14-Night CARIBBEAN CRUISE

Wind Surf

This 14-night Caribbean (Eastern) cruise aboard the Wind Surf by Windstar Cruises departs St. Maarten (Philipsburg) on February 20, 2027, calling at Charlestown Nevis, Roseau, Mayreau Island, and 9 more ports, and returns March 6, 2027. Cabin prices start from $5,580 per person.

Days
14 nights
Departs
Feb 20, 2027
Ports
12
Returns
Mar 6, 2027
Sea days
0
Distance
2,606nm
Itinerary
Embark Port Sea
Day 1
Feb 20
Embark
St. Maarten (Philipsburg)
dep 19:00

St. Maarten cruise port is one of the busiest in the Caribbean, with ships docking at the A.C.

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Day 2
Feb 21
Charlestown Nevis, Nevis Island
arr 08:00 · dep 17:00
Day 3
Feb 22
Roseau, Dominica
arr 08:00 · dep 16:00
Day 4
Feb 23
Mayreau Island, Grenadines
arr 08:00 · dep 17:00
Day 5
Feb 24
Terra de Haut, Guadeloupe
arr 12:00 · dep 18:00
Day 6
Feb 25
Basseterre St Kitts, Port Zante
arr 08:00 · dep 22:00

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.

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Day 7
Feb 26
Gustavia St Barths, Saint-Barthelemy Island France
arr 08:00 · dep 22:00
Day 8
Feb 27
St. Maarten (Philipsburg)
arr 06:00 · dep 19:00

St. Maarten cruise port is one of the busiest in the Caribbean, with ships docking at the A.C.

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Day 10
Mar 1
Day 11
Mar 2
Day 12
Mar 3
Gustavia St Barths, Saint-Barthelemy Island France
arr 08:00 · dep 22:00
Day 13
Mar 4
Anguilla
arr 08:00 · dep 18:00
Day 14
Mar 5
Falmouth, Jamaica
arr 08:00 · dep 17:00

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.

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Day 15
Mar 6
Disembark
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1Embark/Debark3Port of CallRoute
Distance
≈ 2,606nm
At sea
0 of 14 nights
Type
Round-trip
Price history

Ocean View cabin

$5,580▼ $19 (0.3%) vs Apr 16
Low
$5,404
High
$6,350
Average
$5,803
Vs avg
−4%
$5,309$5,593$5,877$6,161$6,445Apr 16Jul 6Sep 26$5,599 · Apr 16$5,856 · May 10$6,176 · May 24$5,856 · May 28$5,976 · Jun 2$5,856 · Jun 6$5,976 · Jun 9$5,856 · Jun 10$5,976 · Jun 16$5,856 · Jun 17$6,178 · Jun 23$5,404 · Jun 26$5,460 · Jun 28$5,580 · Jun 29$5,460 · Jul 1$5,740 · Jul 9$5,964 · Jul 10$5,804 · Jul 12$5,964 · Jul 15$5,804 · Jul 16$5,964 · Jul 17$5,824 · Jul 18$5,608 · Jul 19$5,824 · Jul 22$5,608 · Jul 23$5,720 · Jul 24$5,748 · Jul 26$5,936 · Jul 29$5,804 · Jul 30$5,964 · Aug 1$5,852 · Aug 2$5,496 · Aug 7$5,524 · Aug 13$5,804 · Aug 16$5,524 · Aug 19$5,772 · Aug 31$6,070 · Sep 2$6,210 · Sep 4$6,350 · Sep 5$6,000 · Sep 10$5,510 · Sep 16$5,790 · Sep 20$5,510 · Sep 24$5,580 · Sep 26

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Other Caribbean (Eastern) departures

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Starting from
$5,580/person
Incl. taxes & port fees
Checked 2 days ago · Sep 26
Last change Sep 26: $5,510 → $5,580 (+$70)
Ocean View
$399/night
$5,580
Suite
$504/night
$7,050

Track prices

Get emailed when double occupancy drops below your target.

Wind Surf
Your ship
Wind Surf
Windstar Cruises · 5-Masted Motor Sailing Ship class · Built 1990
Passengers
386
Tonnage
14,745
Length
187m
Crew
214
Onboard
PoolHot TubWhirlpoolCasinoTheaterLive Music VenueLibrarySpaSaunaFitness CenterHair SalonSpecialty Restaurant
Full ship profile →
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