The Schooner (boat bar in the Lobster House) is our favorite drink spot on island! We'd recommend that or the Raw Bar (first-come first-serve local seafood restaurant) at the Lobster House. Local tip: I would not wait to get into the main dining room - the food + drinks are better on the Schooner / Raw Bar and no wait!
Great shopping at Tommy's Folly or head into the outdoor mall and visit our favorite shopping spot Cash and Clive For food - The Blue Pig Tavern, Tisha's, Uncle Bills, George's, The Mad Batter, The Ugly Mug and the Ebbitt Room are all right there