Frank Schwartz and the rest of the Sailor Oyster Bar team came back stronger after fire wiped out the popular Annapolis spot. Photo: Susan Moynihan

Welcome Home, Sailor! An Oyster Bar Comes Back to Life

When a beloved restaurant closes, it leaves a hole in the community. So when a fire shut down Sailor Oyster Bar in Annapolis, word spread quickly and the community grieved almost as much as the owner, Scott Herbst, and his team. They vowed to rebuild, but in a 128-year-old building on West Street, it wouldn’t be simple.

From the day of the fire to the day of reopening, the process took two years and ten months, said Herbst. “We had many unforeseen corrections we had to do to a building from 1896 to make it structurally sound.”

The restaurant building comprises two conjoined former row homes built in 1896. When they got down to work, they realized the building didn’t have a true foundation, so that had to be addressed. They also worked carefully to change what made sense while staying true to the look and feel of the original eatery, which recalled oyster bars of old.

Jay’s New Fashion

2 oz. “123” Organic Reposado tequila

.25 oz. habanera agave

2 dashes chocolate bitters (we use The Bitter Truth brand)

Add ingredients to a stir glass, stir until chilled. Strain over a large ice cube and garnish with an expressed orange peel.

An upstairs apartment was razed to expand the dining room, and the dropped ceiling was taken out, opening up a loft-style space. In the prep kitchen, they lifted the ceiling, expanded counterspace and added a window, creating a comfortable, light-filled space for the chefs to work their magic. There’s still no stove or oven—in Sailor’s unique take, everything is done on two induction cooktops and a sous vide machine, in lieu of a traditional kitchen.

Downstairs, they took out two half-walls that separated the dining room, allowing for more seating without impacting flow.  And they added two low wheelchair accessible seats at the bar, something they’d wanted but hadn’t managed to do before. The community donated photos to replace some of what was lost (including Playboy pages in the bathrooms) and local artist Skribe created the sign that says “Welcome back.”

When the restaurant closed, the community stepped in and did a lot of fundraising—to the tune of $110K, which Herbst used to pay his staff for as long as he could. As the renovation stretched from months to years, many went on to find other jobs, but then came back to join Sailor for its reopening. Herbst also added a new chef, Sean McCardle, to join returning chefs Lorenza Aznar and Daniel Zegas. There’s a dedicated shucker and a runner, making the largest team to date.  

Sailor Oyster Bar’s nightly staff meeting before opening time. They waited nearly three years for Sailor’s triumphant return. Photo: Susan Moynihan

We went three weeks after the reopening, on a Friday afternoon. At the pre-opening staff meeting, Herbst went over the evening’s specials, which included a vegan tinned enoki mushroom “snow crab” that got applause from the team. They take obvious pride in what they do, which is part of Sailor’s magic.

By 3:45 pm, people had already begun to line up outside, waiting for the doors to open at 4 pm. Inside, the team tended to the last of the kitchen prep work, lit candles and fine-tuned the placement of menus and seats, and turned up Lou Reed on the stereo before opening the doors. It filled up fast. 

Jay’s New Fashion, as photographed and sampled by the author.

“On our first Saturday, every seat was filled by 4:06 pm,” said beverage director Frank Schwartz, as he crafted a Jay’s New Fashion, their tasty play on an old fashioned made with organic tequila, habanero agave and chocolate bitters (he generously shares his recipe with Chesapeake Bay Magazine: see sidebar).

The menu is mostly the same as it was, much to my relief. The raw bar features freshly shucked oysters, always local selections alongside ones from further afield. Instead of mignonette served in a ramekin, they have it chilled and bottled, alongside traditional cocktail and hot sauces, so you can spritz before you slurp.  The “bloney” sandwich made with mortadella and aged gouda is still there; “That’s not going anywhere,” Herbst laughed. Specials included a sous vide salmon, glazed and torched, and boqueron toast with aged anchovies and dark chocolate. We did the yellowfin crudo, served simply with olive oil, sea salt and crumbled nori, and the tinned salmon, served with thick slabs of buttered, salted sourdough. One bite reminded me of how much I’d missed that taste, and the power of simple, expertly prepared ingredients.

One of Sailor’s unexpected signature dishes: tinned salmon. Photo: Susan Moynihan

Around me, the dining crowd was as happy as the team about the reopening. There were hello hugs from the staff for favorite customers, and cries of “We missed you!” from both sides. 

The couple next to us had come in from Pasadena for the afternoon, and got there early to get two coveted seats at the bar. Over shrimp cocktail and oysters, they asked Frank Schwartz how the fire started.  

“We didn’t start the fire, it was always turning,” Schwartz quipped, citing Billy Joel. “Actually it was our passion for the community that started it,” he smiled.

In truth, it was a cigarette that started the fire, but the staff’s passion will keep Sailor Oyster Bar going strong into its new iteration. Welcome back.


SOB doesn’t take reservations, so you need to get there early, or expect a wait, especially on the weekends. With the renovation, they expanded from 59 seats to 108. That said, when the seats and standing spots at the rail bars are filled, the door closes. Per the fire code they could pack in more people, but they don’t want to; they’d rather keep the vibe mellow and comfortable, and leave plenty of room for the staff to get around. For the waitlist, they’ll take your name and number and send you down the street to Metropolitan, where you can get 20% off of drinks while you wait for dinner.  

Come spring they’ll add 10 more seats outside, and bring back their fantastic frosé. They are open Tuesday through Sunday, from 4pm to midnight. Keep an eye on their Instagram @sailoroysterbar for announcements about daily specials and events. 

Sailor Oyster Bar, 196 West Street, Annapolis

Susan Moynihan writes about travel and food, and is the author of 100 Things to Do in Annapolis and the Eastern Shore Before You Die. You can find her on Instagram at @susanmoynihan.