⚓ 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.

14-night Caribbean from Bridgetown

MSC Cruises · MSC Opera

10 ports
Round trip
Sails Nov 19, 2026
From $1,495 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 →

14-night Caribbean from Bridgetown

MSC Cruises · MSC Opera

10 ports
Round trip
Sails Dec 17, 2026
From $2,135 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 →

12-night Bridgetown to Miami

Silversea · Silver Spirit

8 ports
One way
Sails Mar 7, 2027
From $7,700 pp
Luxury

St. Georges Grenada Private Taxi Tour: Your Island, Your Way
Willemstad Private Full-Day Curaçao Island Tour with Local Expert
Port of Oranjestad Aruba: Snorkel with Turtles at WW2 Shipwreck & Sunset BBQ

See the whole trip →

9-night Bridgetown to Miami

Azamara · Azamara Quest

7 ports
One way
Sails Mar 13, 2028
From $3,939 pp
Luxury

St. Georges Grenada Private Taxi Tour: Your Island, Your Way
Castries Cosol Tours: All-Island Private Safari with 7 Stops
Saint-Pierre Île aux Marins: Private Guided Walk on the Ghost Island

See the whole trip →

9-night Bridgetown to Miami

Regent · Seven Seas Grandeur

9 ports
One way
Sails Feb 24, 2028
From $6,499 pp
Luxury

Castries Cosol Tours: All-Island Private Safari with 7 Stops
Fort-de-France Mount Pelée & Saint-Pierre: Volcano, Ghost Town & Dark History
Roseau Boiling Lake Hike: Dominica's Ultimate Volcanic Pilgrimage

See the whole trip →

12-night Bridgetown to Miami

Silversea · Silver Spirit

9 ports
One way
Sails Jan 25, 2027
From $8,300 pp
Luxury

St. Georges Grenada Private Taxi Tour: Your Island, Your Way
Kralendijk Klein Bonaire: Bioluminescence Snorkel at the Marine Park
Willemstad Private Full-Day Curaçao Island Tour with Local Expert

See the whole trip →

17-night Bridgetown to Miami

Azamara · Azamara Journey

14 ports
One way
Sails Dec 28, 2026
From $5,899 pp
Luxury

Port of Oranjestad Aruba: Snorkel with Turtles at WW2 Shipwreck & Sunset BBQ
Willemstad Private Full-Day Curaçao Island Tour with Local Expert
Castries Cosol Tours: All-Island Private Safari with 7 Stops

See the whole trip →

6-night Bridgetown to San Juan

Azamara · Azamara Journey

7 ports
One way
Sails Dec 12, 2026
From $1,479 pp
Luxury

Castries Cosol Tours: All-Island Private Safari with 7 Stops
Roseau Boiling Lake Hike: Dominica's Ultimate Volcanic Pilgrimage
Port of Basseterre Mt. Liamuiga Volcano Crater Hike: Summit the Sleeping Giant

See the whole trip →

12-night Bridgetown to Miami

Silversea · Silver Ray

11 ports
One way
Sails Mar 20, 2028
From $7,650 pp
Luxury

Castries Cosol Tours: All-Island Private Safari with 7 Stops
Fort-de-France Mount Pelée & Saint-Pierre: Volcano, Ghost Town & Dark History
Roseau Boiling Lake Hike: Dominica's Ultimate Volcanic Pilgrimage

See the whole trip →

7-night Bridgetown to San Juan

Azamara · Azamara Quest

8 ports
One way
Sails Nov 28, 2027
From $1,949 pp
Luxury

Castries Cosol Tours: All-Island Private Safari with 7 Stops
Roseau Boiling Lake Hike: Dominica's Ultimate Volcanic Pilgrimage
Port of Basseterre Mt. Liamuiga Volcano Crater Hike: Summit the Sleeping Giant

See the whole trip →

15-night Bridgetown to San Juan

Explora Journeys · EXPLORA III

10 ports
One way
Sails Mar 21, 2027
From $10,710 pp
Luxury

St. Georges Grenada Private Taxi Tour: Your Island, Your Way
Castries Cosol Tours: All-Island Private Safari with 7 Stops
Gustavia Private Open-Top Mini Moke Island Tour of St. Barts

See the whole trip →

12-night Bridgetown to Miami

Silversea · Silver Ray

11 ports
One way
Sails Feb 26, 2027
From $9,100 pp
Luxury

St. Georges Grenada Private Taxi Tour: Your Island, Your Way
Fort-de-France Mount Pelée & Saint-Pierre: Volcano, Ghost Town & Dark History
Deshaies Jardin Botanique de Deshaies at Opening Hour

See the whole trip →

8-night Bridgetown to San Juan

Silversea · Silver Nova

8 ports
One way
Sails Dec 21, 2026
From $4,050 pp
Luxury

St. Georges Grenada Private Taxi Tour: Your Island, Your Way
Fort-de-France Mount Pelée & Saint-Pierre: Volcano, Ghost Town & Dark History
Port of Basseterre Mt. Liamuiga Volcano Crater Hike: Summit the Sleeping Giant

See the whole trip →

7-night Bridgetown to Philipsburg

Seabourn · Seabourn Ovation

7 ports
One way
Sails Jan 23, 2027
From $5,524 pp
Luxury

Castries Cosol Tours: All-Island Private Safari with 7 Stops
Little Bay Soufrière Hills Volcano Exclusion Zone Helicopter Tour
St. John's Private Half-Day Island Adventure & Trunk Bay Beach

See the whole trip →

7-night Bridgetown to Philipsburg

Seabourn · Seabourn Ovation

7 ports
One way
Sails Feb 13, 2027
From $4,334 pp
Luxury

Castries Cosol Tours: All-Island Private Safari with 7 Stops
Little Bay Soufrière Hills Volcano Exclusion Zone Helicopter Tour
St. John's Private Half-Day Island Adventure & Trunk Bay Beach

See the whole trip →

7-night Bridgetown to Philipsburg

Seabourn · Seabourn Ovation

7 ports
One way
Sails Feb 27, 2027
From $4,674 pp
Luxury

Castries Cosol Tours: All-Island Private Safari with 7 Stops
Little Bay Soufrière Hills Volcano Exclusion Zone Helicopter Tour
St. John's Private Half-Day Island Adventure & Trunk Bay Beach

See the whole trip →

7-night Bridgetown to Philipsburg

Seabourn · Seabourn Ovation

7 ports
One way
Sails Mar 13, 2027
From $5,184 pp
Luxury

Castries Cosol Tours: All-Island Private Safari with 7 Stops
Little Bay Soufrière Hills Volcano Exclusion Zone Helicopter Tour
St. John's Private Half-Day Island Adventure & Trunk Bay Beach

See the whole trip →

7-night Bridgetown to Philipsburg

Seabourn · Seabourn Ovation

7 ports
One way
Sails Nov 27, 2027
From $3,994 pp
Luxury

Castries Cosol Tours: All-Island Private Safari with 7 Stops
Little Bay Soufrière Hills Volcano Exclusion Zone Helicopter Tour
St. John's Private Half-Day Island Adventure & Trunk Bay Beach

See the whole trip →

7-night Bridgetown to Philipsburg

Seabourn · Seabourn Ovation

7 ports
One way
Sails Jan 15, 2028
From $3,994 pp
Luxury

Castries Cosol Tours: All-Island Private Safari with 7 Stops
Little Bay Soufrière Hills Volcano Exclusion Zone Helicopter Tour
St. John's Private Half-Day Island Adventure & Trunk Bay Beach

See the whole trip →

7-night Bridgetown to Philipsburg

Seabourn · Seabourn Ovation

7 ports
One way
Sails Feb 12, 2028
From $4,504 pp
Luxury

Castries Cosol Tours: All-Island Private Safari with 7 Stops
Little Bay Soufrière Hills Volcano Exclusion Zone Helicopter Tour
St. John's Private Half-Day Island Adventure & Trunk Bay Beach

See the whole trip →

11-night Caribbean from Bridgetown

Silversea · Silver Spirit

9 ports
Round trip
Sails Dec 17, 2027
From $6,450 pp
Luxury

Castries Cosol Tours: All-Island Private Safari with 7 Stops
St. Georges Grenada Private Taxi Tour: Your Island, Your Way
Willemstad Private Full-Day Curaçao Island Tour with Local Expert

See the whole trip →

12-night Caribbean from Bridgetown

Silversea · Silver Spirit

10 ports
Round trip
Sails Feb 5, 2028
From $6,250 pp
Luxury

Fort-de-France Mount Pelée & Saint-Pierre: Volcano, Ghost Town & Dark History
Gustavia Private Open-Top Mini Moke Island Tour of St. Barts
Philipsburg Random Wind 'Paradise Day Sail' — Schooner Sail, Snorkel & the Original Tarzan Swing

See the whole trip →

7-night Caribbean from Bridgetown

Silversea · Silver Spirit

7 ports
Round trip
Sails Mar 11, 2028
From $5,050 pp
Luxury

Castries Cosol Tours: All-Island Private Safari with 7 Stops
Iles des Saintes Sunrise Hike to Le Chameau's Summit Fort
Philipsburg Random Wind 'Paradise Day Sail' — Schooner Sail, Snorkel & the Original Tarzan Swing

See the whole trip →

10-night Caribbean from Bridgetown

Regent · Seven Seas Grandeur

9 ports
Round trip
Sails Jan 25, 2028
From $6,349 pp
Luxury

Port of Kingstown La Soufrière Volcano Summit Hike: St. Vincent's Crown
Castries Cosol Tours: All-Island Private Safari with 7 Stops
Fort-de-France Mount Pelée & Saint-Pierre: Volcano, Ghost Town & Dark History

See the whole trip →

10-night Caribbean from Bridgetown

Silversea · Silver Spirit

8 ports
Round trip
Sails Feb 18, 2027
From $6,250 pp
Luxury

St. Georges Grenada Private Taxi Tour: Your Island, Your Way
Kralendijk Klein Bonaire: Bioluminescence Snorkel at the Marine Park
Willemstad Private Full-Day Curaçao Island Tour with Local Expert

See the whole trip →

8-night Bridgetown to San Juan

Silversea · Silver Ray

8 ports
One way
Sails Dec 18, 2027
From $5,950 pp
Luxury

Castries Cosol Tours: All-Island Private Safari with 7 Stops
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 →

14-night Bridgetown to Philipsburg

Seabourn · Seabourn Ovation

11 ports
One way
Sails Jan 8, 2028
From $7,564 pp
Luxury

Rodney Bay Full-Day Private Catamaran Sail to Soufrière & the Pitons
Willemstad Private Full-Day Curaçao Island Tour with Local Expert
Port of Oranjestad Aruba: Snorkel with Turtles at WW2 Shipwreck & Sunset BBQ

See the whole trip →

12-night Caribbean from Bridgetown

Silversea · Silver Spirit

10 ports
Round trip
Sails Jan 10, 2028
From $6,550 pp
Luxury

Castries Cosol Tours: All-Island Private Safari with 7 Stops
Kralendijk Klein Bonaire: Bioluminescence Snorkel at the Marine Park
Willemstad Private Full-Day Curaçao Island Tour with Local Expert

See the whole trip →

14-night Caribbean from Bridgetown

Azamara · Azamara Journey

13 ports
Round trip
Sails Nov 14, 2026
From $4,717 pp
Luxury

Castries Cosol Tours: All-Island Private Safari with 7 Stops
Roseau Boiling Lake Hike: Dominica's Ultimate Volcanic Pilgrimage
Port of Basseterre Mt. Liamuiga Volcano Crater Hike: Summit the Sleeping Giant

See the whole trip →

14-night Caribbean from Bridgetown

Azamara · Azamara Quest

13 ports
Round trip
Sails Nov 14, 2027
From $4,019 pp
Luxury

Castries Cosol Tours: All-Island Private Safari with 7 Stops
Roseau Boiling Lake Hike: Dominica's Ultimate Volcanic Pilgrimage
Port of Basseterre Mt. Liamuiga Volcano Crater Hike: Summit the Sleeping Giant

See the whole trip →

10-night Caribbean from Bridgetown

Silversea · Silver Spirit

8 ports
Round trip
Sails Jan 15, 2027
From $4,950 pp
Luxury

St. Georges Grenada Private Taxi Tour: Your Island, Your Way
Port of Oranjestad Aruba: Snorkel with Turtles at WW2 Shipwreck & Sunset BBQ
Willemstad Private Full-Day Curaçao Island Tour with Local Expert

See the whole trip →

14-night Caribbean from Bridgetown

Azamara · Azamara Journey

13 ports
Round trip
Sails Nov 28, 2026
From $4,859 pp
Luxury

Castries Cosol Tours: All-Island Private Safari with 7 Stops
Roseau Boiling Lake Hike: Dominica's Ultimate Volcanic Pilgrimage
Port of Basseterre Mt. Liamuiga Volcano Crater Hike: Summit the Sleeping Giant

See the whole trip →

10-night Caribbean from Bridgetown

Regent · Seven Seas Grandeur

10 ports
Round trip
Sails Jan 15, 2028
From $7,499 pp
Luxury

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

See the whole trip →

10-night Caribbean from Bridgetown

Regent · Seven Seas Grandeur

10 ports
Round trip
Sails Feb 14, 2028
From $6,449 pp
Luxury

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

See the whole trip →

7-night Caribbean from Bridgetown

Seabourn · Seabourn Ovation

5 ports
Round trip
Sails Jan 2, 2027
From $3,279 pp
Luxury

Rodney Bay Full-Day Private Catamaran Sail to Soufrière & the Pitons
Willemstad Private Full-Day Curaçao Island Tour with Local Expert
Port of Oranjestad Aruba: Snorkel with Turtles at WW2 Shipwreck & Sunset BBQ

See the whole trip →

10-night Caribbean from Bridgetown

Regent · Seven Seas Grandeur

9 ports
Round trip
Sails Feb 4, 2028
From $6,249 pp
Luxury

St. Georges Grenada Private Taxi Tour: Your Island, Your Way
Willis Island Zodiac Circumnavigation of Willis Island: Seabirds & Reef
Oranjestad The Natural Pool (Conchi) & Indian Cave 4x4 Jeep Safari through Arikok National Park

See the whole trip →

8-night Caribbean from Bridgetown

Silversea · Silver Spirit

7 ports
Round trip
Sails Dec 19, 2026
From $3,850 pp
Luxury

Fort-de-France Mount Pelée & Saint-Pierre: Volcano, Ghost Town & Dark History
Roseau Boiling Lake Hike: Dominica's Ultimate Volcanic Pilgrimage
Port of Basseterre Mt. Liamuiga Volcano Crater Hike: Summit the Sleeping Giant

See the whole trip →

8-night Caribbean from Bridgetown

Silversea · Silver Spirit

7 ports
Round trip
Sails Dec 27, 2026
From $5,750 pp
Luxury

Fort-de-France Mount Pelée & Saint-Pierre: Volcano, Ghost Town & Dark History
Deshaies Jardin Botanique de Deshaies at Opening Hour
Port of Basseterre Mt. Liamuiga Volcano Crater Hike: Summit the Sleeping Giant

See the whole trip →

10-night Bridgetown to San Juan

Silversea · Silver Shadow

10 ports
One way
Sails Feb 16, 2027
From $7,450 pp
Luxury

St. Georges Grenada Private Taxi Tour: Your Island, Your Way
Castries Cosol Tours: All-Island Private Safari with 7 Stops
Trois Ilets La Savane des Esclaves: Private Guided Cultural Immersion

See the whole trip →

14-night Bridgetown to Lisbon

Silversea · Silver Spirit

7 ports
One way
Sails Mar 18, 2028
From $8,000 pp
Luxury

Mindelo Private Full-Day São Vicente Island Discovery Tour
Las Palmas Roque Nublo & Tejeda: Gran Canaria's Sacred Heart by 4×4
Santa Cruz de La Palma Tajogaite Volcano: Licensed Expert Trek into La Palma's Last Eruption

See the whole trip →

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