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All 305 Annapolis Restaurants

O'Leary's Seafood Restaurant

310 Third St, Eastport, Annapolis, MD 21403-2510
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Ranked #17 of 305 Restaurants in Annapolis
Certificate of Excellence 2014
Price range: $30 - $50
Sun 5:00 pm - 9:00 pm
Mon - Sat 5:00 pm - 10:00 pm
Cuisines: Seafood, Contemporary
More restaurant details
Restaurant details
Good for: Entertaining clients
Dining options: Dinner, Reservations
Dining style: Casual Elegant
Cross street: Severn Avenue
Transit: Water taxi
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166 reviews from our community

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Rating summary
Date | Rating
  • English first
  • Any
English first
Annapolis, Maryland
12 reviews 12 reviews
5 restaurant reviews
6 helpful votes 6 helpful votes
5 of 5 stars Reviewed November 6, 2014

Best variety and quality of seafood in Annapolis. They usually take reservations (recommend in summer). Pricey. Small, nice atmosphere. If you're looking for a more boisterous time eat at the bar at Ruth's across the street or Middleton's next to city market.

Was this review helpful? Yes 1
Bowie, Maryland
Senior Reviewer
6 reviews 6 reviews
3 restaurant reviews
10 helpful votes 10 helpful votes
5 of 5 stars Reviewed November 3, 2014

If you love fish and shellfish, O'Leary's should not be missed if you're visiting Annapolis. Quite small and a bit noisy because of it, that really should not be a deterrent to eating here. Tiny bar area, but with a reservation, you will be seated before having to stand at the bar for long. I have never had anything but... More

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Sarasota, Florida
Top Contributor
495 reviews 495 reviews
378 restaurant reviews
241 helpful votes 241 helpful votes
4 of 5 stars Reviewed October 20, 2014

The tables at O'Leary's are a little too close for comfort and it does make it feel a bit crowded, but the food was excellent... as were the cocktails :-) We had the shark, which was quite a small portion for the price to be fair... Would definitely recommend though - would probably choose the swordfish over the shark next... More

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Top Contributor
102 reviews 102 reviews
50 restaurant reviews
48 helpful votes 48 helpful votes
3 of 5 stars Reviewed October 19, 2014

We have eaten here in the past and have always found the food very good. The atmosphere is crowded and the seating is tightly packed. You essentially will have no privacy in your conversations. This is not a romantic couple restaurant. The restaurant is a converted house into restaurant. Low ceilings, congested and crowding makes the acoustics almost intolerable. But,... More

Was this review helpful? Yes 1
Beaumont, Texas
5 reviews 5 reviews
7 helpful votes 7 helpful votes
2 of 5 stars Reviewed October 9, 2014

First time in Annapolis and we were told o'Learys was the place to eat seafood. We made reservations and showed up on time. We were seated promptly and the waitress came right over to get our drink order, but I left my cheaters in the car and had to go get them to read the menu. Once I got back... More

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Kennett Square, Pennsylvania
18 reviews 18 reviews
6 restaurant reviews
9 helpful votes 9 helpful votes
5 of 5 stars Reviewed October 2, 2014

Loved the ambiance and the food...wines were amazing...martinis fully loaded with the best and biggest olives ever! My husband had the grouper...loved it...I had the crab cake and soft shell crab over fried green tomatoes...amazing! We can't wait to return!

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Top Contributor
94 reviews 94 reviews
40 restaurant reviews
38 helpful votes 38 helpful votes
5 of 5 stars Reviewed September 23, 2014

Went to O'Leary's due to its top rating on Yelp, during a boat trip to Annapolis overnight with another couple. We couldn't stop talking about the meal that night or the next day. It was clearly one of the top two meals we've had this year. Started out very strong with very interesting and flavorful craft cocktails. The English Pauper... More

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Bethesda, Maryland
Top Contributor
261 reviews 261 reviews
129 restaurant reviews
72 helpful votes 72 helpful votes
5 of 5 stars Reviewed September 23, 2014

Beautiful restored cottage on the Eastport waterfront in Annapolis. This place has been a fixture specializing in wonderful fresh seafood since th 80's. Worth a visit.

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Annapolis, Maryland
13 reviews 13 reviews
10 restaurant reviews
6 helpful votes 6 helpful votes
4 of 5 stars Reviewed September 17, 2014

We have eaten at O'Leary's repeatedly for twenty years. At the moment, they are on an upswing. The menu was inventive, creative and just fine in the execution. The ambience is nice, although the tables are close together. Prices were high but not confiscatory. Be aware, however, that this restaurant is more variable over time than many as to the... More

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Chicago, Illinois
Senior Contributor
42 reviews 42 reviews
35 restaurant reviews
18 helpful votes 18 helpful votes
4 of 5 stars Reviewed September 17, 2014

We spend a lot of time in Florida where Grouper is on every menu. But this preparation was so good, we are telling our friends down there to call O'Learys for the recipe. Lobster Bisque cappuccino needs to be on your bucket list as well. We had a large group (from Florida) and the service was excellent. Extensive, reasonable priced... More

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Additional Information about O'Leary's Seafood Restaurant

Address: 310 Third St, Eastport, Annapolis, MD 21403-2510
Phone Number: 410-263-0884
Location: United States  >  Maryland (MD)  >  Annapolis
Open Hours:
Sunday 5:00 pm - 9:00 pm
Monday 5:00 pm - 10:00 pm
Tuesday 5:00 pm - 10:00 pm
Wednesday 5:00 pm - 10:00 pm
Thursday 5:00 pm - 10:00 pm
Friday 5:00 pm - 10:00 pm
Saturday 5:00 pm - 10:00 pm
Average Prices: USD 30 - 50
Cuisine: Seafood, Contemporary

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