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: $7,300 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 · Cruz Bay, St. John, U.S. Virgin Islands
Cruz Bay, St. John, U.S. Virgin Islands
Arrive 8:00 am · Depart 6:00 pm
The yacht-filled harbor of Cruz Bay hugs a tiny strip of land between the mountains and the sea. This is your entree to the pristine island sanctuary of tiny St. John, the most beautiful of the Virgin Islands, surrounded by some of the most spectacular aquamarine waters in the Caribbean.
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Day 3 · Port of Basseterre, St. Kitts, St. Kitts and Nevis
Port of Basseterre, St. Kitts, St. Kitts and Nevis
Arrive 8:00 am · Depart 6:00 pm
This fertile isle is a land of rain forests, tropical flowers, and abundant sugar cane. After a stroll around the charming colonial streets and shops of the capital, Basseterre, tour the island or visit Brimstone Hill Fort, an impressive construction that is one of the wonders of the Caribbean world.
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Day 4 · Iles des Saintes, Guadeloupe
Iles des Saintes, Guadeloupe
Arrive 8:00 am · Depart 5:00 pm
Guadeloupe is the southernmost of the Leeward Islands, just north of the Windward Islands, where Martinique is found...These islands are the perfect place to relax.
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Day 5 · Bequia, Grenadines
Bequia, Grenadines
Arrive 8:00 am · Depart 6:00 pm
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Day 6 · Day at sea
Day at sea
Depart 12:00 am
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Day 7 · St. Thomas, U.S. Virgin Islands
St. Thomas, U.S. Virgin Islands
Arrive 8:00 am · Depart 6:00 pm
Prior to the arrival of the Europeans, the island of St. Thomas was once inhabited by the Ciboney tribes around 1500 BC along with two other tribes, the Taino or Arawaks and the Caribs. Even today you will be able to find evidence of these late tribes. Also before the European began to form a colony on this island, pirates once roam this island. The most common stories of pirates usually include the names of Blackbeard and Bluebeard who have been known for thieving Spanish ships filled with gold coins and other valuables. In 1917, the Danish flag was a thing of the past and the flag of the United States is a thing of the present. Due to the beauty of this island, breath taking attractions are everywhere you look. This island is equipped with historical sites such as the Charlotte Amalie to marine parks and beautiful botanical gardens throughout the island. During your visit make sure you indulge in the Nightlife full of calypso music for your listening pleasure as well as great restaurants for your dining pleasure and semi-block parties for your dancing delight.
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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 2026-12-27 through 2027-01-03.
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Visit San Juan, Puerto Rico, Cruz Bay, St. John, U.S. Virgin Islands, Port of Basseterre, St. Kitts, St. Kitts and Nevis, Iles des Saintes, Guadeloupe, Bequia, Grenadines, St. Thomas, U.S. Virgin Islands.
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 $7,300 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