San Juan to San Juan
- 20th December 2026
- 14 Nights
- San Juan
- Silver Shadow
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Your itinerary
- San Juan
- Great Harbour, Jost Van Dyke, B.V.I
- Little Bay, Montserrat, Bwi
- Castries, St Lucia
- Fort de France, Martinique
- Sopers Hole, Tortola, British
- San Juan
- St. John, Cruz Bay, U.S. Virgin Islands
- St Kitts
- Les Saintes, Guadeloupe
- Bequia
- St Thomas, US Virgin Islands
- San Juan
Day 1
20th Dec '26
San Juan
Sitting on the north coast of this lush, tropical island, San Juan is the second settlement founded by European settlers in the Caribbean, and the oldest city under US jurisdiction. The stocky walls and watchtowers here have stood the test of time, repelling notable invaders – such as Sir Francis Drake – and the pirates who historically looted these islands. With massive fortresses, airy plazas and sheer Caribbean beauty, San Juan is a beach-blessed star of these turquoise waters. View less With more than 500 years of European history, Old San Juan gleams In Puerto Rico’s sunshine, with sugar-almond painted facades and ankle-testing cobbled lanes. Decorative balconies and varnished wooden doors add everyday artistry to streets, dripping with history. Soak up the culture at rum-fuelled parties and salsa dances on this Spanish-culture infused island, or recline into afternoon relaxation sessions on sensational slivers of gleaming sand. Kick back on the beach, or satisfy a lust for adventure by exploring sprawling mangrove forests. The magic of sea kayaking after dark here is an experience you won’t forget. Break the waves with your oar, and watch as the waters illuminate with neon colour, as bioluminescence creates a mystical, peaceful spectacle. Pocked limestone cliffs and karst landscapes add rugged contrast to the serenity of the beaches, and you can walk into folds of the earth in sea-carved caves, or across cliffs to hidden views of the Caribbean’s expanse. Enjoy a taste of the island’s cuisine by sampling Mofongo – a local concoction of green plantains and chicken. Why not indulge and wash it down with an iced mojito, made from crushed mint and locally distilled rum?
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Arrive
0:00
Depart
19:00
Day 2
21st Dec '26
Great Harbour, Jost Van Dyke, B.V.I
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 trees framing a sandy sweep of shaded beach bars. There’s nothing for it but to indulge on a bed of soft pearly-white sand, and soak in the staggering beauty of it all. The wander up to Majohnny Hill is the most exertion needed to explore this four-square-mile island, and it’s worth it to see the heavenly beaches emerging from tranquil waters below. Even the natural sea formations here encourage you to unwind, with waves gurgling and frothing over the rocks to create Bubbly Pool, a natural jacuzzi. Jost Van Dyke has a reputation as the off-the-radar island getaway of choice for celebrities like Keith Richards. A lot of that comes down to the calypso charm of its rustic beach bars – especially the legendary Foxy’s Bar, which is run by island legend Foxy Callwood. Rum-drenched cocktails and icy buckets of beach beers await – sure to get you into the island’s party spirit in no time.
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Arrive
8:00
Depart
18:00
Day 3
22nd Dec '26
Little Bay, Montserrat, Bwi
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 isle”, is not only because of its lush verdant forests lined with lime trees and palms, but because its coasts bear a certain similarity to Ireland. And yes, Guinness is available! Montserratians are optimistic and fun loving and Little Bay locals are the perfect example. Set at the very tip of the island, the town is intended as the new capital, and is being enhanced with the modernity once would expect of such an honour. Little Bay beach is without doubt one of the most beautiful in Caribbean, and is a tonic for the soul.
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Arrive
9:00
Depart
19:00
Day 4
23rd Dec '26
Castries, St Lucia
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 envy generating photograph – rising up exponentially from the calm waters like sharp shark fins. Castries is this heavenly island’s capital, and while the Cathedral Basilica of the Immaculate Conception may seem a little humble from the outside, the soft sounds of soulful hymns emanating from within are sure to draw you in. The astonishing interior glows with bright frescoes, lit up by the sunlight that spills inside, and atmospheric rows of flickering candles. There’s more rich Caribbean colour to behold at the ramshackle Castries Market, where you can take handfuls of fragrant spices, like nutmeg and cinnamon, and enjoy the singsong ritual of bartering, as you move between tables heaving under bounties of green bananas and rosy mangos.
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Arrive
8:30
Depart
18:00
Day 5
24th Dec '26
Fort de France, Martinique
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.
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Less
Arrive
8:00
Depart
18:00
Day 6
25th Dec '26
At Sea
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Arrive
0:00
Depart
0:00
Day 7
26th Dec '26
Sopers Hole, Tortola, British
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Arrive
8:00
Depart
18:00
Day 8
27th Dec '26
San Juan
Sitting on the north coast of this lush, tropical island, San Juan is the second settlement founded by European settlers in the Caribbean, and the oldest city under US jurisdiction. The stocky walls and watchtowers here have stood the test of time, repelling notable invaders – such as Sir Francis Drake – and the pirates who historically looted these islands. With massive fortresses, airy plazas and sheer Caribbean beauty, San Juan is a beach-blessed star of these turquoise waters. View less With more than 500 years of European history, Old San Juan gleams In Puerto Rico’s sunshine, with sugar-almond painted facades and ankle-testing cobbled lanes. Decorative balconies and varnished wooden doors add everyday artistry to streets, dripping with history. Soak up the culture at rum-fuelled parties and salsa dances on this Spanish-culture infused island, or recline into afternoon relaxation sessions on sensational slivers of gleaming sand. Kick back on the beach, or satisfy a lust for adventure by exploring sprawling mangrove forests. The magic of sea kayaking after dark here is an experience you won’t forget. Break the waves with your oar, and watch as the waters illuminate with neon colour, as bioluminescence creates a mystical, peaceful spectacle. Pocked limestone cliffs and karst landscapes add rugged contrast to the serenity of the beaches, and you can walk into folds of the earth in sea-carved caves, or across cliffs to hidden views of the Caribbean’s expanse. Enjoy a taste of the island’s cuisine by sampling Mofongo – a local concoction of green plantains and chicken. Why not indulge and wash it down with an iced mojito, made from crushed mint and locally distilled rum?
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Less
Arrive
7:00
Depart
19:00
Day 9
28th Dec '26
St. John, Cruz Bay, U.S. Virgin Islands
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 island, with the caveat that it become a national park. Thus, velvety green hills slope into picture perfect white sand beaches, which are ringed by turquoise seas. One very definite winner of the tourism hiatus since 2017 has been the marine wildlife. Underwater life was barely affected by the storms and the subsequent lack of tourism has allowed the eco-systems to propagate. The island’s abundant coral reefs were not overly affected by the storms and today the waters are teeming with sea turtles, reef sharks and sting rays.
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Arrive
8:00
Depart
18:00
Day 10
29th Dec '26
St Kitts
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, where glorious crystalline waters invite you to dive with turtles, and explore doomed wrecks like the River Taw ship – which has now exploded with marine life. In Basseterre itself, stop off to see the pea-green Berkeley Memorial clock, which stands in the Circus, surrounded by busy St. Kitts life. Independence Square is also waiting among the city’s charming Georgian buildings. Renamed from Pall Mall on the 19th of September 1983 – to celebrate the island’s independence – the pretty square gravitates around a colourful burbling fountain, and has a dark history, as a former slave market. Wary canons watch out over the waves far below at Brimstone Hill Fortress, a site of significant history, which dates back to 1690. Known as the ‘Gibraltar of the West Indies’ due to its importance at the heart of the British empire, St. Kitts was one of the first island in the West Indies to be colonised. Nowadays, its World Heritage Site fortress offers panoramic views along the coastline it was built to defend.
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Arrive
8:00
Depart
18:00
Day 11
30th Dec '26
Les Saintes, Guadeloupe
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.
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Arrive
8:00
Depart
17:00
Day 12
31st Dec '26
Bequia
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 island is ridged along the centre, and you can earn your beachside bliss with a gentle hike to the top of Mount Peggy, looking out over views of Grenada and St Vincent. At just seven miles long, you can discover the whole island in a few hours – but that would be to miss the point somewhat. Bequia Island coaxes you in to slow the pace and soothe your soul on blissful beaches, where you can revel in the uncomplicated joys of sitting, reading and swimming in heavenly shallow waters. The royally approved Princess Margaret Beach is one of the finest – an arching band of soft sand and cobalt-blue waters. As evening sets in, you may find you’re beckoned to share with communal barbecues of the day’s fresh catch with the locals, or to indulge in rum-heavy cocktails at beachside bars, lashed together from sea-blanched wooden limbs.
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Arrive
8:00
Depart
18:00
Day 13
1st Jan '27
At Sea
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0:00
Depart
0:00
Day 14
2nd Jan '27
St Thomas, US Virgin Islands
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 at Drake’s Seat – said to be Sir Francis Drake’s lookout point, where he could survey for approaching enemy ships. Nowadays, the views over Magens Bay and the infinite sea are always peaceful, and this is a great spot to catch a fiery Caribbean sunset spilling across the sky. Take catamaran cruises to explore the shining coastline, or seek out the glorious coves and caves that are hidden along the island’s perimeter. Land on the secluded shores of tiny islands, before scuba diving and snorkelling above the twisted boughs of lost ships, reclaimed by the waters and inhabited by curious tropical fish life. Kayak over still lagoon waters, or take the chance to lay back on soft beaches strewn with tiny shells, as St Thomas’s beauty washes over you.
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Less
Arrive
8:00
Depart
18:00
Day 15
3rd Jan '27
San Juan
Sitting on the north coast of this lush, tropical island, San Juan is the second settlement founded by European settlers in the Caribbean, and the oldest city under US jurisdiction. The stocky walls and watchtowers here have stood the test of time, repelling notable invaders – such as Sir Francis Drake – and the pirates who historically looted these islands. With massive fortresses, airy plazas and sheer Caribbean beauty, San Juan is a beach-blessed star of these turquoise waters. View less With more than 500 years of European history, Old San Juan gleams In Puerto Rico’s sunshine, with sugar-almond painted facades and ankle-testing cobbled lanes. Decorative balconies and varnished wooden doors add everyday artistry to streets, dripping with history. Soak up the culture at rum-fuelled parties and salsa dances on this Spanish-culture infused island, or recline into afternoon relaxation sessions on sensational slivers of gleaming sand. Kick back on the beach, or satisfy a lust for adventure by exploring sprawling mangrove forests. The magic of sea kayaking after dark here is an experience you won’t forget. Break the waves with your oar, and watch as the waters illuminate with neon colour, as bioluminescence creates a mystical, peaceful spectacle. Pocked limestone cliffs and karst landscapes add rugged contrast to the serenity of the beaches, and you can walk into folds of the earth in sea-carved caves, or across cliffs to hidden views of the Caribbean’s expanse. Enjoy a taste of the island’s cuisine by sampling Mofongo – a local concoction of green plantains and chicken. Why not indulge and wash it down with an iced mojito, made from crushed mint and locally distilled rum?
More
Less
Arrive
7:00
Depart
0:00
Your ship - The Silver Shadow
Description
Food and Drink
Entertainment
Relaxation
Fitness
Recreational
Other
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 e...riences. 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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atrium
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casino
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connoisseur’s corner
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la dame
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la terrazza
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the grill
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the restaurant
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card room/conference room
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panorama lounge
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the show lounge
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pool deck
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zagara beauty spa
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fitness center
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observation library
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boutique
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reception
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zagara beauty salon
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Staterooms
suite
A quiet sanctuary. The sitting area of the Vista Suite has plenty of room to relax. Large picture w ... indows frame panoramic ocean views. The perfect backdrop for breakfast in bed. One bedroom: 287 ft² / 27 m² Large picture window providing panoramic ocean views. Sitting area. Twin beds or queen-sized bed. Marbled bathroom with double vanity, separate shower and full-sized bathtub. Walk-in wardrobe with personal safe. Vanity table(s) with hair dryer. Writing desk. 32” / 81 cm flat-screen television with Interactive Media Library. Unlimited Standard Wifi.
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