Bridgetown to Fort Lauderdale, Florida

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.

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.

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.

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.

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.

Offering an island bounty of electric-blue Caribbean Sea waters, sensational scuba diving, and elevated viewpoints, Philipsburg revels in Caribbean beauty. St. Maarten is an unusual island of dual personality – partitioned into French and Dutch sides. Discovered by Christopher Columbus on his second journey to the Americas in 1493. A truce was eventually brokered in 1648, sharing the island between the French and Dutch – an arrangement that endures today. View less

A Caribbean mirage of soft sand beaches and perfect snorkelling and scuba diving opportunities – arrive on the south of this beautiful island at the Dutch side’s capital, Philipsburg. Squeezed between the bay and the Great Salt Pond, the town offers waterfront strolls in the gentle breeze, duty-free bargains, and plenty of room to sit and drink in the dazzling sea views. Clear, turquoise waters hold underwater worlds of colourful corals and fish, while glorious beaches of typical Caribbean beauty invite you to sprawl out beside the tempting shallow waters. Look out to see occasional jet skis skirting the waters, as you recline on sand flanked by lush vegetation on both sides. Tear into the fresh local produce and taste the island’s sensational seafood – from lobster to red snapper and conch cocktails. Don’t miss the opportunity to try out the island’s favourite tipple, either – guavaberry rum. Beautiful green peaks offer stunning hikes, amid the rich tangle of jungle scenery. Maho Beach may also be on the radar – the tranquillity of this small beach is regularly interrupted by the deafening roar of jet engines, as Princess Juliana International Airport’s runway comes perilously close to the sands. Huge planes skim just above the beach before touching down, and the blasts of departing jet engines blow violent gales out towards the waters.

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?

Beach masterpieces of silky white sand and sparkling water shifting from turquoise to royal blue welcome you to idyllic Grand Turk. Underwater ramparts of coral teem with vibrant marine life, while tranquil beaches reward with a haven of relaxation. Discover relentless Caribbean beauty as you taste the wonders of this tiny, tooth-shaped island paradise. Part of the Turks and Caicos islands group, an enchanting string of islands that share jaw-dropping natural beauty, Grand Turk is a truly divine Caribbean escape. View less

Your first port of call is always likely to be the blissful sand beaches that roll down to that trademark intense sea. Governor’s Beach is a vision of pink sand, lapped by teal waters and a perfect rendering of your most lavish imagination. Submerge into the warm waters or shelter from the sun below soaring casuarina trees. Pillory Beach is another favoured option, nestled a little further to the north. Wade out along the shelf of sand, and part clear seawater that dances with twinkling sunlit patterns. Take your pick from the islands’ blessing of beaches, or strap on a snorkel to float for hours amid the bright tones and curious displays of life below the surface. Graceful stingrays slide through the waters at Gibbs Cay, and you can wander among huge queen conch shells, strewn over its sands. Later, sunset will burn and boom above, as you taste fresh barbecued snapper, mahi-mahi and lobster platters. The stunning coral reefs that attract keen divers from across the globe have been far less welcoming to ships historically, and the wrecks that rest on the seabed attest to their hull-shredding credentials. Flashing out warnings, and standing tall since 1852, Grand Turk Lighthouse is a true icon of this island. Wild donkeys and horses may join you as you roam below the rusting, cast-iron tower, which gazes out protectively over the North Reef.

With its heady mix of Creole culture and French sophistication, there is more than a pinch of je ne sais quoi in Fort de France. The capital of Martinique, and by far the biggest city in the whole of the French West Indies, if you are looking for Paris in the Caribbean, you’ll find it in Fort de France.

The island has been under French govern since 1638 when the first governor of Martinique Jacques Dyel du Parquet commissioned a fort (from which the city takes its name) to keep out invaders. Not even an unsuccessful attack by the British in 1720, nor the French Revolution in 1789, has been able to shake the French govern of the island and today the city’s French and Creole heritage are impossible to untangle. The colonial past is everywhere, take a stroll down the narrow streets and enjoy the remarkable architecture of the Schœlcher Library, St. Louis Cathedral and the Old Town Hall. Among the many legacies Dyel du Parquet left on the island is sugarcane. A drive through the tropical forests will not only reward you with trees bending under the weight of papayas, mangoes and bananas, but will also afford superb vistas of the elegant plant swaying in the breeze. The arrival and subsequent export of sugar brought the French bourgeoisie in their droves and many of their mansions are still standing. Josephine de Beauharnais, the Napoleonic Empress of “not tonight” fame, hails from the island and those interested will find her childhood home, La Pagerie in nearby Trois Ilets.