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O'Leary's Seafood Restaurant

Certificate of Excellence
$$$$
Seafood, Contemporary
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310 Third St, Eastport, Annapolis, MD 21403-2510 (Severn Avenue)
Water taxi
410-263-0884
Website
Today
5:00 pm - 9:00 pm
Closed now
See all hours
Hours:
Sun 5:00 pm - 9:00 pm
Mon - Sat 5:00 pm - 10:00 pm
Dining options: Dinner, Reservations
Good for:
Casual Elegant
Entertaining clients
Dinner
Reservations

TripAdvisor Reviewer Highlights

Read all 175 reviews
Visitor rating
  • 92
    Excellent
  • 45
    Very good
  • 20
    Average
  • 7
    Poor
  • 11
    Terrible
Rating summary
  • Food
    4 of 5 stars
    Service
    4 of 5 stars
  • Value
    3.5 of 5 stars
    Atmosphere
    4 of 5 stars
Most recent review
Best in Annapolis.. At last so far

We're in Annapolis for a few weeks, and decided to eat at O'Leary's tonight. It is also happens to be Annapolis restaurant week so there were some 3-course fixed price menu specials, which we both selected. Though the portions were smaller than their ala carte counterparts, we found them to be... read more

5 of 5 starsReviewed February 24, 2015
Dave G
via mobile
Good for:
  • Casual Elegant
  • Entertaining clients
  • Dinner
  • Reservations
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175 Reviews from our TripAdvisor Community

Date | Rating
  • English first
  • Any
English first
Contributor
14 reviews 14 reviews
13 restaurant reviews
8 helpful votes 8 helpful votes
5 of 5 stars Reviewed February 24, 2015 NEW via mobile

We're in Annapolis for a few weeks, and decided to eat at O'Leary's tonight. It is also happens to be Annapolis restaurant week so there were some 3-course fixed price menu specials, which we both selected. Though the portions were smaller than their ala carte counterparts, we found them to be plenty filling. It also helped the pocketbook, as the... More 

Was this review helpful? Yes 1
Annapolis, MD
Contributor
11 reviews 11 reviews
7 restaurant reviews
6 helpful votes 6 helpful votes
3 of 5 stars Reviewed February 24, 2015 NEW

My husband and I ate here for our anniversary and I was really disappointed. This place used to be great but the food just isn't as good anymore. There were not many creative menu items, my butternut squash soup tasted like it had pumpkin pie spice in it, my husband's mussels were in a heavy cream sauce that did not... More 

Was this review helpful? Yes
Annapolis, Maryland
Contributor
16 reviews 16 reviews
14 restaurant reviews
6 helpful votes 6 helpful votes
5 of 5 stars Reviewed February 18, 2015

O'Leary's is a great little restaurant in the Eastport neighborhood of Annapolis. It's small and intimate, the food is wonderful. It's a great place to have a drink at the bar, or a nice dinner with a significant other.

Was this review helpful? Yes 1
Maryland
Senior Contributor
28 reviews 28 reviews
17 restaurant reviews
19 helpful votes 19 helpful votes
3 of 5 stars Reviewed February 18, 2015

A major flaw was the service and the lack of attentiveness by the manager to the poor service. Food was average for the price...expected the level of service and quality of food from previous years

Was this review helpful? Yes
Washington DC, District of Columbia
Senior Contributor
25 reviews 25 reviews
14 restaurant reviews
7 helpful votes 7 helpful votes
5 of 5 stars Reviewed January 11, 2015

Enjoyed a great seafood dinner on New Year's Eve. We were seated promptly with a reservation. Quaint location in historic home just a block from the water but it's not a huge space so I highly recommend reservations. The restaurant has a private lot so parking was easy and close. We started with a bowl of Butternut Squash Bisque and... More 

Was this review helpful? Yes 1
Annapolis, Maryland
Top Contributor
75 reviews 75 reviews
41 restaurant reviews
24 helpful votes 24 helpful votes
3 of 5 stars Reviewed December 31, 2014

Had dinner there. Generous, free lot parking (a plus for the Annapolis waterfront area). Quaint, comfortably appointed interior, though small. While things started off well with waiter, he seems to have lost his way. Brought the herbal tea the two of us wanted, but then disappeared for 20 minutes and was somewhat aloof when he returned, though basically polite. Bread... More 

Was this review helpful? Yes 1
Blue Bell, Pennsylvania, United States
Senior Contributor
48 reviews 48 reviews
31 restaurant reviews
29 helpful votes 29 helpful votes
5 of 5 stars Reviewed December 27, 2014

This was a return visit to O'Leary's for me (my honey was a first-timer). We were enjoying a quick get-away to Annapolis and I knew that I wanted to celebrate my birthday dinner at O'Leary's. We had their last reservations of the December evening so we were able to enjoy a lovely, quiet restaurant. We shared one of the delicious... More 

Was this review helpful? Yes 1
Senior Contributor
24 reviews 24 reviews
18 restaurant reviews
4 helpful votes 4 helpful votes
5 of 5 stars Reviewed December 21, 2014 via mobile

We just loved O'Leary's Seafood Restaurant, what beautiful decor, wonderful service and oh the food! We started out with calamari perfectly cooked yum and the fried grouper with jumbo shrimp was amazing! We can't wait to go back!

Was this review helpful? Yes 1
Washington DC, District of Columbia
Senior Reviewer
9 reviews 9 reviews
6 restaurant reviews
7 helpful votes 7 helpful votes
4 of 5 stars Reviewed December 12, 2014

Best seafood restaurant in Annapolis. Black bean soup is amazing. All of the fish dishes come with multiple ingredients. So there is nothing boring about their entrees. Service is great. Ambiance lovely. This is a great place to bring out of town guests for a lovely meal.

Was this review helpful? Yes 1
Annapolis, Maryland
Contributor
15 reviews 15 reviews
6 restaurant reviews
7 helpful votes 7 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 2

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Restaurant Details

Location and Contact Information

  • Address: 310 Third St, Eastport, Annapolis, MD 21403-2510
    (Severn Avenue)
  • Public Transportation: Water taxi
  • Location: United States  >  Maryland (MD)  >  Annapolis
  • Phone Number: 410-263-0884

Price and Cuisine

  • Average Prices: USD 30 - 50
  • Cuisine: Seafood, Contemporary

Restaurant Characteristics

  • Dining Style: Casual Elegant
  • Good for: Entertaining clients
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

Questions & Answers

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?