Wind Surf: 14-Night CARIBBEAN
This 14-night Caribbean (Eastern) cruise aboard the Wind Surf by Windstar Cruises departs St. Maarten (Philipsburg) on January 2, 2027, calling at Falmouth, Anguilla, Tortola, and 9 more ports, and returns January 16, 2027. Cabin prices start from $5,580 per person.
How this date compares
1 of 13 dates
Wind Surf sails round trip from St. Maarten (Philipsburg) to these 12 ports on 13 dates between December 2026 and March 2027.
2nd lowest of 12
At $5,580 for a ocean view cabin, this date is the 2nd lowest of the 12 dates from December 2026 to March 2027 in the table below. The lowest is $5,440 on Feb 27, 2027.
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 →St. Maarten cruise port is one of the busiest in the Caribbean, with ships docking at the A.C.
Read more →Basseterre cruise port in St. Kitts uses the Port Zante terminal, a purpose-built cruise facility in the heart of Basseterre, the capital of St. Kitts and Nevis. Port Zante includes two dedicated cruise piers capable of berthing the largest modern ships plus a marina, restaurants, shops, and the Amina Craft Market.
Read more →Ocean View cabin
New to these charts? How to read cruise price history
Wind Surf to these 12 ports on other dates
| Departs | Port order | Ocean view from | vs Jan 2 |
|---|---|---|---|
| Dec 19, 2026 | St. Barthelemy, Falmouth, Anguilla, Tortola, Jost Van Dyke, Jost Van Dyke, Virgin Gorda, St. Maarten (Philipsburg), St. Barthelemy, Nevis, Roseau, Mayreau, Les Saintes, St. Kitts | $6,490 | +$910 |
| Dec 26, 2026 | St. Barthelemy, Nevis, Roseau, Mayreau, Les Saintes, St. Kitts, St. Maarten (Philipsburg), Falmouth, Anguilla, Tortola, Jost Van Dyke, Jost Van Dyke, Virgin Gorda, St. Barthelemy | $6,770 | +$1,190 |
| Jan 2, 2027 | Falmouth, Anguilla, Tortola, Jost Van Dyke, Jost Van Dyke, Virgin Gorda, St. Barthelemy, St. Maarten (Philipsburg), Nevis, Les Saintes, Mayreau, Roseau, St. Kitts, St. Barthelemy | $5,580 | this sailing |
| Jan 9, 2027 | Nevis, Les Saintes, Mayreau, Roseau, St. Kitts, St. Barthelemy, St. Maarten (Philipsburg), Anguilla, Tortola, Jost Van Dyke, Jost Van Dyke, Virgin Gorda, St. Barthelemy, Falmouth | $6,000 | +$420 |
| Jan 16, 2027 | Anguilla, Tortola, Jost Van Dyke, Jost Van Dyke, Virgin Gorda, St. Barthelemy, Falmouth, St. Maarten (Philipsburg), Nevis, Roseau, Mayreau, Les Saintes, St. Kitts, St. Barthelemy | $6,210 | +$630 |
| Jan 23, 2027 | Nevis, Roseau, Mayreau, Les Saintes, St. Kitts, St. Barthelemy, St. Maarten (Philipsburg), Anguilla, Tortola, Jost Van Dyke, Jost Van Dyke, Virgin Gorda, St. Barthelemy, Falmouth | $6,210 | +$630 |
| Jan 30, 2027 | Anguilla, Tortola, Jost Van Dyke, Jost Van Dyke, Virgin Gorda, St. Barthelemy, Falmouth, St. Maarten (Philipsburg), Nevis, Roseau, Mayreau, Les Saintes, St. Kitts, St. Barthelemy | $5,860 | +$280 |
| Feb 6, 2027 | Nevis, Roseau, Mayreau, Les Saintes, St. Kitts, St. Barthelemy, St. Maarten (Philipsburg), Falmouth, Anguilla, Tortola, Jost Van Dyke, Jost Van Dyke, Virgin Gorda, St. Barthelemy | $6,560 | +$980 |
| Feb 13, 2027 | Falmouth, Anguilla, Tortola, Jost Van Dyke, Jost Van Dyke, Virgin Gorda, St. Barthelemy, St. Maarten (Philipsburg), Nevis, Roseau, Mayreau, Les Saintes, St. Kitts, St. Barthelemy | $7,400 | +$1,820 |
| Feb 20, 2027 | Nevis, Roseau, Mayreau, Les Saintes, St. Kitts, St. Barthelemy, St. Maarten (Philipsburg), Tortola, Jost Van Dyke, Jost Van Dyke, Virgin Gorda, St. Barthelemy, Anguilla, Falmouth | $5,720 | +$140 |
| Feb 27, 2027 | Tortola, Jost Van Dyke, Jost Van Dyke, Virgin Gorda, St. Barthelemy, Anguilla, Falmouth, St. Maarten (Philipsburg), Nevis, Roseau, Mayreau, Les Saintes, St. Kitts, St. Barthelemy | $5,440 | −$140 |
| Mar 6, 2027 | Nevis, Roseau, Mayreau, Les Saintes, St. Kitts, St. Barthelemy, St. Maarten (Philipsburg), Falmouth, Anguilla, Tortola, Jost Van Dyke, Jost Van Dyke, Virgin Gorda, St. Barthelemy | $6,070 | +$490 |
Wind Surf, round trip from St. Maarten (Philipsburg), 14 nights. Ocean view cabin, per person, two sharing, taxes and port fees included. Prices checked as of Nov 10, 2026.
Other Caribbean (Eastern) departures
Questions about this sailing
How much does this cruise cost per night?
Ocean view cabins start at $5,580 per person for the 14 nights, about $399 a night, with taxes and port fees included.
Is $5,580 a good price for this sailing?
It is $2,064 above the lowest ocean view price we have recorded for this sailing since April 16, 2026 ($3,516 on June 22, 2026). Among the 12 dates from December 2026 to March 2027 on this route shown above, the lowest is $5,440 on Feb 27, 2027.
Which ports does it visit?
It sails round trip from St. Maarten (Philipsburg) and calls at Falmouth, Anguilla, Tortola, Jost Van Dyke, Virgin Gorda, St. Barthelemy, St. Maarten (Philipsburg), Nevis, Les Saintes, Mayreau, Roseau and St. Kitts.
Are there other dates with the same ports?
Yes. Wind Surf sails this route on 13 dates between December 2026 and March 2027.
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