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Wind Surf Sailing Dates and Sailing Calendar

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146 Departure Dates 31 Unique Itinerary/Itineraries

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Sail Date	Itinerary Name and Ports	Duration	Save to Favorites	Priced From(per person)
Oct 25, 2026 (Sunday)	5 Night Quick Getaways Yachtsmans Harbors of the Rivieras Cruise From Civitavecchia (Rome), Italy to Barcelona, Spain Ports: Civitavecchia (Rome), Portofino, Monte Carlo, Sanary Sur Mer, Palamos, Barcelona Special Promotions Solo Traveler Offer Complimentary Laundry Service The Signature Collection - Exclusive Amenities	5 Nights	Add to Favorites Compare Favorites	$2,236 Oceanview Stateroom (double occupancy) Includes taxes & feesLearn More
Oct 25, 2026 (Sunday)	13 Night Star Collector Enchantment of the Western Mediterranean Cruise From Civitavecchia (Rome), Italy to Lisbon, Portugal Ports: Civitavecchia (Rome), Portofino, Monte Carlo, Sanary Sur Mer, Palamos, Barcelona, Palma de Mallorca, Cartagena, Almeria, Malaga, Gibraltar, Cadiz (Seville), Lisbon Special Promotions Complimentary Laundry Service The Signature Collection - Exclusive Amenities	13 Nights	Add to Favorites Compare Favorites	$6,504 Oceanview Stateroom (double occupancy) Includes taxes & feesLearn More
Oct 30, 2026 (Friday)	8 Night Spanish Symphony Cruise From Barcelona, Spain to Lisbon, Portugal Ports: Barcelona, Palma de Mallorca, Cartagena, Almeria, Malaga, Gibraltar, Cadiz (Seville), Lisbon Special Promotions Solo Traveler Offer Complimentary Laundry Service The Signature Collection - Exclusive Amenities	8 Nights	Add to Favorites Compare Favorites	$4,470 Oceanview Stateroom (double occupancy) Includes taxes & feesLearn More
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 Complimentary Laundry Service	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) Special Promotions Complimentary Laundry Service The Signature Collection - Exclusive Amenities	7 Nights	Add to Favorites Compare Favorites	$2,658 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) Special Promotions Complimentary Laundry Service The Signature Collection - Exclusive Amenities	14 Nights	Add to Favorites Compare Favorites	$6,490 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) Special Promotions Complimentary Laundry Service	7 Nights	Add to Favorites Compare Favorites	$3,027 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 Complimentary Laundry Service	14 Nights	Add to Favorites Compare Favorites	$6,490 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 Complimentary Laundry Service The Signature Collection - Exclusive Amenities	7 Nights	Add to Favorites Compare Favorites	$2,658 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 Complimentary Laundry Service The Signature Collection - Exclusive Amenities	14 Nights	Add to Favorites Compare Favorites	$6,490 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 Complimentary Laundry Service The Signature Collection - Exclusive Amenities	7 Nights	Add to Favorites Compare Favorites	$3,027 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 Complimentary Laundry Service The Signature Collection - Exclusive Amenities	14 Nights	Add to Favorites Compare Favorites	$6,490 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 Complimentary Laundry Service The Signature Collection - A Hosted Sailing	7 Nights	Add to Favorites Compare Favorites	$3,391 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 Complimentary Laundry Service The Signature Collection - Exclusive Amenities	14 Nights	Add to Favorites Compare Favorites	$6,490 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 Complimentary Laundry Service	7 Nights	Add to Favorites Compare Favorites	$3,027 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 Complimentary Laundry Service The Signature Collection - Exclusive Amenities	14 Nights	Add to Favorites Compare Favorites	$6,490 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 Complimentary Laundry Service The Signature Collection - Exclusive Amenities	7 Nights	Add to Favorites Compare Favorites	$2,798 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 Complimentary Laundry Service The Signature Collection - Exclusive Amenities	14 Nights	Add to Favorites Compare Favorites	$6,070 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 Complimentary Laundry Service The Signature Collection - Exclusive Amenities	7 Nights	Add to Favorites Compare Favorites	$3,027 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 Complimentary Laundry Service The Signature Collection - Exclusive Amenities	14 Nights	Add to Favorites Compare Favorites	$6,350 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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