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Wind Spirit Sailing Dates and Sailing Calendar

For more information, prices, and detailed day-by-day Wind Spirit itineraries, please click one of the Wind Spirit sailing dates below.

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Sail Date

Itinerary Name and Ports

Duration

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Priced From(per person)

Nov 27, 2024

(Wednesday)

10 Night Hidden Treasures of the Lesser Antilles Cruise

From Bridgetown, Barbados to Bridgetown, Barbados

Ports: Bridgetown, Basseterre, Gustavia St. Barts, Sopers Hole, Great Harbour, Prickly Pear British Virgin Islands, Iles des Saintes, Pigeon Island, Bridgetown

10 Nights

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$4,077

Oceanview Stateroom (double occupancy)

Includes taxes & feesLearn More
Dec 7, 2024

(Saturday)

7 Night Jewels of the Windward Islands Cruise

From Bridgetown, Barbados to Bridgetown, Barbados

Ports: Bridgetown, Pigeon Island, Castries, The Pitons, Kingstown, Mayreau, St George's, Bequia, Bridgetown

7 Nights

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$2,651

Oceanview Stateroom (double occupancy)

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Dec 7, 2024

(Saturday)

14 Night Star Collector Windward Treasures An Antilles Odyssey Cruise

From Bridgetown, Barbados to Bridgetown, Barbados

Ports: Bridgetown, Pigeon Island, Castries, The Pitons, Kingstown, Mayreau, St George's, Bequia, Bridgetown, Basseterre, Iles des Saintes, Roseau, Anse Mitan, Pigeon Island, Bridgetown

14 Nights

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$4,168

Oceanview Stateroom (double occupancy)

Includes taxes & feesLearn More
Dec 14, 2024

(Saturday)

7 Night Windward Islands Cruise

From Bridgetown, Barbados to Bridgetown, Barbados

Ports: Bridgetown, Basseterre, Iles des Saintes, Roseau, Anse Mitan, Pigeon Island, Bridgetown

7 Nights

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$2,140

Oceanview Stateroom (double occupancy)

Includes taxes & feesLearn More
Dec 14, 2024

(Saturday)

14 Night Star Collector Windward Treasures An Antilles Odyssey Cruise

From Bridgetown, Barbados to Bridgetown, Barbados

Ports: Bridgetown, Basseterre, Iles des Saintes, Roseau, Anse Mitan, Pigeon Island, Bridgetown, Pigeon Island, Castries, The Pitons, Kingstown, Mayreau, St George's, Bequia, Bridgetown

14 Nights

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$5,068

Oceanview Stateroom (double occupancy)

Includes taxes & feesLearn More
Dec 21, 2024

(Saturday)

7 Night Jewels of the Windward Islands Cruise

From Bridgetown, Barbados to Bridgetown, Barbados

Ports: Bridgetown, Pigeon Island, Castries, The Pitons, Kingstown, Mayreau, St George's, Bequia, Bridgetown

7 Nights

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$3,151

Oceanview Stateroom (double occupancy)

Includes taxes & feesLearn More
Dec 21, 2024

(Saturday)

14 Night Star Collector Windward Treasures An Antilles Odyssey Cruise

From Bridgetown, Barbados to Bridgetown, Barbados

Ports: Bridgetown, Pigeon Island, Castries, The Pitons, Kingstown, Mayreau, St George's, Bequia, Bridgetown, St John's, Roseau, Castries, Anse Mitan, Pigeon Island, Bridgetown

14 Nights

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Oceanview Stateroom (double occupancy)

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Dec 28, 2024

(Saturday)

7 Night Windward Islands Cruise

From Bridgetown, Barbados to Bridgetown, Barbados

Ports: Bridgetown, St John's, Roseau, Castries, Anse Mitan, Pigeon Island, Bridgetown

7 Nights

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Oceanview Stateroom (double occupancy)

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Dec 28, 2024

(Saturday)

14 Night Star Collector Windward Treasures An Antilles Odyssey Cruise

From Bridgetown, Barbados to Bridgetown, Barbados

Ports: Bridgetown, St John's, Roseau, Castries, Anse Mitan, Pigeon Island, Bridgetown, Pigeon Island, Castries, The Pitons, Kingstown, Mayreau, St George's, Bequia, Bridgetown

14 Nights

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Oceanview Stateroom (double occupancy)

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Jan 4, 2025

(Saturday)

7 Night Jewels of the Windward Islands Cruise

From Bridgetown, Barbados to Bridgetown, Barbados

Ports: Bridgetown, Pigeon Island, Castries, The Pitons, Kingstown, Mayreau, St George's, Bequia, Bridgetown

7 Nights

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$3,051

Oceanview Stateroom (double occupancy)

Includes taxes & feesLearn More
Jan 4, 2025

(Saturday)

14 Night Star Collector Windward Treasures An Antilles Odyssey Cruise

From Bridgetown, Barbados to Bridgetown, Barbados

Ports: Bridgetown, Pigeon Island, Castries, The Pitons, Kingstown, Mayreau, St George's, Bequia, Bridgetown, Basseterre, Iles des Saintes, Roseau, Anse Mitan, Pigeon Island, Bridgetown

14 Nights

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$5,068

Oceanview Stateroom (double occupancy)

Includes taxes & feesLearn More
Jan 11, 2025

(Saturday)

7 Night Windward Islands Cruise

From Bridgetown, Barbados to Bridgetown, Barbados

Ports: Bridgetown, Basseterre, Iles des Saintes, Roseau, Anse Mitan, Pigeon Island, Bridgetown

7 Nights

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$3,416

Oceanview Stateroom (double occupancy)

Includes taxes & feesLearn More
Jan 11, 2025

(Saturday)

14 Night Star Collector Windward Treasures An Antilles Odyssey Cruise

From Bridgetown, Barbados to Bridgetown, Barbados

Ports: Bridgetown, Basseterre, Iles des Saintes, Roseau, Anse Mitan, Pigeon Island, Bridgetown, Pigeon Island, Castries, The Pitons, Kingstown, Mayreau, St George's, Bequia, Bridgetown

14 Nights

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$5,768

Oceanview Stateroom (double occupancy)

Includes taxes & feesLearn More
Jan 18, 2025

(Saturday)

7 Night Jewels of the Windward Islands Cruise

From Bridgetown, Barbados to Bridgetown, Barbados

Ports: Bridgetown, Pigeon Island, Castries, The Pitons, Kingstown, Mayreau, St George's, Bequia, Bridgetown

7 Nights

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$3,151

Oceanview Stateroom (double occupancy)

Includes taxes & feesLearn More
Jan 18, 2025

(Saturday)

14 Night Star Collector Windward Treasures An Antilles Odyssey Cruise

From Bridgetown, Barbados to Bridgetown, Barbados

Ports: Bridgetown, Pigeon Island, Castries, The Pitons, Kingstown, Mayreau, St George's, Bequia, Bridgetown, St John's, Roseau, Iles des Saintes, Anse Mitan, Pigeon Island, Bridgetown

14 Nights

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$5,498

Oceanview Stateroom (double occupancy)

Includes taxes & feesLearn More
Jan 25, 2025

(Saturday)

7 Night Windward Islands Cruise

From Bridgetown, Barbados to Bridgetown, Barbados

Ports: Bridgetown, St John's, Roseau, Iles des Saintes, Anse Mitan, Pigeon Island, Bridgetown

7 Nights

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$3,216

Oceanview Stateroom (double occupancy)

Includes taxes & feesLearn More
Jan 25, 2025

(Saturday)

14 Night Star Collector Windward Treasures An Antilles Odyssey Cruise

From Bridgetown, Barbados to Bridgetown, Barbados

Ports: Bridgetown, St John's, Roseau, Iles des Saintes, Anse Mitan, Pigeon Island, Bridgetown, Pigeon Island, Castries, The Pitons, Kingstown, Mayreau, St George's, Bequia, Bridgetown

14 Nights

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$6,248

Oceanview Stateroom (double occupancy)

Includes taxes & feesLearn More
Feb 1, 2025

(Saturday)

7 Night Jewels of the Windward Islands Cruise

From Bridgetown, Barbados to Bridgetown, Barbados

Ports: Bridgetown, Pigeon Island, Castries, The Pitons, Kingstown, Mayreau, St George's, Bequia, Bridgetown

7 Nights

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$3,601

Oceanview Stateroom (double occupancy)

Includes taxes & feesLearn More
Feb 1, 2025

(Saturday)

14 Night Star Collector Windward Treasures An Antilles Odyssey Cruise

From Bridgetown, Barbados to Bridgetown, Barbados

Ports: Bridgetown, Pigeon Island, Castries, The Pitons, Kingstown, Mayreau, St George's, Bequia, Bridgetown, Basseterre, Iles des Saintes, Roseau, Anse Mitan, Pigeon Island, Bridgetown

14 Nights

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$6,618

Oceanview Stateroom (double occupancy)

Includes taxes & feesLearn More
Feb 8, 2025

(Saturday)

7 Night Windward Islands Cruise

From Bridgetown, Barbados to Bridgetown, Barbados

Ports: Bridgetown, Basseterre, Iles des Saintes, Roseau, Anse Mitan, Pigeon Island, Bridgetown

7 Nights

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$3,516

Oceanview Stateroom (double occupancy)

Includes taxes & feesLearn More

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