I fell in love with this cute small town when I first arrived in the U.S.A. 3 years ago. I used to live close and take English lessons at St. Mary’s Church. Sometimes, after class me and my friends would go grab a drink or a bite to eat and so I was completely knees down for this place.
Just walking around the docks is already very pleasant, but I put together some tips for you if you decide on visiting.
When visiting Annapolis:
* Take a cab or an Uber to Downtown, you want to be able to walk there and not get stuck in traffic (it’s a small town and very busy with narrow streets), plus if you want to drink, you don’t want to drive.
* The bars close VERY early compared to big cities (expect the lights of the clubs to turn on around 1:30 – 2am and bars will be actually empty by then) so start your night early – you’ll enjoy more and you’re not going to be as tired next day unless you literally “go to town!” haha
WHERE TO STAY
There are few bed and breakfast or AirBnb places that you can find online.
I suggest staying nearby so you don’t have to drive around.
WHERE TO GO
The main street is full of bars / restaurants, stores and boutiques with local products. Really good for shopping.
Even though Annapolis is a small town, there’s a lot to do, some Sundays they close the main street for events, so double check online if you are going to drive there or even if you want to join.
Sitting by the docks and watching the boats on the bay is something relaxing to do and I highly recommend. Perhaps combined with a good book.
Any season is enjoyable in Annapolis, the ducks will be around from the Summer time through Fall and the bars will warm you up with some good food and drinks during the winter.
Take a look online to find many companies, destinations and schedules.
For more information visit: (https://www.usna.edu/Visit/index.php)
RESTAURANTS / BARS:
(Few of the many options in Downtown)
The Blackwall Hitch (http://www.theblackwallhitch.com/) the Brunch here is spectacular!
Naval Bagels (https://www.navalbagelsinc.com/) Talking about a good breakfast?! Ok, or lunch.. I mean, this place is life! It’s definitely my favorite. A MUST!!!
Middleton Tavern (http://www.middletontavern.com/) I love this place, it’s part of Annapolis history because was established in 1750. It’s great for seafood. The Oyster Shooters are a MUST if you’re an Oysters fan (I’m not, but my husband and friends LOVE IT!)
It’s very local, different than anything you ever tried and surprisingly tasty. They are 2 shots, one is the oyster with a cocktail sauce and the other one is a local beer that you use as a chaser. NO you do not get drunk with it, it’s much more like an appetizer than anything else.
They also have the famous Crab balls.
Vegetarians / Vegans also have options here: Fried green tomatoes are De-li-cious! I’m not vegetarian but every time that I go to this place I HAVE to order them, so good.
At night the upstairs part of the bar turns into a fun piano bar, which I really like for hanging out with friends and singing along with the “band”.
Rams Head on Stage (https://www.ramsheadonstage.com/) Brewery, bar, restaurant and concerts / shows.
Ok, the food is Spectacular, I can’t even point out one thing. The beers and drinks are awesome and we have been to a few shows/concerts that was really nice (keep in mind that the menu from the bar/restaurant is different than the one for the stage) Check the website for events when planning on going you might find some interesting shows.
The restaurant Buddy’s (http://www.buddysonline.com/) has the best crab dip and cream of crab / soup of crab and much more, it’s very very casual, much more like a sports bar type thing. Every New Years our friends that host the party order their crab dip and other goodies, one of the reasons that we always attend this party hahaha.
If you’re looking for a nice casual wine bar I’d recommend Red Red Wine (https://www.redredwinebar.com/) (my favorite).
Harry Brownes is a wonderful restaurant (http://www.harrybrownes.com/). I came here with my husband by “accident” a day after walking around one day and we figured out one of the best restaurants in downtown. If you get a chance, order the crab empanadas, I could have a million of those, sooo good!
If you feel like Ice Cream: (http://www.annapolisicecream.com/) the most famous and elaborated Ice Cream in town.
Other options: Chick & Ruth (biggest milk shake) ; Tsunami (sushi bar); El Toro Bravo (Mexican).
Anyway… I’ve NEVER had a bad experience with ANY bar / restaurant in Annapolis, so I wouldn’t be afraid of trying anything out of this list, plus… I really wish I could put much more, but then you’d be bored of reading it haha.
Night clubs are not really clubs, they are bars / restaurants that turn into a bustling place with a space in the middle of the tables that becomes a dance floor.
For options I’m not that familiar with, but I can tell you to try the ones I’ve been before:
Pusser’s; Federal House; Armadillo’s; Stan and Joe’s
Annapolis is in my heart forever and I love being based nearby, so I can go often. It’s my favorite town in the US and this won’t ever change. Not just because of my story, but because of the beauty of this cute little town that I can call home.
I hope you can fall in love when visiting, just like I did.
Good company in a journey makes the way seem shorter. — Izaak Walton