If surfing has always been on your wish list, Nantucket is a great place to learn. (The island has a tendency to bring out an inner The Endless Summer in all who visit.) As the island’s premier school, Nantucket Island Surf School has been teaching students of all abilities for almost 20 years. They offer private and group lessons as well as SUP (stand-up paddleboarding) on Cisco Beach. All equipment and wetsuits are provided, just bring along sunscreen, your bathing suit, and a sense of humor. Reservations are required.