Miami → San Juan (16 nights)

Welcome to Miami and the sweep of South Beach - backdrop to every iconic Miami movie, and forefront of Latin American culture. Stroll through pastel-hued geometric buildings in the art deco district, to graffiti mural masterpieces at Wynwood Walls. Watch Latino life unfold in Little Havana - the heartbeat of this great city - where walk-up windows sell café cortadito, sweet sugarcane juice, hatuey beer and guava ice-cream. Watch passionate locals discuss politics, play dominoes and smoke cigars. Shimmy at a salsa class, shop designer boutiques and race marlin and sharks by speedboat. Then slow your pace to uncover rare and endangered species at the Everglades National Park outdoor oasis. You’ll find the Miami dream is real – and it’s not just Cuban heels that will give you a spring in your step.

Reggae rhythms and Caribbean spices drift through the air in laid-back Ocho Rios, where time is measured in rosy dawns and tangerine sunsets. Browse below the palms on forest-fringed beaches or climb up into the mountainous interior, where old plantations offer a glimpse into the island’s colonial past. Find positive vibrations in the village of Nine Mile, where Nesta ‘Bob’ Marley strummed his first guitar and now rests in a marble Mausoleum. The cooling mists and forest pools of Dunn’s River Falls carry the imagination to lofty heights, while the Green Grotto Caves plunge into a subterranean world of labyrinthine caverns and honeycomb stalactites, historical hideout for indigenous Arawak and stealthy smugglers.

A fringe of shaggy mountains surrounds the wild jungle home of this Mayan empire, where art masterpieces are untouched and in harmony with nature. A stunning shade of crimson still paints the faces of fearsome gods glaring from towering ancient temples in Quiriguá, a UNESCO World Heritage treasure. Hike to a nature preserve where hundreds of species of birds sip from cool waters fed by sparkling waterfalls. An imposing 1600’s stone citadel begs a visit to see how the Spanish thwarted thieving pirates. Prepare to be dazzled by rows of colourful embroidery, beadwork, and handwoven textiles at the lively town market whilst the nutty fragrance and rich flavour of local coffee pairs perfectly with some of the most exquisite chocolate in the world.

Submerged beneath Caribbean waves, the Bonacca Ridge mountains peek above the surface to form spellbinding Roatán and her Bay Island siblings. Bejewelled reefs and an anthology of marine life beckon snorkellers and scuba divers to the pristine underwater world, where rainbow coral and whale sharks cruise the currents. Colourful Garifuna culture blooms in energetic dance and traditional food, while island spirit is bottled at the Roatan Rum Company. Go fast or slow with hiking and fishing trips, paddle boarding or glass-bottomed boat rides. Tune into the tropics in mangrove forests and jungle eco-parks, where sleepy sloths slumber and bright-feathered macaws screech through the branches or pad across silky soft sands on the finest beaches in Central America.

Beguiling Belize fuses diverse culture with an intriguing history. Touch upon spectacular wildlife, underwater wonders, idyllic beaches and ancient Mayan ruins. Call in at the world’s first jaguar reserve, take a jungle tour, head into the Tiger Cave, seek out The Swing Bridge or dip into a chocolate farm. Snooze under thatch, glide through the vibrant Belize Barrier Reef and mingle with locals to uncover nature’s medicinal tonics. And unwind in a pristine Caribbean caye, courtesy of the aptly named Hummingbird Highway.

Key West might end at Florida’s most southern point, but here is the start of real laid-back life. Nearer Cuba than Miami, this last in line of small coral reefed islands is famed for history, culture, fishing, cuisine, and candy-coloured homes. Surf, snorkel, shop by appointment and attend a private seafood tasting. Hop aboard the Old Town Trolley tour, visit Hemingway’s quirky former house, study over 50 different butterflies at the Butterfly & Nature Conservatory and watch leggy flamingos strut their stuff. Key West is not just a deep tan Floridan beach town, it’s a way of life, with the only rule being to come as you please.

Welcome to Miami and the sweep of South Beach - backdrop to every iconic Miami movie, and forefront of Latin American culture. Stroll through pastel-hued geometric buildings in the art deco district, to graffiti mural masterpieces at Wynwood Walls. Watch Latino life unfold in Little Havana - the heartbeat of this great city - where walk-up windows sell café cortadito, sweet sugarcane juice, hatuey beer and guava ice-cream. Watch passionate locals discuss politics, play dominoes and smoke cigars. Shimmy at a salsa class, shop designer boutiques and race marlin and sharks by speedboat. Then slow your pace to uncover rare and endangered species at the Everglades National Park outdoor oasis. You’ll find the Miami dream is real – and it’s not just Cuban heels that will give you a spring in your step.

The queen of the “Silver Coast”, Puerto Plata is treasured for her soaring cloud-shrouded peaks and stunning shining beaches. Once famously plundered by pirates — you too can storm the 16th-century Fortaleza San Felipe fort — now is coveted by modern-day aficionados seeking her bounty of aged rum, robust cigars, and rich chocolate. Adventurers can soar to the top of the Pico Isabel de Torres 793 mt (2,602 ft), dare to off-road to the Waterfalls of Damajagua, or kite-surf, catamaran, and zip-line over the ocean. Pro tip: save time for a buzzy beach club to chill with coconut-fused libations.

Princely Philipsburg reigns as the capital of the Dutch side of the dual-nation island of Sint Maarten/ and French Saint Martin. Lounging beside aptly named Great Bay, the seaside city weaves colourful streets lined with Dutch emporiums brimming with chocolates, cheeses and coveted luxuries. Kayak lapis-blue waters, dive amongst a kaleidoscope of reefs or gallop on horseback along shaded plantation trails. Play ‘lady luck’ in winning casinos or a round of golf beside an eternally blue sea. Every moment embraces the idea that a day in Philipsburg is royal.

In dainty Terre-de-Haute, diminutive sibling of Guadeloupe and queen of the Îles des Saintes, French charm and Caribbean culture are woven together in laid-back towns and sleepy fishing villages. High above, Fort Napoleon and Le Chameau peak are flanked by fragrant forests of fern and frangipani, overlooking picture-perfect landscapes bathed in golden sunlight and sailboats afloat on gin-clear bays.

Formed by volcanoes, St Kitts fertile soil is so rich it turns monkeys green. Trek through miles of rainforest amongst colourful wildlife to conquer the highest peak of Mount Liamuiga so you can peer into the mile-wide crater, or bravely descend to sniff the sulphur. Experience a train ride, sailing trip, cooking class, sky safari zip-line, or creative batik fabric workshops. Visit sugarcane plantations, the Narrows between St Kitts and Nevis and the UNESCO Brimstone Hill Fortress for spectacular views of neighbouring islands. You’ll find this special island small in size yet tall in standing, as well as big on charm.

Explore the oldest US city for a dose of Caribbean history, slice of Spanish culture and twist of American dream. Roam historic Old San Juan alleyways to glimpse centuries-old forts and colourful colonial buildings. Learn how to move, as locals sashay out the salsa to rhythmic reggae beats. Shop the boho streets or glamorous boutiques for artisan goods, decadent designers and hand-rolled cigars. Experience world-class surfing, explore a tropical rainforest, attend a private rum cocktail tasting and polish off empanadas. Then retire to one of the beautiful beaches to soak up crystal clear waters and, perhaps, one last rum cocktail.