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Cruises from Philipsburg (St. Maarten)


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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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$2,105

per person
(double occupancy)
Includes taxes & fees
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Jan 03, 2028

(Monday)

6 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, Gustavia St. Barts, Great Harbour...
Special Promotions

6 Nights


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$2,767

per person
(double occupancy)
Includes taxes & fees
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Mar 19, 2028

(Sunday)

15 Night Ocean Crossing Cruise

Wind Surf
Windstar Cruises
Starts: Philipsburg (St. Maarten), Netherlands Antilles
Ends: Lisbon, Portugal
Ports of Call:
Philipsburg (St. Maarten), Horta, Ponta Delgada, Lisbon
Special Promotions

15 Nights


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from

$2,829

per person
(double occupancy)
Includes taxes & fees
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Dec 12, 2027

(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...
Special Promotions

7 Nights


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from

$2,851

per person
(double occupancy)
Includes taxes & fees
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Nov 28, 2027

(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, Gustavia St. Barts...

7 Nights


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from

$2,851

per person
(double occupancy)
Includes taxes & fees
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Dec 05, 2027

(Sunday)

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...
Special Promotions

7 Nights


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from

$2,867

per person
(double occupancy)
Includes taxes & fees
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Jan 16, 2028

(Sunday)

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...
Special Promotions

7 Nights


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from

$2,967

per person
(double occupancy)
Includes taxes & fees
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Jan 30, 2028

(Sunday)

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...
Special Promotions

7 Nights


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from

$2,967

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

Feb 13, 2028

(Sunday)

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...
Special Promotions

7 Nights


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from

$2,967

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

Feb 27, 2028

(Sunday)

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...
Special Promotions

7 Nights


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from

$2,967

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

Mar 12, 2028

(Sunday)

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...
Special Promotions

7 Nights


Add to Favorites
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from

$2,967

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

Mar 05, 2028

(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...
Special Promotions

7 Nights


Add to Favorites
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from

$3,051

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

Feb 20, 2028

(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...
Special Promotions

7 Nights


Add to Favorites
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from

$3,051

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

Feb 06, 2028

(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...
Special Promotions

7 Nights


Add to Favorites
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from

$3,051

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

Jan 23, 2028

(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...
Special Promotions

7 Nights


Add to Favorites
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from

$3,051

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

Jan 09, 2028

(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...
Special Promotions

7 Nights


Add to Favorites
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from

$3,051

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

Nov 20, 2027

(Saturday)

8 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, St John's, Deshaies, Road Bay, Sopers Hole...
Special Promotions

8 Nights


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from

$3,067

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

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


Add to Favorites
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from

$3,151

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


Add to Favorites
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from

$3,251

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

Dec 27, 2027

(Monday)

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...
Special Promotions

7 Nights


Add to Favorites
Compare Favorites
from

$3,251

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

Dec 19, 2027

(Sunday)

8 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, Gustavia St. Barts, Road Bay, Sopers Hole, Great Harbour...
Special Promotions

8 Nights


Add to Favorites
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from

$3,267

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

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


Add to Favorites
Compare Favorites
from

$3,267

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

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


Add to Favorites
Compare Favorites
from

$3,351

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


Add to Favorites
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from

$3,367

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


Add to Favorites
Compare Favorites
from

$3,367

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



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