Sleeping under a palm tree, strolling on endless beaches and eating ice cream while floating in a turquoise sea. What could be further from your everyday world? When you sail the Caribbean you'll discover how relaxing, entertaining and just plain fun a week really can be. Visit a variety of beautiful islands and escape to paradise on your next vacation.
Book with a professional travel advisor and you may unlock more than what appears in a standard online search. Depending on the supplier and trip, your advisor may have access to preferred or agency-negotiated group rates, special promotions, upgrades, onboard or resort credits, and other added-value benefits that are not always available through direct booking.
During our consultation, we may ask for a few details—such as your country or state of residence, ZIP code, age eligibility, military status, past-guest history, or loyalty memberships. These details can help us identify fares and benefits you may qualify for and compare them against publicly available options.
Not every offer applies to every traveler, and availability varies by supplier, destination, sailing, travel dates, and eligibility. But the more we know about your trip and the qualifications that may apply to you, the more thoroughly we can search for opportunities to enhance your vacation and help you secure the best available overall value not just the first price you see online.
Recent price found was as low as: $6,700 per person. Port charges, taxes, and fees included
Itinerary Overview
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Day 1 · San Juan, Puerto Rico
San Juan, Puerto Rico
Depart 7:00 pm
The fortress of El Morro guards the harbor against long-gone Sir Francis Drake and his British privateers. The colorful streets of Old San Juan retain the Latin flavor of its seafaring past, when this was the heart of the Spanish Main. Sample the fiery rum made here, or indulge in an icy treat made from fresh tropical fruit and enjoy the Caribbean atmosphere.
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Day 2 · Jost Van Dyke, British Virgin Islands
Jost Van Dyke, British Virgin Islands
Arrive 8:00 am · Depart 6:00 pm
If you''re looking for the ultimate laid back island adventure, Jost Van Dyke is the island for you. Jost Van Dyke has amazing beaches, appetizing restaurants, and tempting bars for your indulging pleasure. This four mile long island is known as the "barefoot" island for its casual inviting atmosphere.
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Day 3 · Little Bay, Montserrat, Leeward Islands
Little Bay, Montserrat, Leeward Islands
Arrive 9:00 am · Depart 6:30 pm
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Day 4 · Castries, St. Lucia
Castries, St. Lucia
Arrive 8:30 am · Depart 6:00 pm
Just recently, St. Lucia, and Castries in particular, has become one of the most popular regions for tourists. The accommodations and facilities are top of the line, and the restaurants and activities fabulous. The majority of travelers reside between Castries, which is the capital of St. Lucia, and the northern end of the island. The entire north side of the island is comprised of white-sand beaches to dazzle even the most seasoned and experienced traveler.
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Day 5 · Canouan
Canouan
Arrive 1:00 pm · Depart 10:00 pm
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Day 6 · Day at sea
Day at sea
Depart 12:00 am
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Day 7 · Sopers Hole
Sopers Hole
Arrive 8:00 am · Depart 6:00 pm
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Day 8 · San Juan, Puerto Rico
San Juan, Puerto Rico
Arrive 7:00 am · Depart 12:00 am
The fortress of El Morro guards the harbor against long-gone Sir Francis Drake and his British privateers. The colorful streets of Old San Juan retain the Latin flavor of its seafaring past, when this was the heart of the Spanish Main. Sample the fiery rum made here, or indulge in an icy treat made from fresh tropical fruit and enjoy the Caribbean atmosphere.
Route Illustration - Actual route may differ
Highlights
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Sail aboard Silver Shadow.
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Travel from 2026-12-20 through 2026-12-27.
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Visit San Juan, Puerto Rico, Jost Van Dyke, British Virgin Islands, Little Bay, Montserrat, Leeward Islands, Castries, St. Lucia, Fort-de-France, Martinique.
Recently found pricing
Cabin pricing snapshot
Recent cabin prices we found for this sailing. Pricing is shown per person and may change at any time.
Cabin Types
Inside
Not currently available — cabin inventory may change.
Oceanview
Not currently available — cabin inventory may change.
Balcony
Not currently available — cabin inventory may change.
SuiteRecently found from $6,700 per person
Port charges, taxes, and fees included
Final taxes, fees, promotions, or availability can change.
Additional Information
Price, availability, taxes, fees, promotions, occupancy requirements, and final cabin availability can change until booked. When you book travel through a professional travel advisor, suppliers often provide exclusive value-adds, upgrades, and promotions that are unavailable when booking directly online. These unadvertised or agency-exclusive perks vary by vendor and destination.
Gallery
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Route Illustration - Actual route may differ
Tags
allcruiseCaribbeanSilversea CruisesSilver ShadowSan Juan, Puerto Rico