San Juan → Miami (9 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.

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.

Pretty Point-à-Pitre flutters between the two wing-like islets of of Guadeloupe’s butterfly-shaped island. Meander through the leafy Victory Square to lively markets and chic boutiques or explore the award-winning Memorial ACTe. Cross the bridge to Basse-Terre to explore rain forests, waterfalls, French fort ruins and sleepy La Grande Soufrière volcano. Or venture to the east island, Grand-Terre, to hit the multi-coloured beaches, summit sky-high Castle Point, then seek sanctuary in museums for Nobel-winning poet and diplomat, Alexis Léger for an afternoon of on-point pleasures.

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.

Anchored in San Juan Bay, an inky palette washes the sky and an enchanted evening begins. Stars peep through our ebony ceiling and a feast of finest fare begins. Champagne corks pop and glasses chime as we toast new beginnings and gorge on merry cheer, while San Juan erupts in an incandescent display of fireworks to welcome the New Year.

Anchored in San Juan Bay, an inky palette washes the sky and an enchanted evening begins. Stars peep through our ebony ceiling and a feast of finest fare begins. Champagne corks pop and glasses chime as we toast new beginnings and gorge on merry cheer, while San Juan erupts in an incandescent display of fireworks to welcome the New Year.

A heavenly haven of sun-dappled beaches wrapped in majestic mountains and immersed in lively Hispanic culture. Snorkel, sail, sunbathe, enrol in a local cooking class, or climb and hike through scenic trails in verdant mountains. Pick up some pace to head further offshore by speed boat or use a quad bike to explore little Latino towns, The Mangrove Forest and the caves of Los Haitises National Park. Then re-hydrate and re-vitalise with freshly cracked coconut water as you tumble into sugar-white sands stroked by crystal-clear waters.

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.

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.