Bridgetown to San Juan from Bridgetown, Barbados, 20 Jan 2027 (10 nights)


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Bridgetown, the captivating capital of Barbados, combines faded colonial history, captivating tradition, and vivid white beaches plucked directly from your richest imagination of Caribbean perfection. Recently listed as a UNESCO World Heritage site, thanks to its beautifully preserved colonial architecture, Bridgetown’s mask of modernity covers a core of complex history and fascinating culture. Sherbet coloured buildings line up to overlook the waterfront of the Constitution River at the ‘The Careenage’ - where gleaming ships bob on the blue water, and peaceful strolls along a wooden boardwalk await. Stop for a sobering moment at the commemorative plaque honouring the people traded at this spot, when Bridgetown was the British Empire’s most important harbour, and first stop on the Transatlantic Slave Trade crossing. Just five minutes’ stroll from here is Carlisle Bay - a postcard-perfect place where you'll find crystal-clear, turquoise seawater glowing in the Caribbean sun, and a mile…
An almost mythical utopia of virgin beaches, rustic rum shacks and bays so scenic you feel like you’re intruding - Bequia Island is an island mirage of Caribbean perfection. This is the real, unspoiled experience - and with just 6,000 locals living here, you quickly start to recognise the same smiling faces, welcoming you with outstretched arms. Offering glorious - often deserted - beaches of pure golden sand, and hillside sweeps of forest and almond trees, Bequia Island is an extraordinary feast for the senses. Unlike some of the flashier Caribbean islands, Bequia - a part of the Grenadines - is a rustic, unassuming and off-the-beaten-path choice. The staggeringly picturesque natural harbour, Admiralty Bay, greets you on arrival, and is peppered with day-tripping yachts bobbing on the gentle waves. The island’s tiny capital, Port Elizabeth, sits behind, with its bustling fruit and vegetable market, turtle sanctuary, and stalls selling hand-crafted model ships. This tiny, pretty islan…
Explore a land of vibrant colour, from the tranquil turquoise water that surrounds it, to the verdant green peaks of its famous soaring volcanic plugs - The Pitons; which give this mesmerising island its form. Waterfalls thunder in the jungled interior, should you successfully drag yourself from St Lucia's gleaming beaches and dive spots - where patchworks of colourful fish dance below the waves. Offering the picturesque island luxury of your wildest dreams, St. Lucia is a cinematic, thrilling Caribbean idyl. Marigot Bay served as the tropical backdrop for 1967’s Doctor Dolittle film, and the island's amiable animal life is never too far away - spot flashes of bright red, as parrots zip between palm trees, before catching sight of dolphins splashing playfully offshore. Vigie beach is a charmed spot to lie back and recline in the sun’s glow, watching as overlapping layers of mesmerising blue hues intertwine. St. Lucia’s iconic Pitons mountains deliver as the perfect backdrop to any env…
Martinique is well known as France’s favoured Caribbean isle, but it is the little commune of Trois Ilets where the two cultures really mesh together. Found directly opposite the busy capital Fort de France, Trois Ilets retains its historic culture – much of it due to Marie Josèphe Rose Tascher de la Pagerie, aka Empress Josephine of France aka Mrs Napoleon Bonaparte. In fact, so proud are the Martiniquais of their famous daughter that they have sanctified her childhood sugar plantation home. View less La Pagerie is a fascinating museum housing rich colonial artefacts, including some of Napoleon’s rather risqué love letters to his future wife. Trois Ilets was once an important French colony, and as such played an active role in the slave trade. A trip to the Savane des Esclaves will have you learning of the plight of Neg Marrons – and others like him – slaves who fled the plantations to live alone in the hinterland. Visit the reconstruction of a typical rural shack where Neg and other…
To fully appreciate the island's unspoiled beauty, a trip into the interior is a must. A good part of Dominica's mountainous terrain is covered with dense evergreen rain forest, where rare plants and animals are still found that have long been extinct on neighboring islands. The Smithsonian Institute called the island a giant plant laboratory, unchanged for 10,000 years. Numerous hot springs bear witness to continuing volcanic activity. Dominica is truly a place to discover nature in all her splendor. But it is not an island for those looking for white sand beaches. Around the mouth of rivers and in sheltered bays, the beaches are pebbly and of dark color.
This small group of islands lies opposite the western part of Guadeloupe. They were discovered in November 1493 by Columbus, who named them Los Santos. French settlers established themselves in 1648 and changed the name to Iles des Saintes, commonly known as Les Saintes. Since then the islands have been closely connected with Guadeloupe.
As one of the Caribbean’s most dramatic islands, Montserrat has always done thing a little differently. While the rest of its neighbours were busy promoting tourism in its masses, Montserrat was content to sit back and stay in the (metaphorical) shadow. The island remains relatively undeveloped for the archipelago, with off the beaten path beaches, hidden creeks and so much natural beauty that we fully expect this little island to soon become the next go-to eco-tourism destination. View less Much of Montserrat’s discretion is because it is governed by seismic activity and has endured more volcanic eruptions than any other Caribbean island. These have earned it the nickname the “Pompeii of the Caribbean”, understandably so, as much of the main city was covered in ash after the 1995 eruption. The cause of this is the mighty Soufriere Hills volcano, dormant since 2010 yet still spewing sulphur and smoke. However, it is not all doom and gloom and Monserrat’s other nickname is “the emerald…
St. Kitts verdant volcanic slopes rise from crystal clear Caribbean waters, promising a land of escape, relaxation and rejuvenation. A place for ‘limin’ - the local word for kicking back, Caribbean style, you’ll be welcomed to an island paradise blessed with swarming reefs, hidden white-sand beaches, and irresistible shallow seas. Bigger sibling to nearby Nevis, St. Kitts is a place of unrestrained natural beauty. View less Soak up the dreamy Caribbean bliss, or explore sprawling island rainforests, teeming with hummingbirds and the distant sounds of waterfalls, as you walk the island’s vine-tangled paths. A ride on Basseterre’s scenic sugar train is a rumbling, immersive journey through the heart of this Caribbean island of culture and vivid unspoiled scenery. Carriages that once transported crops of sugar cane to the city sweep around long curving bends, revealing a spectacular introduction to St. Kitts. The landscapes here are beautiful, and things are no less spectacular offshore,…
Cherry red roofs, yacht-sprinkled bays and a sophisticated French flavour all add to the gorgeous Caribbean allure of Gustavia. The island's capital rolls around a horseshoe-shaped harbour, where gleaming yachts hover and fancy boutiques, bars and restaurants fizz with life and clinking cutlery. Head up to red and white Gustavia Lighthouse to look down over the revered waters, which attract many a celebrity guest and diving enthusiast to these shores. View less Christopher Columbus was the first European to discover this volcanic island in 1493, giving it the name St Barthelemy in honour of his younger brother. The island has a unique history as a Swedish colony, following a deal with the French King Louis XVI to exchange the island with Sweden for better trading rights. It was returned to French control in 1878 and is now a French Overseas Collectivity. Learn more of the Swedish legacy at Fort Karl - which sits on a 29-metre-high hill above Shell Beach. The fort now lies in ruins, bu…
Like so many of the islands in the Caribbean, 2017’s double whammy of hurricanes Irma and Maria devastated much of St. John. However, as relief funds get funnelled into rebuilding, normality is gradually being restored, and St. John version 2.0 is emerging - bolder, brighter and better. St. John’s small size might just give it the edge over other desert islands. View less The US purchased the tiny landmass (at just nine miles long, the island is the smallest of the three American Virgin Islands) from the West India and Guinea Company in 1917 and it remains under US govern to this day. Historically speaking however St. John is Danish, who colonised it for almost 250 years before its sale to America. The Virgin Island Nation park covers almost two-thirds the island, meaning visually St. John is stunning, and will remain that way for generations to come. This ‘gift’ to the world comes thanks to Laurence Rockefeller who in 1956 gave the 5,000 acres of lush forest to the people of the isla…
What's included
Fare overview
This sailing is shown as a cruise-only guide fare with Silversea. The fare is linked to the ship, itinerary and cabin category you choose. Drinks packages, gratuities, Wi-Fi, flights, transfers and shore experiences are only treated as included where they are confirmed before booking.

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Silver Shadow
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Award-winning Silver Shadow has all the hallmarks of extreme luxury at sea. With one of the highest space-to-guest ratios at sea, Silver Shadow is a firm favourite in the Silversea fleet. Authentic experiences. Simple pleasures. Shared moments. Silversea’s Millennium Class luxury cruise ships Silver Shadow and Silver Whisper offer you freedom and space to design your day. Slightly larger in size than ships Silver Cloud and Silver Wind, Silver Shadow retains Silversea’s essence – spacious suites, a complement of only 388 guests, superior service – paired with a lively cosmopolitan atmosphere and enhanced amenities. Aboard the Silver Shadow, energize body and soul with complimentary Pilates and yoga in the expanded fitness center. Savour fine wines and French gastronomy in La Dame, enjoy authentic Italian cuisine in La Terrazza, or simply gaze at endless ocean views from The Grill. Not forgetting the regional-inspired The Restaurant, dining at sea has never been so good.
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