Great!! Very knowledgeable waiter explained the oyster choices and their characteristics. Extensive choices of local and imported oysters. We did a dozen local & dozen imported. All were really good - served with hot sauce, cocktail sauce, & mignonette - all House made and perfect compliments. Really enjoyed Meer's Point Maine variety - had 1/2 dozen more. House spiced peanuts were a great nibble/crunch accompanying the oysters . The lobster toast was AMAZING! Cuban was only so so - but good. read more

We came for our 20th anniversary dinner based on Google search/reviews and Instagram. I knew I wanted oysters and my husband knew he wanted the octopus. We were NOT disappointed. We also had Dan's special of the day - sous vide quail, poke and ice cream (peanut butter with chocolate balsamic ganache). Everything was so fresh and tender and flavorful! That balsamic ganache was incredible! All the staff were super friendly and helpful (along with the customers we were seated near), the atmosphere is so fun. I highly recommend Sailor Oyster Bar for any occasion. read more

See all

Love the place, great feel the servers attention to detail food was excellent Wine recommendations were perfect octopus hotdog was amazing read more

Sailor Oyster Bar - Seafood Near Me - Annapolis, Maryland

This was quite the find during happy hour on a Sunday afternoon. Special priced oysters and beer and wine and absolutely terrific service. The place is small so you may want to call ahead and the cool looking window table with the wood seats is a bit rough but have a second brew and you won't feel it as much. Great service with friendly, talkative help that understand the menu and are able to make good recommendations. We loaded up on oysters which are served with three housemade sauces; a vinegar base, a cocktail sauce and a hot sauce. I also had the beets with lemon ricotta and pistachios - yum. read more

Sailor Oyster Bar - AND they are part of the Oyster Recovery Partnership!! - Seafood Near Me - Annapolis, Maryland

A damn can of sardines.... changed my whole damn life!!! And, the bartender was the shhhhhhh!!!! Definitely going back! read more

This is the second time I've been here and the food was just as amazing the first time as it was the second! I highly recommend filling up on their oysters and cocktails. Best customer service I have ever received and will gladly come back for a third and fourth time! We had 2 dozen oysters, the charcuterie board and several cocktails this trip. read more

Sailor Oyster Bar - Charcuterie board - Seafood Near Me - Annapolis, Maryland

Walking just outside of the busy, touristy Main St area has never been more rewarding! After having some oysters earlier in the day at a popular place by the water and feeling underwhelmed, we were told Sailor was a must see - which couldn't have been more accurate! The selection of oysters at SOB was impressive - there was such a variety to choose from and every one was shucked to perfection and tasted fresh and amazing. We also had to try the duck gyro and seasonal octopus dish and wow, just wow. Everything we ate was ridiculously delicious! We also enjoyed some very well made drinks with our dinner - just everything was on point! Additionally, we really enjoy the vibe and staff at Sailor! Every person we talked to was genuine, friendly, and just plain cool. The decor and feeling of the restaurant was also pretty rad We could see ourselves hanging there quite frequently and can't wait to return! read more

Sailor Oyster Bar - New Merch at SOB - Seafood Near Me - Annapolis, Maryland

See all

I googled "Best Oysters In Annapolis" and this place popped up. It was our first stop on a bar crawl in the city and my first time in Annapolis and the best bar on the crawl turned out to be this one by a long shot. This place is SERIOUS about oysters. They have a variety from across the country and local. Fresh. Solid cocktail sauce. They have a GREAT happy hour. $3.50 craft beer drafts, $5 wine and $1 local oysters. And they have it on Saturdays (til 3) and Sundays (all day)! Try the tinned fish options. The Sardines with bread, chive butter and arugula was great. This is the first bar I've ever seen canned fish and it is awesome. They turned one of my favorite camping snacks into a fancy feast. They also know how to make professional cocktails. I didn't order any but I sat at the bar and watched them. They are trained well. Its a REAL bar. I like the atmosphere here. Very nautical. Very clean. From the actual bar to the waiter's striped shirts. Waiter bros were cool. The owner was in the house making sure everything was running smoothly. Very nice. Really cares about the customer and his business. The restaurant is a little pricey, but it is quality. It is shocking I would ever rate a place like this so high, but I just had an A++ experience. The happy hour and the awesome atmosphere/service make this a must visit on any trip to Annapolis. I may go back to Napptown just to hang here again. read more

Sailor Oyster Bar - Sardines at a Bar! $12, so good. They have other canned fancy fish too - Seafood Near Me - Annapolis, Maryland

See all

As noted in some of the other reviews here, this is a cozy place, warm and inviting. Reminds me of a tiny London Pub or NY style restaurant while still being very "Annapolis". Gavin (our new Mayor) suggested we visit this place (before he was Mayor) and check it out. I wish we went sooner! The food is fresh and delicious. They prep it for you right there. We went on a weeknight and it was fairly quiet. Not sure how this would be on a busy night - which we may try tonight. Funny but notable thing is they have two large bathrooms. A lot of these smaller restaurants may have only one bathroom. Suggestion: Park in the city garage nearly across the street. If you live in the City of Annapolis, you can get a book of parking passes at the city parking authority during business hours. This knocks an hour or two off of your parking fee! read more

Innovative use of different flavors and great oysters. The specialty cocktails are very good too.

So, I love oysters. 1 dollar oysters for happy hour is something I almost love just as much as oysters - same with cheap draft. Serving fresh clean shucked oysters with a hot sauce in a dropper(makes it real easy to get the right amount), good cocktail sauce, and some nice sharp lemon all combined is enough to make me frequent an establishment... But these guys didn't stop there, they make bomb sandwiches too! The Merchant Marine sandwich they serve is a phenomenal meld of quality cold cut, cheese, and a few condiments in between some delightful bread. Their tuna tartar is not skimpy, they serve you a hearty amount atop some arugula with crisps to crunch on with a dollop of tuna on top. They were also serving honey inspired cocktails in order to support bees - a portion of the cocktail price went into a donation. Interior was clean, compact, and had cool decor. In the mood for oysters and in Annapolis? Look no further - but get a sandwich too! read more

My favorite place for happy hour oysters. All day Sunday and five dollar wines and beers. The service is also always great and their homemade sauces aren't overpowering. The way the tables are set up allows for maximum space in a close knit environment. Nomnomnom read more

I went to this place by chance about five years ago and never forgot it . I was back in town and found it for a second time . It was just as memorable . This is a special place with a menu you won't find elsewhere. Really solid spot that makes you want to Yelp ! read more

Sailor Oyster Bar - The Boqueron has flavors that opened up with flavor similar to a fine red wine . - Seafood Near Me - Annapolis, Maryland

See all

The husband and I have stopped in here for their weekend happy hour specials a few times now. Who can turn down dollar oysters and drink specials? The oysters, even the dollar ones, have always been on point. My husband can plow through at least a dozen (or two...) so this is a great investment. I have ordered the whiskey cured salmon on a bagel and it's delicious. Topped with generous amounts of salmon, capers, and tomatoes. Definitely a filling treat. Great selection of beers and wines and friendly service! read more

Sailor Oyster Bar - Whiskey cured salmon on a bagel - Seafood Near Me - Annapolis, Maryland

They weren't playing when they said this place is small and perpetually packed. This is for good reason - the moment I walked in, I felt the friendly atmosphere. The drinks were strong, conversation was good and the oysters were phenomenal. I will absolutely be back! read more

A small intimate bar/restaurant that has a neat interior and hipster-feel to it. Happy hour oysters are $1 a piece (local at least) and while the beer menu leaves a little to be desired their cocktail options are plentiful. They oysters were amazing. Definitely do a dash I'd their house-made hot sauce (comes with a dropper ) read more

Sailor Oyster Bar - Fantastic Raw MD oysters - Seafood Near Me - Annapolis, Maryland

I haven't been here for a while, cause it was so small. But it seems they have expanded! For a restaurant without a kitchen, stove or oven; they do an incredible menu! I had plans for dinner at Lemongrass so it was just for a drink and a snack. The scallops were fantastic! Happy Hour offers a few selections of $1 oysters on the half. read more

My partner and I came to this place on a whim while we were running errands in Annapolis and it was one of our best finds! The food was amazing! We highly recommend the Ducketta sandwich! Delicious! We also had raw oysters and the crudo. Everything was fantastic and the service was great! read more

Cool vibe + friendly bartenders + fresh seafood + cheeky bathroom decor= SOB. Stopped in for pre-dinner snack and cocktail and we were lucky to snag two seats at the bar. Bartenders were very warm and helpful with recommendations about food/drinks. Loved the nautical theme. Will definitely stop back in next time in Annapolis. read more

Sailor Oyster Bar - Bathroom decor - Seafood Near Me - Annapolis, Maryland

See all

Okay--- I don't eat oysters.. butttttt I really enjoyed stopping by for some old bay peanuts and a spicy passion fruit mezcal ... Good atmosphere.. 99% kind staff... my server got busy behind the oyster bar so someone else cashed me out... he wasn't as friendly...sort of felt like I annoyed him by asking for a box to take my peanuts But still a cool spot! :) Would def recommend. read more

Great atmosphere and staff is very friendly. But the food is just weird. They don't have a kitchen, so everything is raw, sous-vide, or (literally) torched. My scallops were gelatinous. Great place for a drink, but food needs some work? read more

To park there is a garage or pay to park on the street with a pay mobile app. This is an out of the way super hip foodie place. I would call it a tapas place as all orders were just a couple bites. We had four people and a lot of fun sharing about 10 plates of food. Everything we had was amazing, staff was so friendly and attentive. read more

Definitely go if you're in Annapolis. I'd give the food and cocktail a 4.25 if possible but the whole place gets a 5 because the staff is professional, kind and accommodating. Bravo. read more

Total candor moment here: I really didn't want to write this review. But it's Mother's Day, and my wife totally disagreed with my premise for not writing it, so as an homage to her, here goes: This has very rapidly become our favorite place in town. We'll be returning for Mother's Day making it the fourth time in less than three weeks (and second time this weekend). I can also state this with confidence: this is far and away the best restaurant I've ever eaten in that has no stove (beyond a propane/butane torch). And no oven (beyond a toaster oven). Seriously. An incredibly professional and industrious crew somehow concocts creative and complex combinations of lobster, hamachi, octopus, salmon and so much more. They offer a killer charcuterie and cheese board that we prefer over the board at Grapes' Wine Bar, which had been our "go to" in town. There's a modest selection of soup and salads, but we've not sampled enough to provide feedback that would be useful. Not everything is complex, nor should it be. Oysters are offered fresh (usually six choices encompassing local, East and West coast varieties), without grit and tasting...clean. The usual accoutrements accompany, as well as starch if requested (including GF if need be) and a house blend of jalapeño/habanero sauce (2 drop max fwiw!). And then there's the 'even simpler'--tins of fish. Whether that's a true addition to the menu, a fanciful response to 'how can this place be different from most oyster bars?', an almost self-mocking of the fact they have no stove or oven, or something altogether different, I don't know. I'm not a dessert guy. Until now, and except here. They offer a chocolate peanut butter truffle with sea salt that so hits that sweet-salty spot and puts a figurative cherry on top of a sundae of a dining experience. Modest but very high quality selection of wines and drafts, including an excellent double IPA (Catch and Release), and cocktails and mocktails we need to further expl. Sit near the "kitchen" if you can (not hard, as you'll see in a moment) to watch the mixologists and staff work their magic with an intensity that only adds to the gestalt. So why the hesitance to write a review? The place is tiny and we want our seat! They open up a small upstairs Friday and Saturday nights, but there are maybe 8 tables and as many bar stools. It is loud without being over the top, and we feel oh so impossibly unhip as 50+ adults sporting not a single tattoo between us. The place seems crowded at all times...and glowing reviews aren't likely to make that any better. We're confident the passion for quality will overcome its modest footprint and ensure SOB much success. We're thrilled that it's far enough away from Ego Alley to avoid much of the tourist traffic. I recall a line (roughly) from Broadcast News, when William Hurt posits the question, "what do you do when your reality exceeds your dreams?" To which Brooks replied, "Keep it to yourself." I STILL think that's what I should be doing with SOB! Happy Mother's Day, my dear. Nearly one year later, and we still enjoy SOB....except the new menu, which really disappoints! The rarebit toast, the third iteration of avocado toast, even the ribeye crudo, will not be ordered again...and Ive never said a bad word about ribeye in my life. We still come back for the oysters, the great staff and excellent bar selection (even if they removed my fave double IPA), and still a couple new things that we haven't tried like the octopus hot dog, but all in all, ready for a new menu again! read more

We stumbled upon Sailor for our one night in Annapolis and wow did we luck out! The oysters were so fresh and our minds were blown with so many gems on the menu. Being from SF, it's safe to say we are foodies, so if you're one too, here's what you need to know: the patè is the bomb and you cannot miss the spicy anchovy toast. Holy sh*t, our minds were blown. We felt like locals, hung with the locals and even met the owner. Thanks for making our night so special, Scott and everyone at Sailors! read more

What a gem!!! It's tucked away from the busy streets of downtown Annapolis. Street parking was easy to find on Sunday night. Also it's Happy Hour all day Sunday with $1 oysters till they run out. Sorry. No picture of the oysters bc they got devoured quick!!! read more

Sailor Oyster Bar - Octopus "hot dog" - Seafood Near Me - Annapolis, Maryland

See all

So much fun!! Wonderful oysters, drinks and staff Outside seating in the late afternoon Cannot wait to go back read more

Sailor Oyster Bar (SOB) is without a doubt one of my favorite restaurants not only in downtown Annapolis, but of all time. And I LOVE to eat out and travel. There is something about this place that makes the experience special every single time. Whether it be the intricate and artsy decor that creates the cool atmosphere, the craft cocktails that always pack a punch, the unique and flavorful plates, or the AMAZING, wonderful staff-- all the elements seem to come together and make you feel like you just belong there. And by the way, best oysters in town, bar none. Thank you, SOB. Already looking forward to my next visit. read more

See all

Phenomenal experience! The food was amazing and the service impeccable. Highly recommend. We live in Minnesota but will definitely be back! read more

Love the place. Oysters were so fresh and stuff is sure friendly! Looking forward to coming there again. read more

Best service I've had in a long time. Stick to the seafood, the duck sandwich was average but everything else was fantastic.

This place is so far my favorite spot in Annapolis, I come here from North Bethesda every now and then to enjoy the beers and oysters. So far I have tried their Raw Oysters and Clams, avocado toast, crab toast, tiger prawn and scallops. The avocado toast is my boyfriend's fav bc he loves avocado, cheese and the sourness. Me personally like the crab toast better and it was topped with fish eggs. Oysters are always fresh and juicy--I would appreciate it better if it could be a little less salty The tiger prawn body was cooked but the head was raw(for decoration?) I ate both and ended up liking it raw better bc the meat is sweet and tastes really good just by itself Scallop was really good too but it was sooo overpriced $16 for just one single scallop with some cold corn read more

See all

If you're ever in Annapolis, this place is a must! The oysters were fresh and delicious; the drinks were "well poured"; and from the avocado toast to the rib eye crudo to the Smith Island cake nothing disappointed us! About the service...we were told by a local to ask for Aaron...thank goodness he wasn't working that night because we had the extreme pleasure of meeting our server, the ever so lovely Eleanor! She was phenomenal with her recommendations and conversation! She was right on top of everything w/out being in our face. SHE WAS THE BEST! (P.s. my brothers and I were walking past SOB the next day and she happened to catch us...her sweet smile and knocking on the window to say "hi" melted these old geezers hearts) It took me 30 years since my last visit to beautiful Annapolis and along with Cantler's, Sailors Oyster Bar will surely be on my "Must Go" list of what to do when in town! read more

Such a great meal! We had oysters, the bolney toast, hummus, smoked fish dip, and the choo chee curry. SO GOOD. Everything was on point, especially the martinis. read more

Duck sandwich with flavors of a fine dining New Orleans restaurant. Oysters always on point.

This place is awesome. Super attentive and helpful staff with great food. The menu is small but everything was excellent... had 2 types of MA oysters, the smoked fish dip and spicy hummus all w/ homemade hot sauce. Small place but the bar is a great spot to sit and it's def worth the wait, if there is one!! (Recommend the Frose also, not too sweet and sooooo refreshing on a hot day) read more

Underwhelming & poor quality. They don't even have a kitchen! Just an area to heat & toast lol . Literally spit out the raw tuna because it was bad which I never ever do. My friend is a private chef for affluent DC clients & also noted the tuna was bad not to eat it, so we sent it back with instructions to the chef not to serve it to others. $15-19 for a can of sardines served to you in the can. For what? An experience sitting in a tiny cramped old house eating out of a can? Sat upstairs and the table of 4 next to us was so loud cackling drunk that my friend & I couldn't hear each other speak even when trying. We couldn't even hear the waitress talk to us. The upstairs room is way too small for the acoustics of group tables but it's all for profit in their tiny space. The upstairs room needs to be re-arranged so you're not stuck on top of rude idiots paying for $20 rotten fish appetizers. We left the restaurant with our ears literally buzzing from the noise like I was at a concert a Ramshead. This place isn't all that. Granted I work in DC so maybe this is small town Annapolis standards? read more

Our favorite spot in Annapolis, without question. Amazing oysters every time, great craft drinks, and amazing service. Strongly suggest a visit. Could I give it 6 stars? read more

Undoubtedly one of the most enjoyable solo dining experiences of my life. I had planned my Sunday supper here several weeks in advance, knowing my seafood-adverse friends had other plans that night, and I needed to fend for myself. Despite wandering into the place a stone-cold-stranger from San Francisco, from the moment I walked through the door, I was greeted like a long-time patron and soon knew there was something special about this place. Offered a perch at the middle corner of the grand, arching bar, I jumped at a chance to have a cat bird seat to take in all the oyster shucking, drink mixing, and food blowtorching. My service team was first rate (yes, a team). This place seems to really value the customer/staff interaction experience because over the course of the night no less than 6 friendly, helpful, and downright kind staffers checked in with me, chatted me up about the food, my experience, and what makes the SOB so special. And speaking of the food, it was incredible. The oysters were fresh and nuanced, highlighting exactly the flavor profiles I was told to expect (i ended up downing 2 dozen+). The mushroom salad was the stuff of dreams. Even a casual request for an off-menu mint tea received grand accommodation with fresh mint and lemon. Finally every dish that passed me by, caught my eye, pulled me in, and left me considering whether to order it too! After a leisurely 2.5 hours, it was finally time to pick up my friends. After asking for my check, all the staff members made a point of wishing me well and sending me on my way. I am walking on air a day later, still remembering the SOB and its cold, briny oysters and its warm, welcoming crew. Highly recommended. read more

S.O.B. - The best first impression of any restaurant I have dinned at, in Annapolis. You enter S.O.B with a few strep incline, walking straight into the heart of the restaurant, the "kitchen." The "kitchen" splits 2 long bar seating areas in half. This adds a level of intrigue since the diner has the opportunity to watch Chef James create his art. As a first timer to a new restaurant, I like to experience as many dishes as I can enjoyable consume. Tonight was like none other, starting with a delicious cocktail made by Clancy. Spicy, smoky, tequila prominent, just as I asked for. Now onto the food: Crudo. I can only suggest one thing, try them all. There were 4 crudo dishes on the menu tonight, consisting of Scallop, Ribeye, Salmon, Squid. I started with the scallop crudo dish. The scallop came with a vibrant and smooth poblano cream and sweet eastern shore corn. The crispy quarter sized chorizo added a nice texture and spice. Second was the ribeye. Spicy, sweet, charred and smoky, paired with fresh mint, basil, cilantro, and charred ciabatta. The spice of the ribeye along with the savory marrow butter and fresh herbs created an incredible flavor profile. After the first 2 dishes and phenomenal drinks Clancy was putting together, I was indeed wanting more. I asked for the other 2 crudo options, the salmon and the squid. The flavor of the salmon dish was delightful. Salmon was cured, over a ranch style cream base with capers and fresh dill. The squid dish.... smoky, salty, savory, delicate. Some fresh herbs as a garnish but really add to the overall flavor. After I chewed through the first 4 crudo dishes along with Clancy's unique cocktails, I couldn't end my meal without having one more thing. Octopus hotdog was my final pick and to say it was the perfect closing dish to an incredible meal is an understatement. The octopus was cooked perfect, soft, savory and charred. There was a cabbage slaw which lied next to the octopus in the perfectly toasted potato roll. How could I forget, the pickle on the side, covered with a small drizzle of a sweet chili sauce. As someone who graduated from a culinary arts school but with a business degree, I have had the privilege of being exposed to quality food. Dining at S.O.B. tonight has taken the cake for one of the best overall restaurant experiences I have had in Annapolis which was a product of the food, drinks, and personnel of the restaurant. Thank you all for knocking it out of the park. read more