Leaving behind the lively streets of San Juan, we arrive in the Dominican Republic – first at Punta Cana, home to the longest stretch of white-sand beach in the Caribbean, and then at Santo Domingo, a charming and historically important city where we spend two days. Enjoy your time exploring its cobblestone streets, lined with buildings dating back to the 1500s, including the first cathedral built in the New World. After all that sightseeing, a day at sea brings the chance to relax before Jamaica comes into view. Here, we visit Port Antonio – beloved by the likes of film star Errol Flynn, and celebrated authors Ian Fleming and Noël Coward, for its hidden coves, mountainous coastline, and waterfalls – and then the Montego Bay to recline on its stunning beaches or enjoy a round of golf. Next comes George Town on Grand Cayman for a spot of shopping – a visit to the Cayman Islands National Museum is also rewarding – before one last sea day brings us to our final destination, Fort Lauderdale.