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 9, 2027, calling at Charlestown Nevis, Terra de Haut, Mayreau Island, and 9 more ports, and returns January 23, 2027. Cabin prices start from $7,330 per person.

Days
14 nights
Departs
Jan 9, 2027
Ports
12
Returns
Jan 23, 2027
Sea days
0
Distance
2,605nm
Itinerary
Embark Port Sea
Day 1
Jan 9
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 10
Charlestown Nevis, Nevis Island
arr 08:00 · dep 17:00
Day 3
Jan 11
Terra de Haut, Guadeloupe
arr 07:00 · dep 13:00
Day 4
Jan 12
Mayreau Island, Grenadines
arr 08:00 · dep 17:00
Day 5
Jan 13
Roseau, Dominica
arr 08:00 · dep 16:00
Day 6
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 7
Jan 15
Gustavia St Barths, Saint-Barthelemy Island France
arr 08:00 · dep 22:00
Day 8
Jan 16
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 17
Anguilla
arr 08:00 · dep 18:00
Day 11
Jan 19
Day 12
Jan 20
Day 13
Jan 21
Gustavia St Barths, Saint-Barthelemy Island France
arr 08:00 · dep 22:00
Day 14
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 15
Jan 23
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

$7,330▲ $1,931 (35.8%) vs Apr 16
Low
$4,648
High
$7,820
Average
$5,960
Vs avg
+23%
$4,330$5,282$6,234$7,186$8,138Apr 16Jul 6Sep 26$5,399 · Apr 16$6,217 · Apr 21$5,399 · Apr 22$5,696 · May 10$4,648 · Jun 6$4,768 · Jun 9$4,648 · Jun 10$5,048 · Jun 15$5,626 · Jun 16$4,928 · Jun 17$6,066 · Jun 23$5,544 · Jun 26$5,684 · Jun 28$5,796 · Jul 10$6,020 · Jul 18$6,132 · Jul 24$6,160 · Jul 26$5,460 · Jul 30$5,824 · Aug 2$5,608 · Aug 7$5,776 · Aug 13$5,468 · Aug 22$7,820 · Aug 31$7,400 · Sep 4$6,700 · Sep 5$6,840 · Sep 12$6,700 · Sep 15$6,210 · Sep 16$6,700 · Sep 17$6,350 · Sep 19$6,770 · Sep 24$7,330 · Sep 26

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Other Caribbean (Eastern) departures

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Starting from
$7,330/person
Incl. taxes & port fees
Checked 2 days ago · Sep 26
Last change Sep 26: $6,770 → $7,330 (+$560)
Ocean View
$524/night
$7,330
Suite
$594/night
$8,310

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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