I wanted to love this restaurant but the food was only ok and the prices were pretty pricey for service and quality. Limited children's menu. Fish and chips was only ok, fries were very very greasy. Wait time for entrees was way too long. Fish was flaky and delicious. Calamari were very crustily fried. My son liked them but no need for quite so much breading. Bread was boring. Bloody Mary was small and unmemorable. The rest was enjoyable but nothing extraordinary.

We had a wonderful time here. Sat at the bar and had an excellent time learning from the bartender about all the drinks she created and how she named them all. Food was amazing (followed her recommendations which were on point!). We had the whole fish, and lobster risotto and it was truly wonderful!

We ate at several restaurants while in Annapolis. This was probably our least favorite.
Food was ok, nothing great compared to the other 2. Prices were higher than others.
Service was good. not outstanding. The Hostess was the best part. She was friendly, warm and very good.

We were greeted with, “happy anniversary!” and treated to complimentary champagne. Shared mussels appetizer was wonderful. Grilled scallops and red snapper entrees were visually beautiful and tasted fantastic. Staff recommended a great wine and were attentive with no hint of rushing us. It had been a few years since our last visit and we won’t let that long pass again. Best Annapolis seafood worth the trip across Spa Creek to Eastport!

Unfortunately, our experience was hampered by the noise level in the restaurant. There were six of us dining and we could hardly hear each other. The staff eventually opened some windows and the noise improved some. On a positive note, we all enjoyed our entrees, particularly my husband who ordered the soft shell crab special.

The ambiance was nice but our server was not very friendly. She seemed annoyed that we didn't get an appetizer nor dessert. She was pushing for a higher tip (although I gave her 20%) through her "electronic" billing machine. There are several other places to have a great dining experience in the area.

Food was very good. Service was eclectic. Noise level was unbearable. The 4 members of our party could hardly carry on a conversation. Had to strain to hear and raise our voices to be heard by those next to us. The booth that we sat in was very uncomfortable. Table was almost touching our bodies no room to move.

When I want a place to relaxant get a great meal at a reasonable price there is no better.

Very authentic made-from-scratch seafood creations. I had an elegant but hearty soft-shell crabs dinner with fried green tomatoes cooked to perfection (not greasy) and all topped with a drizzle of something wonderful on a bed of the best cole slaw ever. He had pasta with seafood but the home-made sauce changed that simple dish to incredible. If you want to treat yourself to a five-star experience, O'Leary's is still the best. Service was a little too attentive as I would've loved to linger.

Favorite restaurant in Annapolis and best seafood by far. No pretenses or stuffiness - just creative, honest, fresh and exceptional preparation. Eaten here over a dozen times over the last four years with the same wonderful experience - excellent consistency. Highly recommended.

Seafood menu was good and all dishes were well prepared and tasty.
The wine was reasonably priced.
Excellent bread.
Server was informative, friendly and kind.

Service was excellent.

Brilliant meal and excellent service as always

Well, one out of two isn't bad. My crab cakes were outstanding - big chunks of backfin with just a touch of filler holding them together. On the other hand, my wife's lobster, which was a special, was served at room temperature and was rubbery. Nice atmosphere spoiled by a mediocre dinner.

We had the opportunity to meet and speak with the proprietor. This was our second “special occasion “ at O’Leary’s recently and we were recognized. It gave us the chance to talk about our experience and to give him feedback directly. Our feedback was to keep up the good work. We have been coming to O’Leary’s almost since its opening in 1983 and it always has been very good but recently it has stepped up a notch or two. Try it if you have not already. We think you will come back again and again.

We had a lovely dinner with crab and lobster at O'Leary's. We were visiting from out of town and some locals had recommended it. The food was very good but a bit expensive.

Everything was just ok. Worth another try but wouldn’t race out to go

This restaurant is always excellent. It has been "solid" for years. The food is fresh, well prepared and innovative. The servers are friendly, knowledgable, attentive and courteous.
You can never go wrong eating here.

Fantastic seafood! Fresh ingredients. Recommend highly. Wine is reasonably priced.

We were a challenging guest. Our group grew, then shrunk, then returned to original number. The staff was very kind in accommodating.
We never felt rushed even though we kept messing with their time frame.
Great recommendation on wine.
Wonderful dinner.
Worth the time and money,.

O’Leary’s really knows their stuff. Best soft shell crabs anywhere. The fried fish was also excellent. Easily accessible by boat or car.

Excellent service from the moment we were seated. We indicated we were celebrating our anniversary and were served a glass of champagne as soon as we were settled. Our waitress was very attentive and helpful. Sautéed calamari were delicious - wish more restaurants offered this instead of fried. I enjoyed the diver scallops and my hubby had the barramundi - both excellent. Would definitely return when in the area again

We returned to O’Learys as we had a great meal a year ago. This was our 49th Wedding anniversary so something special after journeying from Delaware.

Unfortunately warm wine, frozen fish did not cut it. ( the special of the day was sold out for our 7.30pm reservation.)

Sadly we will not return.

Excellent experience. Dimitre (sp?) was wonderful.

Outstanding dining experience in an out of the way water view setting. Demetri was terrific, pleasant, and knowledgeable. Food was amazing. Could not ask for better.

Very nice ambiance and great food. We were celebrating our anniversary and the restaurant surprised us with a glass of champagne which was a nice touch.

Food was outstanding. The sommelier made an excellent wine recommendation. We loved it!

First time at O'Learys. The food was very good, service very good and it was quiet enough hold a conversation without having to yell across the table. Everything was fine until the elderly couple at the table behind us asked to see the manager (Will, I think he said his name was). He tried to address their concern (problem with the lobster or the lack of a lobster) but he said "I see I'm not going to satisfy you" and walked away making a snide remark as he left. My wife and I didn't think he handled the situation very well. Regardless, I would recommend O'Learys.

Dimitri was an awesome, very professional waiter and made our Mothers Day dinner a wonderful night out. He deserves a promotion.

The food and service was excellent. The view leaves a little to be desired and as the tables filled the noise level grew as well. Would definitely repeat

We went to Oleary’s for the first time this past Mother’s Day. The dining room is nice and comfortable. The welcome from the host and bartender were warm and gracious. Wine selection was excellent. We started with the Cream of Crab soup which was outstanding. Rich and smooth in texture. The mains were good but the lobster was slightly over cooked, which is not acceptable at the price we were paying. The Barramundi was excellent and fresh. We also had a sautéed calamari that was good if a bit uninspired. The service was great, professional, friendly and efficient. We were never rushed. It was odd to see the booth we were given had big tears in it, unexpected in a restaurant commanding such high prices. We would probably go again, if just for the soup, but be a bit less ambitious in our choices.

Wonderful Mother's Day Brunch. We all chose from the Prix Fixe menu and everything was excellent. This has become our go to spot in Eastport for seafood and special occasions. It doesn't have the views like Carols Creek or Chart House, but the food and drinks are superior and it is a more intimate setting.

Yummy food. Mine was cold, but still good. Great cocktails. And the service was good

Excellent seafood such as oysters, calamari, whole Maine lobster.

My food was lukewarm. I didn't ask for it to be re-heated because, in my experience, when that happens the food is then reheated, and what I really want is a new, fresh dish (and not have to wait for my new dish while my dinner companion is eating). Basically, I'd rather have it be hot the first time around. Also, the entree had very little flavor. The shortcake in the dessert was stale and flavorless and a disappointment. I mentioned that to our waitress and she did take off half the cost of the dessert, but she really should haven't charged us anything at all for it.

Unfortunately, there was a very loud table (with one man in particular with the loudest voice I have ever heard in a restaurant) right next to us, and my husband and I had to practically shout at each other to be heard. I don't know if the restaurant manager should have asked that diner to lower his voice.

I've eaten at this restaurant a number of times, and each time is worse than the last. It is unlikely I will ever go back.

Everything was fine except, there was a table of 4 that was beyond loud. Every other table in the room was disturbed by these people. They were virtually shouting every word. No argument, no discussion. Just outrageously loud. Our server said she couldn't present the specials over the volume created by that table.
I suggested that the manager might ask them to turn it down, but that didn't happen. It was so outrageous that it became funny to everyone other than the offenders. They were oblivious.

My wife and I entertained my nephew (LtCdr in the Navy) and my cousin (a Major in the Army). The food was excellent, the noise level was such the we were able to carry on a very interesting conversation. The wine was excellent and the list was extensive. I recommend this restaurant to all my friends as probably the best seafood restaurant in Annapolis.

Fantastic food. Proves they are one of the top seafood places in Annapolis. Huge fan of the unique bourbon selection.

Dmitri was an excellent waiter and the food from broiled oysters to tiramisu was awesome.

Outstanding food, professional service, warm atmosphere, very solid wine list.