Cobblestone streets, historic captain’s homes, and some of the best boutique shopping, restaurants and galleries. Grab a coffee at Behind the Bookstore and wander!
Right by the ferry in Oak Bluffs, make sure you get Donavan's Dirty Banana.
A picture-perfect spot to relax and snap some iconic Vineyard photos.
Enjoy a cocktail overlooking the harbor at The Atlantic, or sip frosé on the deck at The Seafood Shanty
Wide sandy shores and rolling waves make this the best spot for sunbathing and surf
Calm waters, perfect for swimming. Also home to the Jaws Bridge—if you’re feeling brave, take the leap!
A quieter, hidden gem for watching the sunset.
Take the Chappy Ferry (a 2-minute ride) and explore this peaceful island escape, home to serene gardens and scenic beaches.
Rent bikes and cruise along the scenic trails from Edgartown to Oak Bluffs or Katama.
A dreamy farm-to-table spot in Chilmark with fresh-baked goods and organic cheeses.
Grab a lobster roll and enjoy it on the dock while watching the sunset.
The most stunning views on the island, with striking clay cliffs and a historic lighthouse.
A charming, colorful village straight out of a storybook.