San Juan → Miami (7 nights)

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.

Savour a fusion of heritage in sparkly St Thomas. Roam a flawless Capital teeming with local culture, smart boutiques, American hallmarks, streets bearing Danish names, and former hideouts for the notorious pirates of Blackbeard and Bluebeard. Climb up to historic landmarks, catch the cable car for serious views and savour the Frenchtown quarter famed for its restaurants. Ferry to scenic conservatory of St. John, float around diamond-sand beaches with limpid blue waters and venture on forested yomps through rugged hilltops. Dreamy Caribbean warmth soaked in Danish roots and American influence - this USVI is a curious culture clash with plenty of personality.

Clasped between the Dominican Republic mainland and the jungle-draped hillsides of the Samaná Peninsula, little Cayo Levantado is a jade droplet in sapphire seas. Tread softly across ivory-white sands before crossing the crystalline waters of Samaná Bay towards unscripted adventures. To the north, a primordial world of rainforests, waterfalls and secret coves, where hiking trails thread through lush forests to soul-stirring viewpoints. Travel south to paddle pristine mangroves serenaded by a symphony of birdsong or cruise to powder-soft beaches where coconut groves spill down to cerulean shores. Colourful clapboard houses outshone only by the radiance of bougainvillaea and hibiscus provide the backdrop for fresh fish feasts and rum punch sunsets.

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.

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.

Wander into the reality of a serene Bahamian dream. Alluring, exclusive and eco-friendly, an escape to this island marine reserve is possibly the world’s most coveted invite. Slowly snorkel, gently paddle board or glide over aquamarine waters by boat. Wonder at marine life and nature in its natural habitat, visit the marina, lighthouse, lagoon and pastel-hued buildings. Recline for a beachside massage, settle into a lazy lunch, sip endless rum cocktails and sink into powdery white sands cooled by the soothing sways of palm leaves. If paradise was packaged, this island might be the finest gift.

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.