San Juan to San Juan
Silversea · Silver Shadow
Depart
Dec 20, 2026
Return
Jan 3, 2027
Port
San Juan
Nights
14 nights

At a glance
- Built
- 2019
- Tonnage
- 28258
- Cabins
- 194
- Crew
- 302
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.
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On board

The Grill

The Restaurant
Itinerary
Cruise from San Juan and back
Day 1Cruise departs from San JuanDec 20, 2026 • Departs at: 7 pm
Day 2Jost Van Dyke (British Virgin Islands)Dec 21, 2026 • Arrives at: 8 am • Departs at: 6 pm
Glowing turquoise waters, lazily bowing palm trees, and pristine white sand beaches – it's all waiting for you in Jost Van Dyke's picturesque Caribbean splendour. Slip off your shoes, you won't be needing them too much in these parts, as you wander soft, heavenly sands, and paddle out into impossibly clear waters. The island escape of choice for dallying yachts, which visit to soak up the off-the-beaten-path good life. Join them around the pristine beaches of this tiny celebrity magnet of an island. View less If this is your first experience of the Caribbean's splendour, you may be a little sceptical about the reality of those famed, shockingly bright colours that you see in photographs. If so, Jost Van Dyke will be love at first sight. Splash into water that glows with a bright teal hue and is blotched with occasional swells of deeper royal blue. Snorkellers will adore the explosions of colourful fish beneath the waves. White Bay is a slice of island perfection, with a neat hill of t…
Day 3Little bayDec 22, 2026 • Arrives at: 9 am • Departs at: 7 pm
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…
Day 4Castries (St. Lucia)Dec 23, 2026 • Arrives at: 8:30 am • Departs at: 6 pm
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…
Day 5Fort-de-FranceDec 24, 2026 • Arrives at: 8 am • Departs at: 6 pm
The largest of the Windward Islands, Martinique is 4,261 mi (6,817 km) from Paris, but its spirit and language are decidedly French, with more than a soupçon of West Indian spice. Tangible, edible evidence of the fact is the island's cuisine, a superb blend of French and creole. Martinique is lushly landscaped with tropical flowers. Trees bend under the weight of fruits such as mangoes, papayas, lemons, limes, and bright-red West Indian cherries. Acres of banana plantations, pineapple fields, and waving sugarcane stretch to the horizon. The towering mountains and verdant rain forest in the north lure hikers, while underwater sights and sunken treasures attract snorkelers and scuba divers. Martinique is also wonderful if your idea of exercise is turning over every 10 minutes to get an even tan and your taste in adventure runs to duty-free shopping. A popular cruise-ship excursion goes to St-Pierre, which was buried by ash when Mont Pelée erupted in 1902.
Day 6At SeaDec 25, 2026
Day 7Sopers Hole , British Virgin IslandsDec 26, 2026 • Arrives at: 8 am • Departs at: 6 pm
Day 8San JuanDec 27, 2026 • Arrives at: 7 am • Departs at: 7 pm
Day 9St John , U.S. Virgin IslandsDec 28, 2026 • Arrives at: 8 am • Departs at: 6 pm
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…
Day 10St. Kitts (Basseterre)Dec 29, 2026 • Arrives at: 8 am • Departs at: 6 pm
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,…
Day 11Les Saintes, GuadeloupeDec 30, 2026 • Arrives at: 8 am • Departs at: 5 pm
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.
Day 12Bequia, St. Vincent And The GrenadinesDec 31, 2026 • Arrives at: 8 am • Departs at: 6 pm
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…
Day 13At SeaJan 1, 2027
Day 14St. ThomasJan 2, 2027 • Arrives at: 8 am • Departs at: 6 pm
The steep, spectacular hills that surround St Thomas's exquisite harbour provide a fitting entry point for this island of overwhelming natural splendour. The jungled-mountains reach up above tempting beaches and scuba diving sites, while Charlotte Amalie - the island's capital - sprawls down towards the water, bedecked with shops and tasty restaurants. Part of the beautiful U.S. Virgin Islands - together with St John and St Croix - these lands were purchased by the US in 1917. View less Nowadays, St Thomas is a patchwork of cultures, and a lively welcome to the islands, serving as a gracious host to the many visitors who linger - as well as those who jump on ferries, yachts and catamarans to explore the blessed beaches of the Caribbean's other retreats. A stunning island of dramatic jungled-scenery, keep your camera close to hand as you swing up the Skyride to Paradise Point, to look down over the natural amphitheatre of the dock and city below. Snap some more postcard-perfect shots a…
Day 15Cruise returns to San JuanJan 3, 2027 • Arrives at: 7 am
Cabin options
Compare the cabin types and onboard features shown for this sailing. Final price and availability are confirmed by our team when you inquire.
16 cabin grades listed for this sailing.
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