Very nice dinner, food was excellent. Restaurant is loud so if you're looking for quiet this is not the place.

My wife loved the crab cakes, and I loved the steak. We both had great drinks too. We will be back

Food was fantastic. Got a little warm when the restaurant was full.

Six words: Ahi Tuna & Crispy Rockfish & Dessert Cocktails

The Ahi Tuna Tartare was best I have had anywhere, not just tuna it was topped with avocado cream and lots of lump crabmeat, along with pickled ginger & wasabi. And big enough it would be a lunch entree

Main of crispy rockfish was super awesome, right amount of crunch without being greasy. Perfection

Dessert cocktails were great, I had a coconut drink, wow

Our waiter was the best. He spent time with us explaining the food & wine. He made our experience extra special!

Always terrific!

Waiter was serving to customers who were seated after us , taking our cocktail order after 25 minutes, ridiculous. Waiter also told us crab cakes have a 2 percent filler, not true, 50 percent is more like it. Tuna Tartare appetizer was out of this world. Wanted to go here for many years but never had the time. What a disappointment .Better off going to Middleton

We had not been to O’Leary’s in a few years. Our mistake. The food has always been excellent. The service good to very good. The restaurant itself, nice but not over the top. It lends itself to casual dining in an inviting atmosphere. The last time we were there parking was nearly impossible. That has changed for the better and I mean “much” better. I have eaten in many of the restaurants in Annapolis and I include this one among my favorites in spite of not eating there frequently. My mistake and I hope to correct it.

Our dinner was delicious and the atmosphere was relaxing. My husband and I highly recommend OLeary for special occasions.

Our server, Dimitri, was phenomenal. He was attentive, knowledgeable and engaging. Our meal was delicious from the cocktails to the appetizers and entrees as well as the dessert. We will definitely be back.

A wonderful place that we have enjoyed for special events. Excellent food and excellent service!

Excellent service with attention to detail. Fabulous food.

Stellar seafood choices - we had the Ahi Tuna Tartare which included avocado and lump crab meat, a fish soup with creamy sauce that included some carrots and other vegetables, the entree with crab cakes that was split into a single serving, divers scallops entree with crab risotto and sautéed spinach. We were full and skipped dessert but the dessert menu looked very inviting. The only thing not available tonight were oysters in the raw or grilled because of non delivery. Drinks including sparkling water, Prosecco, and excellent Pinot Noirwere our beverages of choice but a wide range of choices for cocktails, beer and wine available. Prices were reasonable for the quality of food served with appetizers in the $10 to 15 and entrees in the $20 to $39 range. This is not a chain restaurant so emphasis is on quality and freshness plus service.

Service and ambience are fine. This restaurant's food quality is excellent. The central ingredients of each dish are allowed to come through without any of the contrivances many other restaurants employ. Thus, the ingredients have to be both fresh and high quality.

Crab cakes, fish and meat dishes are all well prepared.

Good, solid wine list designed to be 'food-friendly' - meaning they compliment the cuisine, the wines do not overpower the natural flavors of the excellent preparations.

Lovely restaurant with great food. So appreciate the fact that you can have a conversation...

Food was great. Server was pleasant and service was very good. I had the crab cakes and they were mostly crab, virtually no filler. My husband had bkackened coho salmon, which was delicious. Will definitely recommend this restaurant to friends.

Everything was outstanding from beginning to end. There was something for every discerning palate. You need to go to O’Leary’s and we will certainly be going again.

Delicious but on the expensive side ($50 for dinner, without wine or cocktails) and the servings were not particularly generous.

O’Leary’s has a menu that is as dependable as it is tasty. The food is always prepared well and presented thoughtfully. The drinks are excellent and wine selection is very good. Dmitri, in particular, is very knowledgeable about all wines and exceptional at recommending pairings.

Mixed Review - we went for Easter Sunday with a reservation and were seated relatively quickly. We waited an incredibly long time for our food. It just wasn't coming out. We know it was a holiday and weren't in a rush but it took over an hour to get served. Our wait staff was overwhelmed and we knew it wasn't her fault, but she kept ignoring us because she likely didn't know what to say. It took 45 minutes before a manager came to apologize for the kitchen back up or whatever the problem was. The manager comped our entire meal which was the right thing to do. The food was very good and I'd go back. My only recommendation for the restaurant is for the wait staff or manager to come out much earlier. Offer us a drink or an appetizer that doesn't require cooking, something.

They must have been having a bad day on Easter Sunday. People waited hours for their food. When it arrived it was not the correct order and the food was cold. Clearly a problem in the Kitchen. The Chef was pulling attitude, they ran out of stocked items, had to run to the store to buy eggs. It was a colossal failure. Where they failed the most was not letting customers know what was going on. There was no offer of bread, a salad, or even fruit while waiting. None of the staff seemed the slighted bit interested in addressing it however, on a side note, our waiter did ask for status a couple of times. We were told it was a problem with the "hood" in the kitchen but we think it was a problem the help in the kitchen. We waited for an hour and finally asked for bread which came with disgusting soupy garlic butter. Another guest said they waited 2.5 hrs. Really? We finally left 1.5 hrs later without food. We drove to the ice cream shop down the street and finally had a new version of brunch. That was good.
Would I ever go back? Probably not. I understand a kitchen issue but I don't understand how poorly the restaurant handled it. So, no... probably not.

Great..Dmitri (food maestro) and Jennifer (drink maestro) are stars....

Cocktails, food, and service were all great. It’s a little expensive for frequent visits, but all of the restaurants in that part of Eastport/Annapolis are close to comparable in price, but not equal in quality. The server (Jessica,) knew the dishes, the cocktails, and even the craft beers. Will definitely go back. Highly recommend.

This was our second anniversary visit in six years. I’m not sure how they knew this was our anniversary but they had special (and complimentary) anniversary wine ready for us. The food was amazing and they even created a dish based on something I had ordered the first time I came (which wasn’t on the menu). Our waitress was very polite, attentive, and her suggestions were perfect. Will visit again when I have some extra money to blow!

Phenomenal seafood dishes!

Great food and great service. Fantastic night out!

I really liked this place, and definitely will be going back soon.

Loved our booth...cozy and the artwork is fun to look at. We had a fabulous waitress, Jessica. I would ask for her again. Our food was cooked perfectly and the presentation was awesome. I have nothing negative to say. We will def be back.

We love dining there and the food never disappoints!

We have had many wonderful meals at O'Leary's for special occasions and just for a weeknight treat. Excellent wine list and the meals are always special. The staff is warm, friendly and accommodating.

Thoroughly enjoyed our 4 different seafood dinners. There were no appealing appetizers, it was all seafood. And if you don’t want mussels or clams etc. not much to choose. Service was professional and we would go back. Wish it didn’t always cost $100 for 2 no matter where we go - 2 drinks, 2 entrees and 2 coffees.

We were on a date and the atmosphere was just what I expected. The service was excellent and the people were really nice. I will be dining at O'Leary's again.

Food and service were outstanding. A bit expensive but well worth it. The only drawback - the space is small, a bit crowded and a bit noisy. That drawback notwithstanding, I recommend highly. We had Red Snapper, Salmon and Shrimp and Grits - all were exceptionally good and exceptionally well presented.

Awsome food great service shrimp and grits and the oysters were crazy good

We (unknowingly) went during restaurant week; some from our party ordered off of the restaurant week, and others did not. The scallop appetizer was wonderful, as was the tuna tartar. The crabcake was a bit bland (missing some chesapeake bay flavor), but the rockfish was wonderful. Small, tight restaurant, can get very noisy.

Superb from start to finish!

Many promise you the finest crabcakes, but O'Leary's delivers! Although, really, you cannot go wrong with whatever you order. It's pretty expensive, especially if you add wine to your meal, but it's our favorite special occasion restaurant in Annapolis, and for a special occasion it's totally worth it.

very disappointing experience. the waitress was awful. I specifically told her nothing spicy and asked for recommendations. The dish that came was too spicy to eat. I sent it back. At that point, you would think the maitre'd, who was stationed right behind our table would have come over to check if everything was ok when the new meal came out (it was meh), but he didn't and neither did the waitress. She did, however grab out bread plates (without asking, of course) before the main course even arrived, and I had to ask for more bread and another plate.
Not going back!

A friend and I enjoyed dinner here during Restaurant Week. We had reservations and our table was ready on arrival. The acoustics could be improved but otherwise the ambiance enhanced our experience. Our meals were both excellent and a good value given the prix fixe menu this week. Our server was truly lovely and served dessert with lit candles having observed a gift on the table. The only issue was the length of time we had to wait for each course. In another scenario, perhaps it would not have been an issue but my friend had an early appointment in the morning and we ended up rushing through dessert because each course took so long to arrive. Overall, though, I would highly recommend this neighborhood gem.

During Annapolis Restaurant week, I try to find a new location that controls my spending and lets me see different ways to present meals. This is a perfect find - has a "return to the scene" feel, with a great menu and excellent staff.