Edgartown
Elegant but relaxed, Edgartown is known for brick sidewalks, white captains' homes, boutique shops, and one of the prettiest harbors in New England.
Worth Knowing: Walk to the Chappaquiddick ferry just to watch it shuttle back and forth. It's one of those simple Vineyard traditions that never gets old.
Don't miss South Beach, Katama Airfield, or Jaws Bridge, yes, that Jaws.
Oak Bluffs
Oak Bluffs is where the Vineyard comes alive. Colorful cottages, harbor views, restaurants, nightlife, and the Flying Horses Carousel, the oldest operating carousel in America.
Worth Knowing: Visit Circuit Avenue early in the morning before it fills with visitors. It feels like a completely different town.
It's also one of the island's primary ferry ports, making it an easy place to begin exploring.
Chilmark & Menemsha
This is where life slows down.
Menemsha Harbor is famous for fresh seafood, working fishing boats, and sunsets that draw both locals and visitors.
Worth Knowing: Pick up dinner from Larsen’s or Menemsha Fish Market and eat it on the beach while the sun goes down.
Aquinnah
At the western edge of the island, Aquinnah feels almost untouched. Towering clay cliffs, quiet beaches, and panoramic views create one of the Vineyard's most unforgettable landscapes.
Worth Knowing: Come for the scenery, but stay for the silence. This is where the Vineyard truly exhales.
Tisbury / Vineyard Haven
Home to the island's year-round ferry terminal, Vineyard Haven blends a historic harbor with independent bookstores, cafés, and a quieter pace than neighboring Oak Bluffs.
Worth Knowing: Grab a coffee and wander the harbor before the first ferry crowds arrive.
West Tisbury
If someone asks where the Vineyard still feels like the "old Vineyard," chances are they're talking about West Tisbury.
Rolling farmland, winding roads, and Alley's General Store, serving Islanders since 1858, make this one of the island's most authentic corners. And don’t miss Lucy Vincent Beach.
Worth Knowing: If you’re visiting in August, the Agricultural Fair, a true island tradition that’s been bringing locals together for generations.