2. Martha’s Vineyard, Massachusetts
One of the most popular weekend getaways from Boston, Martha’s Vineyard is a world-famous island located off Cape Cod. Its enchanting coast is sprinkled with windswept beaches, lighthouses and cliffs. Because tourism is so heavy during the summer, Martha’s Vineyard is home to plenty of cozy hotels, inns and B&Bs. There are also cottage rental options if you want to enjoy a more private or long term trip. There are upscale eateries and fish & chip shacks, swanky boutiques and cottage craft shops. Don’t miss sites like South Beach, Edgartown Lighthouse and Gay Head Cliffs. Daytrippers flock to Martha’s Vineyard in the summer, but if you can swing a few nights here, you’ll get to experience mornings and evenings without the tourist crowds. Go in the off-season (October to May) to really discover the quiet charms of this island.