Dining on vacation is an art. And like any popular destination, Nantucket is riddled with tourist traps. You don't want to eat somewhere touristy, but you don't necessarily want somewhere as gritty as Sayle's. Shopping poses a similar dilemma. You don't want to buy something you could easily get at home. But you also don't want something you can only use in the vacation environment (a Nantucket basket carried off-island is try-hard). There is no problem if you're looking to pick up an oversand vehicle permit tee at any of the t-shirt hawkers on South Water Street. But if you're looking for a memento or a dining experience that is memorable and authentic - take heed.
[Photo via @juliahengel]