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14-Night Repositioning Cruise
Departs Lisbon, Portugal
Sailing Nov 18 - Dec 2, 2025
Windstar Cruises - Wind Surf
Prices from
$2,499

14-Night Repositioning Cruise

Windstar Cruises - Wind Surf
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Inside

From
$4,149

Oceanview

From
$2,499

Suite

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Cruise Itinerary

Departs Lisbon, Portugal
Sailing Nov 18 - Dec 2, 2025
Day 1
Nov 18
Lisbon
Portugal
Day 2
Nov 19
Day 3
Nov 20
Day 4
Nov 21
Day 5
Nov 22
Day 6
Nov 23
Day 7
Nov 24
Day 8
Nov 25
Day 9
Nov 26
Day 10
Nov 27
Day 11
Nov 28
Day 12
Nov 29
Day 13
Nov 30
Day 14
Dec 1
San Jose
Costa Rica
Arrives 8:00AM
Day 15
Dec 2
Saint Maarten (Phillipsburg)
Netherlands Antilles
Arrives 6:00AM
Wind Surf
Year Refurb
2010
Passenger Capacity
312
Number of Crew
191
Gross Tonnage
14745
Decks
6
Suite Cabins
21
Balcony Cabins
0
Oceanview Cabins
150
Inside Cabins
0

Wind Surf, a 310-guest flagship, glides majestically into the most exclusive ports-of-call with its towering sails billowing. Just like all of the ships from Windstar’s impressive fleet, Wind Surf’s smaller size allows access to unique ports-of-call that the average cruise ship would not be able to maneuver its way into. Wind Surf has some of the most beautiful public spaces at sea, which is immediately noticeable in its newly renovated reception area. The exquisite décor only continues as you make your way into your cabin where fine details await. Inside you’ll find signature bowls of flowers and fresh fruit, along with rich tufted headboards, welcoming seascape colors, all new upholstery, and fine count Egyptian cotton linens. Windstar’s award-winning service and style give its guests the luxury of choice. Travelers onboard Wind Surf can enjoy live music and cocktails at Compass Rose or work out on the state-of-the-art equipment in the Fitness Center. When you simply want to relax, take a breather and catch up on your favorite book on the comfortable chaise lounges on deck. Sports enthusiasts can try out the Watersports Platform which includes kayaking, waterskiing, and windsurfing. The options are diverse and abundant! Experience these wonderful amenities onboard the majestic Wind Surf.

4.7 (146)
* 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 consistently receives high praise for its exceptional service, outstanding food, and intimate, yacht-like atmosphere. Guests highlight the attentive and friendly crew, well-maintained ship, and unique itineraries that visit less-crowded ports. While most reviews are overwhelmingly positive, some guests note areas for improvement such as the need for ship updates, expensive extras (like WiFi and excursions), and occasional issues with specialty diets or cabin amenities. Overall, Wind Surf delivers a luxurious, relaxed cruise experience that exceeds expectations for most travelers.

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Service

Service is frequently described as attentive, friendly, and personalized, with many guests noting that crew members remember names and go above and beyond to accommodate requests.

"But best of all are the crew members - attentive, courteous, funny and they remember your names!"
"The Windstar Cruise line exceeded my expectations in every way, especially the personal treatment from the staff."
"The service and accommodations on board really made it feel like traveling with friends on a private yacht."
“of”
3 Stars
Cruise Date: 01/18/2025
Destination: Caribbean
The food was great, but the weather was rough and windy. Disappointing, however, no fault of Windstar.
Reviewed 4 months ago by Richard
“Barcelona to Lisbon”
5 Stars
Cruise Date: 07/28/2024
Destination: Europe
Wonderful journey. Outside of twisting my knee on coming off a step down in the lounge, we enjoyed the whole experience. Staff was very professional and caring. Kudos and praise to Eri who took care of stateroom and our needs and to Rudy, our waiter in the restaurant, Superb service by both Food was delicious. Gift shop was disappointing We enjoyed the entertainment
Reviewed 9 months ago by Francine
5 Stars
Cruise Date: 07/21/2024
Destination: Europe
Great ship, wonderful time sailing the Mediterranean!
Reviewed 10 months ago by Paul
“Sicilian Splendors”
5 Stars
Cruise Date: 07/11/2024
Destination: Europe
The cruise itinerary was amazing and the excursion offerings were wonderful! The staff onboard Wind Surf was attentive, friendly, and lovely. Would highly recommend Windstar and will book many more cruises with them.
Reviewed 10 months ago by Kippalee
“SPRING CROSSING ON THE WINDSURF”
5 Stars
Cruise Date: 03/30/2024
Destination: Transatlantic/Repositioning
This was a very good crossing. Weather was surprisingly good for entire 14-day cruise. This was my 24th crossing with Windstar, 23 of which were on the Surf. The other one was on the WindSpirit. Several things that I have voiced concern about on previous crossings were either remedied or improved satisfactorily. The meals were considerably improved from the Fall Crossing. I think there are still many things that Windstar still needs to do to bring the level back to what it once was. I have cruised with Windstar since 2000, and the Spring Crossing was the 28th cruise with this line, including
Reviewed about 1 year ago by Edward
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