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Cruise itinerary

14 night star collector caribbean explorations

Ask your friends: Should I go?

Ship: Wind Surf (details)
Cruise line: Windstar Cruises

Departure date: Saturday, December 26, 2026
Return date: Saturday, January 09, 2027
Departure port: Philipsburg
Ports of call: St. Barts, Charlestown, Roseau, Mayreau, Iles Des Saintes, Basseterre, Falmouth, Road Bay, Sopers Hole, Great Harbour
Return port: Philipsburg

Cruiseable's travel advisors can often find you additional savings & lower fares than the public prices listed here.

Day Location

1
Philipsburg
2
Philipsburg
3
St. Barts
4
Charlestown
5
Roseau
6
Mayreau
7
Iles Des Saintes
8
Basseterre
9
Philipsburg
10
Falmouth
11
Road Bay
12
Sopers Hole
13
Great Harbour
14
British Virgin Islands
15
St. Barts
16
Philipsburg
17
Philipsburg

Visitors jumping from rocks to the sea in St. Maarten.

Want an adrenaline rush? Head to Loterie Farm for a zipline adventure on St. Maarten.

The bridge over the river Galion on the tropical island of Guadeloupe.

A vendor selling pepper shrimp in Jamaica.

Fort Louis Delgrès in Basse-Terre, capital of Guadeloupe.

Rent a bike and take to the road on St. Maarten.

Grab a towel and hit the beautiful beaches of St. Maarten.

Gotta have nectar! An electric green-colored hummingbird in Jamaica.

A tropical flower in Jamaica.

A beach on Guadeloupe in the Caribbean.

Near Cupecoy Beach, St. Maarten.

Selling textiles in St. Maarten in the Caribbean.

A scene along the beach and tropical waters of Falmouth, a popular cruise destination in Jamaica.

For a snack try some tasty Jamaican plantain tarts (they look like turnovers but the locals call them tarts).

A dramatic landscape on St. Maarten.

One of the beautiful beaches in Basse-Terre, Guadeloupe.

White Witch Golf Course near Falmouth, Jamaica.

A couple watches one of Jamaica's scenic sunsets.