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Cruise itinerary

11 night masterpieces at sea gems of the leeward islands

Ask your friends: Should I go?

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

Departure date: Wednesday, October 28, 2026
Return date: Sunday, November 08, 2026
Departure port: San Juan (Puerto Rico)
Ports of call: Cruz Bay- St. John- U.S. Virgin Isl, St. Barts/Gustavia, French West Indies, Basseterre, Falmouth, Iles Des Saintes (Guadeloupe), Pigeon Island, St. George's- Grenada, Great Harbour (British Virgin Islands)
Return port: San Juan (Puerto Rico)

Prices:

Outside $4,257

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Balcony $6,677

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Suite $9,157

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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 (Puerto Rico)
2
San Juan (Puerto Rico)
3
Cruz Bay- St. John- U.S. Virgin Isl
4
St. Barts/Gustavia, French West Indies
5
Basseterre
6
Falmouth
7
Iles Des Saintes (Guadeloupe)
8
Pigeon Island
9
St. George's- Grenada
10
Great Harbour (British Virgin Islands)
11
British Virgin Islands
12
San Juan (Puerto Rico)
13
San Juan (Puerto Rico)

Go street shopping in St. Barthélemy (aka St. Barts or St. Barths) during a shore excursion on your Windstar cruise.

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

Necker Island in a sea of turquoise, near Virgin Gorda in the British Virgin Islands.

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.

The cliffs of La Trace des Falaises on Grand Terre, Guadeloupe.

Gather a group to kayak the peaceful waters of St. John in the U.S. Virgin Islands.

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.

The Baths on Punta Gorda in the British Virgin Islands.

Swanky Saba Rock Resort in the British Virgin Islands.

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

The overlook at Trunk Bay, with its vivid vista of jungle and water, may be one of your top highlights when visting St. John in the U.S. Virgin Islands.

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

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.

A beach on Guadeloupe in the Caribbean.

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.

Anagarda in the British Virgin Islands

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.

Seven Sisters Waterfalls on Grenada.