Wind Surf: 7-Night Caribbean
This 7-night Caribbean (Eastern) cruise aboard the Wind Surf by Windstar Cruises departs St. Maarten (Philipsburg) on January 2, 2027, calling at Falmouth, Anguilla, Tortola Island BVI, and 3 more ports, and returns January 9, 2027. 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. In the table below, February 13, 2027 and March 13, 2027 call at them in the same order.
Cheapest of 7
At $2,658 for a ocean view cabin, this date is the 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 Jan 2 |
|---|---|---|---|
| Dec 19, 2026 | Gustavia St Barths, Falmouth, Anguilla, Tortola Island BVI, Jost Van Dyke, Jost Van Dyke, Virgin Gorda Island BVI | $3,218 | +$560 |
| Jan 2, 2027 | Falmouth, Anguilla, Tortola Island BVI, Jost Van Dyke, Jost Van Dyke, Virgin Gorda Island BVI, Gustavia St Barths | $2,658 | this sailing |
| Jan 16, 2027 | Anguilla, Tortola Island BVI, Jost Van Dyke, Jost Van Dyke, Virgin Gorda Island BVI, Gustavia St Barths, Falmouth | $2,868 | +$210 |
| Jan 30, 2027 | Anguilla, Tortola Island BVI, Jost Van Dyke, Jost Van Dyke, Virgin Gorda Island BVI, Gustavia St Barths, Falmouth | $3,183 | +$525 |
| Feb 13, 2027 | Falmouth, Anguilla, Tortola Island BVI, Jost Van Dyke, Jost Van Dyke, Virgin Gorda Island BVI, Gustavia St Barths | $2,833 | +$175 |
| Feb 27, 2027 | Tortola Island BVI, Jost Van Dyke, Jost Van Dyke, Virgin Gorda Island BVI, Gustavia St Barths, Anguilla, Falmouth | $3,428 | +$770 |
| Mar 13, 2027 | Falmouth, Anguilla, Tortola Island BVI, Jost Van Dyke, Jost Van Dyke, Virgin Gorda Island BVI, Gustavia St Barths | $3,148 | +$490 |
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 Oct 21, 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 $1,030 above the lowest ocean view price we have recorded for this sailing since March 9, 2026 ($1,628 on June 20, 2026). It is also the 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 Falmouth, Anguilla, Tortola Island BVI, Jost Van Dyke, Virgin Gorda Island BVI and Gustavia St Barths.
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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