It depends what you're looking for. I'd recommend the Boatyard Bar and Grill as a casual place. If you're looking higher end...I'd say don't bother. Really. Unless the new Hell Point seafood opens by then and lives up to expectations, or you could also try O'Leary's, which has had some up and downs over the years, but I hear they are in an up period. What type of restaurants are you looking for?
I disagree with the statement that "higher end" does not exist in Annapolis. A place that I find often goes unnoticed is Les Folies. Although it is not downtown it is only a few minutes away and is still in Annapolis. Really authentic French cuisine...from foie gras with carmelized apples to their bouillabaisse to the coq au vin. Additionally, Harry Browne's is a great option for a special occasion type of dinner if you want to stay downtown. It's not on main street but it is a short walk from the city dock. The beef carpaccio is my favorite among the appetizers and the ribeye and the grouper stand out as my favorites from the entree selection. I would also submit that they serve the BEST dry martini in Annapolis. Of course, as said before, Lewnes' is the best bet for serious carnivores. While Annapolis doesn't really boast a list of contemporary fusion restaurants or places that serve foams or sous vides, there certainly are suitable options for a special meal if that is what you're seeking.
If you're looking for a more casual bite to eat, Sammy's Deli on Randall Street occupies the same space as a great cheese shop and they serve unbelievable sandwiches and freshly baked baguettes are always available. And as JR explains below, Galway Bay on Maryland Ave is a great casual spot for lunch.....and a whiskey if you're in the mood.
Two things to note. Sammy's does not have seating, and while Harry Browne's has higher end pricing, the service and food are both poorly executed. It's not that it's not contemporary (it's not), but the food tends to be one dimensional, oversweet, the meat tends to be overcooked, the seasoning tends to be...overbland. And the wait staff is the opposite of what you would expect at a high-end non-contemporary restaurant. They don't practice any formality that you would expect in this range. I don't mind pouring my own wine, I just wouldn't expect that would be that the case at this stodgy establishment. Giolitti's is pretty good for an Italian deli with seating, if that's preferred.
Sammy's is great, Bob the owner and his Wife are such nice people, the sandwiches they make are very good, they make a veggie sandwich that is great, and their deli meats are really good. I used to eat there all the time when it was in the market place. I don't know if they take more now, they used to only take cash and now and then I would be low so I would order a PB&J and Bob would make me something good like Turkey and Havarti instead and tell me not to worry.
Galway Bay is close and has good entree salads and crabcakes.
There is a bagel place by Grawl's Market that if it doesn't close to be bought up by developers soon has very good bagels.
The Annapolis Ice Cream Company makes a very good blackberry cobbler ice cream.
I don't know if the little Italian hole in the wall place is still out behind the Bank Of America "sail" building and Remax at West St. and Rt 2. but it was great and cheap.
Paul's Homewood Cafe is another option for cheaper good food.
There are a couple Thai places, I like Lemongrass, but none are extremely stellar, but definitely good and not too expensive for a good portion of thai.
I also love Potato Valley's stuffed baked potatoes, I don't know what they do to those potatoes, but they are the best I have ever had and they stuff them full of veggies, or chicken and put greens on top, they are just lovely. It is only open weekdays, but I really enjoy it.
City Dock has good coffee and muffins.
Hope this helps some.
"There is a bagel place by Grawl's Market"
- That's Graul's Market :) on the corner of Rowe and Taylor, and it has a very good butcher and bakery.
"I don't know if the little Italian hole in the wall place is still out behind the Bank Of America "sail" building."
- That's Giolitti's Deli, on Somerville Road across from the Whole Foods in the new Parole Center, and it is very much still open, (and the "sail" bank is Sun Trust, not BoA.) I'm worried that Whole Foods is going to gobble them up and spit them out. Please support the local shops!
Your post reminded me of this story about John McCain's favorite Annapolis restaurant when visiting his son at the Academy, Pussar's Caribbean Grill: http://www.npr.org/templates/story/st...
I remember it being a nice story about the chef, but I haven't been to the restaurant and don't remember if it's been mentioned here. I'd be curious what people here think of it.
There's a nice long thread about Annapolis that might also be helpful -- if you can't find it, I think I can find it for you.
Please report back this summer about where you go!!
I'd second Lewnes's ,, best steak in town by far (better than the big chain place up the st).. 1/2 block down is O'leary's one of the better upscale seafood places, good and pricey too . Wild Orchid is a nice cozy little place in Eastport. Paul's Homewood on West St. is a non-touristy gem with excellent Med influenced bistro style dining. Both Paul's and the Orchid are real values and affordable. For a true MD crab experience -- there is nothing like, Cantler's Riverside Inn (out-of-town, about 15 mins from the Yard). Want a "pub" experience? Galway Bay stands out in a town overloaded with Irish Pubs (visit the bar here - great draughts and super selection of Irish whiskey & Scots whisky)
Galway's crab cakes are some of the best in Annapolis.... who would think it? Fish and chips are great as you would expect.
Someone mentioned Pusser's -- I think like many waterfront or view oriented places, the food is not real the focus so don't expect too much. Buddy's being a prime example.
Agree on Boatyard - nice vibe. Nearby Rockfish fun and good, but a bit pricey.
Near Academy, consider Cafe Normandie - very solid. Nearby, try YinYankee.
Further out (east) Jalapenos for tapas etc. - undistinguished location but a class guy (Gonzolo) runs it. We've lived here 15 years and it's go-to place for honored visitors (but not pricey)
In general, agree with other posters. Pusser's is a rathole, however.
What makes Pusser's a rathole? Go there to sit outside and enjoy a painkiller with the view.
The Wild Orchid is also a good choice. It is in Eastport, just over the drawbridge from Annapolis. I agree with Lewnes, O'Leary's, Sammys deli, Tsunami, Jalapenos, Joss, and Boatyard as the better (best) places in Annapolis.
I had a really great meal at Harry Browne's recently so I have to beg to differ with one of the previous posters. I am a closet chef and have eaten at many great places and found their preperation, service, taste, and execution to be quite admirable. I admit that consistancy is key but 99% of eateries flunk this test at some time.
Osteria 177 on Main Street in Annapolis is great. Loved the atmosphere and the mediterranean food was delicious, creative and fresh. Higher end, for sure, but I thought it was worth the money.
Ditto for Les Folies on Riva Road near all the malls, an unbelievable raw bar, and quite well executed french county meals. Jalapenos nearby with its small plates menu and blend of Spanish and Mexican cuisine hits it on the spot most of the time. Not your average Latin place. The flavors are tremendous and the selection excellent.
If you would like some cheap eats, try Davis' Pub in Eastport. A perfect hole in the wall next to the water serving juicy burgers, cold beer and shoestring fries. Leeward market, also in Easport, is about as casual as you can get, but they use organic produce and meats and have some interesting sandwich combinations. Lastly, the newer Philly Flash on West Street, in the new condo complex bordering Chinquapin Road, is a family owned place that serves up great Philly Cheesesteaks and other home style specialties.
If you would like to go the chain route, Annapolis has just had an explosion of new restaurants including: Gordon Biersch brew pub, PF Changs, Metro Silver Diner, Cheesecake Factory, Greystone Gille, Brio Tuscan Grille, Fado Irish Pub, Carpaccio's, Morton's Steakhouse, and Austin Grill. There are more opening as we speak, so the variety of chain eateries will continue to expand.
Also, the new Wholefoods just opened up in Annapolis Towne Center. It was supposed to be the second largest in the country, but they scaled down during construction. Nevertheless, they offer all kinds of hot and cold buffets (bbq, asian, salad, seafood) and also have a grill and pizza oven, where they serve freshly prepared burgers with local beef and store baked buns. You can eat at the location itself, as they have cafe style seating within the store.
I just wanted to mention that Philly Flash does make a pretty fantastic Cheesesteak. The bread's still more Maryland style, not Philly style, but the meat quality and meat to cheese ratio are both great. Add on the well cooked and seasoned crinkle cut fries, and it's a great meal. FYI: It looks like they're either opening up a second location or moving the store to the Annapolis Town Center.
Annapolis, MD, Annapolis, MD
I second (or third) the motion on Folies for very good basic French cusine, though it is in an uninspiring environment in the Annapolis burbs. Check out their website.
On the Annapolis dock, Aromai d'Italia is a modest cafeteria-like eatery with great gelato, very good breakfasts and decent cheap Italian (pizza, sandwiches, Italian desserts). Reminds me a bit of lunch places in Italy. Owned and run by an Italian native I believe.