Miami, FL to Miami, FL

Sitting on the north coast of this lush, tropical island, San Juan is the second settlement founded by European settlers in the Caribbean, and the oldest city under US jurisdiction. The stocky walls and watchtowers here have stood the test of time, repelling notable invaders – such as Sir Francis Drake – and the pirates who historically looted these islands. With massive fortresses, airy plazas and sheer Caribbean beauty, San Juan is a beach-blessed star of these turquoise waters. View less With more than 500 years of European history, Old San Juan gleams In Puerto Rico’s sunshine, with sugar-almond painted facades and ankle-testing cobbled lanes. Decorative balconies and varnished wooden doors add everyday artistry to streets, dripping with history. Soak up the culture at rum-fuelled parties and salsa dances on this Spanish-culture infused island, or recline into afternoon relaxation sessions on sensational slivers of gleaming sand. Kick back on the beach, or satisfy a lust for adventure by exploring sprawling mangrove forests. The magic of sea kayaking after dark here is an experience you won't forget. Break the waves with your oar, and watch as the waters illuminate with neon colour, as bioluminescence creates a mystical, peaceful spectacle. Pocked limestone cliffs and karst landscapes add rugged contrast to the serenity of the beaches, and you can walk into folds of the earth in sea-carved caves, or across cliffs to hidden views of the Caribbean’s expanse. Enjoy a taste of the island’s cuisine by sampling Mofongo – a local concoction of green plantains and chicken. Why not indulge and wash it down with an iced mojito, made from crushed mint and locally distilled rum?

Like so many of the islands in the Caribbean, 2017’s double whammy of hurricanes Irma and Maria devastated much of St. John. However, as relief funds get funnelled into rebuilding, normality is gradually being restored, and St. John version 2.0 is emerging - bolder, brighter and better. St. John’s small size might just give it the edge over other desert islands. View less The US purchased the tiny landmass (at just nine miles long, the island is the smallest of the three American Virgin Islands) from the West India and Guinea Company in 1917 and it remains under US govern to this day. Historically speaking however St. John is Danish, who colonised it for almost 250 years before its sale to America. The Virgin Island Nation park covers almost two-thirds the island, meaning visually St. John is stunning, and will remain that way for generations to come. This ‘gift’ to the world comes thanks to Laurence Rockefeller who in 1956 gave the 5,000 acres of lush forest to the people of the island, with the caveat that it become a national park. Thus, velvety green hills slope into picture perfect white sand beaches, which are ringed by turquoise seas. One very definite winner of the tourism hiatus since 2017 has been the marine wildlife. Underwater life was barely affected by the storms and the subsequent lack of tourism has allowed the eco-systems to propagate. The island’s abundant coral reefs were not overly affected by the storms and today the waters are teeming with sea turtles, reef sharks and sting rays.

St. Kitts verdant volcanic slopes rise from crystal clear Caribbean waters, promising a land of escape, relaxation and rejuvenation. A place for ‘limin’ - the local word for kicking back, Caribbean style, you’ll be welcomed to an island paradise blessed with swarming reefs, hidden white-sand beaches, and irresistible shallow seas. Bigger sibling to nearby Nevis, St. Kitts is a place of unrestrained natural beauty. View less Soak up the dreamy Caribbean bliss, or explore sprawling island rainforests, teeming with hummingbirds and the distant sounds of waterfalls, as you walk the island’s vine-tangled paths. A ride on Basseterre’s scenic sugar train is a rumbling, immersive journey through the heart of this Caribbean island of culture and vivid unspoiled scenery. Carriages that once transported crops of sugar cane to the city sweep around long curving bends, revealing a spectacular introduction to St. Kitts. The landscapes here are beautiful, and things are no less spectacular offshore, where glorious crystalline waters invite you to dive with turtles, and explore doomed wrecks like the River Taw ship – which has now exploded with marine life. In Basseterre itself, stop off to see the pea-green Berkeley Memorial clock, which stands in the Circus, surrounded by busy St. Kitts life. Independence Square is also waiting among the city’s charming Georgian buildings. Renamed from Pall Mall on the 19th of September 1983 - to celebrate the island’s independence - the pretty square gravitates around a colourful burbling fountain, and has a dark history, as a former slave market. Wary canons watch out over the waves far below at Brimstone Hill Fortress, a site of significant history, which dates back to 1690. Known as the ‘Gibraltar of the West Indies’ due to its importance at the heart of the British empire, St. Kitts was one of the first island in the West Indies to be colonised. Nowadays, its World Heritage Site fortress offers panoramic views along the coastline it was built to defend.

The archipelago of the British Virgin Islands, commonly known as B.V.I., numbers more than 60 islands, of which only about 16 are inhabited. Discovered by Columbus in 1493, the first settlers were Spanish and Dutch planters, followed by the British in the 17th century. Tortola became notorious as the haunt of buccaneers; nearby Norman Island is said to have provided the inspiration for Robert Louis Stevenson's Treasure Island. Approximately 80 percent of the population lives on Tortola, the largest island in the archipelago. The capital, Road Town, is the administrative and business centre of the B.V.I. Its Main Street features typical island-style buildings. Banks, government offices and a small craft village are built on filled land, named Wickhams Cay.