San Juan → Bridgetown (15 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.

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.

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".

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".

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.

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.

A low-lying cay with a laid-back luxe vibe, pretty Provo is the cosmo-cool jewel of the Turks and Caicos Islands. Encircled by virgin coral and pristine beaches, the cosy cay is crowned with glorious Grace Bay Beach and swoon-worthy Provo Golf Club. Charter a fast boat to a remote island to find the perfect slice of sand then crack open lunch at the infamous Da Conch Shack for its name-sake delicacy. Live on the edge and discover the widest blue hole, the largest dry cave system, or the unforgettable Wall. Best of all is taking it slow, being gloriously cradled in paradise.

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.

Soak up the ultimate wellbeing experience at a real life “Nature Island.” Oxygenate in lush rainforests, revive under waterfalls, convene in thermal sprint waters, and detox in volcanic mud baths. Trek Morne Trois Pitons National Park, a UNESCO jewel with the Mother Nature’s rarest flora and fauna. Stir-up true Caribbean soul food; taste callaloo soup; sip spiced rum; and learn how herbs can heal. To cap it all, you can even snorkel in the bubbles of uber-healthy Champagne Reef.

Summon your inner Robinson Crusoe on remote Bequia. Secret lagoons. Castaway picnics. Warm waters in shades of blue that beg to be snorkelled through. Stake your flag in the sweet Bequia breeze just as the Union Jack did for almost 200 years. Usher in deep tranquillity on lovely Princess Margaret Beach. Ascend Mount Peggy with sunny views of St. Vincent. Stoll Belmont Boardwalk to Margret Beach for hand-whittled mahogany boat models then prowl the concrete catwalk that runs along Port Elizabeth for home-churned nutmeg ice cream. Support a sterling turtle sanctuary protecting the rare hawksbill or ferry to nearby Mustique, the favourite holiday romp for Prince William and Kate Middleton.

Gently breeze into the vibrant capital of Barbados. Steeped in fascinating history, with architecture to match, uncover the wonderfully laid-back West Indian ambiance. Embrace the slow Bajan rhythm of this welcoming island; surf, snorkel and try spotting turtles in balmy azure waters. Explore subterranean Harrison’s Cave, Jacobean St Nicholas Abbey and zipline high above bountiful tropical flora. Then return to restore on pastel pink sands at palm-studded beaches, where you’ll discover cocktail hour is endless, and measures of rum are copious.