All cruises › Windstar cruises from Bridgetown
Most popular first
Ranked by what people search for and where the cruise lines send the most ships.
Windstar · Wind Star
- 9 ports
- One way
- Sails Nov 24, 2026
- From $7,896 pp
- Luxury
- Bequia Tobago Cays & Mystique Full-Day Private Sail
- St. Georges Grenada Private Taxi Tour: Your Island, Your Way
- Kralendijk Klein Bonaire: Bioluminescence Snorkel at the Marine Park
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
- Bequia Tobago Cays & Mystique Full-Day Private Sail
- Mayreau Salt Whistle Bay: Dawn Swim Before the Boats Arrive
Windstar · Star Legend
- 4 ports
- One way
- Sails Mar 2, 2027
- From $2,946 pp
- Luxury
- Funchal Pico do Arieiro to Pico Ruivo: Madeira's Rooftop Ridge Walk
- Casablanca Private Guided Tour of Casablanca with Hassan II Mosque Entry
- Lisbon Sintra: Pena Palace, Cabo da Roca & Cascais (small-group day trip)
Windstar · Star Legend
- 7 ports
- Round trip
- Sails Nov 27, 2026
- From $2,594 pp
- Luxury
- Anses D'arlet Small-Boat Snorkel with Wild Sea Turtles, Anse Noire
- Rodney Bay Full-Day Private Catamaran Sail to Soufrière & the Pitons
- Casablanca Private Guided Tour of Casablanca with Hassan II Mosque Entry