San Juan → San Juan (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.

Restore in blissfully quiet yet sophisticated laid-back island life. Roam amongst wildlife, learn fascinating insights into Anguilla's quirky history and gently wander to the limestone cavern of Katouche cave. Embark on a guided quad bike tour for a glimpse of island life and sail over electric blue seas to reach remote paradise at private Little Bay, where jagged cliffs flank pristine sands. Casually kayak or paddle board through warm breezes and calm waters to secluded coves and indulge in refreshing cocktails with butter-soaked grilled lobster at enticing beach bars, with toes submerged in the softest, whitest and finest sand.

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.

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.

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.

Mango-scented reveries on flour-soft beaches. Tinkling ice cubes in rummy cocktails. Rainbow marine life in crystalline coral gardens. Welcome to Catalina Island, an earthly paradise where trails meander through fragrant forests and merengue rhythms drift on the breeze. Fortune awaits in the sunken wreckage of Captain Kidd’s ship, home of silent sponges and sentinel seahorses, an underwater kingdom awaiting discovery.

Named for a Dutch pirate who once encamped here, Jost Van Dyke is a petite jewel with a bounty of lush landscapes and beautiful beaches. Hike (or water taxi) to Bubbly Pool, a natural jacuzzi created as waves at high tide crash through a crevasse. Kick back on the powder-fine sands of White Bay, swimming the turquoise shallows, finding zen at the floating spa or succumbing to the infamous Painkiller, the dark rum and coconut cocktail created in the 1970s at the Soggy Dollar Bar, polestar of the cheerful island vibe.

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.

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.

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.