We wanted a good seafood meal the other day and found O'Leary's online. We were able to call and get a reservation in 20 minutes so off we went. The ability to call ahead and get a fast reservation was enough foreshadowing to tell us this is a great restaurant. But the food soon clinched the deal. I had the crispy rockfish. Really good! Three big pieces of rockfish served atop black beans and rice. The side was 3 large shrimp perched on a slightly spicy salsa. A good aioli sauce finished off the dish nicely. I will say that the breading on the rockfish was not so crispy - rather, it was a tad on the soft side and bit too moist for my liking. But the fish inside was pure and white as expected. The serving was very large. My spouse had the crab cake dinner and he says that it is the best crab cake he has ever had. He even entered it into his restaurant contacts on his phone. This is high praise coming from a native Marylander who loves good Chesapeake Blue Crab. From my perspective, I could see that each of the 2 crab cakes was HUGE!!!! Just 1 alone might have been enough for a meal. The crab cakes were served on top of fried green tomatoes which he gobbled up. The balance of luxuriously silky crab salad against the fried green tomatoes was perfect. You know what else was perfect? The bread service! We each got 1 nicely sized roll, still warm and easy to pull apart. But the butter was enough to make me lick it off my knife. Garlic butter or chive butter - we could not quite decide - but it was so tasty that I wanted more. We both drank Arnold Palmers. He thought it was the best Arnold Palmer ever while I did not care for mine. I guess that is what makes the world go around, right? To each his own. Whatever you think of the crab cakes or the Arnold Palmer, O'Leary's Seafood is a great place. I highly recommend it for a great seafood meal. read more

My wife had a nice birthday dinner with me. Food was good but on the expensive side. 13 to 15 dollar bottle if wine was 46. It was a basic fess parker california riesling. Sailors old fashioned 16 was small. Ice tea 4 dollars never refilled Hailbut at 52 was good but expensive. Mininal accompaniments. Lobster special at 62 dollars was good Surprised they charged 16 dollars for the birthday we got a key line bar. The lit candle was free. Service was ok, but could have been better; per my wife. Waiter was sarcastic. Manager/owner was nice. Like the easy parking in their lot. Soup and salad was fine. Close to harbor read more

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Came to Annapolis for the day and decided on this restaurant for dinner based on reviews. I'm not sure why this place is rated so high. We started the complimentary bread which was served with garlic butter. Garlic is a strong taste so we would have preferred regular butter. Then we ordered the calamari which was fine. For entrees we got the rockfish and lobster (1lb) with risotto. The rockfish would have been better steamed and not fried (the breading wasn't our preference) and the lobster wasn't fully cooked. Half of it was rubbery and literally inedible (see photos) which is disappointing for such an expensive meal. Service overall was great but I wouldn't recommend. read more

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I am so sad this place is closing!! The calamari is good, their half dozen oysters are a great price, and their entrees are stunning and delicious. The rockfish is a personal favorite, pupusas and gazpacho were great, scallops are another star! The crabcakes are good but a little different than my preferred prep. Service is kind and I hope the best for them read more

O'Learys Seafood Restaurant - Seafood Near Me - Annapolis, Maryland

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Will miss this place so much!!! Also had a wonderful time dining here. The food is delicious- my favorite was the shrimp and grits and the lobster risotto. We dined on a quarter of their menu last night! Enjoyed the oysters from Virginia as well as their crab cakes, lobster, shrimp and rockfish. Also had the strawberry shortcake for dessert! Sad that it was our last meal there. Farewell and thanks for the memories! read more

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A great dining experience. We were greeted walking in and seated within a minute or so, the place was packed on the evening of our dining. Seafood is whats in order here. Reservations are necessary most nights. The interior is sea themed and lots of open windows, comfortable and leans towards fine dining. Oysters on the half shell to get us started, fresh and plump juicy oysters. We had two dozen to get our table of four going. After giving the menu a good read I opted for the Halibut, it was an excellent choice. Superbly prepared and beautifully presented, I love halibut and this meal was an excellent one. A Napa vallet Chardonnay "Aviary" was rich, buttery and full bodied and again an excellent choice for our meal. After our meal, my dining partner and I split the Flourless chocolate cake, it was hot and creamy luscious with a full cocao flavor. A great choice and easily splitable. 4.5 Stars rounded up for the great host and staff 01109 read more

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The food was unbelievable. Yes expensive, so much flavor though. I ordered the ahi tuna because it was on my mind from the previous restaurant we tried, Chart House, which wouldn't let us in due to the dress code. We had a group of eight, some came from the boat show, and not all of us were able to change. It's okay though, O'Leary's was definitely more our style. I love the paintings and after the sun set black lights brought out the different colors. read more

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This seafood joint was very nice, and the food was perfectly prepared and cooked well. I had the crab cakes and rockfish, as well as calamari. The crab cake was all crab with no filling and along with the rockfish was moist to the taste. The calamari had a preparation I had not seen previously, or perhaps they perfected it. They had a hot pepper and a sauce that gave the dish a little kick and great depth of flavor. Great work on the overall appearance, presentation, and execution of the meal. read more

Really good spot for drinks and dinner. Lots of great seafood on the menu . I like to try regional specialties when I travel so I had the crab cake and it was excellent. Big pieces of Maryland crab... no bread filler. Delicious! Served on top of a fried green tomato. We had martinis, which were good Very good bread . The only thing that missed the mark was the strawberry shortcake dessert. None of us liked it. But the food was so good otherwise we didn't mind. Three of us had the crab cakes and my husband had the salmon and we're were all very pleased. Service was attentive. read more

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10/10 waiter named John 9/10 crab cakes Bread was fantastic Oyster virgins enjoyed them Quick service Good ambiance read more

O'Learys Seafood Restaurant - 50/50 dish - Seafood Near Me - Annapolis, Maryland

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What a birthday dinner? I picked O'Learys due to its reputation and past experience. Alas, it was a wilted rose. Dinner started off okay--but slid quickly and didn't get better. It was my birthday--so the waiter brought myself and wife a small pour of champagne but none for my 24 year old daughter. Hmmm. Next, I had perused their website's wine menu since I hate trying to choose a good wine while at the table. Alas, the didn't have my choice any longer. I was able to find a good wine--at the expense of being Mr. Boring while researching the list. We ordered dinner and our entrees were served in reasonable order. The lobster and halibut were very good--but my medium rare Delmonico steak was overcooked to medium well. It was a shame to waste a $100 steak--but was not even close to order. We notified the waiter who had the steak replaced. Something came to the table 30 minutes later--but it was a chewy rump end of what was previously ruined. It seemed like the chef was determined to get even for sending the first steak back. I chewed through half of the steak before boxing the rest (to take home for our pet). The waiter was nice enough to offer free dessert for the error--but noted that they were out of Key Line pie and chocolate brownie--so we had our choice of Tres Leches, bread pudding, or butterscotch pudding. I felt bad for laughing--but those choices were worse than over cooking the steak. Not impressed for a $400 meal and not going back. I hope my review saves you the same pain. read more

Have contacted this restaurant several times in hopes of arranging a buy-out for a wedding dinner that will occur a year from now. They don't respond to phone calls or emails. We'll be spending our money (a good five figures) elsewhere. read more

Originally from the area and haven't been here in years. Celebrated a special occasion and couldn't be more pleased. Ambiance was awesome and the food fresh and spectacular. The only thing sub par was the Cream of Crab soup. Unique flavor with a lot of meat, but having claw when they stared it was lump. Definitely not lump. Thoroughly enjoyed the service, vibes, and meal. Thank you !!! read more

The food was delicious and the ambiance was comfortable yet elegant. Our waiter was very attentive and considerate of our conversation. read more

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I tried to return to this restaurant for a long time this Sunday was the perfect opportunity my wife and I had a wonderful experience at our dinner the service was excellent, the food was fantastic, the scallops were cooked sublimely, My wife delighted the shrimps and Grits, not before sharing with her some appetizers and desserts with coffee to finish, funny the same dishes from the menu the first time we went to try that establishment , all this w the immaculate service of Patric to make our dining experience memorable, definitely had to be back soon to try the rest of the menu selection read more

My wife and I went here for Valentine's Day and had a wonderful experience. We started off with drinks. We both ordered the Smoke and Mirrors, it was a very well balanced drink that we both enjoyed. For an appetizer we ordered the Pupusas and they were pretty tasty, especially with the sauce that came with it. For our entrees my wife ordered the Whole Maine Lobster Special and I ordered the Creekstone Farms Delmonico Steak Special. My wife let me try her Lobster and it was delicious! My steak was also amazing, very flavorful and juicy. We were both very satisfied with how good the food was. Our server was very good, super attentive, and gave great recommendations. This was such a great experience for a Valentine's Day date night. read more

O'Learys Seafood Restaurant - Whole Maine Lobster - Seafood Near Me - Annapolis, Maryland

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Great food! Went for our anniversary and they gave us a glass of champagne which was kind. Server was knowledgeable and food was very tasty! Great wine selection. read more

O'Learys Seafood Restaurant - O'learys Crab Cakes - Seafood Near Me - Annapolis, Maryland

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Had dinner here Sunday night. The best thing about this place is the ambiance. The interior is beautiful. It also overlooks at the harbor. Its a beautiful place to have a dinner date and enjoy the vibe. The food is decent, but not the best we've had in Annapolis. We had the steamed mussel pasta, which was okay, though far from the best I've had. The pasta was a bit overcooked for my taste and the mussels had a bit too much of a sea smell (though someone might prefer it that way). As a second dish we had sea bass with some shrimp and risotto. Again, decent but not in any way notable. We also didn't like the dessert menu (there were three or four kind of random choices) so we didn't have any. Service was good. Overall, I would recommend it for the enjoyable vibe, but wouldn't expect too much from food. read more

O'Learys Seafood Restaurant - Dining area - Seafood Near Me - Annapolis, Maryland

Delicious food, great recommend from our waitress and lovely atmosphere. Bonus: Location within walking distance to the dock! read more

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I love love love seafood so when I saw O'Learys offered a whole lobster, I knew I had to try it! The lobster was already removed from the shell which made it easier to eat. Lobster was on the smaller size but sweet and juicy. Grilled lemon and butter made it better. I'm not a big fan of risotto so to me it was just meh. Overall, not sure if it was worth the price tag but I enjoyed the lobster itself and service was good. read more

O'Learys Seafood Restaurant - lobster risotto - Seafood Near Me - Annapolis, Maryland

Everything was great! I'd even go back for the bread. Haha! New Year's Eve. We were at the tail end of the crowd but business was steady. However, Christina and the rest of the crew kept us covered. We started with the mussels. Indeed, they came out arranged like on the website photos. I ordered the whole sea bass. My beautiful wife had the haddock. We wrapped it up with the tres leches crème brûlée and the flourless chocolate cake. As I said, everything tasted good. However, I'm not sure all the items went together. For example, the cilantro paste was a surprise pairing for jolaf rice and okra. Similarly, the seaweed salad and sticky rice weren't my first thought for Mediterranean Sea bass. Nevertheless, it was tasty and I look forward to going back. read more

O'Learys Seafood Restaurant - Crème Brule with a flourless chocolate cake in the background - Seafood Near Me - Annapolis, Maryland

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Regrettably Disappointing. We came for dinner on a Saturday, and found the entrees to be pretty disappointing. My wife had the grilled whole fish which was not very flavorful. I had the scallops on top of orzo -- the scallops were perfect, but they were served on top of a very bland orzo that did not go. We had wine by the glass, which was okay. Their calamari is excellent -- it's not too breaded, has a great sauce, and the pickled onions are a nice twist. Service was good. We came here for a treat for my wife who loves seafood. We were expecting much better, especially given the great reviews and price point. Disappointing overall and we will not return. read more

We came here for a birthday dinner on a Sunday night and it definitely hit the celebration marks. We did not have a reservation but we were seated immediately. The entrance is a bit narrow but actual inside is spacious and has a beautiful view of the bay. The service was spectacular. Our server recommended drinks and helped guide us through the menu. I ordered the mas mango cocktail. When it came out, it had the half and half and mango separated, so the first sip was basically just half and half. After mixing it, it was much better, a little tangy but just the right amount sweet. They also served us each a roll that came with a chive butter, it was delicious. I could have eaten like 10 more of them! We ordered oysters on the half shell which were delicious, very briny. I liked the mignonette although it was a little difficult to pour, I actually did not think that the oysters needed any because they were flavorful enough as is. We also ordered the buffalo oysters which were phenomenal! I had no idea what to expect but they were very flavorful and you could still tell they were oysters, but with buffalo sauce, blue cheese, and pickled red onions. I'd come back for that alone. For my main, I ordered the whole fish of the day. It was beautifully prepared and was very tasty. The fish itself was very mild and felt a little overpowered by the peperonata sauce it was served with, but I still enjoyed it. read more

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Dinner was excellent and so was the ambience and the service. Only giving three stars because the desserts we ordered(the butterscotch pudding and flourless chocolate cake) were extremely small portions; especially the flourless chocolate cake. Definitely could never split a dessert with someone in fact, I could've eaten myself a double portion it was so small and they should know better than to give such small portions. also, there was a drink we had with dessert which was made with a lot of butter and water served hot which was truly horrible and I think $15. read more

Definitely enjoyed my time here. Entrance is a bit weird. Super narrow space and nowhere really for the hostess to stand. I ordered the lobster and crab risotto special. Lobster was great, nicely cooked. The rice I had was definitely not a risotto. Not creamy and overcooked. It was also just above room temperature. There was a bit of crab in the "risotto" as well. Drawn butter on the side was a weird addition. It made me feel like I shouldn't be eating the lobster with the risotto but instead dipping it in the butter and then having a bite of the risotto. Not cohesive imo. Crab cakes my party had were very good. Lots of crab and a very sharp mustard sauce. Fingerling potatoes were a nice compliment. Haricot verts were undercooked. Love al dente for veg but this was under that. Desserts were ok. Didn't understand the tres leches creme brulee. Tasted like any other creme brulee I've had but with a much thicker sugar crust on top. Super thick. Bread pudding was a huge disappointment. Wasn't soaked in enough liquid before baking. Just didn't come together. Not a bad spot. For the price point, I expected more finesse in the kitchen. Make sure to make a reservation. read more

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My boyfriend and I went here for our anniversary. The ambiance was nice with white tablecloths and low lighting, it felt peaceful and the right vibe for an anniversary. Our waiter was also nice and helpful. To drink I got the fresh cut which I knew wouldn't be super sweet but it was more savory than I expected and I wasn't a fan. We told our waiter and he was nice enough to get me a new drink, the summer sangria, but this wasn't very good either. My boyfriend got the smoke & mirrors and he enjoyed it. For apps, we got the oysters which were fresh but not the best we've had. The complimentary bread and butter was good but not anything special. For our mains, my boyfriend got the wild halibut which was ok, there wasn't much flavor but the sides were good. Then I got the crab cakes which again was not much flavor or seasoning and the best part was the sauce with it. For dessert, we got the berry shortbread which was very good. Probably the best part of the meal. Wish our food and drinks were better but it was a nice experience despite that. read more

O'Learys Seafood Restaurant - Grilled Oysters on the Half Shell, Fresh Cut, Smoke & Mirrors - Seafood Near Me - Annapolis, Maryland

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I had a great dinner here. The cocktails were good. The diver scallops were tasty and the crispy rockfish was interesting. I haven't had rockfish prepared that way with the shrimp and rice before, but it was good. The butterscotch pudding dessert tasted a bit bland to me. But overall I had a great experience. The restaurant also had a cozy and elegant vibe. read more

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Great sipper buffalo oysters crab cakes lobster an crab rodeo's plus bottle of wine and great service mage a reservation and get over to a great dinner spot read more

We were passing thru Annapolis yesterday Friday n it was nearing dinner time. Checked on Yelp for a restaurant n came across O'Learys seafood restaurant w great reviews and thought we'd head there 4 dinner. Made a good choice. Nice restaurant in Annapolis. Friendly welcoming staff. Clean restaurant. We had the beet salad, crab risotto and calamari which were v tasty. The bread rolls were fresh n warm w butter. We had the lobster dish w crab risotto, crispy rockfish which was fried with a delicious sauce and the fish of the day which was grilled Black Sea bass w tomatoes n olives. We enjoyed every bit of the dishes . They were so yummy. Not a morsel left. And topped it off w crème brûlée n butter scotch desert. Mmmm yummy. Thank you for a great dinner. Will sure stop by at O'Leary's when we r in the area the next time. read more

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The Food and Service are excellent. If not the best restaurant in Eastpoint one of the best. Whole fresh fish the best around. Don't miss the bone in Pork Chop. read more

My birthday was just a few days ago, and in the mood for seafood, I hit up O'Leary's. It's located in the heart of Annapolis, surrounded by many other restaurants, and practically on the water. The restaurant has its own parking area, with ample parking, which is really nice in this pretty crowded area. O'Leary's was busy when we got there, but they seated us right away, and the server was awesome. Very friendly, knowledgeable, and gave great recommendations. He steered me to my drink choice, beehive on a hill. It's a little sweet compared to, say, straight liquor, but it went great before the meal, and I loved it. The first thing to hit at any seafood restaurant, for me, is the raw bar, and I gobbled down a half dozen raw oysters. They were really well shucked, extremely flavourful, fresh, and just delicious. The only odd part is that they came with a vat of mignonette (vinegar), but no little spoon to dip it with. I poured, but they were a smaller variety, and it was hard to not drown them. They didn't really need it. On a whim, I ordered "Buffalo Oysters." Personally, I think that the easiest way to ruin an oyster is to cook it, so I didn't have any hope for these... but they turned out to be the best part of the meal (which is saying something). They're perfectly fried, breaded, and just nicely spicy with some buffalo sauce on it. I could have eaten just them. Next up was a special seafood soup. This was the weakest link in the meal, but it was still fantastic. The broth exploded with the flavour of a ten thousand little bits of seafood, and the vegetables were also great. My minor gripe is that, despite being a seafood soup, it was a little light on actual pieces of seafood. I finished up with softshell crab. I could have a lot more of these they were so good! Just a little crunchy, but not too crunchy, and served on a bed of vegetables. read more

Always a treat, BUT don't count in parking in the lot! Having a parking lot makes dining here easy but tonight at 6:15pm, the lot was full. We arrived to only 6 seated tables but zero parking spots? Service shines here and our services had a trainee so we got extra attention! Maryland Crab soup sorely missed on the menu. The show stopping Lobster entree has been scaled back but still wonderful. Don't miss the duck fat fingerling potatoes. read more

O'Learys Seafood Restaurant - Scallops - Seafood Near Me - Annapolis, Maryland

Went to O'Leary's on Friday evening to celebrate Father's Day a bit early . We were seated promptly and given bread and butter right away. Our waiter was quite busy but he did a great job. Sorry I didn't remember his name . The food , what a bit expensive was really delicious. And actually I guess it's really not that bad for what you get . My husband and son in law both got crab cake platters that they loved. They were very large and came with corn relish . My daughter got scallops with orzo and she loved hers . I got a whole lobster taken out of the shell and served with crab risotto- it was really delicious! . We all got cocktails that were very good and a bottle of wine to share . They were gracious enough to let us taste before we chose . We were too stuffed for dessert. Overall it was great! read more

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I love Annapolis, so I was eager to try O'Learys. This restaurant is nestled near the water(no water view ) with parking which was a plus. The food was good. We had the 50/50 which was delicious. The pork chop lacked flavor and I was not impressed with the way it comes plated. Service can use a little bit of work however the manager was extremely friendly. She came over to the table and checked in on us. read more

O'Learys Seafood Restaurant - Pork chop with brussel sprouts and potatoes - Seafood Near Me - Annapolis, Maryland

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Last evening my family and I celebrated my husband's birthday. We have always loved O'Learys; however, the service provided by Pat was shockingly unprofessional and borderline racist. Our entire time there for dinner was riddled with rude comments by Pat and constant sarcasm. After patronizing the restaurant for over a decade, we have decided not to visit again. This decision does not come lightly since we deem O'Learys a neighborhood gem. One highlight was John's Martinis. Do better, Pat, you bragged about how long you've been employed there, perhaps it is time to retire. read more

The staff were very friendly. Thomas our waiter was knowledgeable and answered questions regarding food prep and ingredients that would accommodate my food allergies. We both had the crab cakes for dinner. Best crab cakes ever! The sauce complimented the perfectly cooked crab well. The fingerling potatoes and green beans were also cooked perfectly and delicious. Thomas' timing was impeccable when checking on us after cocktails and food arrived. The ambiance was nice. We will definitely come back when we're in town! read more

Came in for dinner with my brother and sister-in-law the other night. The 1st thing I noticed was that they have their own parking lot which is a huge plus in Annapolis! We had 6pm reservations on a Saturday night and got seated right away. Cozy place, nicely decorated with big windows for some nice views. Our server didn't make us wait and we were drinking cocktails pretty quickly. Everyone liked their meal! For out-of-towners, I highly recommend the lump crab dinner ("when in Rome"). The pictures say it all! Very good food here. read more

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Really disappointed in what O'Learys has become! First and foremost, they charge a 2% credit card surcharge without disclosing this policy (maybe its in fine print somewhere?) to customers. Just bad form. Secondly while their dishes are good to great, their menu is overpriced and their service is pedestrian. After going to this restaurant religiously for the past 10 years for great rockfish, we've taken this restuarant off of the list. FYI, on a holiday weekend the restaurant was only at 25% of capacity on a pleasent evening in Annapolis. My conclusion is everyone else got the memo on the diminished "dining experience" and we didn't. read more

Fantastic food. Great drinks, among the very best seafood in Annapolis. My drink order is very specific and many bartenders get it wrong. O'Learys was perfect read more

We had the lobster over Parmesan risotto. It was so amazing. Also, their version of the espresso martini called the insomniac Yum- O. They're fresh hot baked ciabatta was to die for. Our server was very attentive. The view was beautiful as the sunset. Highly recommend it is off the beaten path, but was highly recommended by a local so we gave it a try. Glad we did. read more