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14-Night Caribbean
Cruise
Departs
Saint Maarten (Phillipsburg), Netherlands Antilles
Sailing
Jan 9 - 23, 2027
Windstar Cruises - Wind Surf
Prices from
$6,019
14-Night Caribbean Cruise
Windstar Cruises -
Wind Surf
Speak To A Vacation Planner
1-888-447-8459
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Oceanview
From
$6,019
Suite
From
$11,719
Deals on this Cruise
- Spring Into Travel Sale!
- Yacht Club Past Guest Rewards – Save up to 10%, up to $100 Free Onboard Credit, Private Cocktail Reception PLUS More!
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1-888-447-8459
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Cruise Itinerary
Departs
Saint Maarten (Phillipsburg), Netherlands Antilles
Sailing
Jan 9 - 23, 2027
Day 1
Jan 9
Philipsburg
Sint Maarten
Departs
7:00PM
Day 2
Jan 10
Charlestown
Nevis, St. Kitts And Nevis
Arrives
8:00AM
|
Departs
5:00PM
Day 3
Jan 11
îLes Des Saintes
Guadeloupe, France
Arrives
7:00AM
|
Departs
1:00PM
Day 4
Jan 12
Mayreau
Saint Vincent And The Grenadines
Arrives
8:00AM
|
Departs
5:00PM
Day 5
Jan 13
Roseau
Dominica
Arrives
8:00AM
|
Departs
4:00PM
Day 6
Jan 14
Basseterre
St. Kitts, St. Kitts And Nevis
Arrives
8:00AM
|
Departs
10:00PM
Day 7
Jan 15
Gustavia
Saint Barthélemy, France
Arrives
8:00AM
|
Departs
10:00PM
Day 8
Jan 16
Philipsburg
Sint Maarten
Arrives
6:00AM
|
Departs
7:00PM
Day 9
Jan 17
Road Bay
Anguilla
Arrives
8:00AM
|
Departs
6:00PM
Day 10
Jan 18
Sopers Hole
Tortola, British Virgin Islands
Arrives
8:00AM
|
Departs
6:00PM
Great Harbour
Jost Van Dyke, British Virgin Islands
Arrives
7:00PM
Day 11
Jan 19
Great Harbour
Jost Van Dyke, British Virgin Islands
Departs
10:00PM
Day 12
Jan 20
Prickly Pear
British Virgin Islands
Arrives
8:00AM
|
Departs
10:00PM
Day 13
Jan 21
Gustavia
Saint Barthélemy, France
Arrives
8:00AM
|
Departs
10:00PM
Day 14
Jan 22
Falmouth Bay
Antigua, Antigua And Barbuda
Arrives
8:00AM
|
Departs
5:00PM
Day 15
Jan 23
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
Windstar's Wind Surf 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. Some criticisms include the need for ship updates, inconsistent internet service, and extra charges for certain amenities. Excursions and specialty services are generally well-received, though some guests found them overpriced or lacking in variety. Overall, Wind Surf is highly recommended for travelers seeking a luxurious, small-ship cruise experience.
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 7 months ago by
Richard
“Timothy Fussell”
Cruise Date:
06/14/2025
Destination:
Europe
Reviewed 9 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