Martha's Vineyard is an island located just south of Cape Cod. It is well-known for being a (not so secret) hideaway for the rich and famous and for the filming of Jaws. So you know this island means business: in terms of money and great white sharks. There is always a tradeoff between visiting a popular destination in peak season versus shoulder (or off-season). On one hand, the only way to enjoy the fabulous beaches in the Vineyard is during the summer months. But you'll be sharing with swarms of other people. And if you visit during the shoulder season, temperatures are too cool to enjoy the water, but the roads, restaurants, and trails are noticeably quieter. We went with the quieter option and visited in October.