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 2, 2027, calling at Falmouth, Anguilla, Tortola Island BVI, and 9 more ports, and returns January 16, 2027. Cabin prices start from $6,420 per person.

Days
14 nights
Departs
Jan 2, 2027
Ports
12
Returns
Jan 16, 2027
Sea days
0
Distance
2,593nm
Itinerary
Embark Port Sea
Day 1
Jan 2
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 3
Falmouth, Jamaica
arr 08:00 · dep 18:00

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 3
Jan 4
Anguilla
arr 08:00 · dep 18:00
Day 5
Jan 6
Day 6
Jan 7
Day 7
Jan 8
Gustavia St Barths, Saint-Barthelemy Island France
arr 08:00 · dep 22:00
Day 8
Jan 9
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 10
Charlestown Nevis, Nevis Island
arr 08:00 · dep 17:00
Day 10
Jan 11
Terra de Haut, Guadeloupe
arr 07:00 · dep 13:00
Day 11
Jan 12
Mayreau Island, Grenadines
arr 08:00 · dep 17:00
Day 12
Jan 13
Roseau, Dominica
arr 08:00 · dep 16:00
Day 13
Jan 14
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 15
Gustavia St Barths, Saint-Barthelemy Island France
arr 08:00 · dep 22:00
Day 15
Jan 16
Disembark
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1Embark/Debark3Port of CallRoute
Distance
≈ 2,593nm
At sea
0 of 14 nights
Type
Round-trip
Price history

Ocean View cabin

$6,420▲ $1,121 (21.2%) vs Apr 16
Low
$3,516
High
$7,120
Average
$5,548
Vs avg
+16%
$3,155$4,237$5,318$6,400$7,481Apr 16Jul 6Sep 26$5,299 · Apr 16$5,599 · Apr 26$5,299 · May 1$5,599 · May 4$5,299 · May 5$5,616 · May 10$5,936 · May 11$5,616 · May 13$5,736 · May 15$5,616 · May 18$5,936 · Jun 2$4,088 · Jun 6$4,208 · Jun 9$4,088 · Jun 10$4,208 · Jun 12$4,088 · Jun 15$4,208 · Jun 16$4,088 · Jun 17$4,906 · Jun 19$3,516 · Jun 22$5,226 · Jun 24$3,516 · Jun 25$4,956 · Jun 26$5,068 · Jun 28$5,188 · Jul 1$5,068 · Jul 4$5,188 · Jul 5$5,068 · Jul 7$5,824 · Jul 10$5,944 · Jul 12$5,824 · Jul 13$6,112 · Jul 15$5,992 · Jul 16$5,404 · Jul 18$5,524 · Jul 19$5,404 · Jul 20$5,524 · Jul 21$5,404 · Jul 22$5,636 · Jul 24$6,151 · Jul 26$5,656 · Jul 27$6,160 · Jul 28$6,196 · Jul 30$6,076 · Jul 31$6,000 · Aug 1$5,600 · Aug 2$5,880 · Aug 3$3,941 · Aug 5$5,916 · Aug 7$5,468 · Aug 11$5,636 · Aug 13$6,140 · Aug 19$6,131 · Aug 22$5,636 · Aug 24$6,131 · Aug 26$5,636 · Aug 27$6,420 · Aug 31$6,978 · Sep 4$6,000 · Sep 5$6,560 · Sep 8$6,280 · Sep 10$6,840 · Sep 12$6,978 · Sep 15$7,120 · Sep 16$6,560 · Sep 17$6,420 · Sep 24$6,420 · Sep 26

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Starting from
$6,420/person
Incl. taxes & port fees
Checked 2 days ago · Sep 26
Last change Sep 24: $6,560 → $6,420 (−$140)
Ocean View
$459/night
$6,420
Suite
$569/night
$7,960

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
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