San Juan → San Juan (14 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.

A tropical utopia with soaring peaks for climbing, waves for surfing, wrecks for snorkelling, and cocktails with locally sourced rum. All around Road Town, the capital of the British Virgin Islands, are streets lined with brightly coloured buildings built during the days of colonial Dutch and British rule. Check out Pusser’s Painkiller Bar for a namesake punch before venturing into the humid embrace of the high-canopied forest of Sage Mountain. Beyond are adventures at every turn; zip-line through treetops; dive coral-laden lagoons, explore jungles with 4x4’s, or lounge on countless postcard-perfect beaches. And, since this is the so-called “sailing capital of the Caribbean,” don’t miss catching a catamaran navigating to a scattering of uninhabited islands.

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.

Mingle amongst other discerning guests on this French isle that exudes relaxed glamour. Wander along secluded beaches, harbourside Creole huts, drop into bohemian bars and snorkel gently through warm turquoise waters. Visit La Tourmente, the peaceful salt ponds and admire uninterrupted views on a local boat trip. And as you sip your second (or third) glass of champagne to the lull of the gentle waves, it might be time to learn the French for "paradise found".

Take your time, for happy hour is infinite here. Embrace the radiant warmth as you absorb the island’s history within sparkling turquoise seas that join sapphire skies. Discover the iconic salt flats, visit old-world villages, taste conch and look out from the lighthouse. Snorkel and dive through calm crystal-clear waters and revel at a rum punch party aboard a catamaran. Or perhaps you’d prefer a little snooze beneath some bougainvillea shade – a compliment to the slower, more measured pace of life.

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.

Spidery tendrils of the coast are dotted with quiet coves and hidden harbours in sublime Saint John, the smallest of the US Virgin Islands. Tune in to island time on Trunk Bay, where turquoise waters caress powder-soft sands; this is what Caribbean dreams are made of. The motherly arms of Virgin Islands National Park embrace two-thirds of the isle, an emerald expanse of protected forest etched with mountain valleys, indigenous rock art and the ruins of old sugar plantations, crisscrossed by a web of scenic hiking trails. Kayak into the knotted mangroves around Hurricane Hole or plunge below the waves at Maho Bay, where turtles and rays sluice through crystal-clear waters.

An adrenaline rush awaits. Swim with stingrays. Zip-line through lush forests. Walk across a gorge on a scenic suspension bridge. Sip excellent aged rums. Taste the island with a chef. Or stroll St. John's old town to tour cottages laden with cheerful fretwork. Explore British forts atop Shirley Heights and Goat Hill. Then rest and rejuvenate at one of the snow-white beaches.

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.

Mingle amongst other discerning guests on this French isle that exudes relaxed glamour. Wander along secluded beaches, harbourside Creole huts, drop into bohemian bars and snorkel gently through warm turquoise waters. Visit La Tourmente, the peaceful salt ponds and admire uninterrupted views on a local boat trip. And as you sip your second (or third) glass of champagne to the lull of the gentle waves, it might be time to learn the French for "paradise found".

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.