No Avoya Fees on Cruises or Tours. Book, change, or cancel without paying any Avoya fees. Plus, our Low Price Guarantee! No Avoya Fees on Cruises or Tours.
Click Here!
No Avoya Fees on Cruises or Tours. Book, change, or cancel without paying any Avoya fees. Plus, our Low Price Guarantee! No Avoya Fees on Cruises or Tours.
Click Here!
14-Night Caribbean
Cruise
Departs
Saint Maarten (Phillipsburg), Netherlands Antilles
Sailing
Dec 26, 2026 - Jan 9, 2027
Windstar Cruises - Wind Surf
Prices from
$4,099
14-Night Caribbean Cruise
Windstar Cruises -
Wind Surf
Speak To A Vacation Planner
1-888-447-8459
1-888-447-8459
Unlock Avoya Member pricing for free to see if you qualify for special deals.
Cruise prices are constantly changing click here to get live pricing.
Inside
From
$9,799
Oceanview
From
$4,099
Suite
From
$10,199
Deals on this Cruise
- 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!
Cruise Itinerary
Departs
Saint Maarten (Phillipsburg), Netherlands Antilles
Sailing
Dec 26, 2026 - Jan 9, 2027
Day 1
Dec 26
Philipsburg
Sint Maarten
Departs
7:00PM
Day 2
Dec 27
Gustavia
Saint Barthélemy, France
Arrives
8:00AM
|
Departs
10:00PM
Day 3
Dec 28
Charlestown
Nevis, St. Kitts And Nevis
Arrives
8:00AM
|
Departs
5:00PM
Day 4
Dec 29
Roseau
Dominica
Arrives
8:00AM
|
Departs
4:00PM
Day 5
Dec 30
Mayreau
Saint Vincent And The Grenadines
Arrives
8:00AM
|
Departs
5:00PM
Day 6
Dec 31
îLes Des Saintes
Guadeloupe, France
Arrives
12:00AM
|
Departs
6:00PM
Day 7
Jan 1
Basseterre
St. Kitts, St. Kitts And Nevis
Arrives
8:00AM
|
Departs
10:00PM
Day 8
Jan 2
Philipsburg
Sint Maarten
Arrives
6:00AM
|
Departs
7:00PM
Day 9
Jan 3
Falmouth Bay
Antigua, Antigua And Barbuda
Arrives
8:00AM
|
Departs
6:00PM
Day 10
Jan 4
Road Bay
Anguilla
Arrives
8:00AM
|
Departs
6:00PM
Day 11
Jan 5
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 6
Great Harbour
Jost Van Dyke, British Virgin Islands
Departs
10:00PM
Day 13
Jan 7
Prickly Pear
British Virgin Islands
Arrives
8:00AM
|
Departs
5:00PM
Day 14
Jan 8
Gustavia
Saint Barthélemy, France
Arrives
8:00AM
|
Departs
10:00PM
Day 15
Jan 9
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, and unique itineraries that visit smaller, less crowded ports. Guests consistently praise the crew's friendliness and professionalism, the ship's cleanliness, and the intimate, relaxed atmosphere. While most aspects are highly rated, some guests mention areas for improvement such as the need for ship updates, better vegan dining options, and more inclusive pricing for extras like Wi-Fi and excursions. Overall, the Wind Surf delivers a memorable, yacht-like cruise experience that exceeds most guests' expectations.
AI-generated from the text of customer reviews
select to learn more
“Timothy Fussell”
Cruise Date:
06/14/2025
Destination:
Europe
Reviewed 3 months ago by
Timothy
“of”
Cruise Date:
01/18/2025
Destination:
Caribbean
Reviewed 8 months ago by
Richard
“Barcelona to Lisbon”
Cruise Date:
07/28/2024
Destination:
Europe
Reviewed about 1 year ago by
Francine
Cruise Date:
07/21/2024
Destination:
Europe
Reviewed about 1 year ago by
Paul
“Sicilian Splendors”
Cruise Date:
07/11/2024
Destination:
Europe
Reviewed about 1 year ago by
Kippalee