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Wind Surf Sailing Dates and Sailing Calendar

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143 Departure Dates 29 Unique Itinerary/Itineraries

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Sail Date	Itinerary Name and Ports	Duration	Save to Favorites	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)	14 Nights	Add to Favorites Compare Favorites	Call For Price Inside (double occupancy) Learn More
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) The Signature Collection - Exclusive Amenities	7 Nights	Add to Favorites Compare Favorites	$3,876 Oceanview Stateroom (double occupancy) Includes taxes & feesLearn More
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) The Signature Collection - Exclusive Amenities	14 Nights	Add to Favorites Compare Favorites	$7,148 Oceanview Stateroom (double occupancy) Includes taxes & feesLearn More
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)	7 Nights	Add to Favorites Compare Favorites	$4,770 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)	14 Nights	Add to Favorites Compare Favorites	$7,148 Oceanview Stateroom (double occupancy) Includes taxes & feesLearn More
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) Special Promotions Solo Traveler Offer $300 Reduced Deposit Free All-Inclusive Package The Signature Collection - Exclusive Amenities	7 Nights	Add to Favorites Compare Favorites	$3,876 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) Special Promotions $300 Reduced Deposit Free All-Inclusive Package The Signature Collection - Exclusive Amenities	14 Nights	Add to Favorites Compare Favorites	$6,378 Oceanview Stateroom (double occupancy) Includes taxes & feesLearn More
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) Special Promotions $300 Reduced Deposit Free All-Inclusive Package The Signature Collection - Exclusive Amenities	7 Nights	Add to Favorites Compare Favorites	$3,930 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) Special Promotions $300 Reduced Deposit Free All-Inclusive Package The Signature Collection - Exclusive Amenities	14 Nights	Add to Favorites Compare Favorites	$6,868 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) Special Promotions $300 Reduced Deposit Free All-Inclusive Package The Signature Collection - A Hosted Sailing	7 Nights	Add to Favorites Compare Favorites	$4,401 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) Special Promotions $300 Reduced Deposit Free All-Inclusive Package The Signature Collection - Exclusive Amenities	14 Nights	Add to Favorites Compare Favorites	$7,288 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) Special Promotions $300 Reduced Deposit Free All-Inclusive Package	7 Nights	Add to Favorites Compare Favorites	$4,420 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) Special Promotions $300 Reduced Deposit Free All-Inclusive Package The Signature Collection - Exclusive Amenities	14 Nights	Add to Favorites Compare Favorites	$7,428 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) Special Promotions $300 Reduced Deposit Free All-Inclusive Package The Signature Collection - Exclusive Amenities	7 Nights	Add to Favorites Compare Favorites	$4,506 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) Special Promotions $300 Reduced Deposit Free All-Inclusive Package The Signature Collection - Exclusive Amenities	14 Nights	Add to Favorites Compare Favorites	$7,708 Oceanview Stateroom (double occupancy) Includes taxes & feesLearn More
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) Special Promotions $300 Reduced Deposit Free All-Inclusive Package The Signature Collection - Exclusive Amenities	7 Nights	Add to Favorites Compare Favorites	$4,735 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) Special Promotions $300 Reduced Deposit Free All-Inclusive Package The Signature Collection - Exclusive Amenities	14 Nights	Add to Favorites Compare Favorites	$7,988 Oceanview Stateroom (double occupancy) Includes taxes & feesLearn More
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) Special Promotions $300 Reduced Deposit Free All-Inclusive Package	7 Nights	Add to Favorites Compare Favorites	$4,821 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) Special Promotions $300 Reduced Deposit Free All-Inclusive Package	14 Nights	Add to Favorites Compare Favorites	$7,568 Oceanview Stateroom (double occupancy) Includes taxes & feesLearn More
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) Special Promotions $300 Reduced Deposit Free All-Inclusive Package The Signature Collection - Exclusive Amenities	7 Nights	Add to Favorites Compare Favorites	$4,245 Oceanview Stateroom (double occupancy) Includes taxes & feesLearn More

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Wind Surf Sailing Dates and Sailing Calendar

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Wind Surf

Wind Surf Sailing Dates and Sailing Calendar

Sail Date

Itinerary Name and Ports

Duration

Save to Favorites

Priced From(per person)

Price Alerts Confirmed

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Browse Wind Surf Itineraries by Month ▼

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