Wind Surf February 2027 Itinerary

For more information, prices, and detailed day-by-day Wind Surf itineraries in February 2027, please click one of the scheduled Wind Surf sailing dates below.

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Sail Date

Itinerary Name and Ports

Duration

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Priced From(per person)

Feb 6, 2027

(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, Iles des Saintes, Basseterre, Gustavia St. Barts, Philipsburg (St. Maarten)

7 Nights

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$2,651

Oceanview Stateroom (double occupancy)

Includes taxes & feesLearn More
Feb 6, 2027

(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, 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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$4,319

Oceanview Stateroom (double occupancy)

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Feb 13, 2027

(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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$2,767

Oceanview Stateroom (double occupancy)

Includes taxes & feesLearn More
Feb 13, 2027

(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, Mayreau, Iles des Saintes, Basseterre, Gustavia St. Barts, Philipsburg (St. Maarten)

14 Nights

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$4,419

Oceanview Stateroom (double occupancy)

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Feb 20, 2027

(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, Iles des Saintes, Basseterre, Gustavia St. Barts, Philipsburg (St. Maarten)

7 Nights

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$2,751

Oceanview Stateroom (double occupancy)

Includes taxes & feesLearn More
Feb 20, 2027

(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, Iles des Saintes, Basseterre, Gustavia St. Barts, Philipsburg (St. Maarten), Sopers Hole, Great Harbour, Prickly Pear British Virgin Islands, Gustavia St. Barts, Road Bay, Falmouth Harbour, Philipsburg (St. Maarten)

14 Nights

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$4,519

Oceanview Stateroom (double occupancy)

Includes taxes & feesLearn More
Feb 27, 2027

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

7 Nights

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$2,867

Oceanview Stateroom (double occupancy)

Includes taxes & feesLearn More
Feb 27, 2027

(Saturday)

14 Night Star Collector Caribbean Explorations Cruise

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

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

14 Nights

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$4,408

Oceanview Stateroom (double occupancy)

Includes taxes & feesLearn More

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