With more surviving 18th century buildings than any other city in the United States, visiting Annapolis is like stepping back in time to the days when the city was a colonial seaport. Known as America’s Sailing Capital, the city is located on the shores of the Chesapeake Bay and is a paradise for water lovers, famous for its crab cakes, lighthouses, and 500 miles of gorgeous shoreline. Tour the campus of the US Naval Academy, or the Maryland State House, the oldest state capitol still in use.
Things to do in Annapolis
4.5 based on 603 reviews
We love their imaginative pizzas and combinations, including butternut squash with goat cheese and prosciutto. Great fresh salads to start and excellent wine choices, including a $5/glass (during lunch?) Be ready for a wait or better yet go very early- as soon as they open -or late, at the end of the night.
4.5 based on 482 reviews
We have taken our son, daughter-in-law, and young grand-daughter here several times and always enjoyed it thoroughly. The tapas are many and varied, and always delicious. We always order several and share them. Entrees are equally delicious, and perfectly cooked. Do make reservations, as they get quite busy!
4.5 based on 157 reviews
A modern industrial take on a Prohibition- era speakeasy. A place where you would sneak a bourbon, craft beer and gourmet comfort food meal if Prohibition were still the law of the land today.
Some hits and misses: they couldn’t make a bloody mary to save their life and clearly skimped on alcohol when you order say, Grey Goose versus house vodka. On the meals the brioche buns on the sliders were just stale and nasty. Fries came out luke warm and soggy.
BUT, this is still a great place with a speakeasy vibe and upscale crowd. Stick to burgers and whiskeys and nothing fancy and you will leave happy. But this is no Iron Rooster food wise.
4.5 based on 1 reviews
The Boatyard is where local sailors, fishermen and lovers of the Chesapeake enjoy pint drinks, great crab cakes and the freshest local seafood. Specialties include smoked fish of the day (on premise), cream of crab and Maryland crab soups and an extensive list of crab and seafood specialties. The First Lady came from the White House to enjoy our crab cakes. The Boatyard has the most extensive raw bar in the area including a variety of oysters, clams, shrimp and mussels. The Boatyard receives awards for being most family friendly and having the best burger on the Bay. Its weekend brunch is the best in the area. The Boatyard is located in the historic maritime district of Eastport-a short walk or water taxi from Annapolis City Docks. Its photo boat films the local sailing races and shows them nightly. Named by Coastal Living, Sailing World and Sail Magazine as one of world's top sailing/boating restaurants.
That rare place where both locals and touristas hang, so what else do you need to know?! Solidly above average everything, great beers on tap, very nice oyster selection, great location (if you park in downtown Annapolis somewhere, just walk over the Eastport bridge, which is easy and recommended, take the first left and you’re two blocks away). Dick has been a supporter of all things local (such as the Maritime Museum) since Moses was a newborn. That’s not the reason to go, but it’s nice to know you’re supporting the gestalt of Annapolis/Eastport when you do!
4.5 based on 1 reviews
We had lunch there on a Saturday and waited about 40 mins for a table for two. I very much enjoyed my crab hash. The hash browns were very crispy, though the amount of crab in the crab hash was less than optimal. Service was good and I enjoyed the decor.
4.5 based on 192 reviews
Excellent local eatery offering Mexican and Latin cuisne.
We have dined here several times and it has been excellent each and every visit. The food is very fresh and authentic. The restaurant is always crowded and lively. I really like that they combine dishes from several countries in South/Central America which adds even more diversity and interesting items to the menu!!
4.5 based on 377 reviews
The Lewnes family has been serving fine food at this location since 1921. We trust that your dining experience with us will be a memorable one!
My husband and I had dinner recently to celebrate our anniversary. We remembered eating there in the past and we're prepared to be blown away. Instead we found the food good and our waiter friendly but we waited longer then we would like to request things such as a new drink etc. Over all we've eaten in better steak houses. The wine selection and recommendations were great.
4.5 based on 477 reviews
We celebrated the new year at Osteria. The price fixed dinner was simply spectacular—carefully conceived, wonderfully cooked, graciously served. There was a special menu for the occasion, but it was a reflection of the great meals we have always had here. Probably the best restaurant in Annapolis and a terrific go-to place for special occasions.
The wait staff knows the food well. It’s impossible to go wrong taking their advice.
4.5 based on 345 reviews
We are six locals from Annapolis. We really want a great seafood house and want this restaurant to fix this problem so we can support it! O'Leary's last night was somewhat disappointing. The food was spotty in quality. My fish was cooked perfectly and presentation was very nice. My neighbor's fish was terrible and uneatable. Same fish dish! After showing this to the waitstaff it was redone but every other person was finished their dinner. The Scallop special was not served hot but tasted fine. And their signature rockfish was thought to be heavily battered and unappetizing. This restaurant is very cute and cosy. Great service, a nice wine list and parking! The impression was that the kitchen needs to do a better job if you want repeat local customers. No one in the group after spending a fair amount of money on drinks, wine and food are in a hurry to return here. It's really a shame! The restaurant for a Friday night was far less than full the whole time we were seated. Maybe they need to look into the reasons why.
4.5 based on 235 reviews
Mason's serves Fresh Maine Lobster, Crab, and Shrimp Rolls, Chowders, Bisques, and Maine Root soda's all direct from Maine!
This small unpretentious place is a true find for a delicious moderately priced lobster lunch.
Various styles of lobster roll and lobster salad are offered...prices around $14 per. Good quantity of fresh--not frozen--lobster meat assures you of a quality lobster roll. You'll probably want a second one, so consider getting the jumbo or an assortment of three if you're really into lobster!
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