San Juan to Bridgetown

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.

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.

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.

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.

Columbus discovered St. Kitts (short for St. Christopher) and Nevis on his second voyage in 1493. Arawak and Carib Indians who had moved up through the islands from South America already inhabited both islands. While European immigrants massacred many of them, the Caribs continued to stage fierce battles, which became legendary. In 1632, the West Indies’ first British settlement was established on the island, which soon developed into an important colony thanks to its sugar industry.
France and England shared St. Kitts for some time, but the partition ended with the Peace of Utrecht in 1713. After being declared a British colony in 1783, St. Kitts and Nevis, along with Anguilla and the British Virgin Islands, were administered as a single colony until 1871 when the Leeward Islands Federation was formed. This continued up to 1957 when St. Kitts and Nevis were granted self-government, with Britain remaining responsible for external affairs and defense. Both islands became an independent state within the Commonwealth in 1983.

Basseterre, St. Kitts’ capital, still shows signs of colonial architecture. However, its setting against the emerald green hills ensures a distinct Caribbean ambiance. Many travelers agree that Basseterre is one of the prettiest of the Caribbean’s small capitals.

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.

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.

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.