14-night Eastern Caribbean Featuring Les Saintes & St. Barts Cruise From San Juan, Puerto Rico

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A panoramic view of Gustavia, Saint Barthélemy, featuring a bay filled with luxury yachts and sailboats, framed by lush, green hillsides dotted with houses.
Silversea Cruises Silver Shadow cruise ship exterior
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Sailing Dec 23, 2028 - Jan 27, 2029

Your 14-night Caribbean Cruise at a Glance

Sailings aboard Silver Shadow depart from San Juan, Puerto Rico with 10 stops in ports-of-call including St. John (U.S.V.I.), Iles des Saintes, and Virgin Gorda. The Cruise Web can help you find the best deals and stateroom prices on any of the 2 upcoming sailings in 2028 and 2029.

Departure Port

San Juan, Puerto Rico

A lively Caribbean departure hub where historic streets, oceanfront fortresses, and vibrant island culture create the perfect start to your cruise vacation. Before you depart San Juan, Puerto Rico, we can help you plan travel and accommodations for your Caribbean cruise.

Destination

Caribbean

Stops on your Caribbean voyage will include St. John (U.S.V.I.) on day 2 and Basseterre, St. Kitts on day 14. We can help you with excursions and making the most of any itinerary.

Cruise Ship

Silver Shadow

Silver Shadow, built in 2000 and refurbished in 2019, carries 388 passengers with a crew of 302.

Silversea's luxurious small-ship cruises and expedition voyages sail the world for unique and in-depth experiences in remote locales. We can help you maximize deals on Caribbean cruises aboard Silver Shadow or 11 of Silversea’s other ships.