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Cruises from Philipsburg (St. Maarten)


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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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$2,645

per person
(double occupancy)
Includes taxes & fees
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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, Mayreau, Iles des Saintes, Basseterre...

7 Nights


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$3,044

per person
(double occupancy)
Includes taxes & fees
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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), Charlestown, Roseau, Mayreau, Iles des Saintes, Basseterre...

7 Nights


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$3,044

per person
(double occupancy)
Includes taxes & fees
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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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$3,160

per person
(double occupancy)
Includes taxes & fees
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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), St John's, Road Bay, Sopers Hole, Great Harbour...

7 Nights


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$3,160

per person
(double occupancy)
Includes taxes & fees
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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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from

$3,160

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

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, Deshaies, Basseterre...

7 Nights


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$3,244

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

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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$3,303

per person
(double occupancy)
Includes taxes & fees
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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from

$3,319

per person
(double occupancy)
Includes taxes & fees
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, Prickly Pear British Virgin Islands...

7 Nights


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$3,319

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
4.3 based on 8 ratings
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...

7 Nights


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$3,329

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

Jan 24, 2026

(Saturday)

7 Night Beach Fun and Sun A Remote Caribbean Getaway Cruise

Wind Spirit
Windstar Cruises
4.3 based on 6 ratings
Starts: Philipsburg (St. Maarten), Netherlands Antilles
Ends: Philipsburg (St. Maarten), Netherlands Antilles
Ports of Call:
Philipsburg (St. Maarten), St John's, Road Bay, Prickly Pear British Virgin Islands, Sopers Hole...

7 Nights


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from

$3,353

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

Feb 14, 2026

(Saturday)

7 Night Beach Fun and Sun A Remote Caribbean Getaway Cruise

Wind Spirit
Windstar Cruises
4.3 based on 6 ratings
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...

7 Nights


Add to Favorites
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from

$3,353

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

Feb 21, 2026

(Saturday)

7 Night Beach Fun and Sun A Remote Caribbean Getaway Cruise

Wind Spirit
Windstar Cruises
4.3 based on 6 ratings
Starts: Philipsburg (St. Maarten), Netherlands Antilles
Ends: Philipsburg (St. Maarten), Netherlands Antilles
Ports of Call:
Philipsburg (St. Maarten), St John's, Road Bay, Prickly Pear British Virgin Islands, Sopers Hole...

7 Nights


Add to Favorites
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from

$3,353

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

Dec 21, 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, Mayreau, Iles des Saintes, Basseterre...

7 Nights


Add to Favorites
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from

$3,444

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

Dec 28, 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


Add to Favorites
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from

$3,460

per person
(double occupancy)
Includes taxes & fees
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, Prickly Pear British Virgin Islands...

7 Nights


Add to Favorites
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from

$3,460

per person
(double occupancy)
Includes taxes & fees
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


Add to Favorites
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from

$3,464

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

7 Nights


Add to Favorites
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from

$3,649

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

Jan 14, 2026

(Wednesday)

10 Night Blue Waters of the Leeward Islands Cruise

Wind Spirit
Windstar Cruises
4.3 based on 6 ratings
Starts: Philipsburg (St. Maarten), Netherlands Antilles
Ends: Philipsburg (St. Maarten), Netherlands Antilles
Ports of Call:
Philipsburg (St. Maarten), Basseterre, Roseau, Castries, Anse Mitan, Iles des Saintes, Charlestown...

10 Nights


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$3,833

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

Jan 18, 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


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$3,944

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

Feb 08, 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


Add to Favorites
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from

$3,944

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

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...

7 Nights


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from

$3,960

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

Apr 04, 2026

(Saturday)

14 Night Ocean Crossing and Ponta Delgada Azores Cruise

Wind Surf
Windstar Cruises
4.3 based on 8 ratings
Starts: Philipsburg (St. Maarten), Netherlands Antilles
Ends: Lisbon, Portugal
Ports of Call:
Philipsburg (St. Maarten), Ponta Delgada, Lisbon

14 Nights


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from

$4,012

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

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...

7 Nights


Add to Favorites
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from

$4,060

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



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