Annapolis, MD - Top 3 Restaurants
Unfortunately your options for trendy and upscale are extremely limited in Annapolis. I'd suggest O'Leary's or taking a chance on the brand new Hell Point Seafood. I know there's one negative review on here about Hell Point, but it just opened two weeks or so ago, and has a very good pedigree. If I were you, I'd take the chance since the other high end prospects are dismal and about as untrendy as you can get (I'm thinking of Harry Brownes and Wild Orchid).
If you like trendy and upscale put Tsunami on your list.
I would also suggest giving Hellpoint a try or Jerry's seafood on West St. for the Crab Bomb.
I like Carrol's Creek for classics, but it isn't trendy or modern, or Cantler's for crabs if you are up for a bit of a drive, traditional MD crab shack.
Lewnes restaurant has great prime steaks and seafood, Tsunami has pretty good sushi and eye candy, Prussers Pub in the Marriott is a nice place to down a couple drinks and chow a couple appetizers while waterfront and watching the boats sail by, If you get adventurous, take the roads to route 50 east, go over the bay bridge to Kent Island and grab some live music and drinks waterside at the Red eye dock bar, then eat some fresh seafood waterfront at either Harris Crab House or The Crab Deck,
Agree with most people on here about the restaurants: Here's my recommendations:
Lewne's (For steak)
Joss (best sushi)
Other worthy candidates include either Tsunami or Yin Yankee for sushi. This is not a food town. If it doesn't have a burger or crabcake sandwich on the menu, it wouldn't be Annapolis. Avoid anything Italian.
Annapolis is very dog friendly. In fact, one of the recommended restaurants Harry Browne's will let you dine with your pup outside. They only have about 5 tables, so it's slim pickins on a popular night. But we have dined there quite often with our 95 lb choco lab and they are oh so accommodating.
Just a few doors down is a really nice pet boutique named "Paws". It may be on the pricier side but the owners do so much for local animal charities such as fundraisers, parades, and such that we are happy to give them our business. You may want to take a peek inside.
Loews is an awesome hotel and they host a "yappy hour" on the last Friday of the month for dogs and their owners. It always benefits a great local animal cause.
You may want to go to www.visitannapolis.com and see if they have a category for pet friendly lodging. I know there are other places, inns, and such that do accept pets, but the names escape me now.
Defintiely go for a drink at Jerry's (mentioned) but stay away from eating there. They have a great roof top bar. The food is so over priced, and I doubt they will be in business for long. Osteria 177 is my favorite. We had an awesome dinner there recently. Kind of a sleeper place is Sam's on the Waterfront. It is tucked away a few miles from town, but it is in a beautiful marina with lovely yachts, has an outdoor deck and the recent chef change has brought about some favorable reviews.
Definitely go to Pussers for a drink. You can't get any closer to the water on their deck nor closer to all the boat traffic on Ego Alley.
There is a nice wine bar called the Purple Tooth, right next to Loews, that you may want to try as well. I wish our experience with OB Prime was great, but we had some issues. Nevertheless, I think it is one of the nicest atmospheres of all the restaurants in Annapolis(waterfront ones excluded). Maybe a drink before dinner? They used to have a cigar lounge but I am sure that has been removed, but the ambiance reminded me of some cool place in the Big Apple.
Frankly the other restaurants I would recommend are not in the historic district. They are Jalapenos (spanish tapas with some mexican), and Les Folies Brasserie (obviously French with an awesome raw bar). Both may look kind of dull from the outside, but the atmosphere is pretty nice inside.
Ram's Head Tavern is also kind of fun. They have a really nice beer garden, and the place has a lot of ambiance. You can dine with your pup outdoors in front, but the food is just ok.
Lewnes Steakhouse is awesome. Although it specializes in steak they do serve seafood and do it well. Trendy and upscale is not usually a term used to describe any venue in Annapolis. Afterall, it is a very historic, bayside town that caters to locals, boaters, and throngs of athletic shoe clad visitors. Think Colonial, historical, pubcentric, "George Washington drank here" kind of places. Water means casual and you can just about go to any eatery and be accepted in shorts and a T-shirt.