Always a great experience at this Eastport Gem. We try to get here at least once a summer and we live in PA!

The service was excellent and the food was simply delicious. My date had the soft shell crabs and they were fantastic. Very fresh and served perfectly. I had the jumbo lump crab cakes and they were super. This is one seafood restaurant you do not want to miss when you are in Annapolis. A great place to take someone for a casual dinner or a special occasion. The wine selection was excellent and the bourbon selection was also great. Save room for dessert , if you can , that is.... Simply one great place to dine in Annapolis.

Was treated very well for our anniversary. Great food and service and excellent wine recommendation.

Was a lovely evening, great service and an excellent meal. This was worth the drive.

Great food. Great service.

Excellent ,, food was sooooo good and service was just as good ,,

As a crab snob from MD, only the best will do. Having lived in PA for the last decade or so, I never order a crab cake when I'm out because it is almost always dissapointing and can't compare to my mom's. This place though! All backfin meat! No filler! Just the right amount of Old Bay. It was excellent. My wife's lobster was great too (she's from RI). I would recommend this place to anyone who loves great seafood, and a solid wine selection. We will be back.

The food was wonderful. A good place for parties of up to four. A small space with tables closely packed in. The service was good but the waitress wasn't readily available because of the large number of tables she was covering. Go for the food not the ambiance or view.

Was a good meal except one order of fish was overcooked. The other three meals were excellent

It was pretty good, decent seafood. The crab cakes and sauce were quite tasty. Hubby had the crispy fish with shrimp. The fish was good, but I wasn’t crazy about the shrimp; it was a bit too sweet. The waitstaff were very attentive, friendly, and knowledgeable. It was a pretty quick dining experience from start to finish so you may want to keep that in mind if you want something more leisurely. ( try to space things out on purpose).

The food was wonderful. Ambiance was a bit noisy. Watch the wine menu--markup pretty stiff.
Took a while for the waiter to take our order.

What separates O'Learys from other Annapolis fish restaurants is the quality of the fish and food. How do you do this when they probably all have the same distributor? Is it because they are smaller and can focus on each dish? Don't know and don't care. The fish swam to my plate and the soft shell crab was fat and tender. The risotto was smoky with mushrooms and the corn salad was amazingly fresh. I know the corn was picked that day. I am a corn snob and I only eat corn while in season and the corn salad at O'Learys confirms my snobbness is righteous. We went for a special occasion but I would eat there every day after I win the lottery!! Two cocktails, two wines, one appetizer, two specials, one dessert, coffee, tip and free parking = $180. Not a bad deal.

My soft shell crabs were sautéed perfectly and my wife’s lobster was exceptional. Service was attentive, but not intrusive. Demetri (perhaps incorrectly spelled here) is well known as among the best wait staff in Annapolis. The half-price wine night was a pleasant surprise. We will definitely return and bring friends.

My party of 7 had a wonderful Sunday brunch experience at O'Leary's! I made a reservation and when we arrived our table was all set up and waiting for us even including the highchair for my granddaughter. Dimitri was our waiter and he was absolutely fabulous! This was our first time dining here and he explained the menu very well and provided top notch service. To start most of us ordered the delicious Transfusion Bloody Mary and we devoured the pancake stix for our appetizer. The entrees were served in perfect timing after we had sufficient time to finish the appetizer. Everyone very much enjoyed their entrée with no complaints whatsoever. I had the Eastportorican - a soft boiled egg wrapped inside a delicious lump crab cake - one of the best meals I've ever had anywhere! The food and service here are AMAZING! Will definitely be back and would like to try the dinner menu next time.

Everything I expected and then some. Cozy and warm ambiance, the only thing missing here is a water view. Craft cocktails to start were excellent and unique. These folks know how to prepare seafood! Everything else was amazing. The mussels appetizer was "extra bread worthy" could have made a meal with a loaf of bread and the velvety sauce. The mussels were plump juicy and fresh. I order the shelled 1/2 lb butter poached lobster special served over a gorgeous creamy parmigiano risotto with mushrooms, bok choy with crisp pieces of pancetta elevated the dish to sublime!! Being the nosy diner I am, everything that came out of the kitchen looked top notch. A "Do Not Miss" restaurant in Annapolis' Eastport section of the harbor.

From the moment we walked in it was a wonderful experience. Everyone that worked there couldn’t have been nicer and attentive. Great service and great food!

Loved the cozy adult vibe of O’Leary’s and the all seafood menu. I opted for a fish special of branzino Mediterranean. It was a whole fish and there was no offer to have it filleted. This is a rather new experience for me to eat fish whole. I was disappointed that the Mediterranean aspect was a cold orzo medley sitting beneath the fish. Somehow I thought it might be different. Husband’s scallops were a bit bland even though it sounded good. I guess I liked this place more for the atmosphere and nearby view of the port.

We had been wanting to try O’Leary’s for quite some time so we made the choice to celebrate birthdays there. I will say the front of house staff was the highlight of the evening not the food. We expected the food to be outstanding given the price and raving reviews. It was average and not all the quality we were expecting. Very disappointing.

Probably the best service I have had in years. Food was stellar except the rockfish which was slightly old and fishy. Some of the best crab cakes on the bay.

Seafood, Seafood, Seafood. Besides one steak and a couple of salads everything is seafood at Oleary's - which is what we wanted for our Anniversary dinner. The menu featured at least 8 kinds of fish, crab cakes, soft crabs, scallops, lobster, seafood pasta and shrimp and grits. Choosing our entrees from all the great offerings was very difficult. After starting with two very good specialty cocktails from the bar, we shared the fried smelts which were large and meaty, perfectly cleaned and crisply fried. My wife had the Grilled Divers Scallops served over crab risotto and I chose the red snapper with mussels and shrimp served over dirty rice. The scallops were tremendous and the risotto paired wonderfully with the sauce which was a lemon butter sauce reminiscent of hollandaise but much lighter. The snapper was cooked ideally with wonderfully crisp skin and the shrimp, mussels and rice gave the dish a nice Cajun feel.

We had a very nice dinner at O'Leary's on a Monday night. It was kind of cool and rainy and very quiet in town. The weight staff appeared knowledgeable and attentive and made excellent suggestions. The food was well prepared and elegantly served. Would recommend to friends and foodies alike. Would return in the future.

Very friendly service, great ambiance. We tried the smelt appetizer that was very tasty. Broiled oysters were good, but cheese overpowered them. Not the best crab cakes I ever had, but they were good. Next time I’ll try fish or scallops. Chocolate mousse dessert was exquisite.

Meal here was perfect in every way. Go for a special occasion.

Very Very TASTIE. GOOD FOOD .(period) Server most knowable and accommodating. Will return.

Excellent meal and service. Highly recommend. For dinner. Very knowledgeable wait staff.

The restaurant atmosphere felt cold and unwelcoming, similar to our waitress. We got the feeling that our waitress was not happy to wait on us, she was a lot nicer and dedicated more time to her other tables. I’m not sure if it had to do with our age or appearance (lots of tattoos). Whatever her problem was, it caused her to get a low tip. Thank God the food was excellent, best shrimp & grits I have ever had! My husband really enjoyed the blackened ahi tuna as well. Great wine selection also.

This is a beautiful restaurant, one located near the Annapolis waterfront. Our dinners were quite good, but they were overpriced. However, this may be true of Annapolis restaurants in general. If I were rating O'Leary's on a 5-point scale, it would receive a 4. We had better dinners at a lower price in Williamsburg and Rehoboth Beach during our vacation. In short, it's a good restaurant, but be prepared to spend.

My children took me to O’Leary’s to celebrate a belated Father’s Day. It was a terrific evening. We were seated at a comfortable table next to a window and enjoyed our drinks and appetizers as the sun set. The quality of the food and the presentation of the selections were marvelous. We enjoyed Ahi tartar and muddles as starters, a salad course and then crab cakes, rockfish and soft crabs as our entrees. They were sumptuous and wonderfully delicious. Also, our server, Dimitri, was great... knowledgeable about the preparation of each dish and very helpful with wine selections. It was a memorable evening, and I ( and my children) could not have been more pleased with O’Leary’s!

Excellent app of ahi tuna, crab & avacado. It was so big I saved half and had it with the beet salad. Wonderful flavor combinations. Sweetness had the pasta, yummy. Added it to our list of favorite restaurants.

Was in Annapolis to take a Sailing course with a friend. We heard that O'Leary's had the best seafood in town, so made a reservation there for our last night. It was very expensive. Though the seafood was great (grilled fish and scallops), it wasn't worth the price. Perhaps if there had been a view of the water or a warmer atmosphere in the restaurant, I would have felt differently. We ate less than in other restaurants, primarily because we couldn't afford appetizers in addition to the entrees. Even though we ate less and drank less, we both had indigestion that night. Could be the richness of the food or just the lack of satisfaction in the dinner experience.

We have had many good dinners at O'Leary's but this was not one on July 8th. To begin with I ordered a half dozen oysters on the half shell and they are supposed to cut the oyster from the shell which was not done. Both of our dinners came out lukewarm and my Tuna that was supposed to be medium rare was medium well. My wife ordered the bali barramundi florentine and the florentine sauce was very bland.

O’Learys never disappoints! Whenever we come to Eastport/Annapolis we always stop here for dinner.

Excellent dining experience, wonderful service. The lobster special with crab risotto was delicious. Would definitely return to try other menu items.

This was recommended by several locals in the area. Amazing food and Dimitri is an amazing Sommelier as well an amazing server. Knew the menu and answered every question with expertise. Could tell he was very proud to work there and knew everything he would be serving is top notch! Will be back when I am back in the area! Thank you O'Learys and Dimitri for an amazing last evening in Annapolis! What a GEM!!

The broiled scallops and crab risotto was delicious

Great intimate get away restaurant in downtown Annapolis

Waited 45 minutes for two orders of bacon, eggs over easy, and home fries. Four other people at another table. After 30 minute wait we asked about our food and were told it would be out soon. It arrived 15 minutes later with eggs cooked so that the yolks were hard as could be. We were then told that because of the wait we would get free desert. It was then that I pointed out that there were no home fries on the plates. When those came out we were told we would not be charged for the meal. My wife accepted the offer of the desert while I did not.
I cannot understand how the three people working there could ignore us for so long. I guess they just did not care!

A awful amount for pasta , shrimp & scallops . Have eaten here before and never had a regret.

Great food & cocktails, great service Excellent for everyday & special occasions.

Dmitri was a great waiter!