14-Night CARIBBEAN CRUISE

Wind Surf

This 14-night Caribbean (Eastern) cruise aboard the Wind Surf by Windstar Cruises departs St. Maarten (Philipsburg) on January 16, 2027, calling at Anguilla, Tortola Island BVI, Jost Van Dyke, and 9 more ports, and returns January 30, 2027. Cabin prices start from $8,310 per person.

Days
14 nights
Departs
Jan 16, 2027
Ports
12
Returns
Jan 30, 2027
Sea days
0
Distance
2,605nm
Itinerary
Embark Port Sea
Day 1
Jan 16
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
Jan 17
Anguilla
arr 08:00 · dep 18:00
Day 4
Jan 19
Day 5
Jan 20
Day 6
Jan 21
Gustavia St Barths, Saint-Barthelemy Island France
arr 08:00 · dep 22:00
Day 7
Jan 22
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 8
Jan 23
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 9
Jan 24
Charlestown Nevis, Nevis Island
arr 08:00 · dep 17:00
Day 10
Jan 25
Roseau, Dominica
arr 08:00 · dep 16:00
Day 11
Jan 26
Mayreau Island, Grenadines
arr 08:00 · dep 17:00
Day 12
Jan 27
Terra de Haut, Guadeloupe
arr 12:00 · dep 18:00
Day 13
Jan 28
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 14
Jan 29
Gustavia St Barths, Saint-Barthelemy Island France
arr 08:00 · dep 22:00
Day 15
Jan 30
Disembark
Loading map...
1Embark/Debark3Port of CallRoute
Distance
≈ 2,605nm
At sea
0 of 14 nights
Type
Round-trip
Price history

Ocean View cabin

$8,310▲ $2,711 (48.4%) vs Apr 16
Low
$5,599
High
$8,310
Average
$6,764
Vs avg
+23%
$5,327$6,141$6,955$7,768$8,582Apr 16Jul 6Sep 26$5,599 · Apr 16$5,719 · Apr 23$5,599 · Apr 24$5,719 · May 8$5,599 · May 9$5,856 · May 10$6,176 · May 18$6,296 · Jun 9$6,176 · Jun 10$6,296 · Jun 16$6,176 · Jun 17$6,626 · Jun 23$6,048 · Jun 26$6,636 · Jun 28$6,468 · Jul 10$6,832 · Jul 18$7,224 · Jul 24$7,308 · Jul 26$6,664 · Jul 30$7,084 · Aug 2$6,840 · Aug 7$6,728 · Aug 13$6,420 · Aug 22$8,170 · Aug 31$8,100 · Sep 3$7,680 · Sep 5$8,030 · Sep 12$7,820 · Sep 15$7,470 · Sep 16$8,030 · Sep 24$8,310 · Sep 26

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Other Caribbean (Eastern) departures

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Starting from
$8,310/person
Incl. taxes & port fees
Checked 2 days ago · Sep 26
Last change Sep 26: $8,030 → $8,310 (+$280)
Ocean View
$594/night
$8,310
Suite
$709/night
$9,920

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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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