I grew up in New England and had the fortune of going on summer vacations on the coast. There is something really special about coastal resort towns in New England that I have never experienced anywhere else in the world.
When I moved to Boston I would have my summer vacations on Martha's Vineyard.
Martha's Vineyard is a place of stark beauty amid all the commotion of changing from a sleepy island of 15,000 year-round residents to a summer population of over 100,000 people.
The Vineyard has six towns, each one having its own feel and flavor. Oak Bluffs is the party town with its bars and arcade (and is one of the port towns) and is home to the camp meeting religious community and their famous gingerbread houses.
Vineyard Haven (also called Tisbury) is the other port town and has the most densely populated year-round residents.
Edgartown is the upscale town with it's white houses with black trim and next to it is Chappaquiddick Island, a very upscale and reclusive neighborhood (actually not considered it's own town, part of Edgartown).
Chilmark is a rural town with a fishing community and West Tisbury is where most of the farming is done, and Aquinnah is the southern most town and known for its famous Gay Head Cliffs.
There is a thriving artist community and the beaches are the best in all of New England.
Take a ferry from Cape Cod or even from Long Island and be transported to a place you will want to come back to again and again.