Legendary Road Trips: Annapolis - Oysters, Sardines, Hockey and Cold

A free ticket to the Washington Capitals outdoor game at the Naval Academy finally got me off my lazy butt and out to a city I've been wanting to go to for the past 15 years...and no this isn't like wanting to go to Honolulu, this is Annapolis, just an hour down the road...why haven't I been!?

The trip didn't turn out exactly the way I wanted it to, but there were sardines involved so I had a great time...here's what happened.

Due to my last minute decision to make this trip, every hotel was booked in downtown Annapolis. Just 3 miles away I found a really bad $50 hotel for $100 and figured with Uber we were basically staying inside the stadium...this will not be the case as you will see later...

After finally checking into the hotel 30 minutes after arrival when an employee finally showed up, I had oysters and happy hour on my mind. Using the world wide web and aggregating data from several sites, the analytics told me Sailor Oyster Bar.

The Uber dropped us off out front and I was a little disappointed that it wasn't closer to the water...however, that turned out to be one of the better things about this place.

Sailor Oyster Bar is a tiny little hipstery (to overuse a word) restaurant that kind of makes you feel like you are in the cabin of a boat. From the decorations to the nautical theme to the smarmy (j/k really friendly) waiters wearing striped sailor shirts I was digging the ocean vibes.

I was expecting to pay some steep prices, especially for Oysters on a Saturday and was shocked to find they have a happy hour on Saturdays and Sundays and it includes $1 oysters and $3.50 craft beer drafts!

After a dozen delicious local oysters (they have oysters from all over the country, they ship them in every morning and they get whatever is the freshest, so the selection will change) and trying to drink my Flying Dog Oyster Stout (see Legends Crawl for why I was moving so slow), I noticed a very strange section on the menu...Tinned Fish.

At the moment I saw this, and saw that Sardines was one of the choices, I had never been happier in a bar. This was my new favorite place and I hadn't even tried them yet. (Other options included $75 Caviar and Squid in Ink). I didn't care that the price was $13 I had to have them...and they didn't disappoint.

The owner of the bar was on hand and he was quite impressed with my fine selection. He gave me the top secret way to combine the sardines with the chive butter, the arugula and the bread to form the perfect bar snack. It was delicious.

We hung around for a couple hours, enjoying watching the hard working shucker do his thing while the bartenders actually made professional bar cocktails...like professionals (shocking at a bar I know).

Overall the place would be a little pricy outside of happy hour, but the drink craftsmanship the oyster knowledge/selection, the great service and the cool atmosphere all come together to make it well worth it.

While I could have stayed there all day, I instead decided, that while I'm here I should experience more of what Annapolis had to offer.

It is at this point in most of the Legend's stories that more crazy exciting things happen...however we peaked too early. When the best bar of the crawl is the first bar, it is only downhill from there.

After we left we walked down to the water and past dozens of cool looking bars filled with drunk hockey fans screaming the F word at other drunk hockey fans. A few of the recommended places in Annapolis were overrun, and sadly we couldn't get the full Napptown experience.

In fact we only made it to 1 other bar, a mediocre pizza spot, before just giving up and going to the hockey game way too early and freezing our butts off.

The game was really awesome, particularly the pageantry of the Naval Academy and the awesome flyover. But after a while it was just plain cold.

And in the end, due to limited Uber availability, we paid $50 for a 3 mile ride back to the hotel, which we didn't even use because we were able to drive home to a real bed due to the failure of the bar crawl.

Soooooo. My first trip to Annapolis didn't turn out to be as epic as I had hoped. However, I'm now primed for a return trip, with a long layover at my favorite bar in Annapolis, Sailor Oyster Bar.


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