Miami, FL to Bridgetown

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?

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.

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.

Bright and brilliant colours coat the waterfront buildings of Willemstad, gleaming attractively below the generous Caribbean sun. The capital of the Carribean island Curacao, Willemstad is famous for its technicolour UNESCO World Heritage Site city centre, and a narrow channel connects the sea with the Schottegat harbour, which expands inland like a blooming flower. Settled by the Dutch in the 1630s, they brought colourful architecture, lavish red-roofed mansions, and gorgeous European-style waterfront buildings to this beautiful Caribbean island. View less Watching over the entrance to this luxurious port is Rif Fort - a 19th-century fortress, which looms above the Sint Anna Bay channel. From here, wind your way to the Queen Emma Bridge - a pontoon bridge known as the Swinging Old Lady, which was built in 1888 to connect Otrobanda and Punda. Enjoy the wonderful views of Willemstad's lavish, pastel-coloured Punda waterfront set before you. Visit the small boats that pull up side by side to sell juicy fruits and vegetables, in a floating market on the waters below. At sunset, the gingerbread stretch bathes in lights, glowing evocatively as the last of the evening's light ebbs away. Wander Willemstad to discover the lemon-shaded Mikve Israel-Emanuel Synagogue, said to be the oldest synagogue in the Americas, see the historic liqueur distillery or head for Queen Wilhelmina Park - where the letters 'DUSHI' are spelt out in a standing sign. You'll hear this word a lot - the island's favourite way of describing the little things that make life worth living. The beaches of Curacao are certainly 'dushi', with tempting sandy curves on practically every corner. Snorkel in the turquoise waves, among dashing fish life and sleek sea turtles.

Bonaire's small, tidy capital city (population 3,000) is five minutes from the airport. The main drag, J.A. Abraham Boulevard, turns into Kaya Grandi in the center of town. Along it are most of the island's major stores, boutiques, and restaurants. Across Kaya Grandi, opposite the Littman’s jewelry store, is Kaya L.D. Gerharts, with several small supermarkets, a handful of snack shops, and some of the better restaurants. Walk down the narrow waterfront avenue called Kaya C.E.B. Hellmund, which leads straight to the North and South piers. View less In the center of town, the Harbourside Mall has chic boutiques. Along this route is Ft. Oranje, with its cannons. From December through April, cruise ships dock in the harbor once or twice a week. The diminutive ocher-and-white structure that looks like a tiny Greek temple is the produce market, where one can find plenty of fresh produce brought over from Venezuela. Pick up the brochure Walking and Shopping in Kralendijk from the tourist office to get a map and complete list of all the monuments and sights in the town.

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.