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23-Night Repositioning Cruise
Departs Lisbon, Portugal
Sailing Nov 5 - 28, 2027
Windstar Cruises - Wind Surf
Prices from
$4,697

23-Night Repositioning Cruise

Windstar Cruises - Wind Surf
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Oceanview

From
$4,697

Suite

From
$9,197

Cruise Itinerary

Departs Lisbon, Portugal
Sailing Nov 5 - 28, 2027
Day 1
Nov 5
Lisbon
Portugal
Day 2
Nov 6
Day 3
Nov 7
Day 4
Nov 8
Funchal
Madeira Islands, Portugal
Arrives 8:00AM
Day 5
Nov 9
Day 6
Nov 10
Day 7
Nov 11
Day 8
Nov 12
Day 9
Nov 13
Day 10
Nov 14
Day 11
Nov 15
Day 12
Nov 16
Day 13
Nov 17
Day 14
Nov 18
Day 15
Nov 19
Jost Van Dyke
British Virgin Islands
Arrives 8:00AM
Day 16
Nov 20
Saint Maarten (Phillipsburg)
Netherlands Antilles
Arrives 6:00AM
Day 17
Nov 21
Saint Barthelemy (Gustavia)
Guadeloupe
Arrives 8:00AM
Day 18
Nov 22
San Jose
Costa Rica
Arrives 8:00AM
Day 19
Nov 23
Deshaies
Guadaloupe, French Caribbean
Arrives 7:00AM
Day 20
Nov 24
Road Bay
Arrives 8:00AM
Day 21
Nov 25
Jost Van Dyke
British Virgin Islands
Arrives 7:00PM
Sopers Hole
British Virgin Islands
Arrives 8:00AM
Day 22
Nov 26
Jost Van Dyke
British Virgin Islands
Day 23
Nov 27
Virgin Gorda
British Virgin Islands
Arrives 8:00AM
Day 24
Nov 28
Saint Maarten (Phillipsburg)
Netherlands Antilles
Arrives 6:00AM
4.7 (148)
* 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
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“A small ship is the best way to cruise”
5 Stars
Cruise Date: 08/19/2025
Destination: Europe
Reviewed 5 months ago by Richard
“Timothy Fussell”
5 Stars
Cruise Date: 06/14/2025
Destination: Europe
Reviewed 7 months ago by Timothy
“of”
3 Stars
Cruise Date: 01/18/2025
Destination: Caribbean
Reviewed about 1 year ago by Richard
“Barcelona to Lisbon”
5 Stars
Cruise Date: 07/28/2024
Destination: Europe
Reviewed over 1 year ago by Francine
5 Stars
Cruise Date: 07/21/2024
Destination: Europe
Reviewed over 1 year ago by Paul
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