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23-Night Repositioning
Cruise
Departs
Lisbon, Portugal
Sailing
Nov 5 - 28, 2027
Windstar Cruises - Wind Surf
Prices from
$5,251
23-Night Repositioning Cruise
Windstar Cruises -
Wind Surf
Speak To A Vacation Planner
1-888-447-8459
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Oceanview
From
$5,251
Suite
From
$8,931
Deals on this Cruise
- Avoya's Exclusive Deals with Windstar Cruises!
- 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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to be connected with a
travel professional today!
Cruise Itinerary
Departs
Lisbon, Portugal
Sailing
Nov 5 - 28, 2027
Day 1
Nov 5
Lisbon
Portugal
Departs
5:00PM
Day 2
Nov 6
At Sea
Day 3
Nov 7
At Sea
Day 4
Nov 8
Funchal
Madeira, Portugal
Arrives
8:00AM
|
Departs
3:00PM
Day 5
Nov 9
At Sea
Day 6
Nov 10
At Sea
Day 7
Nov 11
At Sea
Day 8
Nov 12
At Sea
Day 9
Nov 13
At Sea
Day 10
Nov 14
At Sea
Day 11
Nov 15
At Sea
Day 12
Nov 16
At Sea
Day 13
Nov 17
At Sea
Day 14
Nov 18
At Sea
Day 15
Nov 19
Great Harbour
Jost Van Dyke, British Virgin Islands
Arrives
8:00AM
|
Departs
6:00PM
Day 16
Nov 20
Philipsburg
Sint Maarten
Arrives
6:00AM
|
Departs
7:00PM
Day 17
Nov 21
Gustavia
Saint Barthélemy, France
Arrives
8:00AM
|
Departs
10:00PM
Day 18
Nov 22
St. John's
Antigua, Antigua And Barbuda
Arrives
8:00AM
|
Departs
10:00PM
Day 19
Nov 23
Deshaies
Guadeloupe, France
Arrives
7:00AM
|
Departs
5:00PM
Day 20
Nov 24
Road Bay
Anguilla
Arrives
8:00AM
|
Departs
6:00PM
Day 21
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 22
Nov 26
Great Harbour
Jost Van Dyke, British Virgin Islands
Departs
10:00PM
Day 23
Nov 27
Prickly Pear
British Virgin Islands
Arrives
8:00AM
|
Departs
5:00PM
Day 24
Nov 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, 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 8 months ago by
Richard
“Timothy Fussell”
Cruise Date:
06/14/2025
Destination:
Europe
Reviewed 11 months ago by
Timothy
“of”
Cruise Date:
01/18/2025
Destination:
Caribbean
Reviewed over 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 almost 2 years ago by
Paul