Amazing food and service. They have old fashioned on tap!!! 1. Reservations: first come, first serve. They have outdoor and indoor seatings. 2. Ambience: rustic, old school, fun As their name suggests, it is a sailor's bar and has lots of old playboy covers on the wall or in the bathroom for decor. Quite fun. 3. Food - amazing Oysters - great. they have good selection, servers know what they have well. Lobster toast - very simple looking, but tastes great Octopus - torched and comes with hummus, it is a delight. 4. Drinks - amazing Their on tap old fashioned has spices that are unique. Plus, have you ever heard of old fashioned on TAP?! Cocktails in general are great here. You can request the bartender for your special drink, beyond that of the menu and they do a great job too. 5. Service - attentive, friendly and welcoming What I like most about their service is the whole team works together. You don't just wait for your specific server, everyone is willing to take your order and bring your check. You can clearly see the team works are a team instead of one waiter getting mad at another for jumping on my table attitude, which is prominent in other places. 6. Ambience - cosy, small venue with lots of character. I think it is a great dating or hang out with your friends spot. You can't really do business dinner meetings here. I would highly recommend this place to everyone who enjoys good food, drinks and mostly seafood. read more

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So so good. Frank provided phenomenal service and was very knowledgeable about every menu item. Highly recommend. read more

Sailor Oyster Bar - Boqoeron toast with anchovies - Seafood Near Me - Annapolis, Maryland

I love oysters on the half shell and what does one do after the doctor says you have an iron deficiency? Eat aaalll the oysters you can find, LOL... as though I really needed an excuse... Sailor Oyster Bar is the best SOB I've ever met and I hate that I'm just learning about this Annapolis gem, but now that I've found this spot, I'll definitely be frequenting this place. I loved the braised duck I had on toast and the perfectly made Caesar salad with anchovies and egg, too. The star of the show was of course the perfectly shucked assortment of oysters my party and I indulged in that paired nicely with the martinis we enjoyed during our visit. Sailor Oyster Bar is not a very large location and the dining area and bar fill up quickly. They super packed inside, so you should anticipate a bit of a wait and be mindful that this place would not be well suited for a large party. The seating could also be a little tight but they are well worth the wait for the great food and drinks and even better staff that were so warm and friendly and all treated our party like we were family. The hospitality from them truly was impressive and made me want to come back just to hangout with the awesome people that work there. You won't go wrong getting there early and checking them out when looking for a variety of delicious oysters and amazing service experience in Annapolis. Park in the garage and walk over to SOB. read more

Tastiness: This is listed as a cocktail bar but the food is phenomenal. The fresh oysters and seafood are the main stars of the show, but they offer salads and appetizers for the non-seafood crowd. This is also a great place if you just want to have a cocktail and/or appetizers. This place is well-worth the drive from DC. Presentation: Take a look at the pictures taken by other customers: in keeping with the vibe of the restaurant, plating is done in a chic but effortless style. Ambiance: This place exhibits a nonchalant cool vibe. Staff wear sailor tshirts with a hipster attitude and an eye for creativity. Cleanliness/COVID prevention: The restaurant is clean but in July 2021 the staff was mostly not wearing masks. Price: Fair for a cool place with fresh seafood in Annapolis Overall: I plan to return here whenever I'm in Annapolis! It is THAT good, that I'm not really interested in exploring other restaurants as I'll probably be disappointed. read more

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

We stopped by SOB while visiting Annapolis because we heard so much about their $1 oysters during their Saturday Happy Hour. The happy hour special runs from 12pm-3pm and offers $5 select beers, $5 selected wines BTG, and $1 oysters! Not only were the oysters cheap, but they were extremely tasty, ranging in flavor from sweet to mildly salty. We highly recommend the Warshores oysters. They were saltier than the other oysters we tried (Cannon Coves, North Shore Golds), but had a sweet finish. SOB is definitely worth a visit if you're an oyster lover or just looking for an affordable happy hour with great food. read more

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Had a great time at the bar. Oysters were clean and delicious. Spencer behind the bar gave excellent service and made our night.

An absolute taste experience. Enjoy the panoply of herbs and spices. Can be crowded, so call ahead or come early.

I cannot say enough great things about this place. From the unique flavor combinations to the incredibly kind staff, this has become my go to in Annapolis! read more

Tucked away in row of scattered storefronts this gem could nearly have be missed if it weren't for the happy patrons seated outside and the whimsical sounds of laughter which verified I had finally reached my destination. It provided the perfect escape from the daily grind! Atmosphere: Welcoming and relaxed. A great place to unwind and relax along with the added benefits the Sailor Oyster Bar offer such as service and the high quality food. The decor was light and cleverly displayed and the subtle neuances are surely to widen your smile. Staff: All members of the staff I had the pleasure of encountering were not only friendly and welcoming, but also very knowledgable and were more than willing to help make my experience a memorable one. In this day and age it is refreshing to see individuals who seem to care about people and clearly take pride in their work. Food: No other description will suffice, it was absolutley AMAZING! I had the Kusshis oysters from BC and they were not only fulfilling but were some of the best oysters oyster I have ever had. I will be a returning patron! Treat yourself! read more

Sailor Oyster Bar - Kusshis Oysters - Seafood Near Me - Annapolis, Maryland

First time we have been back since the fire two years ago. SOB is again outstanding with their food and service. Got to sit in one of the two window seats for two. Oysters were outstanding along with a draft of a beer from St. Michaels. We also had both of their new deserts. Wonderful. Glad to see some of the staff back after the fire. Outstanding early dinner tonight! GrandPa Walking, AT 2000 Miler! read more

Service was great and staff was nice! The food was also great. I like the upstairs way more than the downstairs. It's a nice style.

Super quaint little place in Annapolis. It was crowded at about 8:15 pm on a Friday night. They were able to squeeze me in at the end of the bar. I started with a half dozen sea stones oysters. Great quality, Great flavor. They are served with a shaker of vinaigrette and a dropper of some sort of hot sauce. They did not bring horseradish with them. I then ordered the ahi poke with aioli, Serrano peppers, and shaved cured egg. It is served with crackers. It was really pretty good. Decent draft beer and a decent old fashioned. Frank was my server/ bartender. He was amazing. Everyone was really friendly. Cool vibe neat building. Pretty limited menu. They do not seem to have any warm food. If you are in Annapolis, go here! read more

Sailor Oyster Bar - Old Fashioned with craft Ice. - Seafood Near Me - Annapolis, Maryland

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Bottom Line: Hipster-ish crew in sailor inspired stripe tees serving fresh oysters, brews and artfully prepared cuisine. For starters, it's important to know that Sailor Oyster Bar is intimate and that between 3pm and 4pm it's happy hour but they only serve oysters. I love oysters but when my husband and I rolled in at 3:05pm starving, we were so disappointed that we couldn't order from the real menu! We killed 55 minutes by eating 1/2 priced oysters, drinking discounted cocktails and eyeing up the Playboy covers in the bathroom. The staff was very nice so we stuck around until the magic hour of 4pm. By 4pm we were famished and drooling (ok, that's a bit dramatic) and we promptly placed our order - avocado toast and the Merchant Marine sandwich. Good things come to those who wait . . . our food was excellent! I was expecting the avocado toast to be avocado smushed and smeared on some toast with some stuff dropped and drizzled on top. Instead it was a gorgeous work of art that tasted even better than it looked. My husband had the Merchant Marine sandwich which was salty, savory, meaty and delicious. The food was worth the wait! read more

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Wednesday dinner date with the sweetie was absolutely incredible! The drinks were delicious, the food was super tasty, and the service Brice provided us with was simply superb! First of all, Brice set the tone for a great evening with his sunshiny personality. He was happy to be there and so attentive... it really set the mood for the amazing food coming out of the kitchen. The chef really honored the ingredients presented by letting them shine without drowning them in sauces. The different textures and mix of salty and sweet, acid and fat sent our taste buds into a frenzy. If you're a fan of Rose's Luxury, this is 100% your spot here in Annapolis... Great for date night or a night out with the girls. We'll be back soon! read more

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Delicious oysters, an interesting menu, and amazing customer service. We really enjoyed how pleasant and kind the host was and our waiter on the second floor was very personable and made great suggestions. This restaurant feels like a labor of love and it was a great experience. read more

I was unexpectedly in town so I didn't have very much time to plan anything or anywhere to eat and came across this quaint neighborhood gem that offers a variety of tapas items. Franklin is this adorable sociable knowledgeable person in the bar that provided us with great service. The local raw oysters were simply delicious. The octopus was controversially tasty because I've had better and I've had worse. The tuna tataki was also mediocre but what I loved is the friendliness of the place which gave me a cheers vibe. If I lived in the area, I would definitely return. read more

Love that they are trying to do something a little different here. Don't expect to find your typical pub fare and be ready to step out of your comfort zone. It is all eclectic stuff like oysters, sardines, and a host of other stuff. It is a welcome change from the monotony of bar food that we all know and quite honestly love. We sat at the bar and enjoyed ourselves. It is a little tight in here but still fun. They have a few different kinds of oysters. We tried both the east coast and west coast oysters. Both were delicious on their own without the condiments. That is the true sign of quality. The sardines were different but also had a nice flavor to them. I would highly recommend checking this place out. It is not exactly downtown but still worth coming. Check it out. read more

Sailor Oyster Bar - Seafood Near Me - Annapolis, Maryland

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Loved everything about this place. It was so good that I ditched my plans for trying another restaurant on our long weekend trip and went here twice. In general there is just a great vibe in the place. The servers were all wonderful and they all seemed extremely happy to work there which transfers to the customers. The food is interesting to say the least since they don't have a kitchen. Everything is either raw, sous-vide, or torched. But everything I had was delicious. My wife and I split the beat salad which was very tasty. The smoked pistachios were a nice crunchy touch. I also tried the Uni toast which was on the specials menu. Excellent Unit flavor. I also had on the second night a dozen oysters and the Maryland Crab toast. The oysters were delicious. The Crab toast was also very good. But the best thing I had at SOB was the Octopus "Hot Dog". Octopus happens to be one of my favorite dishes and this was an interesting way to serve it. It was cooked perfectly, tender with a nice crunch. Also, the sauce had a nice kick to it. Highly recommend it. read more

Best of the best in Annapolis! Great food, service, atmosphere. Just perfection from start to finish. Can't wait to return and we will recommend to anyone visiting the area. read more

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YOOOO THIS PLACE IS FIRE!!! Apparently I've been sleeping on Annapolis. Everything that touched my tongue was creative and delicious down to the recommendation on what order to eat the oysters in. We doubled down on the boucheron because it was that amazing. This was one of the best meals I've had in some time - not just in Annapolis but in general. Amazing, attentive staff, great cocktails, and excellent food. What else can you ask for??? *chefs kiss* read more

Sailor Oyster Bar - Seafood Near Me - Annapolis, Maryland

One of the most incredible dining experiences we have ever had! We ate there this evening- the ambience, the staff (thanks to the owner, Scott, for being so attentive to us) and then the food, from one dish to the next, is just amazing. This place is a gem and can't wait to come back! read more

Came here with the bf and a friend when we were in town a few weeks ago. This place was recommended to us by some locals, and since it was a very short walk from where we were staying, we figured we might as well check it out. We got here a little after 5PM, so we didn't have to wait for a table, but we did notice that the place filled up pretty quickly after we got seated. As the name would suggest, they're known for their oysters, so you're in luck if you happen to be a seafood fan. They also have a wide variety of cocktails, beers, and wines to choose from. I opted for their New Last Word cocktail and their sole vegetarian offering for the day, which happened to be a mushroom and goat cheese salad, while the bf and my friend opted for other drinks and food items. Our drinks and food came out promptly, and everything tasted pretty good. I appreciated that their cocktails were touted as not being too sweet, and they were as described and refreshing. The salad I had was fantastic as well, and my party raved about their food choices as well. It looks like their menus change often, so check beforehand to make sure they have something for your dietary concerns and/or your fancies for the day. Great friendly service, reasonably priced offerings, and fun décor. A nice place to visit if you happen to be in Annapolis. read more

Tight seating but delicious oysters, great music and wonderful staff. Would definitely recommend for before or after dinner, small plate apps. read more

Sailor Oyster Bar - Seafood Near Me - Annapolis, Maryland

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Most amazing and fun dinner since going to the San Jacinto Inn in Houston for the 1979 Liberty Bowl. Five of us sat outside fit three hours and had a ball. Even when there was a downpour the staff brought us umbrellas. The canned Grilled Bronzino was swoon worthy. The Tartar and Ceviche were tasty and super fresh. The Halle berry toast was so unique. The house pickles disappeared in seconds. On and on. By the end the owner was making creative mocktails got me and my niece n nephew. Soo go in. read more

Date night happy hour. Just 2, then some friends stopped by. We moved tables several times. Everyone one was so nice and helped us. Drinks were delish, oysters fresh and fabulous. Staff was knowledgeable about the oysters and the cocktails! Highly recommend! read more

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

When we got to Sailor, there was a wait and we were told it would be at least 35 minutes, not bad for a Friday night! But, it actually turned out to be maybe 15 minutes! We had oysters, first MD, then VA. Very fresh and delicious! We had spicy margaritas to go with the oysters. The service was friendly and excellent. I would definitely go back! read more

I randomly selected an oyster bar, and picked the best one I've ever been to! 10 kinds of oysters, and a knowledgeable staff to steer you to what you like! Great old school atmosphere, tasty local beers, great craft cocktails, and the Smoked Fish Dip is to die for. One of the best seafood/oyster type places I have EVER been to! 10/10!!! read more

Great experience as last time. The only thing is that I liked their old lobster toast with the sweet mango sauce with the caviar on top better than this one topped with spicy jalapeños. But it was still really good. The oyster are amazing as always and so are the really beautiful, refreshing, drinks and the friendly wonderful staff. This is "The" place to go to for great drinks and amazing food! read more

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In Annapolis for the weekend and my friend had recommended this spot. We had already eaten at 2 different spots prior (big foodie ppl over here lol) so we only went for oysters / drinks and got a cheese platter Super cute dive bar! Great staff, great oysters, their homemade spicy sauce is a 10/10 and honey on the cheese board was to die for Didn't get a chance to take a pic of their awesome bathroom wall paper which means you'll just have to check it out by yourself read more

Sailor Oyster Bar - Seafood Near Me - Annapolis, Maryland

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Visited SOB for the first time yesterday with a large group and the staff could not have been more accommodating. The oysters were amazing---Whitestone from VA were a big hit. They also had some great recommendations on some favorites apps including the smoked white fish dip and the Tinned Octopus--both were delicious! Overall just a fantastic experience from start to finish. Additionally the service was so quick and pleasant. Will definitely go back. read more

I go to Sailor Oyster Bar at least two Sunday's out of the month. Why Sunday? Well that's because they have an all day oyster happy hour on Sundays. ($1 oysters) I absolutely love this place. The food is always sooo good. The service is top notch. The prices are very reasonable. There is literally nothing bad I can say about this restaurant. If you're in Annapolis you have to stop by. I recommend this restaurant to people all the time. read more

Let me start by saying that I love this place. It's my new favorite restaurant. Terrific cocktail menu. And once you get into dinner, there's no stopping you from a memorable meal. The boqueron were the best thing I've had all year. Sardines in a tin were terrific, tuna tartare was great, and the Halle berry toast closed it out on a perfect note. Great oysters too. Great staff. Not to be missed, come on in! read more

Sailor Oyster Bar - Sardines in a tin. So good! - Seafood Near Me - Annapolis, Maryland

Probably one of the best places in Annapolis to visit for dinner. Some local friends took me and I'm already planning my next trip back so I can stop by again. Go with a group of friends and snag a window nook or sit solo at the bar. Either way, the oysters are fresh, the drinks are delicious, and the all the food is on point. They don't have big entrees but it's the perfect spot to share food or get a few small plates/oysters. I'll be back! read more

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Quaint little spot in Annapolis. Seating arrangements are cozy and felt like I was in close quarters with those around me and had to be pretty cautious with my movements. This was probably the case because we got the tiny table for 2 people. I don't know why restaurants have these tables - theres barely space on the table for food let alone drinks. I think it takes away from business because it limits you from ordering everything you want. So we just had the ceviche and raw oysters. The ceviche was plated beautifully but was not as appetizing. Definitely recommend coming here for the oysters! They were fresh and they have HH deals ($1 oysters) on the weekend which is pretty rare to find! read more

Sailor Oyster Bar - Seafood Near Me - Annapolis, Maryland

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

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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