Which town is best? All have unique landmarks and separate histories. The down-island towns, Oak Bluffs, Vineyard Haven and Edgartown, are close to beaches, lodging, shopping and dining. The up-island towns, West Tisbury, Chilmark and Aquinnah, are located in remote parts of the island. Insider Tip: If you want a cocktail with meals, only restaurants in the “wet towns” serve alcoholic beverages.