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    Sailor Oyster Bar

    4.7 (308 reviews)
    Closed 4:00 pm - 12:00 am (Next day)
    Updated 1 week ago

    Sailor Oyster Bar Photos

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    SAILOR OYSTER BAR ATMOSPHERE

    What's the vibe?
    Moderate noise
    Hipster
    Casual
    Trendy

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    Octopus
    Caroline H.

    Very delicious food and not wildly over priced. Great atmosphere for date night or large groups. Recommend the charcuterie board for large groups, it's very big and tasty. The caviar sandwich was delicious. The oysters were fabulous, definitely recommend! The martinis were great and service was swift and friendly. Would go back!

    Pickles
    Anuva S.

    About time for a place like this to exist in Annapolis! Sailor is located downtown and is a solid, no frills, oyster bar. The regular menu is solid bar food and they do different specials often along with a great happy hour option of discounted oysters and champagne. They offer a wide variety of oysters and their cocktail list is very impressive. You can tell they take pride in their craft and it's a great place to support downtown.

    Tinned fish
    Dean R.

    Sam was absolutely amazing. As I have said, eating challenges, but after me explaining, Sam was dead on with her recommendations. Oysters were really good but the "tinned fish" was off the chart tasty. All because of Sam's suggestion. They put their house made mignonette and hot sauce in little bottles. Who does that? A great touch Who would have thought tinned fish would be a thing. Again, Sam was dead on with her suggestion. Annapolis is a great city with great options but you have to go to Sailor. Just to see Sam would be worth it.

    Chorizo toast
    Alexis B.

    Someone in Baltimore recommended Sailor Oyster Bar to me over a year ago, and I've had it on my to try list since that recommendation. I finally managed to stop by for dinner last night with my husband, and wow. I'm in love. It might be the best meal I've had so far this year. Sailor Oyster Bar is (you guessed it) all about the seafood. But it's also incredibly fun and creative on top of being delicious seafood. Their menu is a variety of small plates, and we tried quite a few of them. We shared: half a dozen raw oysters; a mini caviar sammy (kettle chips, chive butter, and caviar on a Hawaiian roll); shrimp cocktail (with aji amarillo cocktail sauce); hamachi sashimi (with ponzo and serrano chile); yellowfin tuna crudo (with extra virgin olive oil, dukkah, chives, lemon zest); chorizo toast (with honey-cured egg yolk and manchego); and the boqueron toast (aged anchovy, honey butter, dark chocolate, and fresno chiles on sourdough). Everything was outstanding. If I have two mini pieces of feedback, they're that I didn't taste aji amarillo in the shrimp cocktail at all (still delicious, but tasted totally classic) and that the egg yolk on the chorizo toast was over-cured and couldn't serve as a sauce the way they intended). The mini caviar sammy was a dream and a treat. The sashimi and the crudo were both delicious. The bonqueron toast was wild and shouldn't work but totally did. It's a perfect example of their food overall - creative, surprising, and wild without sacrificing any flavor! It's not style over substance here. Sailor has them both in spades. The restaurant is comfortable and dark and cool. The service was outstanding - several servers and staff delivered dishes, asked if we needed refills, checked in on us, and made us feel totally welcome. I meant when I said it's one of the best meal I've had so far in 2025. I can't wait to head back for another creative, delicious meal at Sailor Oyster Bar!

    Rachel S.

    One of my fave spots for amazing seafood! Never a boring time here! Food is delicious, staff is friendly and fun!

    Goodness

    look, if you want to feel loved and accepted...show up. come once, surrender to the flow and the sublimely sweet and subtly beautiful people here will LITERALLY hug you for being you. old, young, hip, square...you're in. just have fun. be nice and dig in. this isn't only a bar and a restaurant it's a vibe. SOB is your new home. the warm fuzzy after leaving here lasts for days. Go get you some. Let Dan cook. Alex will satiate your oyster and clam needs . Seriously, get the clams. Talk to everybody because chances are you are less than a Kevin bacon separation from everyone here.

    Pickled Mussels
    Sydney S.

    If there's was only one restaurant I could go to for the rest of my life, Sailor Oyster bar would be my choice. The service is outstanding, the food is delicious, and the vibe is very dimly lit. Think gritty-chic meets upscale. The servers, bartenders, and all the staff are always smiling and happy to help! The drinks are delicious, I always get a spicy margarita with tajin on the rim, and it always is delicious! The snacks are very good, the tinned fish is to die for, and the oysters are freshly shucked!! 10000% recommend!

    Bloney sandwich
    Cynthia F.

    Went searching for an oyster bar to visit on a trip to Annapolis and found Sailor Oyster Bar! Husband and I visited on a Sunday and were happily surprised that they have an all day oyster happy hour on Sundays. They had good deals on bubbly, beer, and oysters for happy hour. We also opted to share warm olives, smoked whitefish dip, tuna crudo, and the "bloney" sandwich. The whitefish dip was my fav! Very Smokey and a decent portion for the price. Overall, we had a really nice meal! The bartender was friendly and provided great recommendations. Looking forward to coming back soon!

    Local oyster
    Jacqueline K.

    Love it here! We ordered 6 of the happy hour oysters which were $1.50 each (what an amazing deal for such fresh lovely oysters), and then 2 happy hour ESB Amber oysters for $2.50 each. The rest of the oysters were full price and definitely pricier. We also ordered drinks - their Skull Puncher cocktail was my favorite and the Jay's New Fashioned was an interesting twist on an Old Fashioned.

    The Waltz
    Anna F.

    Sailor Oyster Bar opened nine weeks ago after being closed for over a year because of a fire. Colton was our server and recommended the sparkling red. I've never had a sparkling red so I decided to try it. We ordered the Waltz, which is the seafood tower with raw oysters, shrimp, caviar, brioche and champagne. The price point was high to what we really got. We also got the smoked fish, tinned sardines and toast. The food was good and so were the cocktails and wine. The atmosphere is casual and they didn't rush us out after we paid the check. The service was great too. The only downside are the Playboy magazine pictures in the gender neutral bathroom. I don't remember the bathrooms before the fire so this may be a new thing.

    Smoked whitefish dip
    Sara C.

    Five stars all around! I stopped in solo and had such a lovely experience at Sailor Oyster Bar. The oysters were incredibly fresh--clean, briny, and beautifully presented. I followed that up with the smoked whitefish dip, which was creamy, smoky, and totally hit the spot. I also had some of the best dirty martinis I've had in a while--perfectly chilled and just the right amount of salty. I sat at the bar and was taken care of by Avery, who was friendly, attentive, and made the whole experience feel easy and welcoming. The ambiance is chill, stylish, and relaxed--great for a solo night or a low-key date. I'll definitely be back next time I'm in Annapolis!

    Caesar Salad

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    7 days ago

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    7 months ago

    Heaven for oyster lovers with a broad and expertly crafted supporting menu. Best bartenders in all Annapolis.

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    2 years ago

    The service and selection of oysters was awesome! The staff was great with wine selections!

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    2 years ago

    Terrific oysters and seafood, great and friendly service, sweet potato humus and tinned octopus delish. Tasty cocktails!

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    Leo Annapolis

    Leo Annapolis

    4.6
    (113 reviews)
    0.0 mi

    Leo has only gotten better since their opening a few years ago ... this was our second visit (we…read moredined previously the week of the opening). Really impressed with the elevated food at Leo - ambiance was elegant and service friendly. Though we sat at a table, we'd note that bar looked great! We ordered the (Snakehead) Fish & Grits .. excellent dish and great flavor profile - you'll love it! Also got the scallops at the recommendation of the server - very nice. These were complimented by a starters including oysters, a salad and a side of Brussel Sprouts. HITS: Fish & Grits, Oysters

    Went here with friends on a Saturday night after listening to live music. We didn't have…read morereservations and waited for a table. We didn't have to wait long as a family with a baby was about to leave. I looked around and the space is modern and clean. There is a bar area that is well lit and inviting if I was dining by myself. The menu isn't your typical Italian menu. There was a chicken fried tofu appetizer, steak frites, smash burgers and snakehead. I don't know what snakehead is so ai went with the catfish carbonara, my friend had the steak frites and my other friend had the Brussel sprouts appetizer and pear salad. We also shared a bottle of red wine. Our dessert was a deconstructed sundae with cannoli bits and delicious. Our server was Brendan and he was fantastic. He answered our questions and checked in and chatted with us for a bit. Highly recommend this restaurant.

    Photos
    Love the ambiance!
    Love the ambiance!
    The brussel sprouts are quite good.
    The brussel sprouts are quite good.
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    Vin 909

    Vin 909

    4.4
    (756 reviews)
    1.0 mi
    $$

    Great people, great atmosphere, and prices that are actually fair, which is rare these days. This…read morespot fills up fast, so if you're trying to walk right in and sit down, get there early. Trust me, it's worth it. They've got a small bar area that seats about 4-6 people, which is where I sat, and honestly that's the move if you like a lively vibe. Now let's talk about the pizza--amazing. Fresh, flavorful, and one of those meals where you catch yourself still thinking about it later. I enjoyed every bite and could've easily gone for another round. Overall, this place delivers: good energy, good food, good people. Definitely a spot you want to keep in your rotation.

    We came with a good appetite and left happy. I'd share the menu changes often, according to my…read morefriend who's a regular. I'm glad we narrowed down our group size because 2 and 4 top tables os the setup it has. We had many menu items. I thought after appetizers I'd be full after sharing 1 pizza. Nope, needed a second. This is like middle eastern meets Italian meets Indian influence. It took a mi. To embrace the menu. I liked the crust and flavors of most things we had. This pizza I remembered to picture was Indian influenced. Good service overall. Wait tomes vary an they dont take traditional reservations.

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    Outside
    Outside
    BUTTERSCOTCH PUDDING Pudding, Caramelita Points
    BUTTERSCOTCH PUDDING Pudding, Caramelita Points
    ARUGULA & PROSCIUTTO SALAD Arugula, Prosciutto, Goat Cheese, Crispy Shallots, White Balsamic Vinaigrette

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    ARUGULA & PROSCIUTTO SALAD Arugula, Prosciutto, Goat Cheese, Crispy Shallots, White Balsamic Vinaigrette
    Seasalt

    Seasalt

    4.5
    (66 reviews)
    0.1 mi

    We had a largely positive dinner at Seasalt on April 27. Reservations went smoothly and the…read morerestaurant was not crowded on a Monday evening. We settled into our table and were welcomed by Shannon, our server. (There was a little confusion about this, but it straightened out.) The restaurant is bright and separated from the well-stocked bar. I had a Sagamore rye neat, and B ordered a glass of the Rioja. If there are oysters on the menu, you know I'll order them. There was a pretty good selection, and I opted for a half dozen Rappahanock oysters. They were excellent, sweet and briny. We each ordered a Caesar salad, but Shannon advised us that it was large enough to be shareable. More than enough. B ordered the pasta with clams, and I choose the Seafood chowder. The chowder was delicious, but B found the pasta to be too peppery for her tastes. Worse, three of the clams were unopened. We brought this to Shannon's attention, and she offered to put in a new order, but B demured, as she was full. At this point, Owner John Hogan came over to the table to chat. He told us the clams would be taken off the bill, and gave us a gift card, hoping we'd return. He stayed at our table for nearly 30 minutes, and we had a wonderfully engaging conversation with him. We will definitely be going back.

    This review is only for the sampler dessert. So when you see the three stars it is not a reflection…read moreof their service or main dishes. The service was good, the ambiance is nice they have indoor and outdoor seating. The dessert trio was mediocre at best. The cheesecake was where we mostly lived the others...should have been saved to never been served again. Nothing more, nothing less. Would I go back, yes I would to try the main dishes. Today we just made a mistake by chosen this for dessert stop.

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    Seasalt
    Bluefin tuna tartare
    Bluefin tuna tartare
    Manhattan classic

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    Manhattan classic
    Parley Room

    Parley Room

    4.4
    (50 reviews)
    0.5 mi

    We were here for the 4th of July cookout on the patio. It was Awesome! They had a really nice…read moresetup. This was a buffet which included desserts as well as a nice selection of food. Everything tasted great for the most part. Service was great as well. The outdoor buffet cookout was $20 tickets were purchased on eventbrite. They also had holiday drink specials at $2.49 which was a good deal. They also sold smoked oysters at $1.00 each & the server and bartender was very helpful and friendly. We really enjoyed this event. We would like to go back and check out the other drinks on the menu as well as the food. Definitely bookmarked this spot for a return visit. There is a parking garage about three blocks away. We paid $12.00 for about three hours. Not bad at all.

    Modern, dark, speakeasy vibes on the inside with windows overlooking the Main Street, and a…read morespacious outdoor deck quite literally in the shadow of the gorgeous Maryland State House. All housed in the historic Capital Hotel, newly renovated in November of 2022. The atmosphere here is immaculate. It is a must see when enjoying the sights of Annapolis. My girlfriend and I stopped in on a Thursday afternoon after touring the State House. We each ordered the Monkey Smoke (Penicillin), and she ordered a small plate with avocado and lump crabmeat, which we ordered just in time as the kitchen closed between 3 and 4. The standout of the day for me was the old fashioned, made with plum bitters. One of the best old fashioneds I've ever had. The servers were all very friendly and quick. We will definitely come back the next time we're in town, and definitely recommend this to others.

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    Parley Room
    Parley Room
    Fig Old Fashioned and The O.G. original gimlet.

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    Fig Old Fashioned and The O.G. original gimlet.
    Preserve

    Preserve

    4.3
    (504 reviews)
    0.6 mi
    $$

    At Preserve, consistency is not the point, evolution is. Each visit feels slightly different,…read moreshaped by a menu that shifts with the seasons and refuses to coast on familiarity. That restlessness works in its favor. The space is compact, almost disarming at first. Then it settles around you. There is a quiet intimacy to the room, the kind that feels less designed and more lived in. It leans closer to a welcoming home than a polished dining room, without losing its sense of purpose. The food carries that same balance. Thoughtful, seasonal, and just unpredictable enough to keep you paying attention. Cocktails follow suit, measured and deliberate, never an afterthought. For Annapolis, where good options are not exactly rare, this place still manages to separate itself. It belongs firmly in the top tier of the city's dining scene, and it earns that position every time it changes the menu and starts over again.

    We had made a reservation here for a Sunday brunch at 11. It wasn't overly busy when we came. This…read moreis in downtown Annapolis so there's some street parking around. Bright and open inside with friendly service. We ordered a handful of mimosas and got a couple of small bites to share. Sourdough Foccaccia - this was pretty good, warm and toasted. Pork Bites - I loved the flavor but thought this was pork belly and not ground pork. Overall, flavor was good but the texture wasn't great. Crispy Kale - this is very popular here and we really enjoyed it. The cumin yogurt really brought it together. Pickled Squid - Not what we expected but I actually really liked this dish. We did also order the Coconut Panna Cotta for dessert. The raspberry was pretty prominent here and wasn't as custard like as expected, just a little too soft but the flavor otherwise wasn't bad. Overall, everything was pretty good and I would visit again to try other items on their menu.

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    Seating
    Seating
    Fish Dip
    Fish Dip
    Bar area

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    Bar area

    Sailor Oyster Bar - seafood - Updated July 2026

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