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Nov 27, 2026

(Friday)

7 Night Jewels of the Windward Islands Cruise

Star Legend
Windstar Cruises
Starts: Bridgetown, Barbados
Ends: Bridgetown, Barbados
Ports of Call:
Bridgetown, Anse Mitan, Rodney Bay, Castries, The Pitons, Mayreau, St George's, Bequia, Bridgetown

7 Nights


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$1,942

per person
(double occupancy)
Includes taxes & fees
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Jan 03, 2028

(Monday)

6 Night Beach Fun and Sun A Remote Caribbean Getaway Cruise

Wind Surf
Windstar Cruises
Starts: Philipsburg (St. Maarten), Netherlands Antilles
Ends: Philipsburg (St. Maarten), Netherlands Antilles
Ports of Call:
Philipsburg (St. Maarten), Road Bay, Gustavia St. Barts, Great Harbour...
Special Promotions

6 Nights


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$2,168

per person
(double occupancy)
Includes taxes & fees
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Jan 16, 2028

(Sunday)

7 Night Beach Fun and Sun A Remote Caribbean Getaway Cruise

Wind Surf
Windstar Cruises
Starts: Philipsburg (St. Maarten), Netherlands Antilles
Ends: Philipsburg (St. Maarten), Netherlands Antilles
Ports of Call:
Philipsburg (St. Maarten), St John's, Road Bay, Sopers Hole, Great Harbour...
Special Promotions

7 Nights


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$2,273

per person
(double occupancy)
Includes taxes & fees
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Jan 30, 2028

(Sunday)

7 Night Beach Fun and Sun A Remote Caribbean Getaway Cruise

Wind Surf
Windstar Cruises
Starts: Philipsburg (St. Maarten), Netherlands Antilles
Ends: Philipsburg (St. Maarten), Netherlands Antilles
Ports of Call:
Philipsburg (St. Maarten), Falmouth Harbour, Road Bay, Sopers Hole, Great Harbour...

7 Nights


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$2,273

per person
(double occupancy)
Includes taxes & fees
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Feb 13, 2028

(Sunday)

7 Night Beach Fun and Sun A Remote Caribbean Getaway Cruise

Wind Surf
Windstar Cruises
Starts: Philipsburg (St. Maarten), Netherlands Antilles
Ends: Philipsburg (St. Maarten), Netherlands Antilles
Ports of Call:
Philipsburg (St. Maarten), St John's, Road Bay, Sopers Hole, Great Harbour...
Special Promotions

7 Nights


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$2,273

per person
(double occupancy)
Includes taxes & fees
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Feb 27, 2028

(Sunday)

7 Night Beach Fun and Sun A Remote Caribbean Getaway Cruise

Wind Surf
Windstar Cruises
Starts: Philipsburg (St. Maarten), Netherlands Antilles
Ends: Philipsburg (St. Maarten), Netherlands Antilles
Ports of Call:
Philipsburg (St. Maarten), Falmouth Harbour, Road Bay, Sopers Hole, Great Harbour...
Special Promotions

7 Nights


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$2,273

per person
(double occupancy)
Includes taxes & fees
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Mar 12, 2028

(Sunday)

7 Night Beach Fun and Sun A Remote Caribbean Getaway Cruise

Wind Surf
Windstar Cruises
Starts: Philipsburg (St. Maarten), Netherlands Antilles
Ends: Philipsburg (St. Maarten), Netherlands Antilles
Ports of Call:
Philipsburg (St. Maarten), St John's, Road Bay, Sopers Hole, Great Harbour...
Special Promotions

7 Nights


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$2,273

per person
(double occupancy)
Includes taxes & fees
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Mar 05, 2028

(Sunday)

7 Night Classic Caribbean Cruise

Wind Surf
Windstar Cruises
Starts: Philipsburg (St. Maarten), Netherlands Antilles
Ends: Philipsburg (St. Maarten), Netherlands Antilles
Ports of Call:
Philipsburg (St. Maarten), Charlestown, Roseau, Mayreau, Iles des Saintes, Basseterre...
Special Promotions

7 Nights


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$2,362

per person
(double occupancy)
Includes taxes & fees
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Feb 20, 2028

(Sunday)

7 Night Classic Caribbean Cruise

Wind Surf
Windstar Cruises
Starts: Philipsburg (St. Maarten), Netherlands Antilles
Ends: Philipsburg (St. Maarten), Netherlands Antilles
Ports of Call:
Philipsburg (St. Maarten), Charlestown, Roseau, Mayreau, Iles des Saintes, Basseterre...
Special Promotions

7 Nights


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$2,362

per person
(double occupancy)
Includes taxes & fees
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Jan 23, 2028

(Sunday)

7 Night Classic Caribbean Cruise

Wind Surf
Windstar Cruises
Starts: Philipsburg (St. Maarten), Netherlands Antilles
Ends: Philipsburg (St. Maarten), Netherlands Antilles
Ports of Call:
Philipsburg (St. Maarten), Charlestown, Roseau, Mayreau, Iles des Saintes, Basseterre...
Special Promotions

7 Nights


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$2,362

per person
(double occupancy)
Includes taxes & fees
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Jan 09, 2028

(Sunday)

7 Night Classic Caribbean Cruise

Wind Surf
Windstar Cruises
Starts: Philipsburg (St. Maarten), Netherlands Antilles
Ends: Philipsburg (St. Maarten), Netherlands Antilles
Ports of Call:
Philipsburg (St. Maarten), Charlestown, Roseau, Mayreau, Iles des Saintes, Basseterre...
Special Promotions

7 Nights


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$2,362

per person
(double occupancy)
Includes taxes & fees
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Feb 06, 2028

(Sunday)

7 Night Classic Caribbean Cruise

Wind Surf
Windstar Cruises
Starts: Philipsburg (St. Maarten), Netherlands Antilles
Ends: Philipsburg (St. Maarten), Netherlands Antilles
Ports of Call:
Philipsburg (St. Maarten), Charlestown, Roseau, Mayreau, Iles des Saintes, Basseterre...
Special Promotions

7 Nights


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$2,432

per person
(double occupancy)
Includes taxes & fees
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Mar 06, 2027

(Saturday)

7 Night Classic Caribbean Cruise

Wind Surf
Windstar Cruises
Starts: Philipsburg (St. Maarten), Netherlands Antilles
Ends: Philipsburg (St. Maarten), Netherlands Antilles
Ports of Call:
Philipsburg (St. Maarten), Charlestown, Roseau, Mayreau, Iles des Saintes, Basseterre...
Special Promotions

7 Nights


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$2,432

per person
(double occupancy)
Includes taxes & fees
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Feb 21, 2028

(Monday)

22 Night Star Collector Caribbean Charms to Iberian Shores Cruise

Star Legend
Windstar Cruises
Starts: San Juan, Puerto Rico
Ends: Lisbon, Portugal
Ports of Call:
San Juan, St George's, Bequia, Mayreau, Iles des Saintes, Marigot, San Juan, Agadir, Casablanca...

22 Nights


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$2,451

per person
(double occupancy)
Includes taxes & fees
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Dec 20, 2026

(Sunday)

7 Night Windward Islands Surf and Sunsets Cruise

Star Pride
Windstar Cruises
Starts: San Juan, Puerto Rico
Ends: San Juan, Puerto Rico
Ports of Call:
San Juan, St George's, Bequia, Mayreau, Deshaies, Marigot, San Juan
Special Promotions

7 Nights


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$2,516

per person
(double occupancy)
Includes taxes & fees
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Mar 13, 2028

(Monday)

7 Night Windward Islands Surf and Sunsets Cruise

Star Pride
Windstar Cruises
Starts: San Juan, Puerto Rico
Ends: San Juan, Puerto Rico
Ports of Call:
San Juan, St George's, Bequia, Mayreau, Iles des Saintes, Marigot, San Juan
Special Promotions

7 Nights


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$2,516

per person
(double occupancy)
Includes taxes & fees
Learn More

Mar 20, 2027

(Saturday)

7 Night Classic Caribbean Cruise

Wind Surf
Windstar Cruises
Starts: Philipsburg (St. Maarten), Netherlands Antilles
Ends: Philipsburg (St. Maarten), Netherlands Antilles
Ports of Call:
Philipsburg (St. Maarten), Charlestown, Roseau, Mayreau, Iles des Saintes, Basseterre...
Special Promotions

7 Nights


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$2,537

per person
(double occupancy)
Includes taxes & fees
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Mar 20, 2028

(Monday)

7 Night San Juan and the Virgin Islands Cruise

Star Pride
Windstar Cruises
Starts: San Juan, Puerto Rico
Ends: San Juan, Puerto Rico
Ports of Call:
San Juan, Cruz Bay, Basseterre, Gustavia St. Barts, Philipsburg (St. Maarten), Great Harbour...
Special Promotions

7 Nights


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$2,548

per person
(double occupancy)
Includes taxes & fees
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Mar 19, 2028

(Sunday)

15 Night Ocean Crossing Cruise

Wind Surf
Windstar Cruises
Starts: Philipsburg (St. Maarten), Netherlands Antilles
Ends: Lisbon, Portugal
Ports of Call:
Philipsburg (St. Maarten), Horta, Ponta Delgada, Lisbon
Special Promotions

15 Nights


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$2,580

per person
(double occupancy)
Includes taxes & fees
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Nov 05, 2027

(Friday)

15 Night Ocean Crossing Cruise

Wind Surf
Windstar Cruises
Starts: Lisbon, Portugal
Ends: Philipsburg (St. Maarten), Netherlands Antilles
Ports of Call:
Lisbon, Madeira, Great Harbour, Philipsburg (St. Maarten)
Special Promotions

15 Nights


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$2,580

per person
(double occupancy)
Includes taxes & fees
Learn More

Dec 26, 2026

(Saturday)

7 Night Classic Caribbean Cruise

Wind Surf
Windstar Cruises
Starts: Philipsburg (St. Maarten), Netherlands Antilles
Ends: Philipsburg (St. Maarten), Netherlands Antilles
Ports of Call:
Philipsburg (St. Maarten), Gustavia St. Barts, Charlestown, Roseau, Mayreau, Iles des Saintes...
Special Promotions

7 Nights


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from

$2,607

per person
(double occupancy)
Includes taxes & fees
Learn More

Jan 09, 2027

(Saturday)

7 Night Classic Caribbean Cruise

Wind Surf
Windstar Cruises
Starts: Philipsburg (St. Maarten), Netherlands Antilles
Ends: Philipsburg (St. Maarten), Netherlands Antilles
Ports of Call:
Philipsburg (St. Maarten), Charlestown, Iles des Saintes, Mayreau, Roseau, Basseterre...
Special Promotions

7 Nights


Add to Favorites
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from

$2,607

per person
(double occupancy)
Includes taxes & fees
Learn More

Dec 12, 2027

(Sunday)

7 Night Classic Caribbean Cruise

Wind Surf
Windstar Cruises
Starts: Philipsburg (St. Maarten), Netherlands Antilles
Ends: Philipsburg (St. Maarten), Netherlands Antilles
Ports of Call:
Philipsburg (St. Maarten), Charlestown, Roseau, Mayreau, Iles des Saintes, Basseterre...
Special Promotions

7 Nights


Add to Favorites
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from

$2,607

per person
(double occupancy)
Includes taxes & fees
Learn More

Mar 27, 2028

(Monday)

7 Night Windward Islands Surf and Sunsets Cruise

Star Pride
Windstar Cruises
Starts: San Juan, Puerto Rico
Ends: San Juan, Puerto Rico
Ports of Call:
San Juan, St George's, Bequia, Mayreau, Iles des Saintes, Marigot, San Juan
Special Promotions

7 Nights


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from

$2,621

per person
(double occupancy)
Includes taxes & fees
Learn More

Dec 06, 2026

(Sunday)

7 Night Windward Islands Surf and Sunsets Cruise

Star Pride
Windstar Cruises
Starts: San Juan, Puerto Rico
Ends: San Juan, Puerto Rico
Ports of Call:
San Juan, St George's, Bequia, Mayreau, Deshaies, Marigot, San Juan
Special Promotions

7 Nights


Add to Favorites
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from

$2,621

per person
(double occupancy)
Includes taxes & fees
Learn More



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