21 Federal $$$$
This is the place to see, be seen and spend money for food on Nantucket. Don't let the unassuming Greek Revival exterior fool you, 21 Federal is a big time restaurant. The portobello mushroom pudding is a staff and foodie favorite. Don't have the cash to dine here? Step up to the bar, order a martini and people watch, you won't be disappointed.
LoLa 41 $$$
LoLa just opened in 2006, but it has quickly become an island hot spot, possibly because it is so unique. The theme of this globally inspired restaurant? Anything along the 41st parallel north is fair game, we think. That means Japan, Spain, California and the Northeastern U.S. are all bound to be represented on the menu. Oven roasted Lamb Loin, California crab cakes, and tuna panko rolls are all on the menu. Service is friendly and the best part of all? This is the type of place where you could run into Bill Belichick, a prominent CEO, or a college kid who slings drinks on the island for the summer. Gotta love the contrast.
The Atlantic Cafe $$
Known as the AC this Water Street institution will serve you large portions for a fair price and let you stick around to sample some Cisco Brewery products afterwards.
A cup of Quahog Chowder and the must have Spinach & Artichoke Dip will be enough for many, but if you are here for a full meal give the Roast Beef Au Jus or any of the burgers a go.
Go ahead and skip dessert. The apple pie is nothing special and there are plenty of dessert specialty places in town within easy walking distance.