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Cruise itinerary

14 night star collector lovely leewards

Ask your friends: Should I go?

  • Departure date: Sunday, November 15, 2026
  • Return date: Sunday, November 29, 2026
  • Departure port: San Juan (Puerto Rico)
  • Ports of call: Cruz Bay- St. John- U.S. Virgin Isl, Basseterre, St. Barts/Gustavia, French West Indies, Philipsburg, Great Harbour (British Virgin Islands), British Virgin Islands, St. George's- Grenada, Bequia, Mayreau, Iles Des Saintes (Guadeloupe)
  • Return port: San Juan (Puerto Rico)

Prices:

  • Outside $5,393
  • Balcony $7,813
  • Suite $10,293

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

Day Location
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 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.
Rent a bike and take to the road on St. Maarten.
Grab a towel and hit the beautiful beaches of 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.
Anagarda in the British Virgin Islands
Colorful al fresco dining in Old San Juan, Puerto Rico.
Near Cupecoy Beach, St. Maarten.
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.
A dramatic landscape on St. Maarten.
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.
Selling textiles in St. Maarten in the Caribbean.

Cruise line partners

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