · Crown Princess

5 ports
Round trip
Sails Feb 26, 2027
From $1,399 pp
Premium

San Juan Walk El Morro & Old San Juan's City Walls
St. Maarten Maho Beach: Legendary Extreme Plane-Spotting Experience
Dominica Boiling Lake & Valley of Desolation: Dominica's Epic Hike

See the whole trip →

Fort-de-France

14-night Caribbean from Bridgetown

MSC Cruises · MSC Opera

9 ports
Round trip
Sails Dec 3, 2026
From $1,435 pp
Contemporary

Fort-de-France Mount Pelée & Saint-Pierre: Volcano, Ghost Town & Dark History
Pointe-a-Pitre Death in Paradise Filming Locations & Botanical Garden
Road Town Norman Island: The Indians & Sea Caves Sailing & Snorkel

See the whole trip →

Fort-de-France

14-night Caribbean from Bridgetown

MSC Cruises · MSC Opera

9 ports
Round trip
Sails Feb 11, 2027
From $1,808 pp
Contemporary

Fort-de-France Mount Pelée & Saint-Pierre: Volcano, Ghost Town & Dark History
Pointe-a-Pitre Death in Paradise Filming Locations & Botanical Garden
Road Town Norman Island: The Indians & Sea Caves Sailing & Snorkel

See the whole trip →

San Juan

7-night Caribbean from Bridgetown

Princess · Crown Princess

6 ports
Round trip
Sails Feb 5, 2027
From $1,419 pp
Premium

San Juan Walk El Morro & Old San Juan's City Walls
St. Thomas Private Catamaran Sail & Snorkel at Honeymoon Beach, Water Island
St. Maarten Maho Beach: Legendary Extreme Plane-Spotting Experience

See the whole trip →

Fort-de-France

14-night Caribbean from Bridgetown

MSC Cruises · MSC Opera

9 ports
Round trip
Sails Jan 14, 2027
From $1,825 pp
Contemporary

Fort-de-France Mount Pelée & Saint-Pierre: Volcano, Ghost Town & Dark History
St. John's Private Half-Day Island Adventure & Trunk Bay Beach
Virgin Gorda The Baths National Park: Private Guided Boulders & Devil's Bay

See the whole trip →

Port of Kingstown

14-night Caribbean from Bridgetown

MSC Cruises · MSC Meraviglia

11 ports
Round trip
Sails Feb 22, 2028
From $2,261 pp
Contemporary

Port of Kingstown La Soufrière Volcano Summit Hike: St. Vincent's Crown
Port of Spain Caroni Swamp: Scarlet Ibis Sunset Boat Safari
St. Georges Grenada Private Taxi Tour: Your Island, Your Way

See the whole trip →

San Juan

7-night Caribbean from Bridgetown

Princess · Crown Princess

6 ports
Round trip
Sails Jan 29, 2027
From $1,439 pp
Premium

San Juan Walk El Morro & Old San Juan's City Walls
St. Thomas Private Catamaran Sail & Snorkel at Honeymoon Beach, Water Island
Guadeloupe La Grande Soufrière: Private Guided Summit Hike

See the whole trip →

Fort-de-France

14-night Caribbean from Bridgetown

MSC Cruises · MSC Opera

10 ports
Round trip
Sails Dec 31, 2026
From $2,428 pp
Contemporary

Fort-de-France Mount Pelée & Saint-Pierre: Volcano, Ghost Town & Dark History
St. John's Private Half-Day Island Adventure & Trunk Bay Beach
Road Town Norman Island: The Indians & Sea Caves Sailing & Snorkel

See the whole trip →

Prefer a calendar? →The ports themselves →