10 Martha’s Vineyard
It may be the most obscure choice on this list but this summer is the perfect time to explore the Vineyard’s way of life. It’s designed for an easy-going crowd with relaxing walks on the beach, quaint fishing expeditions and scrumptious goods at local stops like The Black Dog Bakery. The triangle-shaped island – which sits just eight miles off the coast of Cape Cod, Massachusetts – has been a secret hideaway for the rich and famous for years and “Hollywood East” has continued to earn quite the reputation. Its most famous visitors? Reese Witherspoon, David Letterman and Bill Murray are just some of the many but the laid-back atmosphere is what really rules the roost.
Martha’s Vineyard is full of expensive summer homes and exquisite dining but low-key towns like Chilmark, Vineyard Haven and Menemesha offer casual experiences and let you swap your stilettos for sandals. If you just want to keep things simple, opting for a bike ride to explore the smaller parts of the island can also help you experience the Vineyard at its best.