1.) Oak Bluffs (gingerbread houses at the Tabernacle, Circuit Ave., Ocean Park, the beach, the O.B. Harbor, etc.) Plenty of souvenir shops there too.
2.) Tisbury, AKA Vineyard Haven: Coastwise Wharf (which is just the dock next to the Black Dog tavern restaurant, frequented more by touists than locals), shopping downtown
3.) Drive through West Tisbury, stop at Alley's General Store if they want to, walk around the Maley Gallery across the street, and head up to Chilmark to the small fishing village of Menemsha. The HomePort restaurant has great lobster and it's cheaper if you order takeout through their back door. You can walk down to the beach & watch the gorgeous sunsets. There are also 2 seafood stores, and cute burger/clam joints in the area.
4.) Drive up through pretty, hilly Chilmark to Aquinnah (formerly Gay Head) and check out the clay cliffs and the Gay Head Light. There are some Wampanoag souvenir shops at the top of the hill, along with fast food take out spots and one indoor/outdoor restaurant.
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