I've always heard such amazing things about Martha's Vineyard - quaint, charming, Americana at its best. In May 2016, I took a four night trip to the small island and loved it! This is a perfect place for a long weekend getaway.
Nantucket gets all of the publicity but I loved the more rustic charm of Oak Bluffs which was a short bus ride (or easy cycle) from Edgartown.
Edgartown is a perfect afternoon trip. Fill up on lobster rolls and then walk the beach and charming boutiques.
Getting there: Air Canada and Porter fly directly to Boston from Toronto. From there, you can drive or get on a 10 seater plane and scoot over to Martha's Vineyard in about half an hour. We had the plane to ourselves on the way there. Coming back every seat was taken and we flew in dense fog - a nailbiter!
We had a lot of time to stare at the impressive ceiling at the local airport on our return. Fog delayed the flight back. The airport was quiet and very Americana charming.
When to go: We went Victoria Day weekend in Canada (3rd week of May) - the week before the Memorial Day long weekend in the US which is when the crowds spill in and prices skyrocket. It's not swimming weather but you can still walk the beaches and cycle comfortably. Leave your heels at home and pack jeans and a hoodie.
Stay: We stayed in Oak Bluffs vs the more high end Edgartown - a great choice that was more low key. Check out the local B&Bs - our pick, The Oak Bluffs Inn, is an old Victorian house with a coach house, on the edge of the shopping village. The price was right and every afternoon, Erik the owner (a great character!), served up freshly baked chocolate chip cookies. He also invited us for a bonfire on the beach to watch the sunset.
Walk around Martha's Vineyard to check out all of the gorgeous painted houses - so charming and all unique.
I think I ate a lobster roll every day. Obsessed!
Travel tip - Make sure you get health insurance. I had an ear infection and needed to go to the hospital emergency late Sunday night. The visit cost more than $1700US!! Fortunately I was covered by my work benefits but that would have been a terrible way to end my trip.