Although I covered the whole island, my favorite areas were Edgartown and Aquinnah. Edgartown is quaint without being overrun with tourists and visitors, like other towns on the island can be. The original home of Vineyard Vines, Edgartown has lots of souveneir shops, boutiques, art galleries and dining options. I have to make a plug for my favorite Vineyard restaurant, Atria. Grab the six-topper outside near the tree for a dazzling evening under the stars. Another great lunch or dinner option is The Atlantic; you can sit outside on the porch or on the dock overlooking Edgartown Harbor. For brunch, head to Among the Flowers just off of Main and Water Street for coffee and fresh seafood omelettes.
Aquinnah is a rural part of the island known for the stunning Gay Head Cliffs. In addition to the cliffs, there is an old lighthouse which is a great photo op to remember your trip. I love all things nautical, and I adore lighthouses. I don't know why they seem to fascinate me so, but I took many, many pictures of the Aquinnah lighthouse.
Chappaquiddick Island, or Chappy, is famous for a certain Senator's "incident" back in 1969, but it is also a resident-only island just off the Edgartown Harbor. (There is one store, the Chappy Store, which looks like a shed. You need to bring provisions over from the main island.) Chappy is known for its red and white-striped beach cabanas and some really beautiful vacation homes.
If you do make it to the island, I'd suggest renting a car or moped to get around. Although bikes are abundant and a great way to travel, unless you're up for a 25+ mile ride, a motorized vehicle is the way to go. Chilmark, in the center of the island, is a largely residential area; in August 2009, President Obama and his family stayed at Blue Heron Farm, coincidentally owned by a family from my hometown. Chilmark is also home to Chilmark Pottery, where you can find some one-of-a-kind pieces created right on the Island. Chilmark Chocolates is a decadent chocolate shop where, unless you just don't like chocolate, you will fall head over heels for their varieties of chocolates, truffles, and variety of chocolate-covered fruits.
Vineyard Haven is quaint, although a little busier than Edgartown as it is the main point of entry to the Island. There are some great home furnishing stores, as well as Midnight Farm, a funky and bohemian clothing and home goods store co-owned by Carly Simon. Oak Bluffs is also a fun place to visit, although it tends to be busy and crowded during high tourist season. In Oak Bluffs you will find everything from t-shirt shops, fine dining, bed and breakfasts, bars, and the oldest platform carousel still in operation located here, as well as some delightfully, brightly painted Gingerbread Cottages.
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