⚓ 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.

11-night Caribbean from Bridgetown

Silversea · Silver Spirit

9 ports
Round trip
Sails Feb 29, 2028
From $5,450 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 →

11-night Bridgetown to Colon

Windstar · Wind Star

9 ports
One way
Sails Nov 24, 2026
From $7,896 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 →

12-night Caribbean from Bridgetown

Silversea · Silver Spirit

10 ports
Round trip
Sails Feb 17, 2028
From $5,750 pp
Luxury

Castries Cosol Tours: All-Island Private Safari with 7 Stops
Port of Oranjestad Aruba: Snorkel with Turtles at WW2 Shipwreck & Sunset BBQ
Kralendijk Klein Bonaire: Bioluminescence Snorkel at the Marine Park

See the whole trip →

10-night Bridgetown to San Juan

Silversea · Silver Shadow

10 ports
One way
Sails Jan 20, 2027
From $7,150 pp
Luxury

Castries Cosol Tours: All-Island Private Safari with 7 Stops
Trois Ilets La Savane des Esclaves: Private Guided Cultural Immersion
Roseau Boiling Lake Hike: Dominica's Ultimate Volcanic Pilgrimage

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7-night Caribbean from Bridgetown

Silversea · Silver Spirit

7 ports
Round trip
Sails Jan 22, 2028
From $4,950 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
Roseau Boiling Lake Hike: Dominica's Ultimate Volcanic Pilgrimage

See the whole trip →

7-night Caribbean from Bridgetown

Silversea · Silver Spirit

7 ports
Round trip
Sails Jan 29, 2028
From $4,950 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
Roseau Boiling Lake Hike: Dominica's Ultimate Volcanic Pilgrimage

See the whole trip →

14-night Caribbean from Bridgetown

Seabourn · Seabourn Ovation

11 ports
Round trip
Sails Dec 19, 2026
From $7,599 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 →

14-night Caribbean from Bridgetown

Seabourn · Seabourn Ovation

11 ports
Round trip
Sails Jan 9, 2027
From $7,839 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 →

14-night Caribbean from Bridgetown

Seabourn · Seabourn Ovation

11 ports
Round trip
Sails Jan 29, 2028
From $9,094 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 →

14-night Caribbean from Bridgetown

Seabourn · Seabourn Ovation

11 ports
Round trip
Sails Feb 26, 2028
From $8,074 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 →

13-night Caribbean from Bridgetown

Silversea · Silver Spirit

11 ports
Round trip
Sails Dec 28, 2027
From $7,550 pp
Luxury

St. Georges Grenada Private Taxi Tour: Your Island, Your Way
Castries Cosol Tours: All-Island Private Safari with 7 Stops
Kralendijk Klein Bonaire: Bioluminescence Snorkel at the Marine Park

See the whole trip →

11-night Caribbean from Bridgetown

Silversea · Silver Spirit

9 ports
Round trip
Sails Jan 4, 2027
From $4,850 pp
Luxury

Castries Cosol Tours: All-Island Private Safari with 7 Stops
Deshaies Jardin Botanique de Deshaies at Opening Hour
Codrington Barbuda's Pink Sand Beach at Dawn, Private & Empty

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14-night Caribbean from Bridgetown

Seabourn · Seabourn Ovation

11 ports
Round trip
Sails Nov 28, 2026
From $6,399 pp
Luxury

Rodney Bay Full-Day Private Catamaran Sail to Soufrière & the Pitons
Little Bay Soufrière Hills Volcano Exclusion Zone Helicopter Tour
St. John's Private Half-Day Island Adventure & Trunk Bay Beach

See the whole trip →

21-night Caribbean from Bridgetown

Seabourn · Seabourn Ovation

15 ports
Round trip
Sails Dec 18, 2027
From $12,944 pp
Luxury

St. Georges Grenada Private Taxi Tour: Your Island, Your Way
Port Elizabeth Schotia Private Game Reserve: Big Five Safari & Bush Dinner
Saint-Pierre Île aux Marins: Private Guided Walk on the Ghost Island

See the whole trip →

8-night Bridgetown to Port of Oranjestad

Windstar · Star Legend

7 ports
One way
Sails Dec 4, 2026
From $2,940 pp
Luxury

Rodney Bay Full-Day Private Catamaran Sail to Soufrière & the Pitons
Mayreau Salt Whistle Bay: Dawn Swim Before the Boats Arrive
St. Georges Grenada Private Taxi Tour: Your Island, Your Way

See the whole trip →

14-night Caribbean from Bridgetown

Seabourn · Seabourn Ovation

11 ports
Round trip
Sails Mar 11, 2028
From $8,754 pp
Luxury

Rodney Bay Full-Day Private Catamaran Sail to Soufrière & the Pitons
Little Bay Soufrière Hills Volcano Exclusion Zone Helicopter Tour
St. John's Private Half-Day Island Adventure & Trunk Bay Beach

See the whole trip →

17-night Bridgetown to Philipsburg

Seabourn · Seabourn Ovation

14 ports
One way
Sails Dec 11, 2027
From $9,519 pp
Luxury

Rodney Bay Full-Day Private Catamaran Sail to Soufrière & the Pitons
Scarborough Grand Circle Island Private Tour: Dawn to Dusk Tobago
Willemstad Private Full-Day Curaçao Island Tour with Local Expert

See the whole trip →

7-night Caribbean from Bridgetown

Seabourn · Seabourn Ovation

6 ports
Round trip
Sails Dec 12, 2026
From $3,199 pp
Luxury

Port of Basseterre Mt. Liamuiga Volcano Crater Hike: Summit the Sleeping Giant
Terre-de-haut Private Catamaran Sail & Snorkel: Bay of Les Saintes
Saint-Pierre Île aux Marins: Private Guided Walk on the Ghost Island

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7-night Caribbean from Bridgetown

Seabourn · Seabourn Ovation

6 ports
Round trip
Sails Feb 6, 2027
From $5,834 pp
Luxury

Port of Basseterre Mt. Liamuiga Volcano Crater Hike: Summit the Sleeping Giant
Saint-Pierre Île aux Marins: Private Guided Walk on the Ghost Island
Roseau Boiling Lake Hike: Dominica's Ultimate Volcanic Pilgrimage

See the whole trip →

7-night Caribbean from Bridgetown

Silversea · Silver Spirit

7 ports
Round trip
Sails Dec 5, 2026
From $4,550 pp
Luxury

Fort-de-France Mount Pelée & Saint-Pierre: Volcano, Ghost Town & Dark History
Deshaies Jardin Botanique de Deshaies at Opening Hour
Gustavia Private Open-Top Mini Moke Island Tour of St. Barts

See the whole trip →

7-night Caribbean from Bridgetown

Silversea · Silver Spirit

7 ports
Round trip
Sails Dec 12, 2026
From $4,850 pp
Luxury

Castries Cosol Tours: All-Island Private Safari with 7 Stops
Fort-de-France Mount Pelée & Saint-Pierre: Volcano, Ghost Town & Dark History
Deshaies Jardin Botanique de Deshaies at Opening Hour

See the whole trip →

7-night Caribbean from Bridgetown

Silversea · Silver Spirit

7 ports
Round trip
Sails Feb 28, 2027
From $5,150 pp
Luxury

Castries Cosol Tours: All-Island Private Safari with 7 Stops
Gustavia Private Open-Top Mini Moke Island Tour of St. Barts
Cruz Bay Trunk Bay Underwater Snorkel Trail & VI National Park

See the whole trip →

24-night Bridgetown to Buenos Aires

Azamara · Azamara Journey

13 ports
One way
Sails Jan 25, 2027
From $8,265 pp
Luxury

Scarborough Grand Circle Island Private Tour: Dawn to Dusk Tobago
Ile Royale Île Royale Penal Colony: Private Guided History Immersion
Recife Recife & Olinda: Private Historical City Tour in English

See the whole trip →

16-night Bridgetown to Rio de Janeiro

Seabourn · Seabourn Venture

9 ports
Repositioning
Sails Oct 13, 2026
From $6,719 pp
Luxury

Port of Spain Caroni Swamp: Scarlet Ibis Sunset Boat Safari
Devils Island Îles du Salut: Private Guided History & Wildlife Immersion
Fortaleza Private Half-Day Fortaleza Shore Excursion (4–6 hrs)

See the whole trip →

16-night Bridgetown to Rio de Janeiro

Seabourn · Seabourn Venture

9 ports
Repositioning
Sails Oct 9, 2027
From $9,009 pp
Luxury

Port of Spain Caroni Swamp: Scarlet Ibis Sunset Boat Safari
Devils Island Îles du Salut: Private Guided History & Wildlife Immersion
Fortaleza Private Half-Day Fortaleza Shore Excursion (4–6 hrs)

See the whole trip →

20-night Bridgetown to Rio De Janeiro

Silversea · Silver Nova

8 ports
One way
Sails Jan 18, 2027
From $18,850 pp
Luxury

Manaus Meeting of the Waters: Private Amazon Speedboat Expedition
Boca da Valeria Private Motorized Canoe Deep into the Amazon Tributaries
Recife Recife & Olinda: Private Historical City Tour in English

See the whole trip →

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