Wind Surf January 2027 Itinerary

For more information, prices, and detailed day-by-day Wind Surf itineraries in January 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)

Jan 2, 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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$2,567

Oceanview Stateroom (double occupancy)

Includes taxes & feesLearn More
Jan 2, 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, Iles des Saintes, Mayreau, Roseau, Basseterre, Gustavia St. Barts, Philipsburg (St. Maarten)

14 Nights

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$4,319

Oceanview Stateroom (double occupancy)

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Jan 9, 2027

(Saturday)

7 Night Classic Caribbean Cruise

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

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

7 Nights

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$2,851

Oceanview Stateroom (double occupancy)

Includes taxes & feesLearn More
Jan 9, 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, Iles des Saintes, Mayreau, Roseau, Basseterre, Gustavia St. Barts, Philipsburg (St. Maarten), Road Bay, Sopers Hole, Great Harbour, Prickly Pear British Virgin Islands, Gustavia St. Barts, Falmouth Harbour, Philipsburg (St. Maarten)

14 Nights

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$4,719

Oceanview Stateroom (double occupancy)

Includes taxes & feesLearn More
Jan 16, 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), Road Bay, Sopers Hole, Great Harbour, Prickly Pear British Virgin Islands, Gustavia St. Barts, Falmouth Harbour, Philipsburg (St. Maarten)

7 Nights

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$2,967

Oceanview Stateroom (double occupancy)

Includes taxes & feesLearn More
Jan 16, 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), Road Bay, Sopers Hole, Great Harbour, Prickly Pear British Virgin Islands, Gustavia St. Barts, Falmouth Harbour, Philipsburg (St. Maarten), Charlestown, Roseau, Mayreau, Iles des Saintes, Basseterre, Gustavia St. Barts, Philipsburg (St. Maarten)

14 Nights

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$4,519

Oceanview Stateroom (double occupancy)

Includes taxes & feesLearn More
Jan 23, 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
Jan 23, 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), Road Bay, Sopers Hole, Great Harbour, Prickly Pear British Virgin Islands, Gustavia St. Barts, Falmouth Harbour, Philipsburg (St. Maarten)

14 Nights

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$4,219

Oceanview Stateroom (double occupancy)

Includes taxes & feesLearn More
Jan 30, 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), Road Bay, Sopers Hole, Great Harbour, Prickly Pear British Virgin Islands, Gustavia St. Barts, Falmouth Harbour, Philipsburg (St. Maarten)

7 Nights

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$2,667

Oceanview Stateroom (double occupancy)

Includes taxes & feesLearn More
Jan 30, 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), Road Bay, Sopers Hole, Great Harbour, Prickly Pear British Virgin Islands, Gustavia St. Barts, Falmouth Harbour, Philipsburg (St. Maarten), Charlestown, Roseau, Mayreau, Iles des Saintes, Basseterre, Gustavia St. Barts, Philipsburg (St. Maarten)

14 Nights

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$4,219

Oceanview Stateroom (double occupancy)

Includes taxes & feesLearn More

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