14-Night CARIBBEAN CRUISE

Wind Surf

This 14-night Caribbean (Eastern) cruise aboard the Wind Surf by Windstar Cruises departs St. Maarten (Philipsburg) on December 26, 2026, calling at Gustavia St Barths, Charlestown Nevis, Roseau, and 9 more ports, and returns January 9, 2027. Cabin prices start from $7,960 per person.

Days
14 nights
Departs
Dec 26, 2026
Ports
12
Returns
Jan 9, 2027
Sea days
0
Distance
2,592nm
Itinerary
Embark Port Sea
Day 1
Dec 26
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
Dec 27
Gustavia St Barths, Saint-Barthelemy Island France
arr 08:00 · dep 22:00
Day 3
Dec 28
Charlestown Nevis, Nevis Island
arr 08:00 · dep 17:00
Day 4
Dec 29
Roseau, Dominica
arr 08:00 · dep 16:00
Day 5
Dec 30
Mayreau Island, Grenadines
arr 08:00 · dep 17:00
Day 6
Dec 31
Terra de Haut, Guadeloupe
arr 12:00 · dep 18:00
Day 7
Jan 1
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 8
Jan 2
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 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 10
Jan 4
Anguilla
arr 08:00 · dep 18:00
Day 12
Jan 6
Day 13
Jan 7
Day 14
Jan 8
Gustavia St Barths, Saint-Barthelemy Island France
arr 08:00 · dep 22:00
Day 15
Jan 9
Disembark
Loading map...
1Embark/Debark3Port of CallRoute
Distance
≈ 2,592nm
At sea
0 of 14 nights
Type
Round-trip
Price history

Ocean View cabin

$7,960▲ $2,561 (47.4%) vs Apr 16
Low
$4,340
High
$8,380
Average
$5,807
Vs avg
+37%
$3,936$5,148$6,360$7,572$8,784Apr 16Jul 6Sep 26$5,399 · Apr 16$5,691 · May 10$6,011 · May 11$5,691 · May 13$6,011 · May 28$4,340 · Jun 6$4,460 · Jun 9$4,340 · Jun 10$4,460 · Jun 16$4,340 · Jun 17$5,473 · Jun 20$5,320 · Jun 26$5,740 · Jul 10$5,860 · Jul 13$5,936 · Jul 15$5,740 · Jul 18$5,580 · Jul 19$5,964 · Jul 22$5,580 · Jul 23$5,664 · Jul 24$6,048 · Jul 26$6,020 · Jul 30$5,936 · Aug 2$5,608 · Aug 7$5,916 · Aug 13$5,440 · Aug 22$5,160 · Aug 31$5,090 · Sep 4$5,510 · Sep 6$6,840 · Sep 12$7,680 · Sep 16$8,380 · Sep 20$8,240 · Sep 24$7,960 · Sep 26

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Other Caribbean (Eastern) departures

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Starting from
$7,960/person
Incl. taxes & port fees
Checked 2 days ago · Sep 26
Last change Sep 26: $8,240 → $7,960 (−$280)
Ocean View
$569/night
$7,960
Suite
$679/night
$9,500

Track prices

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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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