Always think of O'Leary's as the best seafood in Annapolis. Wish there had been simpler prepared fish on the menu. Crab cakes were $50 and were not hot, come on, that's the worst. Was very excited about the bread pudding and that was no big deal either
Mary Jane
Food was fabulous! We had the half and half--crab cake and rockfish! Entire meal was wonderful. Staff was welcoming and helpful!
Dona
We visited O'Leary's for the first time to celebrate my birthday, and it was amazing from start to finish. I started with the pupusa appetizer, which was outstanding. My husband had the lobster bisque; it was rich, loaded with flavor, and definitely did not disappoint. For my entree, I had the half and half crab cake and rockfish. Everything on the plate was perfectly cooked and seasoned—the smashed fingerling potatoes that came with the meal were amazing, and the green beans were easily the freshest and most perfectly cooked I've ever had. My husband also loved his crab cakes! We finished with the caramel brownie dessert, which was the perfect ending. The drinks were great tasting, and the environment is very friendly and cozy. A huge shoutout to our waiter, who was super attentive and made excellent recommendations that really made the night special. We will definitely be coming back for more!
Rob
Went for a bday celebration and the food & service (Thomas) were excellent. We had a jumbo lump crab cake appetizer and the wild halibut & crispy rockfish with shrimp for our main dishes...followed by the Butterscotch Pudding (House Sous Vide Pudding, Baked Graham Cracker Crumble)....🙌🏻🙌🏻🙌🏻
Brady
O'Leary's is not as good as it used to be. There are better places to get seafood in Annapolis. They need to pay attention to the smaller details of the dining experience, and I think they can get back to where they were. The lobster bisque was really good, but several of the other dishes were nothing special.
Kathy
We've been going to O'Learys for 29 years now! It's always a great experience and we come back again and again! It's always great to see owner Will as well! 
Kevin
Oleary's is a town favorite for seafood and other really great food! The papusas were a great first bite. Service was excellent both at the table and bar with long time bartender John making the drinks. One our local favorite places.
Lisa
Christmas Eve dinner- so good! Enjoyed the lobster with mushroom risotto and a good bottle of Chardonnay!
Maria Park
My visitors and I bumped into O'Leary's Seafood and decided to take a chance. I am so glad we did, what a hidden treasure. The ambience was cozy, our host made us comfortable with his European flair and the food was gourmet level quality. My brother had sea scallops that melted in the mouth. My sister-in-law had a grilled halibut steak which was enormous, accompanied by jollof rice and fried okra. What made the dish special was the Remoulade sauce with fresh cilantro and lime that perfectly set off the grilled halibut. I had the crab cakes with haricot verte, fingerling potatoes and a marvelous sauce. Never in my life, have I had a crab cake that was literally all crab. It was huge, moist and flaky and set off beautifully by the sauce. I had to take the other one home. We topped everything off with a shared cremé brúlé. It literally just dissolved in your mouth, leaving a buttery goodness behind. We all agreed that O'Leary's Seafood was a very special place, offering intimate, gourmet dining in the beautiful city of Annapolis.
Atmosphere: 5
Food: 5
Service: 5
Molly
Food was delicious and service was exceptional. Such a lovely spot for a special occasion.
Started with Buffalo oysters good and p”spicy Lobster over crab risotto and crab cakes for entrees outstanding grub and service make a reservation and head over !
Ffjorren
Impeccable service and lovely food - we will definitely stop in again when we are in the area!
Cynthia
Value for food was middle of the road for cost. I expect warm plates to support a meal as food cools down too quickly if not served on a warm plate. Husbands fish entre had too many seasoning and overwhelmed fish. Creme Brulie was more like a pudding and had too much brown sugar topping.
Pete Marquez
O’Learys has the best seafood in Annapolis without a doubt. It's definitely worth stopping by and giving it a try; you will not be disappointed.
Atmosphere: 5
Food: 5
Service: 5
Alex Berberian
The food here was excellent. Recommended for a classy date night. One thing to note is they have a parking lot on site, so no need to pay for parking at an area lot. The service was excellent as well and the waiter had excellent suggestions. It's a pricier restaurant, but we thought the food was excellent for the price so I'm not going to say it's overpriced. It's properly priced but don't expect bar pricing. The atmosphere was tight but pleasant And we had a nice view of the water.
Always think of O'Leary's as the best seafood in Annapolis. Wish there had been simpler prepared fish on the menu. Crab cakes were $50 and were not hot, come on, that's the worst. Was very excited about the bread pudding and that was no big deal either
Food was fabulous! We had the half and half--crab cake and rockfish! Entire meal was wonderful. Staff was welcoming and helpful!
We visited O'Leary's for the first time to celebrate my birthday, and it was amazing from start to finish. I started with the pupusa appetizer, which was outstanding. My husband had the lobster bisque; it was rich, loaded with flavor, and definitely did not disappoint. For my entree, I had the half and half crab cake and rockfish. Everything on the plate was perfectly cooked and seasoned—the smashed fingerling potatoes that came with the meal were amazing, and the green beans were easily the freshest and most perfectly cooked I've ever had. My husband also loved his crab cakes! We finished with the caramel brownie dessert, which was the perfect ending. The drinks were great tasting, and the environment is very friendly and cozy. A huge shoutout to our waiter, who was super attentive and made excellent recommendations that really made the night special. We will definitely be coming back for more!
Went for a bday celebration and the food & service (Thomas) were excellent. We had a jumbo lump crab cake appetizer and the wild halibut & crispy rockfish with shrimp for our main dishes...followed by the Butterscotch Pudding (House Sous Vide Pudding, Baked Graham Cracker Crumble)....🙌🏻🙌🏻🙌🏻
O'Leary's is not as good as it used to be. There are better places to get seafood in Annapolis. They need to pay attention to the smaller details of the dining experience, and I think they can get back to where they were. The lobster bisque was really good, but several of the other dishes were nothing special.
We've been going to O'Learys for 29 years now! It's always a great experience and we come back again and again! It's always great to see owner Will as well! 
Oleary's is a town favorite for seafood and other really great food! The papusas were a great first bite. Service was excellent both at the table and bar with long time bartender John making the drinks. One our local favorite places.
Christmas Eve dinner- so good! Enjoyed the lobster with mushroom risotto and a good bottle of Chardonnay!
My visitors and I bumped into O'Leary's Seafood and decided to take a chance. I am so glad we did, what a hidden treasure. The ambience was cozy, our host made us comfortable with his European flair and the food was gourmet level quality. My brother had sea scallops that melted in the mouth. My sister-in-law had a grilled halibut steak which was enormous, accompanied by jollof rice and fried okra. What made the dish special was the Remoulade sauce with fresh cilantro and lime that perfectly set off the grilled halibut. I had the crab cakes with haricot verte, fingerling potatoes and a marvelous sauce. Never in my life, have I had a crab cake that was literally all crab. It was huge, moist and flaky and set off beautifully by the sauce. I had to take the other one home. We topped everything off with a shared cremé brúlé. It literally just dissolved in your mouth, leaving a buttery goodness behind. We all agreed that O'Leary's Seafood was a very special place, offering intimate, gourmet dining in the beautiful city of Annapolis.
Atmosphere: 5
Food: 5
Service: 5
Food was delicious and service was exceptional. Such a lovely spot for a special occasion.
Restaurantji Recommends
Started with Buffalo oysters good and p”spicy Lobster over crab risotto and crab cakes for entrees outstanding grub and service make a reservation and head over !
Impeccable service and lovely food - we will definitely stop in again when we are in the area!
Value for food was middle of the road for cost. I expect warm plates to support a meal as food cools down too quickly if not served on a warm plate. Husbands fish entre had too many seasoning and overwhelmed fish. Creme Brulie was more like a pudding and had too much brown sugar topping.
O’Learys has the best seafood in Annapolis without a doubt. It's definitely worth stopping by and giving it a try; you will not be disappointed.
Atmosphere: 5
Food: 5
Service: 5
The food here was excellent. Recommended for a classy date night. One thing to note is they have a parking lot on site, so no need to pay for parking at an area lot. The service was excellent as well and the waiter had excellent suggestions. It's a pricier restaurant, but we thought the food was excellent for the price so I'm not going to say it's overpriced. It's properly priced but don't expect bar pricing. The atmosphere was tight but pleasant And we had a nice view of the water.
Atmosphere: 5
Food: 5
Service: 5
Recommended dishes: Crab Risotto, Diver Scallops, Beet Salad
Loading...