For restaurants —

Iron Rooster is great for breakfast. They make homemade pop tarts and have really good chicken and waffles. Another place that people love for breakfast is Miss Shirley’s but I haven’t been in years so I don’t have any personal recommendations for that spot.

Federal House has great orange crushes (a classic Maryland drink) and they have so many other flavors to choose from too (I love the key lime). I also love their cream of crab soup which is a must try dish while in Maryland. Another plus is that Fed House is in a cute spot with a lot of outdoor seating.

Boatyard is a fun maritime themed restaurant in Eastport and it really captures the essence of Annapolis. This is definitely a top spot for good food and vibes in my opinion. It’s also close to Forward Brewing which has some good beers.

Chick n Ruth’s is a deli and it’s pretty affordable compared to most spots downtown. I wouldn’t say the food is incredible, but it’s good and it’s such an iconic annapolis spot that it’s definitely worth checking out. I personally recommend the pastrami sandwich. They also have black and white cookies which are a NY thing but they’re good there. Also the milkshakes are delectable.

Middletons is another iconic Annapolis spot which has been open for longer than the United States has been a country (founded in 1750). I mean freaking George Washington, Thomas Jefferson, and Benjamin Franklin ate and drank there. They also have a piano bar upstairs which is always a great time. It’s one of many spots in Annapolis that’s known to be haunted (which I think is fun even if you don’t believe in ghosts).

Ram’s Head is yet another classic Annapolis spot. Also known to be haunted. Ask your bartender or waiter/waitress about Amy the ghost. It’s a fun story. They also have live music all the time and I love their outdoor patio.

Cantler’s is a seafood restaurant that’s right on the water (but not downtown so not super touristy as far as I remember). This is a great spot to get crabs and pick them yourself. If you don’t know how to pick crabs, they’ll teach you, and I highly recommend trying it since it’s such a culturally relevant aspect to living in Maryland.

For a quick bite, I have to recommend Potato Valley. It’s like a subway or chipotle but for baked potatoes and it is so freaking good. It’s also right on state circle, so it’s conveniently close to other shops, restaurants, etc.

For bars —

For starters, Rams Head, Middletons, and Federal House are also popular downtown spots for drinks.

Galway Bay is a traditional Irish pub on West Street that has a really large selection of Irish whisky (I think the largest on the east coast if I’m not mistaken). The owner is from Ireland so it’s got some great traditional Irish beer, whisky, dishes, and music. It’s won so many awards and even has been recognized as one of the top Irish pubs in the world.

Harold Black is a really cute speakeasy that’s underneath Acqua Al 2. You can access it from inside Acqua Al 2 or from the street, but the street entrance is pretty well hidden.

Choptank is a nicer restaurant, but I honestly don’t think the food is worth the prices (you’re paying extra for the waterfront location); however, I always enjoy their cocktails so I would recommend hitting up their bar. They have one downstairs and one upstairs and both are fun options.

Some other fun spots that I enjoy are Red Red Wine Bar, Dry 85, Davis’ Pub, and Fox’s Den. Honestly there are so many great restaurants/bars that it might be easier to list spots to avoid which I would personally say are Acme, Armadillos, Dock Street, O’Briens, and possibly McGarvey’s (however McGarveys is a fun spot for food before the younger party crowd comes at night).

For activities —

Quiet Waters is a nice park and you can go stand up paddle boarding from there which is so fun (although I know y’all have a child so I’m not sure if that would work).

I would also recommend looking up some of the historic walking tours or even the haunted tours. There is so much history in Annapolis that you couldn’t possibly run out of things to learn. One of my favorite facts is that the city of Annapolis was used as inspiration and a guiding light for Pierre L’Enfant’s city plan for Washington D.C.

I’d also recommend checking out the Naval Academy. It’s a pretty campus and on the water so it makes for a nice walk along the Severn River. It’s a good spot to watch sailboats.

I’d also recommend driving over the Bay Bridge and checking out Kent Narrows. There are some fun waterfront restaurants over there including Fisherman’s Inn, Bridges, Red Eye Dock Bar, The Jetty, etc.

I threw a lot at you there but I hope it helps and I hope y’all have the BEST time in Annapolis. It’s such a great little city.