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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, Virgin Gorda, Gustavia St. Barts...

5 Nights


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Lowest from

$1,899

per person
(double occupancy)
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Mar 01, 2025

(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, Virgin Gorda...

7 Nights


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Lowest from

$2,199

per person
(double occupancy)
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Mar 08, 2025

(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, Virgin Gorda...

7 Nights


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Lowest from

$2,199

per person
(double occupancy)
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Mar 22, 2025

(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, Virgin Gorda...

7 Nights


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Lowest from

$2,299

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), Charlestown, Roseau, Pigeon Island, Iles des Saintes...

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), Charlestown, Roseau, Pigeon Island, Iles des Saintes...

7 Nights


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Lowest from

$2,299

per person
(double occupancy)
Learn More

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), Charlestown, Roseau, Pigeon Island, Iles des Saintes...

7 Nights


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Lowest from

$2,299

per person
(double occupancy)
Learn More

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, Virgin Gorda...

7 Nights


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Lowest from

$2,399

per person
(double occupancy)
Learn More

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, Virgin Gorda...

7 Nights


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Lowest from

$2,399

per person
(double occupancy)
Learn More

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, Virgin Gorda...

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)
Learn More

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, Virgin Gorda...

7 Nights


Add to Favorites
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Lowest from

$2,399

per person
(double occupancy)
Learn More

Jan 25, 2025

(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, Virgin Gorda...

7 Nights


Add to Favorites
Compare Favorites
Lowest from

$2,399

per person
(double occupancy)
Learn More

Feb 01, 2025

(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, Virgin Gorda...

7 Nights


Add to Favorites
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Lowest from

$2,399

per person
(double occupancy)
Learn More

Feb 15, 2025

(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, Great Harbour, Virgin Gorda, Sopers Hole...

7 Nights


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Lowest from

$2,399

per person
(double occupancy)
Learn More

Feb 22, 2025

(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), Charlestown, Roseau, Pigeon Island, Iles des Saintes, Basseterre...

7 Nights


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Lowest from

$2,399

per person
(double occupancy)
Learn More

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)
Learn More

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)
Learn More

Jan 04, 2025

(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), Charlestown, Roseau, Pigeon Island, Iles des Saintes...

7 Nights


Add to Favorites
Compare Favorites
Lowest from

$2,399

per person
(double occupancy)
Learn More

Jan 11, 2025

(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, Gustavia St. Barts, Sopers Hole, Great Harbour...

7 Nights


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Lowest from

$2,499

per person
(double occupancy)
Learn More

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, Sint Maarten, Charlestown, Gustavia St. Barts, Great Harbour, Virgin Gorda, San Juan

6 Nights


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Lowest from

$2,499

per person
(double occupancy)
Learn More

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), Sint Maarten, Gustavia St. Barts, Basseterre...

7 Nights


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Lowest from

$2,499

per person
(double occupancy)
Learn More

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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Compare Favorites
Lowest from

$2,499

per person
(double occupancy)
Learn More

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


Add to Favorites
Compare Favorites
Lowest from

$2,499

per person
(double occupancy)
Learn More



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