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14-Night Caribbean
Cruise
Departs
Saint Maarten (Phillipsburg), Netherlands Antilles
Sailing
Mar 14 - 28, 2026
Windstar Cruises - Wind Surf
Prices from
$3,999
14-Night Caribbean Cruise
Windstar Cruises -
Wind Surf
Speak To A Vacation Planner
1-888-447-8459
1-888-447-8459
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Cruise prices are constantly changing click here to get live pricing.
Inside
From
$9,699
Oceanview
From
$3,999
Suite
From
$10,099
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!
Call
1-888-447-8459
1-888-447-8459
to be connected with a
travel professional today!
Other dates for this cruise
Sail Date
Brochure
Our Price
Savings
Deals
Cruise Itinerary
Departs
Saint Maarten (Phillipsburg), Netherlands Antilles
Sailing
Mar 14 - 28, 2026
Day 1
Mar 14
Philipsburg
Sint Maarten
Departs
7:00PM
Day 2
Mar 15
Falmouth Bay
Antigua, Antigua And Barbuda
Arrives
8:00AM
|
Departs
6:00PM
Day 3
Mar 16
Road Bay
Anguilla
Arrives
8:00AM
|
Departs
6:00PM
Day 4
Mar 17
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
Mar 18
Great Harbour
Jost Van Dyke, British Virgin Islands
Departs
10:00PM
Day 6
Mar 19
Prickly Pear
British Virgin Islands
Arrives
8:00AM
|
Departs
5:00PM
Day 7
Mar 20
Gustavia
Saint Barthélemy, France
Arrives
8:00AM
|
Departs
10:00PM
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 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.
AI-generated from the text of customer reviews
select to learn more
“of”
Cruise Date:
01/18/2025
Destination:
Caribbean
Reviewed 3 months ago by
Richard
“Barcelona to Lisbon”
Cruise Date:
07/28/2024
Destination:
Europe
Reviewed 9 months ago by
Francine
Cruise Date:
07/21/2024
Destination:
Europe
Reviewed 9 months ago by
Paul
“Sicilian Splendors”
Cruise Date:
07/11/2024
Destination:
Europe
Reviewed 9 months ago by
Kippalee
“SPRING CROSSING ON THE WINDSURF”
Cruise Date:
03/30/2024
Destination:
Transatlantic/Repositioning
Reviewed about 1 year ago by
Edward