Marthas Vineyard is not your typical uptight beachfront island retreat. As you walk down the picturesque streets and beaches, youll see not only the famous purple hydrangeas, but also fathers building sand castles with their children, families riding bikes on the street, and ice cream smiles smeared across many faces. Fried food is plentiful and ocean-view dinners with butter-dripped lobster bibs are a nightly affair. The island attracts many elite families throughout the summer, including the First Family. Despite its distinguished vacationers, the atmosphere remains relaxed and casual. That is part of the Vineyards charm, the chance to revel in normalcy.

WHERE TO STAY: Harbor View Hotel in Edgartown. Sitting in a great location, walking distance to shops and restaurants, this hotel has fantastic views of the harbor, paired with superb service.

WHERE TO EAT: Art Cliff Diner in Vineyard Haven. This is the kind of diner that is small and casual but with a big reputation.

WHAT TO DO: Kids love the the fairytale reminiscent land of 300 gingerbread houses at Oak Bluffs, where each Victorian style cottage is brightly painted and given a whimsical name.

HOW TO GET THERE:?You can get to the vineyard by ferry from various locations within Massachusetts or fly direct from Boston, New York City and D.C.

Insider Tip: With hot summers and busy beaches, it is best to rent a private ocean front home.


Read the Massachusetts vacation guide for The Berkshires, Marthas Vineyard, Cape Cod and Cape Ann.Let’s be friends: Follow me on Instagram, Twitter, Pinterest and like me on Facebook.


Picture 1, 2, 3.