Harold Black - Annapolis

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 spot in Annapolis that is just a little different. Drinks were top notch. Jake the bartender knows his spirits and makes great recommendations as well as drinks. Definitely try the Mai tai (it’s not your sugary punch version) and the NY sour. Cheeseburger was good. Staff was very friendly, and we will return!

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.

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.

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.

Very cool speakeasy new to downtown Annapolis. The drinks are pricey and not overly strong but the atmosphere and service make the visit worth it if you’re looking for a fun night out. Would love to see more of these restaurant/speakeasy’s in downtown in the future.

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.

Great atmosphere. Amazing whiskey sours!

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.

We visited Annapolis for a long weekend and made a Saturday night reservation at HB. We were slightly confused at first on how to enter, because yes the place is supposed to be a bit hidden but a few more signs could've helped (or info when we made the reservation). I do agree with another reviewer that the music was way too loud. We were there at 6pm for pre-dinner drinks and the music volume definitely felt more like late evening club tunes. Hard to communicate even just for our party of 2. We were seated at a booth which was nice. Our server, Gabriel, was very attentive and very friendly. We enjoyed our selection of cocktails and thought the prices were fair. We also ordered some of the French fries which were good. We left to tend to our reservation upstairs, however, we probably would have stayed at HB to eat had the Acqua menu been offered. Feels like a veteran move to be able to order from that menu and we were first timers. Overall, I would say we will definitely be back when visiting Annapolis again. The ambiance (aside from music) and service were spot on.

My brother and I found Harold Black on a Saturday night and were thrilled to get a table without a reservation! It's a very cozy and dimly lit space under Acqua. Definitely recommend for a night cap or even getting the night started! I had a buffalo trace Manhattan which honestly tasted more like an old fashion- but I wasn't complaining haha. They definitely make their drinks alcohol forward and I found their pricing to be very reasonable. I'll definitely be stopping by again!

My first speak easy experience. We sat at the bar and were able to order dinner from the full Italian restaurant menu. The place has a really cool vibe and the bartenders were fun to watch and chat with. I don't drink alcohol but they made me a virgin mojito. The place has great ambience and I loved the decor too -- especially the glass and metal screen at the back of the bar.

Nice speakeasy. Visit here after dinner and had a good time. It's pretty small and if you don't have a reservation be prepared to wait, the place is small so if you arrive on a night that's busy you will have a wait. It's pretty dark (I guess to keep up with the whole speakeasy theme) but it is a pretty cozy spot. The food isn't too bad, but nothing to really brag about. The drinks are good as well. To be honest I'll probably be back when I'm the area and I just want a cocktail with someone.

From the time you are greeted with a smile to the excellence of the cocktails...Harold Black is an excellent experience every time. If you want to feel the essence of a reimagined Annapolis... Check this place out. In love...

For DC people, visiting Harold Black again is such a special experience as this was a long-time favorite of ours on Capitol Hill. The added bonus of this new location is that you can order the full Acqua al 2 menu from upstairs. We thoroughly enjoyed a dinner of the pesto gnocchi and linguine and clams (both favorites from their days in DC). The service was super quick and the atmosphere was almost as good (although much bigger) than its predecessor.

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.

Very nice speak easy venue. Decor is nice. Would never knew this place exist unless the staff of Aqua Al 2 mention it. Drinks good. Haven't try the food here yet. 2 different venue run by the same owner with 2 different theme. Love it. Will be back.

Great speakeasy. Cool vibe. Played great 90s music the nights we've been there. Cool , old black and white Annapolis photos on the walls; adds to the vibe with the black leather booths. Oh, drinks are yummy too.

Speaking easy....super cute spot that plays 90's hip hop. The service is awesome - I wish I could remember our server's name - and everyone is super cool while they bob heads to the music. Grab some friends and chill at this hidden gem !

If you where a Fan of the Old Harold black, when it was in DC, then you will be extremely Disappointed. Although the ambiance is "quaint"in its own right; this iteration of Harold Black is less "mystique" than its predecessor. The Good: It's placement in the back basement of the restaurant gives it the Speakeasy vibe that it was going for. You will be pleasantly surprised by the menu and the skills of the bartender. As much as I enjoyed the skills, my one complaint was how tight the restaurant was. There is not a lot of standing room and when the place gets a little crowded it feels like people are standing right on top of you. I live the is place with an average size crowd but on a weekend it isn't the place for you if don't like people right next to you getting loud. Additionally, the music gets turned up to compensate for the noise, and hard to hear your conversation... hence the removal of the star. If I could give 3.5 I would, but it was an easy round up.

Food is basic. We ordered shrimp, fries and calamari, None of us finished our food. Service and and ambiance is great We had a good time

An expensive and very disappointing dinner. Music was loud and not conducive to conversation and we had to ask that it be lowered to avoid screaming at our table. Our server lowered the music, but the management put it back up a few minutes later to an inappropriate volume. Song being played were more for a dance club than dinner (B-52 Roam, Prince Purple Rain, Fine Young Cannibals You Drive Me Crazy). Food was ala carte and portions were very small. Cocktails were average and there was zero speak-easy appeal. Salt was stuck in the shaker, we were told that butter was not normally served with the bread, and the tables were metal and freezing. Our server stated that she was 20 and had no experience with the cocktail menu. The restrooms were large and nice. Overall, a very disappointing and not worth the money experience. Not even sure why this is called a speak-easy other than the only sign was on a typed piece of paper on the outside of the door. Not worth the hype. They also do not validate parking.

This place is an old 18th century building with a speakeasy in the basement. The service is top notch along with the happy hour menu.

I always love Jasper's. It's a neighbor staple with consistently good food. This order I tried the fish tacos. They were great and very filling. Great value for the cost.

This place has such a great vibe. As soon as we walked in the ambiance was on point with candles lit everywhere and a great hip hop playlist. The French fries hit the spot and the drinks were delicious especially the espresso martini! We will definitely be coming back! Such a hidden gem!

Waited for so long to get in, Refused to serve us because we were already drinking. Never heard somebody reject a group of people so disrespectfully. Wanted To have fun at the speakeasy and they shut us down for no reason. Was really happy to go to this place but honestly it's so stupid. Do not wait to go into this shit show. So rude So annoying Fuck it Grow a pair and be honest, so rude to people that just want to have fun......out

Best "speakeasy" in the DMV. Atmosphere is vibing with GREAT tunes and quality drinks. Just don't tell the tourists!