Annapolis, Maryland: The Perfect Summer Day Trip


I love day tripping or spending the weekend in Annapolis. There is nothing like a small town with medium sized town options. Annapolis is small but quaint and has a lot to offer.

Annapolis has a great waterfront. You can take a boat ride through one of the larger companies (I like Cruises on the Bay and  Schooner Company) or rent a boat for the day. I’ve even seen folks with those motorized inflatable boats from Walmart. I don’t want to be that close to the water but, hey, options are options. The great thing is that the waterfront abuts Main Street and all of its cute restaurants.

I also love Annapolis’s understated art scene – there are galleries along Main Street and West Street in addition to beautiful murals and coffee shops displaying local artwork. It’s pretty neat for a town that most only know for the Naval Academy. Annapolis also has good shopping. All along Main Street there are little boutique stores, even a Francesca’s (for your last minute accessories).

Fair warning, though, like any small town, options start running low around 8pm in which case people without dinner plans resort to drinking their dinner. This means Bridgette and her friend Lori will start to get louder and find the closest male figure to treat as a dance pole. It also means that you will get A+ people watching around 9pm.

I will say as great as the waterfront is, I am always surprised that Annapolis doesn’t have more bars and restaurants right on the harbor. Pusser’s (more on this below) is right on the bay but is about the only place where you are right on the water. I imagine this will change soon. Still, I love the laid back vibes of Annapolis – good for romance, a girls weekend or a solo jaunt. For a smaller town, I think the food options are great. Lots of seafood and good brunch spots. Here is the restaurant rundown:


Hype level: 4

Actual Score: 1

So, I mentioned Pusser’s already mainly because someone will say you have to go here. I know it looks like we’re having a good time but we weren’t. We were making videos to pass the time and avoid the chaos. I don’t know what’s up with Pusser’s but it’s scary as shit. I’m sorry but I don’t like this place. It looks damn near condemned and is full of the drunkest bros and soros (idk what the female equivalent of a bro is). The people here have that glazed over look. Don’t get in Bridgette’s way- you will see her later in Annapolis getting donuts. Aside from the atmosphere that feels like that bad toga party in college, the drinks are also typical college bar drinks with puckers and bad mixes. I didn’t eat here but I did laugh when I saw it’s supposed to be Caribbean food. Everything I saw looked liked bad baby food. It’s a no for me. With one caveat: nice water views. Shrug.

Miss Shirley’s

Hype level: 3

Actual Score: 5 always

Yes, this is the same Miss Shirley’s Cafe as the other locations in Baltimore. It doesn’t get as much acclaim in Annapolis, probably because it’s a little bit of a walk from the waterfront. But there’s still a line and it’s still DELICIOUS brunch food. I have been going to Miss Shirley’s in Baltimore for some time but this one is even closer to D.C. and not as crowded. Anything carb related is a must. They have the best waffles. My other favorite is Shirley’s Affair with Oscar. It’s a play on a Benedict with a fried green tomato as the English muffin, topped with a filet, jumbo lump crab meat and a side of grits. Yeh, it’s intense and ah-mazing.

Boat Yard Bar and Grill

Hype level: 4

Actual Score: 5

Boat Yard has great seafood and a lovely ambiance. I love their crab cakes, shrimp and everything in between including their oysters Rockefeller. I LOVE oysters Rockefeller – am I the only one still ordering these? Yeh? OK, I can live with that. The ambiance is good too. Boat Yard does “casual bar and restaurant” well and hasn’t sunk to Pusser’s level of dinge and degradation. This place does a great job of balancing fresh, tasty seafood with strong drinks.


Hype level: 3

Actual Score: 5

Maybe I missed the O Leary’s chants. So this could be more popular than I’m letting on, but it’s never come highly recommended. It should, though. It’s a touch upscale. I say a touch because the dresss code threw me. One couple was dressed for a nice dinner, another like a day out on the boat, and folks at the bar were “come as you are.” It’s still nice enough where you could easily get a bit dressed. The food is outstanding. Everything is freshly made and flavorful. I had a branzino on special with crab meat and it was amazing. My husband had seafood pasta that I kept “trying” also known as “eating as though I ordered it.” I think this is my favorite restaurant in Annapolis.

49 West Coffeehouse

Hype level: 5

Actual Score: 5

I’m not usually into coffee houses, mainly because I don’t drink much coffee but all of the locals were making a beeline for 49 West so who was I to turn away? I see why people like coming here. You can turn on your whole bohemian personality, listening to a live guitarist singing low, melodic balads while having the fanciest of cafe lattes. It’s also a wine bar so it’s got all bases covered.

The joy of Annapolis is that it’s small so you could visit all of these spots in a day trip plus fit in a visit to a gallery or two. Pro tip: walk everywhere or take bikes. Main Street/West Street is a cluster and you don’t want to deal with all the drunk Bridgettes crossing the road.

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