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Cruise itinerary

14 night star collector lovely leewards

Ask your friends: Should I go?

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

Departure date: Sunday, November 16, 2025
Return date: Sunday, November 30, 2025
Departure port: San Juan
Ports of call: Cruz Bay, Basseterre, St. Barts, Philipsburg, Great Harbour, British Virgin Islands, St. George's, Bequia, Pigeon Island, Iles Des Saintes
Return port: San Juan

Prices:

Suite $5,579

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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
San Juan
2
San Juan
3
Cruz Bay
4
Basseterre
5
St. Barts
6
Philipsburg
7
Great Harbour
8
British Virgin Islands
9
San Juan
10
St. George's
11
Bequia
12
Pigeon Island
13
Iles Des Saintes
14
Marigot
15
San Juan
16
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.

The New World's oldest governor's mansion is still in use. Some 150 consecutive governors have served over the past 300 years. It's at the west end of Calle Fortaleza in Old San Juan, Puerto Rico.

West of San Cristóbal along the coastline is the neighborhood of La Perla in Old San Juan, Puerto Rico. It's part of the area's UNESCO World Heritage Site.

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

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

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

Fort San Felipe del Morro in Old San Juan, Puerto Rico, a UNESCO World Heritage Site.

Selling textiles in St. Maarten in the Caribbean.

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

Near Cupecoy Beach, St. Maarten.

Guard bunks at historic Castillo de San Cristóbal in Old San Juan, Puerto Rico. Completed by Spanish forces in 1783, it was the largest fortification built by Spain in the New World.

Catedral Santiago Apóstol in Fajardo, along the northeast coast of Puerto Rico.

This bronze fountain "Raíces" (for "Roots") in Old San Juan celebrates Puerto Rico’s rich cultural diversity and historical heritage.

Isla Verde Beach, Puerto Rico.

A dramatic landscape on St. Maarten.

Avocado gazpacho at Toro Salao on Calle Tetuan in Old San Juan, Puerto Rico.

Colorful al fresco dining in Old San Juan, Puerto Rico.

Balconies on Calle San Sebastian in Old San Juan, Puerto Rico, a UNESCO World Heritage Site.

A swimming cove in the Condado neighborhood of Puerto Rico.