14-Night CARIBBEAN CRUISE

Wind Surf

This 14-night Caribbean (Eastern) cruise aboard the Wind Surf by Windstar Cruises departs St. Maarten (Philipsburg) on February 6, 2027, calling at Charlestown Nevis, Roseau, Mayreau Island, and 9 more ports, and returns February 20, 2027. Cabin prices start from $6,980 per person.

Days
14 nights
Departs
Feb 6, 2027
Ports
12
Returns
Feb 20, 2027
Sea days
0
Distance
2,593nm
Itinerary
Embark Port Sea
Day 1
Feb 6
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.

Read more →
Day 2
Feb 7
Charlestown Nevis, Nevis Island
arr 08:00 · dep 17:00
Day 3
Feb 8
Roseau, Dominica
arr 08:00 · dep 16:00
Day 4
Feb 9
Mayreau Island, Grenadines
arr 08:00 · dep 17:00
Day 5
Feb 10
Terra de Haut, Guadeloupe
arr 12:00 · dep 18:00
Day 6
Feb 11
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.

Read more →
Day 7
Feb 12
Gustavia St Barths, Saint-Barthelemy Island France
arr 08:00 · dep 22:00
Day 8
Feb 13
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.

Read more →
Day 9
Feb 14
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.

Read more →
Day 10
Feb 15
Anguilla
arr 08:00 · dep 18:00
Day 12
Feb 17
Day 13
Feb 18
Day 14
Feb 19
Gustavia St Barths, Saint-Barthelemy Island France
arr 08:00 · dep 22:00
Day 15
Feb 20
Disembark
Loading map...
1Embark/Debark3Port of CallRoute
Distance
≈ 2,593nm
At sea
0 of 14 nights
Type
Round-trip
Price history

Ocean View cabin

$6,980▲ $1,181 (20.4%) vs Apr 16
Low
$5,768
High
$7,120
Average
$6,313
Vs avg
+11%
$5,632$6,038$6,444$6,850$7,256Apr 16Jul 6Sep 26$5,799 · Apr 16$6,099 · May 6$6,336 · May 10$6,016 · May 11$6,336 · May 21$6,136 · May 28$6,016 · May 29$6,456 · May 30$6,336 · May 31$6,016 · Jun 6$6,136 · Jun 9$6,016 · Jun 10$6,136 · Jun 16$6,016 · Jun 17$6,962 · Jun 20$6,300 · Jun 26$6,412 · Jun 28$6,532 · Jun 29$6,412 · Jul 1$6,532 · Jul 3$6,412 · Jul 4$6,720 · Jul 8$5,888 · Jul 9$5,768 · Jul 10$6,196 · Jul 11$6,076 · Jul 12$6,196 · Jul 14$5,888 · Jul 15$6,076 · Jul 17$6,216 · Jul 18$6,028 · Jul 19$5,908 · Jul 20$6,028 · Jul 21$5,908 · Jul 22$6,300 · Jul 24$6,244 · Jul 26$6,216 · Jul 30$6,692 · Aug 2$6,504 · Aug 13$6,168 · Aug 22$6,350 · Aug 31$6,840 · Sep 4$6,770 · Sep 5$6,840 · Sep 11$6,770 · Sep 16$7,120 · Sep 20$6,910 · Sep 24$6,980 · Sep 26

New to these charts? How to read cruise price history

Similar sailings

Other Caribbean (Eastern) departures

View all →
Starting from
$6,980/person
Incl. taxes & port fees
Checked 2 days ago · Sep 26
Last change Sep 26: $6,910 → $6,980 (+$70)
Ocean View
$499/night
$6,980
Suite
$604/night
$8,450

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 →
Book this cruiseInstant checkout

We may earn a commission when you book through this link, at no extra cost to you.