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Cruise itinerary

14 night star collector leeward and windward caribbean havens

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

Departure date: Sunday, January 04, 2026
Return date: Sunday, January 18, 2026
Departure port: Philipsburg
Ports of call: Falmouth, Road Bay, Sopers Hole, Great Harbour, British Virgin Islands, St. Barts, Basseterre, St. John, Iles Des Saintes, Pigeon Island, Kingstown
Return port: Bridgetown

Prices:

Outside $4,373

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Suite $10,073

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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
Falmouth
4
Road Bay
5
Sopers Hole
6
Great Harbour
7
British Virgin Islands
8
St. Barts
9
Philipsburg
10
Basseterre
11
St. Barts
12
St. John
13
Iles Des Saintes
14
Pigeon Island
15
Kingstown
16
Bridgetown
17
Bridgetown

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.

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

Barbados flower fence.

A sea turtle swims off the coast of Barbados.

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

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

On the beach at the Hilton in Bridgetown on Barbados.

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

The view from St. James in Barbados.

Near Cupecoy Beach, St. Maarten.

Selling textiles in St. Maarten in the Caribbean.

The harbor at Bridgetown, capital of Barbados.

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

St. John Parish Church in Barbados.

A dramatic landscape on St. Maarten.

The sun sets on a catamaran on a quiet bay on Barbados.

The Animal Flower Cave is located under the cliffs at the Northern tip of Barbados.

Parliament building in Bridgetown, Barbados.

Crane beach on Barbados.