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55-Night Caribbean
Cruise
Departs
Saint Maarten (Phillipsburg), Netherlands Antilles
Sailing
Jan 4 - Feb 28, 2026
Windstar Cruises - Wind Surf
Prices from
$21,949
55-Night Caribbean Cruise
Windstar Cruises -
Wind Surf
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Oceanview
From
$21,949
Suite
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Cruise Itinerary
Departs
Saint Maarten (Phillipsburg), Netherlands Antilles
Sailing
Jan 4 - Feb 28, 2026
Day 1
Jan 4
Philipsburg
Sint Maarten
Departs
7:00PM
Day 2
Jan 5
Falmouth Bay
Antigua, Antigua And Barbuda
Arrives
8:00AM
|
Departs
6:00PM
Day 3
Jan 6
Road Bay
Anguilla
Arrives
8:00AM
|
Departs
6:00PM
Day 4
Jan 7
Sopers Hole
Tortola, British Virgin Islands
Arrives
8:00AM
|
Departs
6:00PM
Great Harbour
Jost Van Dyke, British Virgin Islands
Arrives
7:00PM
Day 5
Jan 8
Great Harbour
Jost Van Dyke, British Virgin Islands
Departs
10:00PM
Day 6
Jan 9
Prickly Pear
British Virgin Islands
Arrives
8:00AM
|
Departs
5:00PM
Day 7
Jan 10
Gustavia
Saint Barthélemy, France
Arrives
8:00AM
|
Departs
10:00PM
Day 8
Jan 11
Philipsburg
Sint Maarten
Arrives
6:00AM
|
Departs
7:00PM
Day 9
Jan 12
Basseterre
St. Kitts, St. Kitts And Nevis
Arrives
8:00AM
|
Departs
9:00PM
Day 10
Jan 13
Gustavia
Saint Barthélemy, France
Arrives
8:00AM
|
Departs
10:00PM
Day 11
Jan 14
St. John's
Antigua, Antigua And Barbuda
Arrives
8:00AM
|
Departs
10:00PM
Day 12
Jan 15
îLes Des Saintes
Guadeloupe, France
Arrives
8:00AM
|
Departs
5:00PM
Day 13
Jan 16
Roseau
Dominica
Arrives
8:00AM
|
Departs
4:00PM
Day 14
Jan 17
Mayreau
Saint Vincent And The Grenadines
Arrives
8:00AM
|
Departs
5:00PM
Day 15
Jan 18
Bridgetown
Barbados
Arrives
5:00AM
|
Departs
6:00PM
Day 16
Jan 19
Anse Mitan
Martinique, France
Arrives
9:00AM
|
Departs
11:00PM
Day 17
Jan 20
Castries
St. Lucia
Arrives
8:00AM
|
Departs
4:00PM
Pigeon Island
St. Lucia
Arrives
6:00PM
Day 18
Jan 21
Pigeon Island
St. Lucia
Departs
6:00PM
Day 19
Jan 22
Bequia
Saint Vincent And The Grenadines
Arrives
8:00AM
|
Departs
10:00PM
Day 20
Jan 23
Mayreau
Saint Vincent And The Grenadines
Arrives
8:00AM
|
Departs
6:00PM
Day 21
Jan 24
Saint George's
Grenada
Arrives
7:00AM
|
Departs
2:00PM
Day 22
Jan 25
Bridgetown
Barbados
Arrives
6:00AM
|
Departs
6:00PM
Day 23
Jan 26
Bequia
Saint Vincent And The Grenadines
Arrives
8:00AM
|
Departs
5:00PM
Day 24
Jan 27
Mayreau
Saint Vincent And The Grenadines
Arrives
8:00AM
|
Departs
6:00PM
Day 25
Jan 28
Soufrière
St. Lucia
Arrives
8:00AM
|
Departs
4:00PM
Day 26
Jan 29
At Sea
Day 27
Jan 30
Kralendijk
Bonaire, Netherlands Antilles, Netherlands
Arrives
1:00PM
|
Departs
10:00PM
Day 28
Jan 31
Willemstad
Curaçao, Curaçao
Arrives
8:00AM
|
Departs
6:00PM
Day 29
Feb 1
Oranjestad
Aruba
Arrives
6:00AM
|
Departs
6:00PM
Day 30
Feb 2
At Sea
Day 31
Feb 3
Cartagena
Colombia
Arrives
8:00AM
Day 32
Feb 4
Cartagena
Colombia
Departs
3:30PM
Day 33
Feb 5
At Sea
Day 34
Feb 6
Bocas Del Toro
Panama
Arrives
12:00AM
|
Departs
6:00PM
Day 35
Feb 7
At Sea
Day 36
Feb 8
At Sea
Day 37
Feb 9
Colón
Panama
Arrives
7:00AM
|
Departs
4:00PM
Day 38
Feb 10
Bocas Del Toro
Panama
Arrives
10:00AM
|
Departs
4:00PM
Day 39
Feb 11
San Andrés Island
Colombia
Arrives
1:00PM
|
Departs
7:00PM
Day 40
Feb 12
At Sea
Day 41
Feb 13
At Sea
Day 42
Feb 14
Coxen Hole
Roatán Island, Honduras
Arrives
9:00AM
|
Departs
5:00PM
Day 43
Feb 15
Belize City
Belize
Arrives
9:00AM
|
Departs
7:00PM
Day 44
Feb 16
Costa Maya
Mexico
Arrives
8:00AM
|
Departs
5:00PM
Day 45
Feb 17
Cozumel
Mexico
Arrives
8:00AM
|
Departs
6:00PM
Day 46
Feb 18
At Sea
Day 47
Feb 19
George Town
Grand Cayman, Cayman Islands
Arrives
8:00AM
|
Departs
6:00PM
Day 48
Feb 20
Cayman Brac
Cayman Islands
Arrives
7:00AM
|
Departs
1:00PM
Day 49
Feb 21
Ocho Rios
Jamaica
Arrives
8:30AM
|
Departs
2:00PM
Day 50
Feb 22
At Sea
Day 51
Feb 23
Santo Domingo
Dominican Republic
Arrives
1:00PM
|
Departs
10:00PM
Day 52
Feb 24
La Romana
Dominican Republic
Arrives
7:00AM
|
Departs
5:00PM
Day 53
Feb 25
At Sea
Day 54
Feb 26
Great Harbour
Jost Van Dyke, British Virgin Islands
Arrives
8:00AM
|
Departs
10:00PM
Day 55
Feb 27
Prickly Pear
British Virgin Islands
Arrives
8:00AM
|
Departs
5:00PM
Day 56
Feb 28
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, and unique itineraries that visit smaller, less crowded ports. Guests consistently praise the crew's friendliness and professionalism, the ship's cleanliness, and the intimate, relaxed atmosphere. While most aspects are highly rated, some guests mention areas for improvement such as the need for ship updates, better vegan dining options, and more inclusive pricing for extras like Wi-Fi and excursions. Overall, the Wind Surf delivers a memorable, yacht-like cruise experience that exceeds most guests' expectations.
AI-generated from the text of customer reviews
select to learn more
“Timothy Fussell”
Cruise Date:
06/14/2025
Destination:
Europe
Reviewed 3 months ago by
Timothy
“of”
Cruise Date:
01/18/2025
Destination:
Caribbean
Reviewed 8 months ago by
Richard
“Barcelona to Lisbon”
Cruise Date:
07/28/2024
Destination:
Europe
Reviewed about 1 year ago by
Francine
Cruise Date:
07/21/2024
Destination:
Europe
Reviewed about 1 year ago by
Paul
“Sicilian Splendors”
Cruise Date:
07/11/2024
Destination:
Europe
Reviewed about 1 year ago by
Kippalee