Harold Black - Annapolis

Phenomenal date spot Jake and "Jake" were a hoot. Realy great drinks.

Awesome place! Such a fun atmosphere set in an old bank vault.

Annapolis needed a nice cocktail bar!

Speak easy atmosphere rude bartender

Nice little hidden spot

Great spot! The basement area of the restaurant is well utilized as a hidden speakeasy style bar. There's a small food menu, but you can also ask to order food available at the upstairs restaurant. The bartender was great as she not only knew drinks well enough to recommend something based on what I liked, but also chatted with patrons (few bartenders seem to do anymore) Only downside was the music was a little loud & didn't match the experience

This place was such a a cool vibe. The staff were all SOOO nice! One of our friends has a severe nut allergy, we alerted the servers & staff and they were so kind. They took the time to wash their hands in between handling nuts and touching other glasses, plates, ect. The cocktails were so tasty and the charcuterie board we got was also delicious! Definitely will be coming back here!

This is an unforgettable bar experience. The location, the ambiance, and the menu all work together to transport you to another time and tell you a story. The skill of the bar staff is apparent in every sip. There is irreverence, wit, and passion reflected in the drink menu. This is one of the more expensive sips you will have in Annapolis but it is worth every penny! I cannot wait to go back again.

Excellent cocktails and wonderful service, especially if you are industry-minded. Lenny and Jo-Jo are absolute killers, and I’d trust my them the life of my drinking. Try a Bobsled.

Hands down one of the coolest bars I’ve ever been to in the world. This bar is competing with the architecture and ambiance of speakeasies in historic cities like London, Rome, and Paris. If someone left a bad review for this place, then I don’t trust their taste, to be honest.

Such a great place! We stopped by hoping to grab a couple of seats at the bar and Travis surprised us with a cozy corner table. He was amazing and I can’t say enough about how it made our night! Food was excellent and the drinks were perfect. Great atmosphere!! We’ll be back as often as possible.

Great food and drinks, a gorgeous space, and a high energy atmosphere. The perfect setting for a night out. Harold Black is totally different from anything else in Annapolis-- a welcome addition to the bar/restaurant scene!

Great place and great service from Madison. Didn't have a reservation, but the hostess made an exception once I explained I was visiting from Texas to celebrate my birthday. Even comped us a dessert! What a vibe..

Always amazing food! And the drinks are perfect. Sometimes it gets a little loud

Cocktails: excellent. Food: step below excellent, but good. Slightly pricey side but I think it's standard for downtown, Annapolis. Fun experience!!

Amazing atmosphere with incredible cocktails. We visit every time we are in town.

Awesome bartenders and staff. The cocktails are awesome and the food is great

Excellent atmosphere and drinks. A great "hidden" bar that Annapolis needs

Good vibes if you like cocktails in a dark, basement bar. We’ve gotten the apps/snacks which are fine. I wouldn’t eat a full meal here because the food comes from Acqua Al upstairs (separate review). Cocktails are good, not a big wine or beer selection. Overall, I’ve always liked the atmosphere and the bartenders are friendly. One of our go-tos for cocktails before dinner or late night meetups with friends.

Living in D.C. and frequenting Harold Black on Capitol Hill for years before they closed during COVID, my buddy and I made the 30-minute drive to Annapolis to visit Harold Black, also in Acqua al 2. It was a different experience than the one in D.C. What's the same is that they are both in a good Italian restaurant, but the Annapolis one if in the basement and more of a bar than an actual speakeasy. When we went, it was crowded so we're glad we had a reservation. Service was great! Our server was hilarious, but not as knowledgeable on cocktails. The menus were very basic. Our drinks were not bad, but not at the level of the D.C. Harold Black. I appreciated the Maryland hard cider on the menu. We're glad we went, but the Harold Black in D.C. was special.

Great service from Lenny and Jojo! Highly recommend the burger on the bar menu, it may be $20, but it’s worth it! Cocktails and vibes were on point.

Very cool little gem in the basement of Aqua al 2. Craft cocktails and vintage photos of old Annapolis.

The vibes here are top notch and very unique for Annapolis. You do tend to wait a bit for drinks, think we waited over 10 minutes which was a little tough because we were stopping in here before dinner at another spot. We fortunately were able to walk in late notice. We had a nice cozy little booth, which I think is one of the preferred locations here. You definitely want to be on the outskirts, the bar seemed to brightly lit and a little too bustling in contract to the rest of the dark candle lit speakeasy vibes on the perimeter.

In the basement below Acqua Al 2, Harold Black is a bar/speakeasy for a fun late night spot. I was definitely expecting “more” when you call yourself a speakeasy, but it was fine enough for an after dinner drink. The bartender didn’t seem to know much of drink making and was confused when we shared the ingredients of a drink. Ended up getting poured enough port for three glasses so it all worked out in the end. Will probably try another place next time.

Annapolis has been in need of a place that makes good cocktails for some time. Sadly, as much as I wanted Harold Black to be this, it was not. The atmosphere here is fantastic. Probably one of the coolest spots around town. The service was great, the food was good, the cocktails were… meh. More specifically, they were weak, watered down, and lacking complexity. I don’t mind paying top dollar for a good cocktail, but if I do, I expect them to be just that - good. As much as I hoped this would be a fun new local spot to frequent for good drinks, unless they can up their game, it’s just going to be another tourist spot.

It is a neat experience to enter from an “alley” door into a basement bar. The “look” of this place is really cool. But it is incredibly loud and drinks are nothing special. They pump music into the room, not slow or “classy” music, but modern music. Nothing against that, but at a “speak easy” it doesn’t mesh. Plus, folks have to talk loud over the music. There is nothing in the bar to dampen the sound, so it turns into just loud. Not a place to enjoy a cocktail really. And the cocktails are fine, but you can fine 10 or so other bars in Annapolis making the same quality drinks.

It truly felt like a speakeasy with the hidden door and the lighting/space. However, one big complaint—the music was SO loud which made conversations even louder. I like speakeasy bars for their ambience and intimate settings and while the aesthetics gave speakeasy vibes, the music and noise level definitely did not. A bit disappointed.

This place used to be good but it seems to be going downhill. Sounds like the chef left and it’s very apparent when you order the food. It’s lacking the authenticity it used to hold

The ambience and vibes were pretty cool. Service started off good, but once we closed after one round of drinks our server brought the wrong tab and then disappeared for 20 minutes and we had to close out at the bar. The drinks were kind of disappointing for a cocktail bar, unfortunately.

Not a speakeasy and really disappointing. Instead of the neat, dimly lit, quiet upstairs with intimate nooks in DC, this is an extremely loud and overcrowded basement bar. Why take reservations if you’re gonna let everyone in standing room only? Between the music and yelling, we could barely have a conversation. Server was overwhelmed and struggled to get through the crowd, but was good once he finally made it to the table. Drinks were mediocre, menu is limited, and everything overpriced. Cheeseboard was ok, but came without bread or utensils until we asked. I want the old HB back!

What a cool spot. However, the choice of music that was playing was loud and not what you would expect for a classy joint. Rap music, really?

Went there last night with 5 friends. Although we were 6 of us and going to have dinner they wouldn’t accommodate us to a bigger table because , the hostess said, it was reserved for 8 people but we noticed there was a total of 6. Anyway, that wasn’t the biggest problem , as soon as I sat at the booth, I put my coat behind me and didn’t notice there was an open flame !!!! … so my coat got on fire. It burnt so bad that now it’s trash. All I got as an apology was a round of limoncello for the table and 4 tiny pieces of dessert. The food was good, the waitress very nice but the experience was horrible.

Never again. Without notification was charged $75 for 2 cocktails. Amateurs.

The girl with black hair working in the speakeasy was flat-out rude and gave off the worst attitude I’ve ever encountered in a service job. From the second we walked in, it felt like we were annoying her just by existing. No greeting, no smile — just a blank stare like we were interrupting her personal time. And honestly, we were… because she was glued to her phone the entire night. When we asked questions, she rolled her eyes like we were wasting her time. She acted like everything was a chore — like getting a drink order right or just doing her job was somehow beneath her. At one point, she scoffed when we asked if we could close out. Scoffed. It was unbelievable. She made the whole experience uncomfortable with her nasty attitude, sarcastic tone, and complete disinterest in being helpful. It’s one thing to be inattentive — it’s another to make your customers feel like a burden. There’s absolutely no excuse for that kind of behavior. If this place wants to keep any sort of reputation, they need to seriously rethink who they’re letting represent them.

This place was a major disappointment! We were there Wednesday, Jan 29, at 5:30 and ordered the 50/50 old fashioned and a paper plane. Both drinks were horrible! The paper plane was so unbalanced, with only being able to taste a large amount of Aperol and lemon...I think the bartender didn't add any boubon or Amaro. It was gross. My 50/50 old fashioned was extremely spicy even though nothing in the ingredients would indicate any spice at all. Again, not sure the bartender knew what she was doing. I had to send back my drink and get a regular old fashioned that unfortunately was just as bad (super sweet with no bourbon coming through). The food wasn't any better than the drinks. Calamari smelled un fresh and was rubbery. We barely ate any and the burger was super small, with no flavor and about as basic as you can get. Complete waste of money and time.

We made a reservation for 9:00. They didn’t have a table for us so we finally were seated after waiting 30 minutes. We heard the server expressing his dislike for having to serve our table. He made it very apparent we were a burden and it was very uncomfortable for us. His attitude grew worse as he started huffing and puffing, rolling his eyes, slamming drinks, and blatantly ignoring people at the table. I said something to him when we were just sitting there waiting for any sort of service. Our drinks were empty and it was a pretty crummy experience. Do not recommend this place. So much potential for a subpar establishment.

I can only speak for the Speakeasy part! I am highly upset and recommend a no for this place. The bar tender a female blonde was not friendly and the fish let me not get started. I have no clue what that green soup is. Needless say I sent that ish back to the kitchen and left.

Don’t let the swank atmosphere and vibe fool you. The food is mediocre. With the exception of the wait staff who were excellent, the hostesses and manager had attitudes which should have been a warning. One stop only for our family, and others have said the same.