All cruises › Windstar Caribbean cruises
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Windstar · Wind Surf
- 3 ports
- One way
- Sails Mar 27, 2027
- From $2,805 pp
- Luxury
- Philipsburg Random Wind 'Paradise Day Sail' — Schooner Sail, Snorkel & the Original Tarzan Swing
- Funchal Pico do Arieiro to Pico Ruivo: Madeira's Rooftop Ridge Walk
- Lisbon Sintra: Pena Palace, Cabo da Roca & Cascais (small-group day trip)
Windstar · Star Pride
- 6 ports
- Round trip
- Sails Nov 15, 2026
- From $6,153 pp
- Luxury
- Cruz Bay Trunk Bay Underwater Snorkel Trail & VI National Park
- Port of Basseterre Mt. Liamuiga Volcano Crater Hike: Summit the Sleeping Giant
- Gustavia Private Open-Top Mini Moke Island Tour of St. Barts
Windstar · Star Pride
- 6 ports
- Round trip
- Sails Nov 29, 2026
- From $3,913 pp
- Luxury
- Cruz Bay Trunk Bay Underwater Snorkel Trail & VI National Park
- Gustavia Private Open-Top Mini Moke Island Tour of St. Barts
- Port of Basseterre Mt. Liamuiga Volcano Crater Hike: Summit the Sleeping Giant
Windstar · Star Pride
- 6 ports
- Round trip
- Sails Dec 13, 2026
- From $3,983 pp
- Luxury
- Cruz Bay Trunk Bay Underwater Snorkel Trail & VI National Park
- Gustavia Private Open-Top Mini Moke Island Tour of St. Barts
- Port of Basseterre Mt. Liamuiga Volcano Crater Hike: Summit the Sleeping Giant
Windstar · Star Pride
- 6 ports
- Round trip
- Sails Dec 27, 2026
- From $3,563 pp
- Luxury
- Cruz Bay Trunk Bay Underwater Snorkel Trail & VI National Park
- Gustavia Private Open-Top Mini Moke Island Tour of St. Barts
- Port of Basseterre Mt. Liamuiga Volcano Crater Hike: Summit the Sleeping Giant
Windstar · Star Pride
- 6 ports
- Round trip
- Sails Jan 10, 2027
- From $4,928 pp
- Luxury
- Cruz Bay Trunk Bay Underwater Snorkel Trail & VI National Park
- Port of Basseterre Mt. Liamuiga Volcano Crater Hike: Summit the Sleeping Giant
- Gustavia Private Open-Top Mini Moke Island Tour of St. Barts
Windstar · Star Pride
- 6 ports
- Round trip
- Sails Nov 15, 2027
- From $2,443 pp
- Luxury
- Cruz Bay Trunk Bay Underwater Snorkel Trail & VI National Park
- Port of Basseterre Mt. Liamuiga Volcano Crater Hike: Summit the Sleeping Giant
- Gustavia Private Open-Top Mini Moke Island Tour of St. Barts
Windstar · Star Pride
- 6 ports
- Round trip
- 2 departures Dec 2026 – Jan 2027
- From $3,636 pp
- Luxury
- St. Georges Grenada Private Taxi Tour: Your Island, Your Way
- Mayreau Salt Whistle Bay: Dawn Swim Before the Boats Arrive
- Deshaies Jardin Botanique de Deshaies at Opening Hour
Windstar · Star Pride
- 7 ports
- One way
- Sails Mar 6, 2028
- From $3,069 pp
- Luxury
- Willemstad Private Full-Day Curaçao Island Tour with Local Expert
- Kralendijk Klein Bonaire: Bioluminescence Snorkel at the Marine Park
- Gustavia Private Open-Top Mini Moke Island Tour of St. Barts
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
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
Windstar · Star Pride
- 12 ports
- One way
- Sails Feb 28, 2028
- From $4,233 pp
- Luxury
Windstar · Star Pride
- 9 ports
- Round trip
- Sails Oct 28, 2026
- From $3,930 pp
- Luxury
- Cruz Bay Trunk Bay Underwater Snorkel Trail & VI National Park
- Gustavia Private Open-Top Mini Moke Island Tour of St. Barts
- Port of Basseterre Mt. Liamuiga Volcano Crater Hike: Summit the Sleeping Giant
Windstar · Star Pride
- 6 ports
- Round trip
- Sails Nov 8, 2026
- From $2,411 pp
- Luxury
- St. Georges Grenada Private Taxi Tour: Your Island, Your Way
- Mayreau Salt Whistle Bay: Dawn Swim Before the Boats Arrive
- Les Saintes Sail Into the Bay of Les Saintes at Dawn
Windstar · Star Pride
- 6 ports
- Round trip
- Sails Mar 13, 2028
- From $2,656 pp
- Luxury
- St. Georges Grenada Private Taxi Tour: Your Island, Your Way
- Mayreau Salt Whistle Bay: Dawn Swim Before the Boats Arrive
- Les Saintes Sail Into the Bay of Les Saintes at Dawn
Windstar · Star Legend
- 6 ports
- One way
- Sails Dec 12, 2026
- From $3,246 pp
- Luxury
- Cartagena The Roman Theatre of Cartagena with the Rafael Moneo museum approach
- Bocas Del Toro Isla Zapatillas: Private Speedboat to Panama's Crown Jewel
- San Blas Islands Guna Yala by Private Panga: Cartí Islands & Reef
Windstar · Wind Surf
- 7 ports
- Round trip
- Sails Jan 2, 2027
- From $2,798 pp
- Luxury
- Falmouth Harbour Antigua Stingray City: Private Shallow-Water Encounter
- Road Bay Private Island Hopping: Prickly Pear & Sandy Island by Catamaran
- Sopers Hole The Baths of Virgin Gorda: Private Yacht Day Charter
Windstar · Wind Surf
- 7 ports
- Round trip
- Sails Jan 16, 2027
- From $3,638 pp
- Luxury
- Road Bay Private Island Hopping: Prickly Pear & Sandy Island by Catamaran
- Jost Van Dyke Private Catamaran Charter: White Bay & Sandy Spit by Sail
- Sopers Hole The Baths of Virgin Gorda: Private Yacht Day Charter
Windstar · Wind Surf
- 7 ports
- Round trip
- Sails Feb 27, 2027
- From $3,008 pp
- Luxury
- Sopers Hole The Baths of Virgin Gorda: Private Yacht Day Charter
- Jost Van Dyke Private Catamaran Charter: White Bay & Sandy Spit by Sail
- Virgin Gorda The Baths National Park: Private Guided Boulders & Devil's Bay
Windstar · Wind Surf
- 7 ports
- Round trip
- Sails Mar 13, 2027
- From $2,868 pp
- Luxury
- Falmouth Harbour Antigua Stingray City: Private Shallow-Water Encounter
- Road Bay Private Island Hopping: Prickly Pear & Sandy Island by Catamaran
- Jost Van Dyke Private Catamaran Charter: White Bay & Sandy Spit by Sail