We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.
We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

O'Leary's Seafood Restaurant

310 Third St, Eastport, Annapolis, MD 21403-2510
Improve this listing
Ranked #16 of 298 restaurants in Annapolis
Certificate of Excellence 2014
Reserve with OpenTable
O'Leary's Seafood Restaurant is not available for your requested time. Choose another time, or search restaurants with availability.
The time you selected has already passed.
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
Write a Review

151 reviews from our community

78% Recommend
Rating summary
Date | Rating
  • English first
  • Any
English first
St. Petersburg, Florida
Senior Contributor
25 reviews 25 reviews
12 restaurant reviews
18 helpful votes 18 helpful votes
2 of 5 stars Reviewed August 17, 2014 NEW

The warm greeting when we arrived gave us hope for a nice evening out. Our table was not ready for our 7:30 reservation. In spite of other empty tables in another section of the restaurant, we were directed to the bar. The bar tender was chillier than the ice in the drinks. I ordered the tuna (med rare) it came... More

Was this review helpful? Yes 1
17 reviews 17 reviews
12 restaurant reviews
9 helpful votes 9 helpful votes
4 of 5 stars Reviewed August 5, 2014

A delightful, quiet and very good restaurant away from the crowd. Celebrating my wife's ?? Birthday, the return to O'Learys was nice. The shrimp corn chowder which we shared was superb, intentionally served warm and the flavors came out wonderfully. The rockfish was exceptional along with the polenta. The soft crab/crab cake combination was good, but not great, a bit... More

Was this review helpful? Yes
Springfield, New Jersey
Top Contributor
56 reviews 56 reviews
19 restaurant reviews
23 helpful votes 23 helpful votes
4 of 5 stars Reviewed July 28, 2014

We thoroughly enjoyed the experience of having dinner here. The atmosphere is very nice, though it was very noisy the evening we visited . The waiter was very attentive. The roll served before the meal was very good. I tried the gezpacho which was delicious. We had barbeque mahi mahi, salmon, seafood carbonara and haddock, and loved each dish. If... More

Was this review helpful? Yes
Washington, DC
5 reviews 5 reviews
3 restaurant reviews
8 helpful votes 8 helpful votes
4 of 5 stars Reviewed July 27, 2014

Annapolis is a surprisingly tourist-sloppy town. Hotels are overpriced, the city and state taxes on rooms totaling a shocking 13+% of the charge, the restaurants serve food that's overcooked, fried, unhealthy and dubious as to age, freshness and even sanitation. We were in town sailing for the weekend and I was dreading eating there due to numerous bad experiences. I'd... More

Was this review helpful? Yes 3
Senior Contributor
29 reviews 29 reviews
22 restaurant reviews
8 helpful votes 8 helpful votes
5 of 5 stars Reviewed July 27, 2014

There are plenty of local restaurants in this area but O'Leary's is one of those restaurants that appeals to both casual and fine dining crowds. You will need a reservation and be prepared to wait as table space is limited but well worth the wait. The meals here are exceptional and as soon as they're prepared by their chef, they... More

Was this review helpful? Yes 1
Baltimore, Maryland
14 reviews 14 reviews
7 restaurant reviews
12 helpful votes 12 helpful votes
4 of 5 stars Reviewed July 22, 2014

We discovered O'Leary's a couple of years ago, and keep going back because the food, service, and ambiance are good, reasonably (not cheaply) pricedHe has been very happy with his steak every time he's accompanied us. We usually go as a couple, but there are enough acceptable dishes on the menu for our meat-loving (NOT seafood loving) son. The crabcakes... More

Was this review helpful? Yes 2
Senior Contributor
21 reviews 21 reviews
19 restaurant reviews
9 helpful votes 9 helpful votes
5 of 5 stars Reviewed July 19, 2014 via mobile

O'Leary's remains the best seafood restaurant in Annapolis. Our server, Elaine, was professional, timely, knowledgeable, and a delight. The food was close to perfect. We had 4 different entrees and nobody wanted to share. Grouper, crab cakes, salmon, and shrimp & grits were outstanding. The flash fried oyster appetizers were just as good. We left as happy campers. O'Leary's and... More

Was this review helpful? Yes 1
Tennessee, United States
Top Contributor
51 reviews 51 reviews
34 restaurant reviews
21 helpful votes 21 helpful votes
4 of 5 stars Reviewed June 25, 2014

The crab cakes were wonderful and huge. We had a excellent server who let us know you could order only one if you'd prefer. Easy to walk to O'Leary's from anywhere in the historic area.

Was this review helpful? Yes
Elizabethtown, Pennsylvania
Top Contributor
57 reviews 57 reviews
22 restaurant reviews
21 helpful votes 21 helpful votes
4 of 5 stars Reviewed June 4, 2014

We went on a Monday eve for our first visit to O'Leary's. This was a good choice since the restaurant was not full. Our waitress was very attentive with enthusiastic information on the menu. My husband had a special fish for the day which he loved, my dish was also very satisfying. The atmosphere is pleasant. The prices are very... More

Was this review helpful? Yes
Saint Paul, Minnesota
Top Contributor
78 reviews 78 reviews
52 restaurant reviews
52 helpful votes 52 helpful votes
5 of 5 stars Reviewed May 26, 2014

Despite many trips to Annapolis, we hadn't eaten at O'Leary's for a few years. We weren't disappointed . It is still one of the best if not the best in Annapolis. This time we were there on a Sunday evening and it was much quieter and lot less crowded that on our previous visits which we appreciated. Reservations are a... More

Was this review helpful? Yes

Travelers who viewed O'Leary's Seafood Restaurant also viewed


Been to O'Leary's Seafood Restaurant? Share your experiences!

Write a Review Add Photos & Videos

Owners: What's your side of the story?

If you own or manage O'Leary's Seafood Restaurant, register now for free tools to enhance your listing, attract new reviews, and respond to reviewers.

Manage your listing