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 23, 2027, calling at Charlestown Nevis, Roseau, Mayreau Island, and 9 more ports, and returns February 6, 2027. Cabin prices start from $8,240 per person.

Days
14 nights
Departs
Jan 23, 2027
Ports
12
Returns
Feb 6, 2027
Sea days
0
Distance
2,605nm
Itinerary
Embark Port Sea
Day 1
Jan 23
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 24
Charlestown Nevis, Nevis Island
arr 08:00 · dep 17:00
Day 3
Jan 25
Roseau, Dominica
arr 08:00 · dep 16:00
Day 4
Jan 26
Mayreau Island, Grenadines
arr 08:00 · dep 17:00
Day 5
Jan 27
Terra de Haut, Guadeloupe
arr 12:00 · dep 18:00
Day 6
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 7
Jan 29
Gustavia St Barths, Saint-Barthelemy Island France
arr 08:00 · dep 22:00
Day 8
Jan 30
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 31
Anguilla
arr 08:00 · dep 18:00
Day 11
Feb 2
Day 12
Feb 3
Day 13
Feb 4
Gustavia St Barths, Saint-Barthelemy Island France
arr 08:00 · dep 22:00
Day 14
Feb 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
Feb 6
Disembark
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1Embark/Debark3Port of CallRoute
Distance
≈ 2,605nm
At sea
0 of 14 nights
Type
Round-trip
Price history

Ocean View cabin

$8,240▲ $2,441 (42.1%) vs Apr 16
Low
$5,796
High
$8,660
Average
$6,725
Vs avg
+23%
$5,509$6,369$7,228$8,088$8,947Apr 16Jul 6Sep 26$5,799 · Apr 16$6,016 · May 10$6,456 · May 18$6,336 · May 19$6,456 · Jun 9$6,336 · Jun 10$6,456 · Jun 16$6,336 · Jun 17$5,814 · Jun 20$5,796 · Jun 26$6,440 · Jun 28$6,720 · Jul 10$6,524 · Jul 18$6,412 · Jul 24$6,496 · Jul 26$6,616 · Jul 28$6,496 · Jul 29$6,804 · Aug 2$6,588 · Aug 22$6,840 · Aug 31$6,630 · Sep 4$6,560 · Sep 5$7,750 · Sep 11$8,100 · Sep 16$7,890 · Sep 19$8,660 · Sep 24$8,240 · Sep 26

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Other Caribbean (Eastern) departures

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Starting from
$8,240/person
Incl. taxes & port fees
Checked 2 days ago · Sep 26
Last change Sep 26: $8,660 → $8,240 (−$420)
Ocean View
$589/night
$8,240
Suite
$704/night
$9,850

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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