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Apr 04, 2026

(Saturday)

14 Night Knot Your Average Crossing Cruise

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

14 Nights


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$2,105

per person
(double occupancy)
Includes taxes & fees
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Mar 28, 2026

(Saturday)

16 Night Ocean Crossing Cruise

Wind Spirit
Windstar Cruises
Starts: Bridgetown, Barbados
Ends: Malaga, Spain
Ports of Call:
Bridgetown, Tangier, Malaga

16 Nights


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$2,364

per person
(double occupancy)
Includes taxes & fees
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Mar 22, 2026

(Sunday)

16 Night Ocean Crossing Cruise

Star Pride
Windstar Cruises
Starts: Bridgetown, Barbados
Ends: Amsterdam, Netherlands
Ports of Call:
Bridgetown, Lisbon, Amsterdam

16 Nights


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$2,418

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

(Monday)

7 Night Island Trails Aruba to the Virgin Islands Cruise

Star Pride
Windstar Cruises
Starts: Oranjestad, Aruba
Ends: San Juan, Puerto Rico
Ports of Call:
Oranjestad, Willemstad (Curacao), Bonaire, Gustavia St. Barts, Great Harbour...
Special Promotions

7 Nights


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$2,558

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

(Monday)

14 Night Ocean Crossing Cruise

Star Legend
Windstar Cruises
Starts: Lisbon, Portugal
Ends: San Juan, Puerto Rico
Ports of Call:
Lisbon, Madeira, Great Harbour, San Juan

14 Nights


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$2,639

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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$2,767

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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$2,829

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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$2,829

per person
(double occupancy)
Includes taxes & fees
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Nov 29, 2027

(Monday)

7 Night The Spanish Main Rise of the New World Cruise

Star Pride
Windstar Cruises
Starts: San Juan, Puerto Rico
Ends: Colon, Panama
Ports of Call:
San Juan, Catalina Island, Santo Domingo, Cartagena, San Blas Islands, Colon
Special Promotions

7 Nights


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$2,835

per person
(double occupancy)
Includes taxes & fees
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Feb 28, 2028

(Monday)

15 Night Ocean Crossing Cruise

Star Legend
Windstar Cruises
Starts: San Juan, Puerto Rico
Ends: Lisbon, Portugal
Ports of Call:
San Juan, Agadir, Casablanca, Lisbon

15 Nights


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$2,839

per person
(double occupancy)
Includes taxes & fees
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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


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$2,851

per person
(double occupancy)
Includes taxes & fees
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Nov 28, 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, Gustavia St. Barts...

7 Nights


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$2,851

per person
(double occupancy)
Includes taxes & fees
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Nov 15, 2027

(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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$2,862

per person
(double occupancy)
Includes taxes & fees
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Nov 01, 2027

(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...

7 Nights


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$2,862

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

(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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$2,867

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

(Tuesday)

8 Night Mind Body and Spirit Collection Bermuda Bliss Cruise

Star Pride
Windstar Cruises
Starts: Boston, Massachusetts
Ends: San Juan, Puerto Rico
Ports of Call:
Boston, Hamilton, St George, San Juan

8 Nights


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$2,926

per person
(double occupancy)
Includes taxes & fees
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Nov 08, 2027

(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

7 Nights


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$2,930

per person
(double occupancy)
Includes taxes & fees
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Nov 22, 2027

(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

7 Nights


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$2,930

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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$2,967

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...
Special Promotions

7 Nights


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$2,967

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

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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$2,967

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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$2,967

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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from

$2,967

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

Oct 22, 2027

(Friday)

10 Night Mind Body and Spirit Collection Bermuda Bliss Cruise

Star Pride
Windstar Cruises
Starts: Boston, Massachusetts
Ends: San Juan, Puerto Rico
Ports of Call:
Boston, Hamilton, St George, Gustavia St. Barts, Prickly Pear British Virgin Islands, San Juan
Special Promotions

10 Nights


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$3,026

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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$3,030

per person
(double occupancy)
Includes taxes & fees
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