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O'Leary's Seafood Restaurant

Certificate of Excellence
American, Seafood, Contemporary
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310 Third Street, Eastport, Annapolis, MD 21403-2510 (Severn Avenue)
5:00 pm - 10:00 pm
Closed now
All hours
Sun 10:00 am - 2:00 pm
Sun - Thu 5:00 pm - 9:00 pm
Fri - Sat 5:00 pm - 10:00 pm
More Info
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261 Reviews from our TripAdvisor Community

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Time of year
Showing 260: English reviews
Annapolis, Maryland
Level Contributor
5 reviews
4 restaurant reviews
common_n_restaurant_reviews_1bd8 1 helpful vote
5 of 5 stars Reviewed 2 weeks ago

Absolutely fabulous food, and the menu is great! It's hard to choose what to order here. Exquisite dishes. Friendly, professional and helpful service. Very cool decor. Try the paella (fish stew). It's amazing!

Thank Holly B
Annapolis, Maryland
Level Contributor
65 reviews
54 restaurant reviews
common_n_restaurant_reviews_1bd8 20 helpful votes
5 of 5 stars Reviewed 4 weeks ago

Always wanted to like O'Leary's as it is the only real higher end seafood place in Annapolis. Every 2-3 years we'd go back and try it, be disappointed and not go back. Heard there was a new chef and decided to try it again - everything was fantastic. I had the black sea bass - it couldn't have been cooked... More 

Thank Avansant
Scranton, Pennsylvania
Level Contributor
18 reviews
10 restaurant reviews
common_n_restaurant_reviews_1bd8 5 helpful votes
5 of 5 stars Reviewed 4 weeks ago via mobile

Best seafood in Annapolis! Friendly, casual atmosphere for the best seafood selections. I had crab cakes, and my friend had black bass, both superb. The drinks menu is inventive with herbed cocktails that hit the spot.

Thank Merlinandme2013
Level Contributor
144 reviews
120 restaurant reviews
common_n_restaurant_reviews_1bd8 33 helpful votes
5 of 5 stars Reviewed August 24, 2016 via mobile

Everything was outstanding. We started out with cream of crab soup and mussels. We had scallops and blue cobia florentine for our main courses and fresh berry shortcake for dessert. When we got the bill our wine was 1/2 price since it was Tuesday. Outstanding wine list and parking.

Thank GooseCowboy
Annapolis, Maryland
Level Contributor
16 reviews
10 restaurant reviews
common_n_restaurant_reviews_1bd8 8 helpful votes
5 of 5 stars Reviewed August 24, 2016

We go there for our wedding anniversary almost every year. 33rd this year. Rather small in size, but the menu and food is incredible. I highly recommend getting a reservation. Service is great, not super fast or rushed. In fact if anything it is slow and easy going. I had crispy rockfish (a staple there) and my wife had sopa... More 

Thank Michael K
Level Contributor
9 reviews
7 restaurant reviews
common_n_restaurant_reviews_1bd8 8 helpful votes
5 of 5 stars Reviewed August 13, 2016 via mobile

After a long search of seafood restaurants we ended up here the food was great the atmosphere is very intimate love this place would definitely recommend this to anyone The crispy rock fish was Great also Deep dive scallops

1 Thank RicoBronya
upstate pa
Level Contributor
149 reviews
119 restaurant reviews
common_n_restaurant_reviews_1bd8 43 helpful votes
5 of 5 stars Reviewed July 30, 2016 via mobile

I think O'Leary's Seafood restaurant is one of the best seafood places around. I travel quite a bit and I am shocked when I go to different towns on the Eastern seaboard including Florida that there is no restaurants that compare to this place in Eastport. My hat is off to O'Leary's for running such a great establishment for all... More 

1 Thank twmUpstatePa
Level Contributor
9 reviews
4 restaurant reviews
common_n_restaurant_reviews_1bd8 11 helpful votes
5 of 5 stars Reviewed July 27, 2016

Every time we go to O'Leary's it's spectacular. The service and attention to detail and the quality of the food is the best that Annapolis has to offer. WE have lived here for over 20 years and there isn't a close second.

1 Thank Rob B
Ansonia, Connecticut
2 reviews
common_n_restaurant_reviews_1bd8 1 helpful vote
3 of 5 stars Reviewed July 25, 2016

We were a party of six for dinner with a reservation. When we arrived we were shown to a booth, we asked if a table was available and were told no - parties of six are seated in booths. We took the booth but for six people it was quite uncomfortable. To be fair our server was good too bad... More 

1 Thank Sharon G
Salisbury, Maryland
Level Contributor
4 reviews
common_n_restaurant_reviews_1bd8 4 helpful votes
5 of 5 stars Reviewed July 25, 2016

I requested 3 vegetable side dishes as I'm a vegetarian. The chef spun them together to create a lovely meal. Thank you so much!

1 Thank Kimberly R

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Restaurant Details

Rating summary
  • Food
    4.5 of 5 stars
    4 of 5 stars
  • Value
    3.5 of 5 stars
    4 of 5 stars
Average prices
$28 - $37
American, Seafood, Contemporary
Restaurant features
Takeout, Parking Available, Serves Alcohol, Reservations, Seating, Waitstaff, Free Off-Street Parking, Full Bar, Wine and Beer, Accepts American Express, Accepts Mastercard, Accepts Visa, Accepts Discover, Private Dining, Wheelchair Accessible, Free Wifi
Dining Style
Casual Elegant
Good for
Special occasions, Romantic, Local cuisine, Business meetings
Open Hours
10:00 am - 2:00 pm
5:00 pm - 9:00 pm
5:00 pm - 9:00 pm
5:00 pm - 9:00 pm
5:00 pm - 9:00 pm
5:00 pm - 9:00 pm
5:00 pm - 10:00 pm
5:00 pm - 10:00 pm
Location and Contact Information
  • Address: 310 Third Street, Eastport, Annapolis, MD 21403-2510
    (Severn Avenue)
  • Public Transportation: Water taxi
  • Location: United States  >  Maryland (MD)  >  Annapolis
  • Phone Number: 14102630884

Questions & Answers

Here's what previous visitors have asked, with answers from representatives of O'Leary's Seafood Restaurant and other visitors
1 question
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Rippon, West Virginia
over a year ago

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Questions? Get answers from O'Leary's Seafood Restaurant staff and past visitors.
Posting guidelines
Typical questions asked:
  • Do you have gluten-free options?
  • Is there a dress code?
  • Do you allow dogs on the outdoor patio?