If you want to see what Nantucket was like before the new glam crowds started pouring in, head to this 1847 former guesthouse. The pink-pants-and-deck-shoes crowd has made 21 Federal its unofficial headquarters since 1985—and sunburned, just-off-the-yacht types can still be found here, downing martinis at the clubby wood-paneled bar, hobnobbing on the back patio, and crowding the tables in the homey, rambling collection of dining rooms. Chef Russell Jaehnig, who’s helmed the kitchen for more than a decade, can be creative at times (adventurous types may want to sample his pan-seared foie gras, served atop a banana tarte Tatin); but he never strays too far from the staples: seared local sea scallops; steamed Prince Edward Island mussels; sautéed halibut with lobster risotto; dry-aged sirloin with haricots verts. The one thing that’s consistently surprising about the menu is the price point—entrées cost upwards of $36—but then, observing an increasingly rare species in its native habitat doesn’t come cheap.
Tip: Book as far in advance as you can—tables here are highly coveted.