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Dec 07, 2025

(Sunday)

6 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, Santo Domingo, Cartagena, San Blas Islands, Colon

6 Nights


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$1,854

per person
(double occupancy)
Includes taxes & fees
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Dec 07, 2025

(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...

7 Nights


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$2,051

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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$2,426

per person
(double occupancy)
Includes taxes & fees
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Dec 05, 2026

(Saturday)

14 Night Ocean Crossing Cruise

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

14 Nights


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$2,529

per person
(double occupancy)
Includes taxes & fees
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Jan 02, 2027

(Saturday)

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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$2,567

per person
(double occupancy)
Includes taxes & fees
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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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$2,626

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

7 Nights


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$2,651

per person
(double occupancy)
Includes taxes & fees
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Feb 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...

7 Nights


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from

$2,651

per person
(double occupancy)
Includes taxes & fees
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Feb 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...

7 Nights


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from

$2,651

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...

7 Nights


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from

$2,651

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...

7 Nights


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from

$2,651

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

Mar 13, 2027

(Saturday)

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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$2,667

per person
(double occupancy)
Includes taxes & fees
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Jan 30, 2027

(Saturday)

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), Road Bay, Sopers Hole, Great Harbour...

7 Nights


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$2,667

per person
(double occupancy)
Includes taxes & fees
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Jan 11, 2026

(Sunday)

7 Night Lush and Lovely Islands of the Lesser Antilles Cruise

Wind Surf
Windstar Cruises
Starts: Philipsburg (St. Maarten), Netherlands Antilles
Ends: Bridgetown, Barbados
Ports of Call:
Philipsburg (St. Maarten), Basseterre, Gustavia St. Barts, St John's, Iles des Saintes, Roseau...

7 Nights


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$2,676

per person
(double occupancy)
Includes taxes & fees
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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...

7 Nights


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$2,751

per person
(double occupancy)
Includes taxes & fees
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Dec 13, 2026

(Sunday)

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, Gustavia St. Barts, Basseterre, Philipsburg (St. Maarten), Great Harbour...

7 Nights


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$2,762

per person
(double occupancy)
Includes taxes & fees
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Nov 29, 2026

(Sunday)

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, Gustavia St. Barts, Basseterre, Philipsburg (St. Maarten), Great Harbour...

7 Nights


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$2,762

per person
(double occupancy)
Includes taxes & fees
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Feb 13, 2027

(Saturday)

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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from

$2,767

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

Dec 21, 2025

(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...

7 Nights


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$2,771

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

Mar 27, 2027

(Saturday)

15 Night Ocean Crossing Cruise

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

15 Nights


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$2,829

per person
(double occupancy)
Includes taxes & fees
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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...

7 Nights


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from

$2,851

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

Jan 16, 2027

(Saturday)

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), Road Bay, Sopers Hole, Great Harbour...

7 Nights


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from

$2,867

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

Feb 27, 2027

(Saturday)

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), Sopers Hole, Great Harbour, Prickly Pear British Virgin Islands...

7 Nights


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from

$2,867

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

Mar 28, 2026

(Saturday)

15 Night Knot Your Average Crossing Cruise

Wind Spirit
Windstar Cruises
Starts: Bridgetown, Barbados
Ends: Lisbon, Portugal
Ports of Call:
Bridgetown, Lisbon

15 Nights


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$2,925

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

Nov 10, 2026

(Tuesday)

14 Night Knot Your Average Crossing Cruise

Wind Star
Windstar Cruises
Starts: Lisbon, Portugal
Ends: Bridgetown, Barbados
Ports of Call:
Lisbon, Bridgetown

14 Nights


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$2,925

per person
(double occupancy)
Includes taxes & fees
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