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Wind Surf
Windstar Cruises
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.
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 |
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) |
7 Nights
|
Add to Favorites |
$2,726
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) |
14 Nights
|
Add to Favorites |
$6,470
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 |
$4,024
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 |
$6,680
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
|
7 Nights
|
Add to Favorites |
$2,936
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
|
14 Nights
|
Add to Favorites |
$5,420
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
|
7 Nights
|
Add to Favorites |
$2,694
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
|
14 Nights
|
Add to Favorites |
$5,420
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
|
7 Nights
|
Add to Favorites |
$2,971
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
|
14 Nights
|
Add to Favorites |
$6,400
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
|
7 Nights
|
Add to Favorites |
$3,709
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
|
14 Nights
|
Add to Favorites |
$6,680
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
|
7 Nights
|
Add to Favorites |
$3,286
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
|
14 Nights
|
Add to Favorites |
$6,190
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
|
7 Nights
|
Add to Favorites |
$3,184
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
|
14 Nights
|
Add to Favorites |
$6,050
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
|
7 Nights
|
Add to Favorites |
$3,111
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
|
14 Nights
|
Add to Favorites |
$6,050
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
|
7 Nights
|
Add to Favorites |
$3,184
Oceanview Stateroom (double occupancy) Includes taxes & feesLearn More |
