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Dec 02, 2025

(Tuesday)

5 Night Barefoot Break in the British Virgin Islands Cruise

Wind Surf
Windstar Cruises
4.3 based on 8 ratings
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...

5 Nights


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Lowest from

$1,999

per person
(double occupancy)
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Jan 25, 2025

(Saturday)

7 Night Panama Canal Cartagena San Blas Islands and More Cruise

Star Pride
Windstar Cruises
Starts: Fuerte Amador, Panama
Ends: Oranjestad, Aruba
Ports of Call:
Fuerte Amador, Cruising the Panama Canal, Bocas Del Toro, San Blas Islands, Cartagena, Oranjestad

7 Nights


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Lowest from

$2,199

per person
(double occupancy)
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Dec 07, 2025

(Sunday)

7 Night Classic Caribbean Cruise

Wind Surf
Windstar Cruises
4.3 based on 8 ratings
Starts: Philipsburg (St. Maarten), Netherlands Antilles
Ends: Philipsburg (St. Maarten), Netherlands Antilles
Ports of Call:
Philipsburg (St. Maarten), Roseau, Pigeon Island, Iles des Saintes, Gustavia St. Barts, Basseterre...

7 Nights


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Lowest from

$2,299

per person
(double occupancy)
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Feb 28, 2026

(Saturday)

7 Night Classic Caribbean Cruise

Wind Surf
Windstar Cruises
4.3 based on 8 ratings
Starts: Philipsburg (St. Maarten), Netherlands Antilles
Ends: Philipsburg (St. Maarten), Netherlands Antilles
Ports of Call:
Philipsburg (St. Maarten), Roseau, Pigeon Island, Iles des Saintes, Gustavia St. Barts, Basseterre...

7 Nights


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Lowest from

$2,299

per person
(double occupancy)
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Mar 21, 2026

(Saturday)

7 Night Classic Caribbean Cruise

Wind Surf
Windstar Cruises
4.3 based on 8 ratings
Starts: Philipsburg (St. Maarten), Netherlands Antilles
Ends: Philipsburg (St. Maarten), Netherlands Antilles
Ports of Call:
Philipsburg (St. Maarten), Roseau, Pigeon Island, Iles des Saintes, Gustavia St. Barts, Basseterre...

7 Nights


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Lowest from

$2,299

per person
(double occupancy)
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Mar 07, 2026

(Saturday)

7 Night Beach Fun and Sun A Remote Caribbean Getaway Cruise

Wind Surf
Windstar Cruises
4.3 based on 8 ratings
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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Lowest from

$2,399

per person
(double occupancy)
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Mar 14, 2026

(Saturday)

7 Night Beach Fun and Sun A Remote Caribbean Getaway Cruise

Wind Surf
Windstar Cruises
4.3 based on 8 ratings
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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Lowest from

$2,399

per person
(double occupancy)
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Mar 28, 2026

(Saturday)

7 Night Beach Fun and Sun A Remote Caribbean Getaway Cruise

Wind Surf
Windstar Cruises
4.3 based on 8 ratings
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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Lowest from

$2,399

per person
(double occupancy)
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Feb 28, 2026

(Saturday)

7 Night Lush and Lovely Islands of the Lesser Antilles Cruise

Wind Spirit
Windstar Cruises
4.3 based on 6 ratings
Starts: Philipsburg (St. Maarten), Netherlands Antilles
Ends: Bridgetown, Barbados
Ports of Call:
Philipsburg (St. Maarten), Basseterre, Gustavia St. Barts, Little Bay, Iles des Saintes, Roseau...

7 Nights


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Lowest from

$2,399

per person
(double occupancy)
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Dec 14, 2025

(Sunday)

7 Night Beach Fun and Sun A Remote Caribbean Getaway Cruise

Wind Surf
Windstar Cruises
4.3 based on 8 ratings
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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Lowest from

$2,399

per person
(double occupancy)
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Mar 29, 2025

(Saturday)

7 Night Jewels of the Windward Islands Cruise

Star Pride
Windstar Cruises
Starts: Bridgetown, Barbados
Ends: Bridgetown, Barbados
Ports of Call:
Bridgetown, Pigeon Island, Castries, Anse Mitan, Mayreau, St George's, Bequia, Bridgetown

7 Nights


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Lowest from

$2,399

per person
(double occupancy)
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Feb 22, 2025

(Saturday)

15 Night Ocean Crossing Cruise

Wind Spirit
Windstar Cruises
4.3 based on 6 ratings
Starts: Bridgetown, Barbados
Ends: Lisbon, Portugal
Ports of Call:
Bridgetown, Lisbon

15 Nights


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Lowest from

$2,399

per person
(double occupancy)
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Mar 26, 2025

(Wednesday)

15 Night Ocean Crossing Cruise

Wind Star
Windstar Cruises
4.2 based on 5 ratings
Starts: Bridgetown, Barbados
Ends: Lisbon, Portugal
Ports of Call:
Bridgetown, Lisbon

15 Nights


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Lowest from

$2,399

per person
(double occupancy)
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Apr 05, 2025

(Saturday)

10 Night Ocean Crossing Cruise

Star Pride
Windstar Cruises
Starts: Bridgetown, Barbados
Ends: Santa Cruz de Tenerife, Spain
Ports of Call:
Bridgetown, Santa Cruz de Tenerife

10 Nights


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Lowest from

$2,399

per person
(double occupancy)
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Nov 04, 2025

(Tuesday)

14 Night Ocean Crossing Cruise

Wind Spirit
Windstar Cruises
4.3 based on 6 ratings
Starts: Lisbon, Portugal
Ends: Bridgetown, Barbados
Ports of Call:
Lisbon, Bridgetown

14 Nights


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Lowest from

$2,499

per person
(double occupancy)
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Nov 13, 2024

(Wednesday)

14 Night Ocean Crossing Cruise

Wind Spirit
Windstar Cruises
4.3 based on 6 ratings
Starts: Lisbon, Portugal
Ends: Bridgetown, Barbados
Ports of Call:
Lisbon, Bridgetown

14 Nights


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Lowest from

$2,499

per person
(double occupancy)
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Nov 03, 2024

(Sunday)

6 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, Philipsburg (St. Maarten), Charlestown, Gustavia St. Barts, Great Harbour...

6 Nights


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Lowest from

$2,499

per person
(double occupancy)
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Nov 16, 2024

(Saturday)

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, Charlotte Amalie (St Thomas), Philipsburg (St. Maarten), Gustavia St. Barts, Basseterre...

7 Nights


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Lowest from

$2,499

per person
(double occupancy)
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Nov 23, 2024

(Saturday)

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, Pigeon Island, Iles des Saintes, Philipsburg (St. Maarten), San Juan

7 Nights


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Lowest from

$2,499

per person
(double occupancy)
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Dec 07, 2024

(Saturday)

7 Night Winter Antilles Escape Cruise

Star Pride
Windstar Cruises
Starts: San Juan, Puerto Rico
Ends: Bridgetown, Barbados
Ports of Call:
San Juan, Charlotte Amalie (St Thomas), Gustavia St. Barts, Basseterre, Roseau, Pigeon Island...

7 Nights


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Lowest from

$2,499

per person
(double occupancy)
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Dec 14, 2024

(Saturday)

7 Night Windward Islands Cruise

Wind Spirit
Windstar Cruises
4.3 based on 6 ratings
Starts: Bridgetown, Barbados
Ends: Bridgetown, Barbados
Ports of Call:
Bridgetown, Basseterre, Iles des Saintes, Roseau, Anse Mitan, Pigeon Island, Bridgetown

7 Nights


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Lowest from

$2,499

per person
(double occupancy)
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Dec 14, 2024

(Saturday)

7 Night Windward Ways and Tobago Cays Cruise

Star Pride
Windstar Cruises
Starts: Bridgetown, Barbados
Ends: Oranjestad, Aruba
Ports of Call:
Bridgetown, Man of War Bay, Mayreau, Soufriere , St George's, Willemstad (Curacao), Oranjestad

7 Nights


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Lowest from

$2,499

per person
(double occupancy)
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Jan 04, 2026

(Sunday)

7 Night Beach Fun and Sun A Remote Caribbean Getaway Cruise

Wind Surf
Windstar Cruises
4.3 based on 8 ratings
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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Lowest from

$2,499

per person
(double occupancy)
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Jan 11, 2026

(Sunday)

7 Night Lush and Lovely Islands of the Lesser Antilles Cruise

Wind Surf
Windstar Cruises
4.3 based on 8 ratings
Starts: Philipsburg (St. Maarten), Netherlands Antilles
Ends: Bridgetown, Barbados
Ports of Call:
Philipsburg (St. Maarten), Basseterre, Little Bay, Gustavia St. Barts, Deshaies, Roseau...

7 Nights


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Lowest from

$2,499

per person
(double occupancy)
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Jan 18, 2026

(Sunday)

7 Night Jewels of the Windward Islands Cruise

Wind Surf
Windstar Cruises
4.3 based on 8 ratings
Starts: Bridgetown, Barbados
Ends: Bridgetown, Barbados
Ports of Call:
Bridgetown, Anse Mitan, Castries, Pigeon Island, Bequia, Mayreau, St George's, Bridgetown

7 Nights


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Lowest from

$2,499

per person
(double occupancy)
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