I enjoyed the food and service. Parking can get tricky. Small inside but cute. Great service
Atmosphere: 4
Food: 5
Service: 5
Jessica DuLaney (Nonn)
This was my first time timing despite living in Annapolis for years. We never went because of negative reviews we had heard from a family member. I am glad we gave it a try because it was an amazing dinner date night. The ambiance / decor is beautiful, tables aren’t too close together, we were very comfortable sitting by a window. Our server was incredibly attentive and I even complimented him at the end of the night for his great service! As for the food we literally ate ever single bite - we started with bread service then apps we ordered the buffalo fried oyster - they were amazing. Dinner I ordered crabcakes and my husband ordered a lobster special. See my pictures for how beautiful the presentation was and it was delicious!!! Overall A+ date night and I would return!!
Atmosphere: 5
Food: 5
Service: 5
Recommended dishes: Whole Maine Lobster, O'Learys Crab Cakes, Crab Risotto
K B
A hidden gem in Annapolis! The.entire experience was exceptional. Would not only go back but would highly, highly recommend.
Atmosphere: 5
Food: 5
Service: 5
Stacy Labbe
We hadn't been to O'Leary's in years! Went tonight and the whole experience was wonderful!! We so enjoyed the food, the service and the atomostphere!
Atmosphere: 5
Food: 5
Service: 5
Recommended dishes: Raw Oysters on the Half Shell, Grilled Diver Scallops, King Salmon
carey phipps
I've been frequenting O' Leary's for years and have never been disappointed in a meal. It's menu is full of amazing choices that are fairly priced, staff is always professional and attentive. Side note, it also bosts some Fantastic art work in and out!
Atmosphere: 5
Food: 5
Service: 5
Recommended dishes: Raw Oysters on the Half Shell, Butter Poached Lobster with Risotto, O'Learys Crab Cakes, Tomahawk Ribeye, Shrimp & Grits, Grilled Diver Scallops, Crispy Rockfish, Branzino with Side of Black Beans Sauce and Rice, Crab Risotto
Victoria K
One of if not the best fine dining in Annapolis. The atmosphere is perfect—cozy, inviting, high end but not stuffy, and sets the stage for an excellent meal. Service is always top notch, fantastic wine list and the food is consistently fabulous—and memorable! The rockfish is one of my all time favorite dishes! Have been several times and have never been disappointed. Great for work dinners, date nights or ladies night out. The owners and kitchen staff are also very nice and extremely talented. Highly recommend!
Atmosphere: 5
Food: 5
Service: 5
Recommended dishes: Raw Oysters on the Half Shell, Shrimp & Grits, Cioppino, Crispy Rockfish, Branzino with Side of Black Beans Sauce and Rice
Kimberly Amos
I haven't been to O'Leary's for quite some time and have missed it so much! Our waitress, Chelsea, was hands down one of the best servers we've had in a long time. She was so personable and knowledgeable about the menu. We really enjoyed our drinks and meals. I won't wait so long to return again!
We reserved a table a few months before our travel date. The restaurant was lovely. Our server, Thomas, was knowledgeable, kind, patient and handsome. A truly skilled, professional server, who MADE this a fine dining experience.The food was good, but not first rate, the service, however, was first rate. The lobster was a bit over done and chewy as a result, the scallops were small as was the portion size.I made the reservation online based on what I read about it, I was disappointed overall.I was expecting a more dramatic view, or any view, and first class seafood. Th3 food and service didn’t meet expectations, but the service exceeded!
Atmosphere: 2
Food: 2
Service: 5
Recommended dishes: Crispy Rockfish
Janet D
Really nice atmosphere with great and interesting artwork. It was a bit noisy for me, convival from another point of view. The risotto was delicious and cooked to perfection. Unfortunately, I found my lobster special somewhat undercooked and saved almost all of it to cook more at home. The table next to mine ate every bit. The fish special was nicely cooked and fresh.
If you love seafood, you can't miss at O'Leary's. I had the scallops -- excellent! My sister had the cod, which she doesn't order, but she loved it! Good wine list. We didn't get dessert, but the choices sounded delicious.
Atmosphere: 5
Food: 5
Service: 5
Recommended dishes: Grilled Diver Scallops
Sven U
Very nice place, excellent food and drink. Outstanding service. The restaurant is nicely decorated and has a good vibe. I go there every time when at the boat show. Don’t miss it when in Annapolis.
marygc36
My husband and I stopped in for dinner on a Friday of the crazy Sailboat Show weekend and had such an incredible dinner, we had to come the next night. There were too many delicious items on the menu to try! Emily, the bartender made one of the best Old Fashioneds I'd ever tasted, another reason to come back. Every item on the menu we tried was outstanding and beautifully presented- especially the crab bisque- wow! We had the privilege of speaking with both of the owners, Jennifer and Will, the second night before the restaurant got really busy. The history and evolution of the restaurant to what it is today is such an interesting story and the decor and artwork create such a unique vibe. Any future trips to Annapolis will be certain to include a trip back, or maybe the sole reason we come back to visit Annapolis!
Scott Tominovich
Annapolis resident. Had not been here in years. Expensive. Limited menu. Food was mediocre at best. Disappointing. There are a lot of better options in town.Parking: Accessible parking
Atmosphere: 1
Food: 1
Service: 5
952ginac
Really cute restaurant with a small bar if you want to enjoy a before dinner cocktail. It was a bit loud but the atmosphere made up for it. Our waiter was Peter. He was nice but not very personable. We had some gluten free questions (my husband has Celiac disease & its important to stay gluten free) -- Peter didn't seem knowledgeable nor very eager to ask the kitchen staff which options we had for Gluten free or or offer any GF substitutions as far as sides etc. I really wish more and more restaurants would note GF on their menu these days to make it easier for people to dine. I had the rockfish. It came with a side of red salsa type addition which didn't taste fresh. (it looked like salsa) - I told our waiter about it. But my fish over rice overall was good. Be prepared to spend $$$ -- nothing in Annapolis seems to be reasonable these days.
The best of the best!
Atmosphere: 5
Food: 5
Service: 5
I enjoyed the food and service. Parking can get tricky. Small inside but cute. Great service
Atmosphere: 4
Food: 5
Service: 5
This was my first time timing despite living in Annapolis for years. We never went because of negative reviews we had heard from a family member. I am glad we gave it a try because it was an amazing dinner date night. The ambiance / decor is beautiful, tables aren’t too close together, we were very comfortable sitting by a window. Our server was incredibly attentive and I even complimented him at the end of the night for his great service! As for the food we literally ate ever single bite - we started with bread service then apps we ordered the buffalo fried oyster - they were amazing. Dinner I ordered crabcakes and my husband ordered a lobster special. See my pictures for how beautiful the presentation was and it was delicious!!! Overall A+ date night and I would return!!
Atmosphere: 5
Food: 5
Service: 5
Recommended dishes: Whole Maine Lobster, O'Learys Crab Cakes, Crab Risotto
A hidden gem in Annapolis! The.entire experience was exceptional. Would not only go back but would highly, highly recommend.
Atmosphere: 5
Food: 5
Service: 5
We hadn't been to O'Leary's in years! Went tonight and the whole experience was wonderful!! We so enjoyed the food, the service and the atomostphere!
Atmosphere: 5
Food: 5
Service: 5
Recommended dishes: Raw Oysters on the Half Shell, Grilled Diver Scallops, King Salmon
I've been frequenting O' Leary's for years and have never been disappointed in a meal. It's menu is full of amazing choices that are fairly priced, staff is always professional and attentive. Side note, it also bosts some Fantastic art work in and out!
Atmosphere: 5
Food: 5
Service: 5
Recommended dishes: Raw Oysters on the Half Shell, Butter Poached Lobster with Risotto, O'Learys Crab Cakes, Tomahawk Ribeye, Shrimp & Grits, Grilled Diver Scallops, Crispy Rockfish, Branzino with Side of Black Beans Sauce and Rice, Crab Risotto
One of if not the best fine dining in Annapolis. The atmosphere is perfect—cozy, inviting, high end but not stuffy, and sets the stage for an excellent meal. Service is always top notch, fantastic wine list and the food is consistently fabulous—and memorable! The rockfish is one of my all time favorite dishes! Have been several times and have never been disappointed. Great for work dinners, date nights or ladies night out. The owners and kitchen staff are also very nice and extremely talented. Highly recommend!
Atmosphere: 5
Food: 5
Service: 5
Recommended dishes: Raw Oysters on the Half Shell, Shrimp & Grits, Cioppino, Crispy Rockfish, Branzino with Side of Black Beans Sauce and Rice
I haven't been to O'Leary's for quite some time and have missed it so much! Our waitress, Chelsea, was hands down one of the best servers we've had in a long time. She was so personable and knowledgeable about the menu. We really enjoyed our drinks and meals. I won't wait so long to return again!
Atmosphere: 5
Food: 5
Service: 5
Recommended dishes: Grilled Diver Scallops, Crispy Rockfish
We reserved a table a few months before our travel date. The restaurant was lovely. Our server, Thomas, was knowledgeable, kind, patient and handsome. A truly skilled, professional server, who MADE this a fine dining experience.The food was good, but not first rate, the service, however, was first rate. The lobster was a bit over done and chewy as a result, the scallops were small as was the portion size.I made the reservation online based on what I read about it, I was disappointed overall.I was expecting a more dramatic view, or any view, and first class seafood. Th3 food and service didn’t meet expectations, but the service exceeded!
Atmosphere: 2
Food: 2
Service: 5
Recommended dishes: Crispy Rockfish
Really nice atmosphere with great and interesting artwork. It was a bit noisy for me, convival from another point of view. The risotto was delicious and cooked to perfection. Unfortunately, I found my lobster special somewhat undercooked and saved almost all of it to cook more at home. The table next to mine ate every bit. The fish special was nicely cooked and fresh.
Atmosphere: 5
Food: 4
Service: 5
Restaurantji Recommends
If you love seafood, you can't miss at O'Leary's. I had the scallops -- excellent! My sister had the cod, which she doesn't order, but she loved it! Good wine list. We didn't get dessert, but the choices sounded delicious.
Atmosphere: 5
Food: 5
Service: 5
Recommended dishes: Grilled Diver Scallops
Very nice place, excellent food and drink. Outstanding service. The restaurant is nicely decorated and has a good vibe. I go there every time when at the boat show. Don’t miss it when in Annapolis.
My husband and I stopped in for dinner on a Friday of the crazy Sailboat Show weekend and had such an incredible dinner, we had to come the next night. There were too many delicious items on the menu to try! Emily, the bartender made one of the best Old Fashioneds I'd ever tasted, another reason to come back. Every item on the menu we tried was outstanding and beautifully presented- especially the crab bisque- wow! We had the privilege of speaking with both of the owners, Jennifer and Will, the second night before the restaurant got really busy. The history and evolution of the restaurant to what it is today is such an interesting story and the decor and artwork create such a unique vibe. Any future trips to Annapolis will be certain to include a trip back, or maybe the sole reason we come back to visit Annapolis!
Annapolis resident. Had not been here in years. Expensive. Limited menu. Food was mediocre at best. Disappointing. There are a lot of better options in town.Parking: Accessible parking
Atmosphere: 1
Food: 1
Service: 5
Really cute restaurant with a small bar if you want to enjoy a before dinner cocktail. It was a bit loud but the atmosphere made up for it. Our waiter was Peter. He was nice but not very personable. We had some gluten free questions (my husband has Celiac disease & its important to stay gluten free) -- Peter didn't seem knowledgeable nor very eager to ask the kitchen staff which options we had for Gluten free or or offer any GF substitutions as far as sides etc. I really wish more and more restaurants would note GF on their menu these days to make it easier for people to dine. I had the rockfish. It came with a side of red salsa type addition which didn't taste fresh. (it looked like salsa) - I told our waiter about it. But my fish over rice overall was good. Be prepared to spend $$$ -- nothing in Annapolis seems to be reasonable these days.