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: $4,150 per person. Port charges, taxes, and fees included
Itinerary Overview
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Day 1 · Miami, Florida
Miami, Florida
Depart 6:00 pm
Discover the cosmopolitan beauty of Miami along Florida's fabled Gold Coast. Stroll through carefully preserved Art Deco neighborhoods and witness the trendy lifestyle that is South Beach. Enjoy open-air shopping in the Bayside Marketplace and shop for a bite to eat in Coconut Grove, with its harborside cafes and quaint, artistic settings.
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Day 2 · Day at sea
Day at sea
Depart 12:00 am
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Day 3 · Day at sea
Day at sea
Depart 12:00 am
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Day 4 · Cruz Bay, St. John, U.S. Virgin Islands
Cruz Bay, St. John, U.S. Virgin Islands
Arrive 1:00 pm · Depart 7:00 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 5 · Philipsburg, St. Maarten
Philipsburg, St. Maarten
Arrive 8:00 am · Depart 6:00 pm
Dutch St. Maarten is a great place to stop just to shop. Its capital is Philipsburg and fills a narrow stretch of land between Great Bay and the Great Salt Pond. It is a bustling center of international trade with lively shopping streets, cafes, and hotels. Strangely enough it has two main streets called Front Street and Back Street. On Front Street, which is the main thoroughfare, duty-free shops line the road as far as the eye can see. These duty-free shops offer everything from Italian leather goods and Japanese cameras to native crafts. Don't be afraid to venture the alleyways that will lead you to arcades and courtyards filled with flowers. The Courthouse is the most prominent landmark on Front Street. It is a grand white wooden structure topped with a cupola built in 1793. Front Street also includes the Simartin Museum so that visitors can get and excellent introduction to local St. Maartin history. There are also historical forts that are monuments to Philipsburg's strategic importance in St. Maarten's history. Philipsburg has not been left behind in the time, however. It has combined its historical legacy with 20th century excitement. Since its waterfront has become a popular stop for cruise ships, the shore of this town is covered with restaurants, cafes and nightclubs that offer entertainment well into the night.
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Day 6 · 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 7 · Iles des Saintes, Guadeloupe
Iles des Saintes, Guadeloupe
Arrive 8:00 am · Depart 6:00 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 8 · Fort-de-France, Martinique
Fort-de-France, Martinique
Arrive 8:00 am · Depart 6:00 pm
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Day 9 · Little Bay, Montserrat, Leeward Islands
Little Bay, Montserrat, Leeward Islands
Arrive 8:00 am · Depart 5:00 pm
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Day 10 · 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 11 · 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 2026-12-10 through 2026-12-20.
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Visit Miami, Florida, Cruz Bay, St. John, U.S. Virgin Islands, Philipsburg, St. Maarten, Port of Basseterre, St. Kitts, St. Kitts and Nevis, Iles des Saintes, Guadeloupe, Fort-de-France, Martinique, Little Bay, Montserrat, Leeward Islands, Jost Van Dyke, British Virgin Islands, San Juan, Puerto Rico.
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 $4,150 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.