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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 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, Great Harbour, Prickly Pear British Virgin Islands, Sopers Hole, Gustavia St. Barts, Philipsburg (St. Maarten)

7 Nights

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$4,860

Oceanview Stateroom (double occupancy)

Includes taxes & feesLearn More
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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$4,244

Oceanview Stateroom (double occupancy)

Includes taxes & feesLearn More
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, Prickly Pear British Virgin Islands, Road Bay, Philipsburg (St. Maarten)

14 Nights

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$7,105

Oceanview Stateroom (double occupancy)

Includes taxes & feesLearn More
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, Prickly Pear British Virgin Islands, Road Bay, Philipsburg (St. Maarten)

7 Nights

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$3,319

Oceanview Stateroom (double occupancy)

Includes taxes & feesLearn More
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, Prickly Pear British Virgin Islands, 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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$7,105

Oceanview Stateroom (double occupancy)

Includes taxes & feesLearn More
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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$3,944

Oceanview Stateroom (double occupancy)

Includes taxes & feesLearn More
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, Prickly Pear British Virgin Islands, Gustavia St. Barts, Philipsburg (St. Maarten)

14 Nights

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$7,405

Oceanview Stateroom (double occupancy)

Includes taxes & feesLearn More
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, Prickly Pear British Virgin Islands, Gustavia St. Barts, Philipsburg (St. Maarten)

7 Nights

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$3,649

Oceanview Stateroom (double occupancy)

Includes taxes & feesLearn More
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, Prickly Pear British Virgin Islands, Gustavia St. Barts, Philipsburg (St. Maarten)

7 Nights

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$4,360

Suite (double occupancy)

Includes taxes & feesLearn More
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, Prickly Pear British Virgin Islands, 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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$7,205

Oceanview Stateroom (double occupancy)

Includes taxes & feesLearn More
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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$3,944

Oceanview Stateroom (double occupancy)

Includes taxes & feesLearn More
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, Prickly Pear British Virgin Islands, Sopers Hole, Gustavia St. Barts, Road Bay, Philipsburg (St. Maarten)

14 Nights

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$6,995

Oceanview Stateroom (double occupancy)

Includes taxes & feesLearn More
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, Prickly Pear British Virgin Islands, Sopers Hole, Gustavia St. Barts, Road Bay, Philipsburg (St. Maarten)

7 Nights

Add to Favorites
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$3,319

Oceanview Stateroom (double occupancy)

Includes taxes & feesLearn 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, Prickly Pear British Virgin Islands, 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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$7,105

Oceanview Stateroom (double occupancy)

Includes taxes & feesLearn 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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$3,464

Oceanview Stateroom (double occupancy)

Includes taxes & feesLearn More
Feb 22, 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, Prickly Pear British Virgin Islands, Gustavia St. Barts, Philipsburg (St. Maarten)

14 Nights

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$5,905

Oceanview Stateroom (double occupancy)

Includes taxes & feesLearn More
Mar 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, Prickly Pear British Virgin Islands, Gustavia St. Barts, Philipsburg (St. Maarten)

7 Nights

Add to Favorites
Compare Favorites
$4,060

Oceanview Stateroom (double occupancy)

Includes taxes & feesLearn More
Mar 8, 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, Prickly Pear British Virgin Islands, Gustavia St. Barts, Philipsburg (St. Maarten)

7 Nights

Add to Favorites
Compare Favorites
$4,210

Oceanview Stateroom (double occupancy)

Includes taxes & feesLearn More
Mar 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), Falmouth Harbour, Road Bay, Sopers Hole, Great Harbour, Prickly Pear British Virgin Islands, Gustavia St. Barts, Philipsburg (St. Maarten), Charlestown, Roseau, Pigeon Island, Iles des Saintes, Basseterre, Gustavia St. Barts, Philipsburg (St. Maarten)

14 Nights

Add to Favorites
Compare Favorites
$6,905

Oceanview Stateroom (double occupancy)

Includes taxes & feesLearn More
Mar 15, 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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$4,194

Oceanview Stateroom (double occupancy)

Includes taxes & feesLearn More

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