Wind Surf December 2026 Itinerary

For more information, prices, and detailed day-by-day Wind Surf itineraries in December 2026, 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)
Dec 5, 2026

(Saturday)
14 Night Ocean Crossing Cruise

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

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

Special Promotions
14 Nights

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$3,229

Oceanview Stateroom (double occupancy)

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Dec 5, 2026

(Saturday)
21 Night Star Collector Hearty Ports and Rum Punches A Transatlantic Crossing Cruise

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

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

Special Promotions
21 Nights

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$5,497

Oceanview Stateroom (double occupancy)

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Dec 19, 2026

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

Special Promotions
7 Nights

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$3,567

Oceanview Stateroom (double occupancy)

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Dec 19, 2026

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

Special Promotions
14 Nights

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$5,519

Oceanview Stateroom (double occupancy)

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Dec 26, 2026

(Saturday)
7 Night Classic Caribbean Cruise

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

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

Special Promotions
7 Nights

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$3,351

Oceanview Stateroom (double occupancy)

Includes taxes & feesLearn More
Dec 26, 2026

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

Special Promotions
14 Nights

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$5,219

Oceanview Stateroom (double occupancy)

Includes taxes & feesLearn More

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