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15-Night Caribbean
Cruise
Departs
Saint Maarten (Phillipsburg), Netherlands Antilles
Sailing
Nov 20 - Dec 5, 2027
Windstar Cruises - Wind Surf
Prices from
$4,719
15-Night Caribbean Cruise
Windstar Cruises -
Wind Surf
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Oceanview
From
$4,719
Suite
From
$10,419
Cruise Itinerary
Departs
Saint Maarten (Phillipsburg), Netherlands Antilles
Sailing
Nov 20 - Dec 5, 2027
Day 1
Nov 20
Philipsburg
Sint Maarten
Departs
7:00PM
Day 2
Nov 21
Gustavia
Saint Barthélemy, France
Arrives
8:00AM
|
Departs
10:00PM
Day 3
Nov 22
St. John's
Antigua, Antigua And Barbuda
Arrives
8:00AM
|
Departs
10:00PM
Day 4
Nov 23
Deshaies
Guadeloupe, France
Arrives
7:00AM
|
Departs
5:00PM
Day 5
Nov 24
Road Bay
Anguilla
Arrives
8:00AM
|
Departs
6:00PM
Day 6
Nov 25
Sopers Hole
Tortola, British Virgin Islands
Arrives
8:00AM
|
Departs
6:00PM
Great Harbour
Jost Van Dyke, British Virgin Islands
Arrives
7:00PM
Day 7
Nov 26
Great Harbour
Jost Van Dyke, British Virgin Islands
Departs
10:00PM
Day 8
Nov 27
Prickly Pear
British Virgin Islands
Arrives
8:00AM
|
Departs
5:00PM
Day 9
Nov 28
Philipsburg
Sint Maarten
Arrives
6:00AM
|
Departs
7:00PM
Day 10
Nov 29
Charlestown
Nevis, St. Kitts And Nevis
Arrives
8:00AM
|
Departs
5:00PM
Day 11
Nov 30
Roseau
Dominica
Arrives
8:00AM
|
Departs
4:00PM
Day 12
Dec 1
Mayreau
Saint Vincent And The Grenadines
Arrives
8:00AM
|
Departs
5:00PM
Day 13
Dec 2
îLes Des Saintes
Guadeloupe, France
Arrives
12:00AM
|
Departs
6:00PM
Day 14
Dec 3
Gustavia
Saint Barthélemy, France
Arrives
8:00AM
|
Departs
10:00PM
Day 15
Dec 4
Basseterre
St. Kitts, St. Kitts And Nevis
Arrives
8:00AM
|
Departs
5:00PM
Day 16
Dec 5
Philipsburg
Sint Maarten
Arrives
6:00AM
Ship Reviews
* All reviews are by verified customers that have
traveled by booking through a travel agent in the
Avoya Network
customers say
Wind Surf by Windstar Cruises receives overwhelmingly positive reviews for its attentive service, excellent food, intimate atmosphere, and unique itineraries. Guests consistently praise the crew's friendliness and professionalism, the ship's cleanliness, and the overall value of the experience. While most aspects are highly rated, some guests note areas for improvement such as internet connectivity, occasional maintenance issues, and the cost of extras like excursions and Wi-Fi. The ship's smaller size and relaxed ambiance are highlighted as major advantages over larger cruise lines.
AI-generated from the text of customer reviews
select to learn more
“A small ship is the best way to cruise”
Cruise Date:
08/19/2025
Destination:
Europe
Reviewed 5 months ago by
Richard
“Timothy Fussell”
Cruise Date:
06/14/2025
Destination:
Europe
Reviewed 7 months ago by
Timothy
“of”
Cruise Date:
01/18/2025
Destination:
Caribbean
Reviewed about 1 year ago by
Richard
“Barcelona to Lisbon”
Cruise Date:
07/28/2024
Destination:
Europe
Reviewed over 1 year ago by
Francine
Cruise Date:
07/21/2024
Destination:
Europe
Reviewed over 1 year ago by
Paul