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Cruise itinerary

7 night classic caribbean

Ask your friends: Should I go?

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

Departure date: Sunday, December 21, 2025
Return date: Sunday, December 28, 2025
Departure port: Philipsburg
Ports of call: Charlestown, Roseau, Pigeon Island, Iles Des Saintes, St. Barts
Return port: Philipsburg

Prices:

Outside $2,751

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Suite $5,651

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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
Charlestown
4
Roseau
5
Pigeon Island
6
Iles Des Saintes
7
St. Barts
8
Basseterre
9
Philipsburg
10
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.

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

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

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

Near Cupecoy Beach, St. Maarten.

Selling textiles in St. Maarten in the Caribbean.

A beach on Guadeloupe in the Caribbean.

A dramatic landscape on St. Maarten.

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