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Wind Surf Sailing Dates and Sailing Calendar

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

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Sail Date

Itinerary Name and Ports

Duration

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Priced From(per person)

Dec 7, 2024

(Saturday)

14 Night Ocean Crossing Cruise

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

Ports: Lisbon, St John's, Philipsburg (St. Maarten)

14 Nights

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Inside(double occupancy)

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Dec 21, 2024

(Saturday)

7 Night Classic Caribbean Cruise

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

Ports: Philipsburg (St. Maarten), Charlestown, Roseau, Pigeon Island, Iles des Saintes, Basseterre, Gustavia St. Barts, Philipsburg (St. Maarten)

7 Nights

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$2,999

Oceanview Stateroom(double occupancy)

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Dec 21, 2024

(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, Pigeon Island, Iles des Saintes, Basseterre, Gustavia St. Barts, Philipsburg (St. Maarten), Falmouth Harbour, Road Bay, Sopers Hole, Great Harbour, Virgin Gorda, Gustavia St. Barts, Philipsburg (St. Maarten)

14 Nights

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$5,199

Oceanview Stateroom(double occupancy)

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Dec 28, 2024

(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), Falmouth Harbour, Road Bay, Sopers Hole, Great Harbour, Virgin Gorda, Gustavia St. Barts, Philipsburg (St. Maarten)

7 Nights

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$3,399

Oceanview Stateroom(double occupancy)

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Dec 28, 2024

(Saturday)

14 Night Star Collector Caribbean Explorations Cruise

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

Ports: Philipsburg (St. Maarten), Falmouth Harbour, Road Bay, Sopers Hole, Great Harbour, Virgin Gorda, Gustavia St. Barts, Philipsburg (St. Maarten), Charlestown, Roseau, Pigeon Island, Iles des Saintes, Gustavia St. Barts, Basseterre, Philipsburg (St. Maarten)

14 Nights

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$4,999

Oceanview Stateroom(double occupancy)

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Jan 4, 2025

(Saturday)

7 Night Classic Caribbean Cruise

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

Ports: Philipsburg (St. Maarten), Charlestown, Roseau, Pigeon Island, Iles des Saintes, Gustavia St. Barts, Basseterre, Philipsburg (St. Maarten)

7 Nights

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$2,399

Oceanview Stateroom(double occupancy)

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Jan 4, 2025

(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, Pigeon Island, Iles des Saintes, Gustavia St. Barts, Basseterre, Philipsburg (St. Maarten), Falmouth Harbour, Gustavia St. Barts, Sopers Hole, Great Harbour, Virgin Gorda, Road Bay, Philipsburg (St. Maarten)

14 Nights

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$3,899

Oceanview Stateroom(double occupancy)

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Jan 11, 2025

(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), Falmouth Harbour, Gustavia St. Barts, Sopers Hole, Great Harbour, Virgin Gorda, Road Bay, Philipsburg (St. Maarten)

7 Nights

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$2,499

Oceanview Stateroom(double occupancy)

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Jan 11, 2025

(Saturday)

14 Night Star Collector Caribbean Explorations Cruise

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

Ports: Philipsburg (St. Maarten), Falmouth Harbour, Gustavia St. Barts, Sopers Hole, Great Harbour, Virgin Gorda, Road Bay, Philipsburg (St. Maarten), Charlestown, Roseau, Pigeon Island, Iles des Saintes, Gustavia St. Barts, Basseterre, Philipsburg (St. Maarten)

14 Nights

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$4,299

Oceanview Stateroom(double occupancy)

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Jan 18, 2025

(Saturday)

7 Night Classic Caribbean Cruise

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

Ports: Philipsburg (St. Maarten), Charlestown, Roseau, Pigeon Island, Iles des Saintes, Gustavia St. Barts, Basseterre, Philipsburg (St. Maarten)

7 Nights

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$2,699

Oceanview Stateroom(double occupancy)

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Jan 18, 2025

(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, Pigeon Island, Iles des Saintes, Gustavia St. Barts, Basseterre, Philipsburg (St. Maarten), Falmouth Harbour, Road Bay, Sopers Hole, Great Harbour, Virgin Gorda, Gustavia St. Barts, Philipsburg (St. Maarten)

14 Nights

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$4,299

Oceanview Stateroom(double occupancy)

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Jan 25, 2025

(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), Falmouth Harbour, Road Bay, Sopers Hole, Great Harbour, Virgin Gorda, Gustavia St. Barts, Philipsburg (St. Maarten)

7 Nights

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$2,399

Oceanview Stateroom(double occupancy)

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Jan 25, 2025

(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, Pigeon Island, Iles des Saintes, Basseterre, Gustavia St. Barts, Philipsburg (St. Maarten), Falmouth Harbour, Road Bay, Sopers Hole, Great Harbour, Virgin Gorda, Gustavia St. Barts, Philipsburg (St. Maarten)

14 Nights

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$3,499

Oceanview Stateroom(double occupancy)

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Feb 1, 2025

(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), Falmouth Harbour, Road Bay, Sopers Hole, Great Harbour, Virgin Gorda, Gustavia St. Barts, Philipsburg (St. Maarten)

7 Nights

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$2,399

Oceanview Stateroom(double occupancy)

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Feb 1, 2025

(Saturday)

14 Night Star Collector Caribbean Explorations Cruise

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

Ports: Philipsburg (St. Maarten), Falmouth Harbour, Road Bay, Sopers Hole, Great Harbour, Virgin Gorda, Gustavia St. Barts, Philipsburg (St. Maarten), Charlestown, Roseau, Pigeon Island, Iles des Saintes, Basseterre, Gustavia St. Barts, Philipsburg (St. Maarten)

14 Nights

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$3,999

Oceanview Stateroom(double occupancy)

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Feb 8, 2025

(Saturday)

7 Night Classic Caribbean Cruise

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

Ports: Philipsburg (St. Maarten), Charlestown, Roseau, Pigeon Island, Iles des Saintes, Basseterre, Gustavia St. Barts, Philipsburg (St. Maarten)

7 Nights

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$2,599

Suite(double occupancy)

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Feb 8, 2025

(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, Pigeon Island, Iles des Saintes, Basseterre, Gustavia St. Barts, Philipsburg (St. Maarten), Falmouth Harbour, Great Harbour, Virgin Gorda, Sopers Hole, Gustavia St. Barts, Road Bay, Philipsburg (St. Maarten)

14 Nights

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$3,999

Oceanview Stateroom(double occupancy)

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Feb 15, 2025

(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), Falmouth Harbour, Great Harbour, Virgin Gorda, Sopers Hole, Gustavia St. Barts, Road Bay, Philipsburg (St. Maarten)

7 Nights

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$2,399

Oceanview Stateroom(double occupancy)

Learn More
Feb 15, 2025

(Saturday)

14 Night Star Collector Caribbean Explorations Cruise

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

Ports: Philipsburg (St. Maarten), Falmouth Harbour, Great Harbour, Virgin Gorda, Sopers Hole, Gustavia St. Barts, Road Bay, Philipsburg (St. Maarten), Charlestown, Roseau, Pigeon Island, Iles des Saintes, Basseterre, Gustavia St. Barts, Philipsburg (St. Maarten)

14 Nights

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$3,999

Oceanview Stateroom(double occupancy)

Learn More
Feb 22, 2025

(Saturday)

7 Night Classic Caribbean Cruise

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

Ports: Philipsburg (St. Maarten), Charlestown, Roseau, Pigeon Island, Iles des Saintes, Basseterre, Gustavia St. Barts, Philipsburg (St. Maarten)

7 Nights

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$2,399

Oceanview Stateroom(double occupancy)

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