5. Antigua and Barbuda

The tradewind sailing off Antigua on its cobalt blue Atlantic water is unsurpassed, and the home to Royal Ocean Racing Club Caribbean 600, Antigua Race Week and Classic Yacht Regatta are proof that sailors love this area. A cruise around the island takes you from Nelson’s Dockyard in English Harbour, which is steeped in history, to the capitol of St. John’s to the new marina at Jolly Harbor. If you have time, take a short sail to Barbuda and its stunning beaches and Frigate Bird Sanctuary.