weekend in Annapolis
At this point I would stay away from the newly opened Hell's Point Seafood. Tom S. (can't spell his name correctly) a food critic from the Washington Post gave it a pretty poor rating, and he is well acquainted with the the chef's other restaurant in the District that gets rave reviews. It's just too spotty for food and service at this time to shell out the kind of money they want for mediocre eats.
Osteria 177 on Main St. in the historic district is excellent. The mediteranean menu is diverse, creative and the atmosphere is fun and unusual. I've lived here for 6 years, and have had some of my best meals here. Piccolo Roma, also on Main St. was a well loved Italian place that had closed. News is it has reopened, but no reviews yet.
Definitely concur with Lewnes, great pubby atmosphere and amazing steaks glazed with butter. Not a fan of Chick & Ruth's, if a deli can't make a tasty sandwich, what's the point? If you would like a nice juicy burger with shoestring fries, head to Davis' pub in Eastport. A very local place that is steps from the waterfront that dishes out some good standard grub.
Another casual eatery in Eastport is the Boatyard Bar & Grill. Very popular, eclectic menu, and voted one of the World's top sailing bars. Sailors from all over the world belly up to the bar, and it makes for a lively and fun atmosphere. It's family oriented too, so no conjuring up images of one-eyed, toothless pirates.
If you want a quick bite, head to the Potato Valley Cafe. Folks swear by their piping hot roasted spuds with endless toppings. If you want something sweet, Annapolis has two cupcake shops, many ice cream places and Aromi D'Italia that offers a variety of homemade gelato.
If you like Irish pubs, Galway Bay on Maryland Avenue fits the bill and they make a mean crab cake. If you are just looking to grab a sandwich and eat outside near the harbor, there are a few excellent places to get creative sandwiches and soups. One is in the newly opened Market House, Atwaters, and the other is The Big Cheese/ Sammy's Deli steps off the waterfront on Randall Street. You can find great bread and a variety of hot and cold sandwiches.
Annapolis may not have too many award winning restaurants, but at least there is a nice variety of places, and you don't have to walk too far to experience them.
Also love Lewnes Steak House, it is kinda' old world in the plastic menu city. If you need an all day b'fast or ez lunch, check out Chick & Ruths Delly on mid Main St. It is close to public parking and is a wild: http://www.chickandruths.com/
Last, Yellowfin has a good happy hour with a discout on OK Sushi. I've always had good food and service but note that on the GoogleMaps site, reviews are raves or pans.
Carrol's Creek, Rockfish, Tsunami, McGarvey's (especially for mussels and oysters good crab dip too) are all good. I really like O'Leary's, as well. I used to really like Lemongrass on West St., but I haven't been in a long time.
And if you happen to find yourself out at the mall, Punk's Backyard Grill is very good.
a great place for a drink on a warm afternoon is Prusser's Pub which has waterfront outdoor seating on the harbor and is in the Marriot Hotel
Two restaurants that I really like in Anapolis are Tsunami for upscale and immaginative and fresh sushi. Also love Lewnes Steak House which has prime steaks done right and also has exceptional crab cakes, fish etc.
re: dining with doc
Tara, do a search on this board. Wild Orchid has gotten very mediocre feedback. Hell Point is mixed as well. Pussers does have decent drinks.
I'm an Annapolitan CH, and for me the best seafood is O'Learys. Locally owned, as is Lewnes for great steaks. And if you're staying at one of the hotels/inns near the historic district, both of these places are within walking distance, over the Spa Creek bridge (into Eastport).