⚓ Cruises

Regent Caribbean cruises from Bridgetown

5 itineraries with a bookable sailing ahead, 5 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 › Regent Caribbean cruises from Bridgetown

Most popular first

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

Castries

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

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Port of Kingstown

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 →

St. Georges

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 →

St. Georges

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 →

St. Georges

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

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Prefer a calendar? →The ports themselves →