Relaxed and friendly oyster bar in the heart of Annapolis with such a welcoming vibe and nautical decor (old photos of sailors). Waitstaff is very friendly and accommodating. Menu focuses on both Chesapeake and west coast oysters. They also have a variety of salads, seafood and libations. We ordered a dozen oysters (4 different Chesapeake ones, 3 of each). They came with a vinaigrette and a spicy cocktail sauce. Server explained each one to us. They were fresh, clean tasting and delicious! We also got the smoked whitefish dip. It was creamy and smoky, topped with caviar and came with flatbread style sesame crackers. It was light and savory. My companion ordered the tuna sashimi special. It had melt in your mouth toro marinated in yuzu and sesame sauce. It was topped with seaweed and came with a side of kimchi aioli. It was definitely the star dish. Will need to come back to try other seafood dishes and drinks. read more

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See previous reviews, this place remains solid choice for all your seafood needs. It's worth drive if you don't live in Annapolis. Come early as it's popular, not just for the food but also for the relaxed atmosphere. The staff is always great, my go to for seafood in the DMV. read more

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I continue to absolutely adore Sailor's. Went for an easy date night and had a lovely time. We got a dozen split hh oysters and they were extremelyyyy delicious. The $5 beers/bubs on hh are fabulous for the price. Their tinned fish plates are the key to my heart. I will say the filet bites sauce was far too heavily garlic for me (didn't know there was such a thing!) and aside from being beautifully tender because of the cut, they didn't wow me. Service is spectacular and I'll always come back for more! read more

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Stopped by on Saturday around 5pm for a quick drink and was pleasantly surprised by how easy and welcoming it was. We were sat immediately, and the staff was genuinely friendly, warm, and clearly knew their stuff. The space has a great dim, intimate vibe, and I liked that there are two floors--cozy for date night but still set up to handle larger groups. Definitely planning to come back soon to try more of the menu. read more

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! read more

Sailor Oyster Bar - Octopus - Seafood Near Me - Annapolis, Maryland

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. read more

Sailor Oyster Bar - Pickles - Seafood Near Me - Annapolis, Maryland

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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. read more

Sailor Oyster Bar - Tinned fish - Seafood Near Me - Annapolis, Maryland

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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! read more

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

Sailor Oyster Bar - Seafood Near Me - Annapolis, Maryland

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Absolutely live visiting Sailor Oyster Bar. The staff is super friendly and the food is always amazing. Can't wait to go back!! Highly recommended!!! read more

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. read more

Sailor Oyster Bar - Goodness - Seafood Near Me - Annapolis, Maryland

Okay some of it is a bit pricey, but the food is absolutely delicious. The caviar sandwich is a splurge but a must-try! Great spot for a special night out. Bartenders are great! read more

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! read more

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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! read more

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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. read more

Sailor Oyster Bar - Local oyster - Seafood Near Me - Annapolis, Maryland

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. read more

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

One of my favorite places to grab drinks and eat in Annapolis! So happy that they are back in business after suffering the fire damage. We are so lucky to have Sailor Oyster Bar! read more

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! read more

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This place is a gem. 10/10. A goldmine. The menu is delightful and the food was cooked perfectly (get the pulpo). Beer list was great service was warm and friendly and the atmosphere is fun without being loud and overcrowded. If you are in in Annapolis for a short time and can only pick one spot for dinner this is it. read more

Great service Fantastic food Friendly and wonderful place to visit; felt very welcome on our overnight visit to Anapolis! read more

This place is darling. We were only here for a drink but had a great experience. The bartender was busy and someone came and sub her... That was very helpful to our schedule. Place is really small but quaint. Loved the naval theme... right on with the environment. read more

This place is described by only one word: Awesome! Was a long day of meetings and travel, so I was looking for some good seafood. I popped in after 8 on a Tuesday night and this joint was jumpin'. I managed to find a seat at the bar and was quickly taken care of by the most attentive staff I've ever seen in a casual dining atmosphere. My bartender made me an incredible martini and it was in front of me within a minute or so of walking in the door. Now to the food. Dozen oysters (all from my home state of Maine). Incredibly Fresh and presented well. I love the briney flavor of North Atlantic oysters, and these hit the spot. The Caesar salad was awesome. Two whole romaine stalks. The house dressing was delightful, tangy with a touch of smokiness. The smoked sardines on top, along with the generous portion of freshly shredded Parmesan really completed the dish. I've never filled up on a salad before-but this did the trick. I can't wait to come back here when I pass through Annapolis again. read more

Sailor Oyster Bar - Caesar Salad - Seafood Near Me - Annapolis, Maryland

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We went last night (Sunday). It was snowing and freezing cold. Inside Sailor- it was warm and so very cozy. We saddled up to the bar and was immediately greeted by Lex. She was fantastic! She walked us thru the specials and told us some of her favs off the regular menu. Everything we had was amazing. We started with the fish dip- awesome. Chile lobster awesome and tried the broccoli rabe special- also awesome. Sunday is happy hour all day so $1 oysters and beer and bubbly $5. Most definitely recommend this place to anyone and everyone. Thanks Lex for a great evening. read more

I hate yelp. I love this place. Great service. Better oysters. Extreme woke a Republican can respect and appreciate. read more

Sailor Oyster Bar - Seafood Near Me - Annapolis, Maryland

The only place in Annapolis we enjoyed. Great place for cold martinis and fresh oysters (from Canada!). My fiancé loved the rum punch and I loved my extra dry martini. People are very friendly here too - (which i was surprised to find out is not the standard in Annapolis). Breath of fresh air after a lot of Ls in this town. read more

Sailor Oyster Bar - Rum punch was great as was vodka martini - Seafood Near Me - Annapolis, Maryland

Hands down, best place in Annapolis. James is our go -to bartender (and now friend). I swear he makes perfect cocktails. The food: perfection. Go here if you like food, plain and simple. Oysters, seafood, specially crusted daily dishes; all amazing. Truly! read more

Absolutely amazing flawless service great execution, fresh fresh fresh really great ambience and interior. I would definitely trust eating anything raw from here and I don't say that lightly the owner or manager came to talk to me. I was there for a medical procedure in Annapolis and they really do care about their customers, very personable approach and very unique menu would come back in a heartbeat, actually down there two nights in a row to be honest read more

If you are in Annapolis, you have to come here!! The vibe is cozy and romantic, but not pretentious at all. Our server was able to give us many recommendations and was always there when we needed a drink refilled. What I ordered: we started off with oysters. They had quite a selection and they were a great price. ($20 for 12 east coast.) For my main I had the salmon rillettes. The flavor was amazing. One of the best parts of the meal was the delicious bread and herb butter! I was drinking a red blend with dinner, but the cocktail list also looked amazing. I would 10/10 recommend SOB for dinner and drinks! read more

Sailor Oyster Bar - Salmon rillettes - Seafood Near Me - Annapolis, Maryland

Loved everything about this great spot! Food was delicious and the staff were even sweeter! We had a mixture of plates including oysters. Everything was fresh and well plated. The white fish dip was insanely good. Ambiance was 10/10. Would visit again in a heartbeat! read more

We visited last time we were in Annapolis and were blown away! The ambiance is so cozy and inviting, the service is amazing, and the food is outstanding. We had a great experience and can't wait to go back! read more

Sailor Oyster Bar - Delicious oysters recommended by the bartender. The little sauce bottles are GENIUS! - Seafood Near Me - Annapolis, Maryland

My friend was able to get a table outside even when the place looked super packed. We came based on great reviews and wasn't disappointed! Most of the food is seafood tapas style so very easy to order a bunch of food to share. We got a dozen oysters, salmon ricilette and tuna tartare toast. Everything tasted fresh and delicious! We werent that hungry when we arrived so I def. Want to come back and try more food :) read more

Sailor Oyster Bar - Seafood Near Me - Annapolis, Maryland

Edit: During our first visit to Annapolis in the spring of 2021, my wife and I frequented this bar twice. Despite the small and crowded space, the drinks were excellent. If given the chance, I would definitely return. read more

We had a fantastic time at the upstairs bar! Christian was the bartender and he was so helpful and made great recommendations. We had delicious drinks to start and then the most amazing oysters I've ever had! Christian also recommended the tinned salmon and it was so good and came with fresh bread, butter, arugula and pickled onions. The presentation was great. We also tried the caviar sandwich, a fun way to have a little caviar. It was very good. It's the perfect place for a drink/app before dinner or you could definitely eat enough for a full meal. There were 6 of us and we all were raving about this place. Can't wait to come back for me! read more

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

The food was good, but the service was sold and our waiter forgot to put in an item 2 times even after we reminded her the second time. It was VERY loud upstairs and we had to shout just to hear each other. read more

Sailor Oyster Bar - Oysters and caviar sandwich - Seafood Near Me - Annapolis, Maryland

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Love the new SOB. Very hip great music. Loved sitting at the bar and watching all the action. Service was over the top attentive. Yellowfin Tina #1 was very good. Did not care for seaweed flakes nor still good. Bread pudding was also very unique and good. read more

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Delicious and interesting menu. Fabulous service. Really fun vibe and kind people serving and dining. Highly recommend. One of the best restaurants in Annapolis. read more

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

Craving oysters, we headed for impromptu visit to Sailor Oyster Bar. We were lucky to snag two seats at the upstairs bar where we enjoyed oysters & clams & a well crafted cocktail/beer/wine. After the raw bar choices, we went on to share the mahi mahi cervice & the octopus. Mahi mahi was by far our favorite...just the right amount of zing. I'm personally not a huge fan of octopus & would have loved a little more char on it but my partner thought it was delicous. We had to try the corn custard with cornflakes & caviar. The texture wasn't a hit...but corn & caviar was interesting combo. Service was warm & welcoming. And isn't that what going out is about...not just the food but the atmoshere. Will we be back? Absolutely. My only complaint? I wish it was closer to where I live. read more