Newport Island, Rhode Island
Home to North America’s Volvo Ocean Race (and at one point, America's Cup), Newport is one of the top sailing destinations on the planet. A 40 minute drive from Providence and situated on the southernmost tip of Aquidneck Island, Newport’s legendary Ocean Drive (also known as Ten Mile Drive), includes a journey past elaborate mansions and Fort Adams State Park, which is home of the iconic summertime Newport Folk and Jazz Festivals. Also on Ocean Drive, you past Hammersmith Farm, where JFK and Jackie celebrated their 1953 nuptials. But you're here for the sailing: If you didn't bring your own, be sure to hop aboard an authentic America’s Cup 12-meter yacht with America’s Cup Charters. Unwind later at the Hotel Viking for Top of Newport Spirits & Stogies’ curated dinner experience, which has a rotating weekly spirit and cigar selection paired with a three-course menu.