Wind Surf November 2027 Itinerary

For more information, prices, and detailed day-by-day Wind Surf itineraries in November 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)
Nov 5, 2027

(Friday)
15 Night Ocean Crossing Cruise

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

Ports: Lisbon, Madeira, Great Harbour, Philipsburg (St. Maarten)

Special Promotions
15 Nights

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$2,829

Oceanview Stateroom (double occupancy)

Includes taxes & feesLearn More
Nov 5, 2027

(Friday)
23 Night Star Collector Hearty Ports and Rum Punches A Transatlantic Crossing Cruise

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

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

Special Promotions
23 Nights

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$4,697

Oceanview Stateroom (double occupancy)

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Nov 20, 2027

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

Special Promotions
8 Nights

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$3,067

Oceanview Stateroom (double occupancy)

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Nov 20, 2027

(Saturday)
15 Night Star Collector Caribbean Explorations Cruise

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

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

Special Promotions
15 Nights

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$4,719

Oceanview Stateroom (double occupancy)

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Nov 28, 2027

(Sunday)
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, Gustavia St. Barts, Basseterre, Philipsburg (St. Maarten)
7 Nights

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$2,851

Oceanview Stateroom (double occupancy)

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Nov 28, 2027

(Sunday)
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, 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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$4,519

Oceanview Stateroom (double occupancy)

Includes taxes & feesLearn More

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