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Cruises from Philipsburg (St. Maarten)


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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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$3,051

per person
(double occupancy)
Includes taxes & fees
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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

$3,151

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

$3,151

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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from

$3,151

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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$3,167

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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from

$3,226

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

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

$3,251

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

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

$3,267

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

$3,267

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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from

$3,267

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

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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from

$3,267

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

Mar 28, 2026

(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), St John's, Road Bay, Sopers Hole, Great Harbour...

7 Nights


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from

$3,267

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


Add to Favorites
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from

$3,351

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

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


Add to Favorites
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from

$3,351

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

Dec 19, 2026

(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), Gustavia St. Barts, Falmouth Harbour, Road Bay, Sopers Hole...

7 Nights


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from

$3,567

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

$3,567

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

Mar 14, 2026

(Saturday)

7 Night James Beard Foundation 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

$3,767

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

Mar 21, 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), Charlestown, Roseau, Mayreau, Iles des Saintes, Basseterre...

7 Nights


Add to Favorites
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from

$3,851

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
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


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from

$3,867

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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from

$4,029

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

Feb 28, 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), Charlestown, Roseau, Mayreau, Deshaies, Basseterre, Gustavia St. Barts...

7 Nights


Add to Favorites
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from

$4,351

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

Mar 06, 2027

(Saturday)

14 Night Star Collector Caribbean Explorations 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...

14 Nights


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from

$5,019

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

Feb 27, 2027

(Saturday)

14 Night Star Collector Caribbean Explorations 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...

14 Nights


Add to Favorites
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from

$5,019

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

Feb 20, 2027

(Saturday)

14 Night Star Collector Caribbean Explorations 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...

14 Nights


Add to Favorites
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from

$5,119

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

Feb 13, 2027

(Saturday)

14 Night Star Collector Caribbean Explorations 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...

14 Nights


Add to Favorites
Compare Favorites
from

$5,119

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



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