THE NEW SILVER SEA SHADOW LUXURY SHIP

The 7-Night Caribbean Roundtrip itinerary on Silversea's ultra-luxury ship, the Silver Shadow, departs from and returns to San Juan, Puerto Rico.


This boutique voyage focuses on smaller, less crowded boutique ports across the British Virgin Islands and the Lesser Antilles, taking full advantage of the ship's intimate 392-guest capacity. 



The 7-Night San Juan to San Juan holiday cruise on the Silver Shadow departs on Sunday, December 20, 2026, and returns on Sunday, December 27, 2026. [1]


Quick Facts & Pricing

  • Ship: Silver Shadow (Silversea Cruises)
  • Dates: December 20 – December 27, 2026
  • Starting Price: $2,880 USD per person 

Your Holiday Itinerary Flow

Because this cruise sails over Christmas week, it features a slightly modified, relaxed pacing with an added day at sea compared to standard winter rotations: 

  • Dec 20 (Sun): Embarkation in San Juan, Puerto Rico

  • Dec 21 (Mon): Jost Van Dyke, British Virgin Islands

  • Dec 22 (Tue): Little Bay, Montserrat

  • Dec 23 (Wed): Castries, St. Lucia (Replaces St. John's, Antigua for this sailing)

  • Dec 24 (Thu): Fort-de-France, Martinique

  • Dec 25 (Fri): Day at Sea (Christmas Day) – Enjoy festive dining, champagne, and open-deck relaxation while cruising the Caribbean Sea.

  • Dec 26 (Sat): Soper's Hole (Tortola), British Virgin Islands

  • Dec 27 (Sun): Disembarkation in San Juan, Puerto Rico


  • Jost Van Dyke, B.V.I. – Renowned for its laid-back vibe and Great Harbour. It is home to the world-famous Soggy Dollar Bar in White Bay. 
  • Little Bay, Montserrat – A highly unique cruise stop. Visitors can view the modern "Pompeii of the Caribbean"—the buried former capital of Plymouth, altered by the Soufrière Hills volcano. 
  • St. John's, Antigua – Known for its 365 beaches, colonial history, and nearby Nelson's Dockyard. 
  • Fort-de-France, Martinique – Offers a distinct French-Creole flair, excellent gastronomy, historical fortresses, and access to local rainforests. 
  • Soper's Hole, Tortola, B.V.I. – Located on the quiet West End of Tortola. This colorful, upscale marina features West Indian architecture, boutique shopping, and easy ferry access to nearby bays.


The Silver Shadow Experience

As an ultra-luxury product, booking this itinerary through platforms like Silversea Official or booking partners includes:

  • All-Suite Accommodations: Ocean-view layouts, with a vast majority featuring private teak verandas. 

  • Butler Service: Dedicated butler service assigned to every single suite onboard. 

  • All-Inclusive Fare: Complimentary fine wines, premium spirits, specialty coffees, and soft drinks throughout the ship. Gratuties are entirely included. 

  • Open-Seating Dining: Fine dining venues like La Terrazza (Italian) and The Grill (outdoor stone cooking), alongside 24-hour in-suite dini

SUITES

Silversea's oceanview suites are some of the most spacious in luxury cruising.

All include the services of a butler thanks to the highest service ratio at sea and almost all have a private teak veranda so that you can breathe in the fresh sea air by merely stepping outside your door. 

THE SILVER  SEA  CRUISE EXPERIENCE