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Caribbean (Eastern)

7 Night Caribbean Cruise

Wind Surf

This 7-night Caribbean (Eastern) cruise aboard the Wind Surf by Windstar Cruises departs St. Maarten (Philipsburg) on December 19, 2026, calling at Gustavia St Barths, Falmouth, Anguilla, and 3 more ports, and returns December 26, 2026. Cabin prices start from $3,708 per person.

Days
7 nights
Departs
Dec 19, 2026
Ports
7
Returns
Dec 26, 2026
Sea days
0
Distance
1,889nm
Itinerary
Embark Port Sea
Day 1
Dec 19
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 20
Gustavia St Barths, Saint-Barthelemy Island France
arr 08:00 · dep 22:00
Day 3
Dec 21
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 4
Dec 22
Anguilla
arr 08:00 · dep 18:00
Day 5
Dec 23
Tortola Island BVI, Road Town, UK Virgin Islands08:00 – 18:00
Jost Van Dyke, British Virgin Islands
Day 6
Dec 24
Jost Van Dyke, British Virgin Islands
dep 22:00
Day 7
Dec 25
Virgin Gorda Island BVI, Spanish Town, UK Virgin Islands
arr 08:00 · dep 17:00
Day 8
Dec 26
Disembark
St. Maarten (Philipsburg)
arr 06:00
Loading map...
1Embark/Debark3Port of CallRoute
Distance
≈ 1,889nm
At sea
0 of 7 nights
Type
Round-trip
Price history

Ocean View cabin

$3,708▲ $109 (3%) vs Mar 9
Low
$1,881
High
$4,303
Average
$3,005
Vs avg
+23%
$1,638$2,365$3,092$3,819$4,546Mar 9Jun 17Sep 26$3,599 · Mar 9$3,667 · Mar 17$3,599 · Mar 18$3,667 · Mar 24$3,599 · Mar 25$3,667 · Mar 31$3,599 · Apr 1$3,199 · Apr 2$3,267 · Apr 16$3,199 · Apr 17$3,267 · Apr 24$3,199 · Apr 25$3,267 · Apr 29$3,199 · Apr 30$3,267 · May 3$3,199 · May 4$2,625 · May 8$2,693 · May 16$2,625 · May 18$2,693 · May 19$2,625 · May 20$2,730 · May 31$2,798 · Jun 9$2,730 · Jun 10$2,798 · Jun 15$2,730 · Jun 16$2,870 · Jun 19$2,938 · Jun 20$2,870 · Jun 22$3,113 · Jun 25$3,045 · Jun 26$3,113 · Jun 29$3,045 · Jun 30$3,113 · Jul 1$3,045 · Jul 4$3,078 · Jul 9$3,010 · Jul 10$2,001 · Jul 11$2,975 · Jul 12$2,940 · Jul 15$1,979 · Jul 17$2,870 · Jul 18$2,229 · Jul 19$1,979 · Jul 20$3,008 · Jul 22$1,979 · Jul 23$2,077 · Jul 24$2,420 · Jul 25$2,352 · Jul 26$1,979 · Jul 27$1,881 · Jul 28$2,092 · Jul 29$2,560 · Jul 30$2,092 · Aug 3$2,183 · Aug 5$3,183 · Aug 7$3,603 · Aug 9$2,267 · Aug 11$2,502 · Aug 12$3,813 · Aug 14$2,502 · Aug 15$4,058 · Aug 19$4,163 · Aug 22$2,729 · Aug 24$4,163 · Aug 26$3,953 · Aug 27$2,684 · Aug 31$2,775 · Sep 3$4,303 · Sep 5$4,233 · Sep 11$2,775 · Sep 14$4,093 · Sep 16$4,023 · Sep 19$3,498 · Sep 24$3,708 · Sep 26

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Starting from
$3,708/person
Incl. taxes & port fees
Checked 2 days ago · Sep 26
Last change Sep 26: $3,498 → $3,708 (+$210)
Ocean View
$530/night
$3,708
Suite
$650/night
$4,548

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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
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