Wind Surf: 7-Night Caribbean
This 7-night Caribbean (Eastern) cruise aboard the Wind Surf by Windstar Cruises departs St. Maarten (Philipsburg) on December 19, 2026, calling at St. Barthelemy, Falmouth, Anguilla, and 3 more ports, and returns December 26, 2026. Cabin prices start from $2,658 per person.
How this date compares
1 of 7 dates
Wind Surf sails round trip from St. Maarten (Philipsburg) to these six ports on 7 dates between December 2026 and March 2027.
Tied for cheapest of 7
At $2,658 for a ocean view cabin, this date is tied for cheapest of the 7 dates from December 2026 to March 2027 in the table below.
St. Maarten cruise port is one of the busiest in the Caribbean, with ships docking at the A.C.
Read more →Falmouth's historic port was purpose-built for mega-ships and sits in a town known for its well-preserved Georgian colonial architecture. Popular excursions include Dunn's River Falls, bamboo rafting on the Martha Brae River, and Montego Bay beaches.
Read more →Ocean View cabin
New to these charts? How to read cruise price history
Wind Surf to these six ports on other dates
| Departs | Port order | Ocean view from | vs Dec 19 |
|---|---|---|---|
| Dec 19, 2026 | St. Barthelemy, Falmouth, Anguilla, Tortola, Jost Van Dyke, Jost Van Dyke, Virgin Gorda | $2,658 | this sailing |
| Jan 2, 2027 | Falmouth, Anguilla, Tortola, Jost Van Dyke, Jost Van Dyke, Virgin Gorda, St. Barthelemy | $2,658 | same |
| Jan 16, 2027 | Anguilla, Tortola, Jost Van Dyke, Jost Van Dyke, Virgin Gorda, St. Barthelemy, Falmouth | $3,183 | +$525 |
| Jan 30, 2027 | Anguilla, Tortola, Jost Van Dyke, Jost Van Dyke, Virgin Gorda, St. Barthelemy, Falmouth | $3,288 | +$630 |
| Feb 13, 2027 | Falmouth, Anguilla, Tortola, Jost Van Dyke, Jost Van Dyke, Virgin Gorda, St. Barthelemy | $3,848 | +$1,190 |
| Feb 27, 2027 | Tortola, Jost Van Dyke, Jost Van Dyke, Virgin Gorda, St. Barthelemy, Anguilla, Falmouth | $3,638 | +$980 |
| Mar 13, 2027 | Falmouth, Anguilla, Tortola, Jost Van Dyke, Jost Van Dyke, Virgin Gorda, St. Barthelemy | $3,638 | +$980 |
Wind Surf, round trip from St. Maarten (Philipsburg), 7 nights. Ocean view cabin, per person, two sharing, taxes and port fees included. Prices checked as of Nov 11, 2026.
Other Caribbean (Eastern) departures
Questions about this sailing
How much does this cruise cost per night?
Ocean view cabins start at $2,658 per person for the 7 nights, about $380 a night, with taxes and port fees included.
Is $2,658 a good price for this sailing?
It is $1,036 above the lowest ocean view price we have recorded for this sailing since March 9, 2026 ($1,622 on November 9, 2026). It is also tied for cheapest of the 7 dates from December 2026 to March 2027 on this route shown above.
Which ports does it visit?
It sails round trip from St. Maarten (Philipsburg) and calls at St. Barthelemy, Falmouth, Anguilla, Tortola, Jost Van Dyke and Virgin Gorda.
Are there other dates with the same ports?
Yes. Wind Surf sails this route on 7 dates between December 2026 and March 2027.
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