Wind Spirit Sailing Dates and Sailing Calendar

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Sail Date

Itinerary Name and Ports

Duration

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Priced From(per person)

Dec 6, 2025

(Saturday)

7 Night Costa Rica and Panama Canal Cruise

From Puerto Caldera, Costa Rica to Colon, Panama

Ports: Puerto Caldera, Quepos, Puerto Jimenez, Isla Parida, Fuerte Amador, Cruising the Panama Canal, Colon

7 Nights

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$3,938

Oceanview Stateroom (double occupancy)

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Dec 13, 2025

(Saturday)

7 Night Enchanting Colombia and Panamanian Islands Cruise

From Colon, Panama to Oranjestad, Aruba

Ports: Colon, San Blas Islands, Cartagena, Oranjestad

7 Nights

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$2,174

Oceanview Stateroom (double occupancy)

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Dec 20, 2025

(Saturday)

8 Night An ABC Christmas Cruise

From Oranjestad, Aruba to Bridgetown, Barbados

Ports: Oranjestad, Willemstad (Curacao), Bonaire, St George's, Mayreau, Bequia, Bridgetown

8 Nights

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Oceanview Stateroom (double occupancy)

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Dec 20, 2025

(Saturday)

15 Night Star Collector Merry Christmas and a Happy New Year from the Caribbean Cruise

From Oranjestad, Aruba to Bridgetown, Barbados

Ports: Oranjestad, Willemstad (Curacao), Bonaire, St George's, Mayreau, Bequia, Bridgetown, Basseterre, Iles des Saintes, Roseau, Mayreau, Fort de France, Bridgetown

15 Nights

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Oceanview Stateroom (double occupancy)

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Dec 28, 2025

(Sunday)

7 Night Windward Islands Cruise

From Bridgetown, Barbados to Bridgetown, Barbados

Ports: Bridgetown, Basseterre, Iles des Saintes, Roseau, Mayreau, Fort de France, Bridgetown

7 Nights

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$2,991

Oceanview Stateroom (double occupancy)

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Jan 4, 2026

(Sunday)

10 Night Sublime Southern Caribbean Cruise

From Bridgetown, Barbados to Philipsburg (St. Maarten), Netherlands Antilles

Ports: Bridgetown, Mayreau, Roseau, Anse Mitan, Charlestown, Basseterre, St John's, Falmouth Harbour, Gustavia St. Barts, Road Bay, Philipsburg (St. Maarten)

10 Nights

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Oceanview Stateroom (double occupancy)

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Jan 14, 2026

(Wednesday)

10 Night Blue Waters of the Leeward Islands Cruise

From Philipsburg (St. Maarten), Netherlands Antilles to Philipsburg (St. Maarten), Netherlands Antilles

Ports: Philipsburg (St. Maarten), Basseterre, Roseau, Castries, Anse Mitan, Iles des Saintes, Charlestown, Prickly Pear British Virgin Islands, Great Harbour, Gustavia St. Barts, Philipsburg (St. Maarten)

10 Nights

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Oceanview Stateroom (double occupancy)

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Jan 14, 2026

(Wednesday)

17 Night Star Collector Hidden Gems of the Caribbean Cruise

From Philipsburg (St. Maarten), Netherlands Antilles to Philipsburg (St. Maarten), Netherlands Antilles

Ports: Philipsburg (St. Maarten), Basseterre, Roseau, Castries, Anse Mitan, Iles des Saintes, Charlestown, Prickly Pear British Virgin Islands, Great Harbour, Gustavia St. Barts, Philipsburg (St. Maarten), St John's, Road Bay, Prickly Pear British Virgin Islands, Sopers Hole, Great Harbour, Gustavia St

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17 Nights

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Oceanview Stateroom (double occupancy)

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Jan 24, 2026

(Saturday)

7 Night Beach Fun and Sun A Remote Caribbean Getaway Cruise

From Philipsburg (St. Maarten), Netherlands Antilles to Philipsburg (St. Maarten), Netherlands Antilles

Ports: Philipsburg (St. Maarten), St John's, Road Bay, Prickly Pear British Virgin Islands, Sopers Hole, Great Harbour, Gustavia St. Barts, Philipsburg (St. Maarten)

7 Nights

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Oceanview Stateroom (double occupancy)

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Jan 31, 2026

(Saturday)

7 Night Beach Fun and Sun A Remote Caribbean Getaway Cruise

From Philipsburg (St. Maarten), Netherlands Antilles to Philipsburg (St. Maarten), Netherlands Antilles

Ports: Philipsburg (St. Maarten), St John's, Road Bay, Sopers Hole, Great Harbour, Prickly Pear British Virgin Islands, Gustavia St. Barts, Philipsburg (St. Maarten)

7 Nights

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$3,660

Oceanview Stateroom (double occupancy)

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Jan 31, 2026

(Saturday)

14 Night Star Collector Caribbean Explorations Cruise

From Philipsburg (St. Maarten), Netherlands Antilles to Philipsburg (St. Maarten), Netherlands Antilles

Ports: Philipsburg (St. Maarten), St John's, Road Bay, Sopers Hole, Great Harbour, Prickly Pear British Virgin Islands, Gustavia St. Barts, Philipsburg (St. Maarten), Charlestown, Roseau, Mayreau, Fort de France, Basseterre, Gustavia St. Barts, Philipsburg (St. Maarten)

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14 Nights

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Oceanview Stateroom (double occupancy)

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Feb 7, 2026

(Saturday)

7 Night Classic Caribbean Cruise

From Philipsburg (St. Maarten), Netherlands Antilles to Philipsburg (St. Maarten), Netherlands Antilles

Ports: Philipsburg (St. Maarten), Charlestown, Roseau, Mayreau, Fort de France, Basseterre, Gustavia St. Barts, Philipsburg (St. Maarten)

7 Nights

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Oceanview Stateroom (double occupancy)

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Feb 7, 2026

(Saturday)

14 Night Star Collector Caribbean Explorations Cruise

From Philipsburg (St. Maarten), Netherlands Antilles to Philipsburg (St. Maarten), Netherlands Antilles

Ports: Philipsburg (St. Maarten), Charlestown, Roseau, Mayreau, Fort de France, Basseterre, Gustavia St. Barts, Philipsburg (St. Maarten), St John's, Road Bay, Sopers Hole, Great Harbour, Prickly Pear British Virgin Islands, Gustavia St. Barts, Philipsburg (St. Maarten)

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14 Nights

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Oceanview Stateroom (double occupancy)

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Feb 14, 2026

(Saturday)

7 Night Beach Fun and Sun A Remote Caribbean Getaway Cruise

From Philipsburg (St. Maarten), Netherlands Antilles to Philipsburg (St. Maarten), Netherlands Antilles

Ports: Philipsburg (St. Maarten), St John's, Road Bay, Sopers Hole, Great Harbour, Prickly Pear British Virgin Islands, Gustavia St. Barts, Philipsburg (St. Maarten)

7 Nights

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$3,860

Oceanview Stateroom (double occupancy)

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Feb 21, 2026

(Saturday)

7 Night Beach Fun and Sun A Remote Caribbean Getaway Cruise

From Philipsburg (St. Maarten), Netherlands Antilles to Philipsburg (St. Maarten), Netherlands Antilles

Ports: Philipsburg (St. Maarten), St John's, Road Bay, Prickly Pear British Virgin Islands, Sopers Hole, Great Harbour, Gustavia St. Barts, Philipsburg (St. Maarten)

7 Nights

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Oceanview Stateroom (double occupancy)

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Feb 21, 2026

(Saturday)

14 Night Star Collector Leeward and Windward Caribbean Havens Cruise

From Philipsburg (St. Maarten), Netherlands Antilles to Bridgetown, Barbados

Ports: Philipsburg (St. Maarten), St John's, Road Bay, Prickly Pear British Virgin Islands, Sopers Hole, Great Harbour, Gustavia St. Barts, Philipsburg (St. Maarten), Basseterre, Gustavia St. Barts, Falmouth Harbour, Iles des Saintes, Roseau, Mayreau, Bridgetown

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14 Nights

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Oceanview Stateroom (double occupancy)

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Feb 21, 2026

(Saturday)

22 Night Star Collector A Lesser Antilles Odyssey Cruise

From Philipsburg (St. Maarten), Netherlands Antilles to Bridgetown, Barbados

Ports: Philipsburg (St. Maarten), St John's, Road Bay, Prickly Pear British Virgin Islands, Sopers Hole, Great Harbour, Gustavia St. Barts, Philipsburg (St. Maarten), Basseterre, Gustavia St. Barts, Falmouth Harbour, Iles des Saintes, Roseau, Mayreau, Bridgetown, Basseterre, St John's, Iles des Saintes,

Special Promotions
22 Nights

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Oceanview Stateroom (double occupancy)

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Feb 21, 2026

(Saturday)

28 Night Star Collector 2026 Grand Caribbean Adventure Cruise

From Philipsburg (St. Maarten), Netherlands Antilles to Bridgetown, Barbados

Ports: Philipsburg (St. Maarten), St John's, Road Bay, Prickly Pear British Virgin Islands, Sopers Hole, Great Harbour, Gustavia St. Barts, Philipsburg (St. Maarten), Basseterre, Gustavia St. Barts, Falmouth Harbour, Iles des Saintes, Roseau, Mayreau, Bridgetown, Basseterre, St John's, Iles des Saintes,

Special Promotions
28 Nights

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Oceanview Stateroom (double occupancy)

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Feb 28, 2026

(Saturday)

7 Night Lush and Lovely Islands of the Lesser Antilles Cruise

From Philipsburg (St. Maarten), Netherlands Antilles to Bridgetown, Barbados

Ports: Philipsburg (St. Maarten), Basseterre, Gustavia St. Barts, Falmouth Harbour, Iles des Saintes, Roseau, Mayreau, Bridgetown

7 Nights

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$3,820

Oceanview Stateroom (double occupancy)

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Feb 28, 2026

(Saturday)

15 Night Star Collector Antilles Adventures Cruise

From Philipsburg (St. Maarten), Netherlands Antilles to Bridgetown, Barbados

Ports: Philipsburg (St. Maarten), Basseterre, Gustavia St. Barts, Falmouth Harbour, Iles des Saintes, Roseau, Mayreau, Bridgetown, Basseterre, St John's, Iles des Saintes, Roseau, Mayreau, Anse Mitan, Bridgetown

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15 Nights

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Oceanview Stateroom (double occupancy)

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