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Cruise itinerary

17 night star collector bermuda and caribbean island explorer

Ask your friends: Should I go?

Ship: Star Pride (details)
Cruise line: Windstar Cruises

Departure date: Friday, October 22, 2027
Return date: Monday, November 08, 2027
Departure port: Boston
Ports of call: Hamilton, St. George, Gustavia St. Barts, Prickly Pear British Virgin Islands, San Juan, Cruz Bay, Basseterre, Philipsburg
Return port: San Juan

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

Day Location

1
Boston
2
Boston
3
Hamilton
4
St. George
5
Gustavia St. Barts
6
Prickly Pear British Virgin Islands
7
San Juan
8
Cruz Bay
9
Basseterre
10
Gustavia St. Barts
11
Philipsburg
12
Great Harbour
13
Prickly Pear British Virgin Islands
14
San Juan
15
San Juan

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.

Businessmen in Hamilton, Bermuda, wearing — yes — Bermuda shorts. You'll spot the colorful, comfy shorts all around the island.

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.

Selling textiles in St. Maarten in the Caribbean.

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

Near Cupecoy Beach, St. Maarten.

The Fairmont Hamilton Princess Hotel overlooks picturesque Hamilton Harbor in Pembroke Parish, Bermuda.

Gombey dancers in Par-la-Ville Park, Hamilton, Bermuda.

A beach on Guadeloupe in the Caribbean.

A dramatic landscape on St. Maarten.

Historic Front Street in Hamilton, the capital of Bermuda.

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

An aerial view of popular Hamilton Harbor in Bermuda. Several cruise lines make stops here.