November 16, 2020
NOTE: Sailor Oyster Bar suffered a fire on June 8, 2022 and is temporarily closed.
My name is Alexandra and I’m the face of @annapolitan_eats. I’m currently a senior at Loyola University Maryland where I study history, French, and Arabic (sadly, they don’t offer a degree in food). In my free time, I love going out to eat (duh), skiing, paddle boarding, and spending time with my family. As a native Annapolitan, I’m an ardent cheerleader for all things Annapolis (hence why I love the Naptown Scoop!)
And now, a review of what I believe to be the best oyster bar in Annapolis.
Sailor is a small but well-decorated space. The bold nautical theme complemented by dark woods and industrial pipes is super cozy. If you want natural light, sit next to the heaters outside or at one of two window tables at the front. It can feel a bit crammed, so it’s safer for date nights or small parties than large groups.
Every time I’ve been, the service has been nothing short of excellent. The staff are super relaxed and laid-back. But they work hard to ensure your needs are met. On all my visits, especially the most recent, they routinely came to refill our drinks and make sure we had everything we needed. Our main waiter was attentive and friendly. He even took the time to make genuine conversation with us—a cherry on top of an already wonderful experience.
If you’re anything like me you love a good buck-a-shuck deal (even if it’s just so you get to say “buck a shuck!”). Go between 4:00 – 5:30 PM Tuesday through Friday for $1 select oyster Happy Hour. Don’t expect a huge meal. The menu is mostly small plates, sandwiches, snacks, and (you guessed it) oysters. It’s a common occurrence to begin an evening at Sailor and finish with a larger meal elsewhere.
Pig and fig toast, tinned fish, sous-vide torched octopus... sounds like normal restaurant fare, right? At Sailor, it’s not only normal, it’s making the best of what they have (and doing a masterful job). Sailor doesn’t have a traditional kitchen (that’s right—a restaurant without a kitchen, you have now heard it all). All they have, I’ve been told, is a toaster and a blow torch
Regardless, I can promise you this—at no point will you be saying “Darn, I wish they had a regular kitchen!” They don’t need it. Trust me.
My top recommendations:
The highlight of our entire dining experience was Dan’s Taco Tuesday special. In the words of my beloved boyfriend and taco enthusiast, “This is, like, the best taco I’ve ever had.” I couldn't help but concur after biting into the hot, house-made chorizo taco with butternut squash, goat cheese, and shaved Fresno peppers.
Seriously. It was the best taco either of us have ever had—and we've had a lot. The only bad thing? It was a special, perhaps never to be seen or heard from again. Darn you, Dan Zegas!
Sailor Oyster Bar could go toe-to-toe with any oyster bar in DC or Baltimore (or New York for that matter). It’s hip, it’s trendy (you have to check their Instagram for each day's menu!), and it capitalizes on one of Annapolis' most popular local foods. Sure, other places in town do oysters and raw bars. But nobody does it like Sailor.
Editor's note: please follow @annapolitan_eats on Instagram. Word of warning: don't look at her pictures on an empty stomach.
The Naptown Scoop rates restaurants on the same scale as Michelin stars:
Just like Michelin stars, not every restaurant will earn scoops. This does not mean they aren't good.
Alexandra has decided to award Sailor Oyster Bar a single scoop.
We're that funny, deal finding, hip and relevant friend you wish you had. And we'll email you all the Annapolis news and events every Monday, Wednesday, and Friday morning. For free.