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Wind Surf Sailing Dates and Sailing Calendar

For more information, prices, and detailed day-by-day Wind Surf itineraries, please click one of the 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 25, 2025

(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
7 Nights

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$4,260

Oceanview Stateroom (double occupancy)

Includes taxes & feesLearn More
Feb 1, 2025

(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
7 Nights

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$4,960

Oceanview Stateroom (double occupancy)

Includes taxes & feesLearn More
Feb 1, 2025

(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, Pigeon Island, Iles des Saintes, Basseterre, Gustavia St. Barts, Philipsburg (St. Maarten)

Special Promotions
14 Nights

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Suite (double occupancy)

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Feb 8, 2025

(Saturday)

7 Night Classic Caribbean Cruise

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

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

Special Promotions
7 Nights

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$4,184

Oceanview Stateroom (double occupancy)

Includes taxes & feesLearn More
Feb 8, 2025

(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, Pigeon Island, Iles des Saintes, Basseterre, Gustavia St. Barts, Philipsburg (St. Maarten), Falmouth Harbour, Great Harbour, Prickly Pear British Virgin Islands, Sopers Hole, Gustavia St. Barts, Road Bay, Philipsburg (St. Maarten)

Special Promotions
14 Nights

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$7,105

Oceanview Stateroom (double occupancy)

Includes taxes & feesLearn More
Feb 15, 2025

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

Special Promotions
7 Nights

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$4,260

Oceanview Stateroom (double occupancy)

Includes taxes & feesLearn More
Feb 15, 2025

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

Special Promotions
14 Nights

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$7,105

Oceanview Stateroom (double occupancy)

Includes taxes & feesLearn More
Feb 22, 2025

(Saturday)

7 Night Classic Caribbean Cruise

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

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

Special Promotions
7 Nights

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$4,244

Oceanview Stateroom (double occupancy)

Includes taxes & feesLearn More
Feb 22, 2025

(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, Pigeon Island, 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
14 Nights

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$7,205

Oceanview Stateroom (double occupancy)

Includes taxes & feesLearn More
Mar 1, 2025

(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
7 Nights

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$4,360

Oceanview Stateroom (double occupancy)

Includes taxes & feesLearn More
Mar 8, 2025

(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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$3,174

Oceanview Stateroom (double occupancy)

Includes taxes & feesLearn More
Mar 8, 2025

(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, Pigeon Island, Iles des Saintes, Basseterre, Gustavia St. Barts, Philipsburg (St. Maarten)

Special Promotions
14 Nights

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$7,005

Oceanview Stateroom (double occupancy)

Includes taxes & feesLearn More
Mar 15, 2025

(Saturday)

7 Night Classic Caribbean Cruise

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

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

Special Promotions
7 Nights

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$4,194

Oceanview Stateroom (double occupancy)

Includes taxes & feesLearn More
Mar 15, 2025

(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, Pigeon Island, 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
14 Nights

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$6,955

Oceanview Stateroom (double occupancy)

Includes taxes & feesLearn More
Mar 22, 2025

(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
7 Nights

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$4,160

Oceanview Stateroom (double occupancy)

Includes taxes & feesLearn More
Mar 29, 2025

(Saturday)

14 Night Ocean Crossing and Ponta Delgada Azores Cruise

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

Ports: Philipsburg (St. Maarten), Ponta Delgada, Lisbon

Special Promotions
14 Nights

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$4,012

Oceanview Stateroom (double occupancy)

Includes taxes & feesLearn More
Mar 29, 2025

(Saturday)

22 Night Star Collector Atlantic Interludes and Iberian Indulgences Cruise

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

Ports: Philipsburg (St. Maarten), Ponta Delgada, Lisbon, Cadiz (Seville), Gibraltar, Malaga, Almeria, Cartagena, Palma de Mallorca, Barcelona

Special Promotions
22 Nights

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$9,966

Oceanview Stateroom (double occupancy)

Includes taxes & feesLearn More
Apr 12, 2025

(Saturday)

8 Night James Beard Foundation and Wine Cruise Spanish Symphony Cruise

From Lisbon, Portugal to Barcelona, Spain

Ports: Lisbon, Cadiz (Seville), Gibraltar, Malaga, Almeria, Cartagena, Palma de Mallorca, Barcelona

Special Promotions
8 Nights

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$6,353

Oceanview Stateroom (double occupancy)

Includes taxes & feesLearn More
Apr 12, 2025

(Saturday)

15 Night Star Collector Enchantment of the Western Mediterranean Cruise

From Lisbon, Portugal to Civitavecchia (Rome), Italy

Ports: Lisbon, Cadiz (Seville), Gibraltar, Malaga, Almeria, Cartagena, Palma de Mallorca, Barcelona, Port Vendres, Sanary Sur Mer, Monte Carlo, Cannes, Portofino, Portoferraio, Civitavecchia (Rome)

Special Promotions
15 Nights

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$10,189

Oceanview Stateroom (double occupancy)

Includes taxes & feesLearn More
Apr 12, 2025

(Saturday)

23 Night Star Collector Riviera Rhapsody Cruise

From Lisbon, Portugal to Venice, Italy

Ports: Lisbon, Cadiz (Seville), Gibraltar, Malaga, Almeria, Cartagena, Palma de Mallorca, Barcelona, Port Vendres, Sanary Sur Mer, Monte Carlo, Cannes, Portofino, Portoferraio, Civitavecchia (Rome), Sorrento, Giardini Naxos, Kotor, Dubrovnik, Split, Rovinj, Venice

Special Promotions
23 Nights

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$15,429

Oceanview Stateroom (double occupancy)

Includes taxes & feesLearn More

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