Bridgetown to San Juan Cruise

Day 1 - Barbados

Arrive: Wed 20 January 2027 / Depart: Wed 20 January 2027 at 23:00

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 of soft white powder sand. A treasure trove for divers, the shipwrecks scattered below the shallow water’s waves are now inhabited by turtles and swirling, rainbow-coloured tropical fish. Head to the backstreets, where street food vendors serve up spicy chicken soup, barbecued pigtails and thirst-quenching coconut water. There are bargains aplenty to be had on Broad Street, where duty-free malls and souvenir stalls cram together, vying for your attention. Roebuck Street is the spot where one of the Caribbean’s favourite drinks, rum, was discovered - having been created here from the by-products of the island’s booming sugarcane trade. Nowadays, it’s lined with bars splashing every variety of the deliciously spicy dark libation imaginable into glasses. For a touch more culture, visit one of the oldest synagogues in The Americas - Nidhe Israel Synagogue, which was built in 1654. The adjoining museum tells the story of Barbados’ Jewish immigrants, who were instrumental in the island’s development.

Day 2 - Bequia

Arrive: Thu 21 January 2027 at 08:00 / Depart: Thu 21 January 2027 at 18:00

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.

Day 3 - Castries, St. Lucia

Arrive: Fri 22 January 2027 at 08:00 / Depart: Fri 22 January 2027 at 18:00

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.

Day 4 - Trois Ilets, Martinique

Arrive: Sat 23 January 2027 at 08:00 / Depart: Sat 23 January 2027 at 18:00

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 others managed to survive by living off the land and by their wits. Like many Caribbean villages, life is centred around the church square. Colourful wooden houses with locally thrown pottery tile rooves flank the typical creole village, while the church itself (where Empress Josephine was baptised) takes pride of place. In fact, so important is pottery to the local culture that the entire village referred to as “Le village de la poterie” in the 18th century. Unsurprisingly though, the islands natural beauty takes a front seat. Many world class beaches are found here including the lovely l’Anse a l’Ane, and the peninsula of Pointe du Bout (literally End Point). This latter place is where you’ll find most of the seaside fun. Think Hobbie-Cats, kayaking, windsurfing and jet skiing for island exploration – the Genipa Mangrove at the end of the island begs discovery if you like to take to the waterways. If your idea of heaven involves the more simple pleasures of reading and strolling under the shade of the palms, then look no further.

Day 5 - Roseau

Arrive: Sun 24 January 2027 at 08:00 / Depart: Sun 24 January 2027 at 19:00

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.

Day 6 - Guadeloupe

Arrive: Mon 25 January 2027 at 08:00 / Depart: Mon 25 January 2027 at 18:00

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 7 - Little Bay, Montserrat

Arrive: Tue 26 January 2027 at 08:00 / Depart: Tue 26 January 2027 at 18:00

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.

Day 8 - St. Kitts

Arrive: Wed 27 January 2027 at 08:00 / Depart: Wed 27 January 2027 at 19:00

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.

Day 9 - Gustavia

Arrive: Thu 28 January 2027 at 08:00 / Depart: Thu 28 January 2027 at 23:00

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, but you'll meet wandering iguanas, and the views down of sweeping sea and emerald coastline are some of the island's finest. Down below, a delightful spread of tiny pebbles and shell fragments are scattered like confetti and lapped by crystal-clear water. A little exploration uncovers countless other glorious beaches and natural wonders. Colombier Beach is a little out of the way but cradles silky-smooth sands and typically turquoise waters. If you have chance, find somewhere to settle and sip fruity rum cocktails as the sunset flares across the waves.

Day 10 - St John, U.S.Virgin Islands

Arrive: Fri 29 January 2027 at 08:00 / Depart: Fri 29 January 2027 at 18:00

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.

Day 11 - San Juan

Arrive: Sat 30 January 2027 at 07:00 / Depart: Sat 30 January 2027