Silversea Sets Sail for Its Grand 2025/2026 Caribbean Season: 32 Destinations, 19 Countries, and Four Elegant Ships

Silversea Cruises, the world’s leading ultra-luxury and expedition cruise line, has launched its highly anticipated 2025/2026 Caribbean and Central America season, promising guests a deep dive into the region’s rich culture, colourful charm, and breathtaking landscapes. With 32 iconic and off-the-beaten-path destinations across 19 countries, Silversea’s elegantly intimate ships offer access to ports that larger vessels simply can’t reach — from the tranquil Little Bay in Montserrat to the picturesque Les Saintes in Guadeloupe.
Departing from Miami on November 18, 2025, the beloved Silver Shadow kicked off the first of 33 curated voyages, marking the start of an immersive season that runs through March 2026. With four ships — Silver Ray, Silver Spirit, Silver Shadow, and Silver Dawn — sailing through turquoise waters and golden shores, this season defines the ultimate in bespoke luxury cruising.

Authentic Caribbean Discovery with a Silversea Touch

Silversea’s 2025/2026 season has been carefully crafted to capture both iconic highlights and hidden treasures of the Caribbean.
“Our guests can expect an extraordinary collection of voyages that reveal the Caribbean’s authentic soul and vibrant flavours like never before,” said Bert Hernandez, President of Silversea. “Exploring boutique ports accessible only to smaller ships allows our guests to feel the region’s genuine rhythm and charm.”
Aboard every Silversea ship, guests can indulge in luxurious comfort, all-suite ocean-view accommodation, and Silversea’s hallmark personalized butler service. Ashore, they’ll uncover the region’s lush mountains, white-sand beaches, and distinctive local heritage — paired with unforgettable S.A.L.T. (Sea and Land Taste) culinary experiences that connect them to each destination through immersive regional cuisine.

Highlights of Silversea’s 2025/2026 Caribbean Voyages

Silver Ray – Fort Lauderdale to Fort Lauderdale (December 2–12, 2025)
Silversea’s newest Nova Class ship, Silver Ray, begins her Caribbean journey with a 10-day Eastern Caribbean voyage. Guests can experience the vibrant cultures of San Juan, St. John, St. Barts, St. Kitts, and Tortola, balanced with relaxing days at sea for enriching S.A.L.T. cooking classes inspired by the Caribbean’s diverse culinary heritage.
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Silver Ray – Fort Lauderdale to Fort Lauderdale (January 27–February 6, 2026)
This 10-day round-trip escape combines two serene sea days with immersive exploration in San Juan, St. John, St. Barts, St. Kitts and Nevis, and Virgin Gorda. From Devil’s Bay National Park to the granite boulders of The Baths, this itinerary blends relaxation and adventure in perfect harmony.
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Silver Spirit – Barbados to Barbados (December 8–15 & December 15–22, 2025)
Embark on two seven-day round-trip sailings from Bridgetown, Barbados, exploring the Caribbean’s most dazzling jewels — St. Lucia, Martinique, St. Barts, Dominica, Grenada, and St. Vincent and the Grenadines. Guests can enjoy lush rainforests, mountain biking adventures, exclusive wine tastings in St. Barts, and snorkelling safaris amid crystal-clear waters.
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Silver Shadow – Barbados to Saint Maarten (February 12–19, 2026)
Celebrate Valentine’s week aboard Silver Shadow with a seven-day journey from Barbados to Saint Maarten. Discover the distinct character of each port — from the French-Caribbean elegance of Trois Ilets in Martinique to the tropical adventures of Dominica and Antigua. Culinary travellers will delight in A Taste of Martinique, featuring rhum tastings and French-Creole cuisine guided by Chef Julien Fournet at La Suite Villa.
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Silver Shadow – Saint Maarten Roundtrip (February 19–26, 2026)
This breathtaking seven-day roundtrip from Saint Maarten explores an enchanting selection of islands, from bustling St. John’s, Antigua to unspoiled Montserrat, St. Lucia, and Guadeloupe. Guests can hike Mount Morel, snorkel in Les Saintes Bay, or relax on white-sanded beaches — discovering the Caribbean’s hidden natural wonders.
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Explore the Caribbean with Silversea Cruises

Silversea’s 2025/2026 Caribbean and Central America season invites travellers to go beyond the ordinary. Each voyage blends luxury, discovery, and authentic Caribbean charm — perfect for those seeking both relaxation and cultural connection in one unforgettable journey.

Experience the best of the tropics aboard Silversea’s boutique ships and discover why this line continues to set the standard in luxury small-ship cruising.

Find the full collection of sailings at Silversea Caribbean Cruises.