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14-Night Caribbean Cruise
Departs Saint Maarten (Phillipsburg), Netherlands Antilles
Sailing Dec 21, 2025 - Jan 4, 2026
Windstar Cruises - Wind Surf
Prices from
$4,899

14-Night Caribbean Cruise

Windstar Cruises - Wind Surf
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Oceanview

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Other dates for this cruise

Brochure
-
Our Price
$3,699
Savings
-
Deals
1 Deals

Cruise Itinerary

Departs Saint Maarten (Phillipsburg), Netherlands Antilles
Sailing Dec 21, 2025 - Jan 4, 2026
Day 1
Dec 21
Philipsburg
Sint Maarten
Departs 7:00PM
Day 2
Dec 22
Charlestown
Nevis, St. Kitts And Nevis
Arrives 8:00AM  |  Departs 5:00PM
Day 3
Dec 23
Roseau
Dominica
Arrives 8:00AM  |  Departs 4:00PM
Day 4
Dec 24
Mayreau
Saint Vincent And The Grenadines
Arrives 8:00AM  |  Departs 5:00PM
Day 5
Dec 25
îLes Des Saintes
Guadeloupe, France
Arrives 12:00AM  |  Departs 6:00PM
Day 6
Dec 26
Basseterre
St. Kitts, St. Kitts And Nevis
Arrives 8:00AM  |  Departs 10:00PM
Day 7
Dec 27
Gustavia
Saint Barthélemy, France
Arrives 8:00AM  |  Departs 10:00PM
Day 8
Dec 28
Philipsburg
Sint Maarten
Arrives 6:00AM  |  Departs 7:00PM
Day 9
Dec 29
Falmouth Bay
Antigua, Antigua And Barbuda
Arrives 8:00AM  |  Departs 6:00PM
Day 10
Dec 30
Road Bay
Anguilla
Arrives 8:00AM  |  Departs 6:00PM
Day 11
Dec 31
Sopers Hole
Tortola, British Virgin Islands
Arrives 8:00AM  |  Departs 6:00PM
Great Harbour
Jost Van Dyke, British Virgin Islands
Arrives 7:00PM
Day 12
Jan 1
Great Harbour
Jost Van Dyke, British Virgin Islands
Departs 10:00PM
Day 13
Jan 2
Prickly Pear
British Virgin Islands
Arrives 8:00AM  |  Departs 5:00PM
Day 14
Jan 3
Gustavia
Saint Barthélemy, France
Arrives 8:00AM  |  Departs 10:00PM
Day 15
Jan 4
Philipsburg
Sint Maarten
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.

Reviews

4.7
146 Reviews
* All reviews are by verified customers that have traveled by booking through a travel agent in the Avoya Network
“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 3 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 8 months ago by Francine
5 Stars
Cruise Date: 07/21/2024
Destination: Europe
Great ship, wonderful time sailing the Mediterranean!
Reviewed 9 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 9 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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