14-Night CARIBBEAN CRUISE

Name: 14-Night Windstar Cruises Cruise from St. Maarten (Philipsburg) on Wind Surf
Brand: Windstar Cruises
Price: 8030 USD
Availability: InStock

Dec 19, 2026 – Jan 2, 2027·14 nights·Wind Surf

This 14-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 9 more ports, and returns January 2, 2027. Cabin prices start from $8,030 per person.

Days

14 nights

Departs

Dec 19, 2026

Ports

Returns

Jan 2, 2027

Sea days

Distance

2,591nm

Itinerary

Embark Port Sea

Day 1

Dec 19

Embark

St. Maarten (Philipsburg)

dep depart 19:00

St. Maarten cruise port is one of the busiest in the Caribbean, with ships docking at the A.C.

Day 2

Dec 20

Gustavia St Barths, Saint-Barthelemy Island France

arr arrive 08:00 · dep depart 22:00

Day 3

Dec 21

Falmouth, Jamaica

arr arrive 08:00 · dep depart 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.

Day 4

Dec 22

Anguilla

arr arrive 08:00 · dep depart 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 depart 22:00

Day 7

Dec 25

Virgin Gorda Island BVI, Spanish Town, UK Virgin Islands

arr arrive 08:00 · dep depart 17:00

Day 8

Dec 26

St. Maarten (Philipsburg)

arr arrive 06:00 · dep depart 19:00

St. Maarten cruise port is one of the busiest in the Caribbean, with ships docking at the A.C.

Day 9

Dec 27

Gustavia St Barths, Saint-Barthelemy Island France

arr arrive 08:00 · dep depart 22:00

Day 10

Dec 28

Charlestown Nevis, Nevis Island

arr arrive 08:00 · dep depart 17:00

Day 11

Dec 29

Roseau, Dominica

arr arrive 08:00 · dep depart 16:00

Day 12

Dec 30

Mayreau Island, Grenadines

arr arrive 08:00 · dep depart 17:00

Day 13

Dec 31

Terra de Haut, Guadeloupe

arr arrive 12:00 · dep depart 18:00

Day 14

Jan 1

Basseterre St Kitts, Port Zante

arr arrive 08:00 · dep depart 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.

Day 15

Jan 2

Disembark

St. Maarten (Philipsburg)

arr arrive 06:00

Loading map...

1Embark/Debark3Port of CallRoute

Distance

≈ 2,591nm

At sea

0 of 14 nights

Type