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Cruise itinerary

8 night beach fun and sun a remote caribbean getaway

Ask your friends: Should I go?

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

Departure date: Sunday, December 19, 2027
Return date: Monday, December 27, 2027
Departure port: Philipsburg
Ports of call: St John's, Gustavia St. Barts, Road Bay, Sopers Hole, Great Harbour, Prickly Pear British Virgin Islands
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 John's
4
Gustavia St. Barts
5
Road Bay
6
Sopers Hole
7
Great Harbour
8
Prickly Pear British Virgin Islands
9
Charlestown
10
Philipsburg
11
Philipsburg

You can rent a car in Philipsburg to more fully explore St. Maarten.

A rocky beach on St. Maarten.

As the sun sets on St. Maarten, visitors take one last leap into the sea.

A dramatic landscape on St. Maarten.

The methodist church of Philipsburg, St. Maarten.

Try your luck at one of St. Maarten's three casinos.

Segways are available for rental in Philipsburg, St. Maarten.

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

Shopping on Front Street in Philipsburg, St. Maarten.

A cigar rolling demonstration in St. Maarten.

Catamaran tour of St. Maarten.

Shopping at the Marigot Market in St. Maarten.

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

The beautiful aquamarine waters of St. Maarten.

Near Cupecoy Beach in St. Maarten.

Visitors explore hilltop ruins on St. Maarten.

Sun, sand and surf on St. Maarten.

Near Cupecoy Beach, St. Maarten.

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

A couple near Cupecoy Beach in St. Maarten.