Sailing to St. Michael’s, MD

On the first leg of our journey, we traveled from Annapolis, MD to St. Michaels, MD.

annapolis to st michaels

It took 6 hours, a combination of sailing and motoring. Sail-motoring. I would venture to say it’s not really easy to get to St. Michaels by car either. On previous sailing trips we have seen houses with seaplanes. 

We docked, and after a quick investigation, I decided to get into the pool because I’m still pretending I’m in Key West. It was cold, and that didn’t last long. We had a crab dinner, and then endured one of the loudest nights I’ve ever had sailing. The way the dock was set up meant that we were approximately 10 feet away from a bar that was having a wedding reception with a live band. I understand, I guess we just had bad luck in our spot. But the reception ended, and then it was just the usual drunks and loud music. Imagine trying to sleep on the patio of a rambunctious bar, and that’s exactly what it was like. Ah well…

The Church

Despite getting little sleep the night before, of course I woke up at an ungodly hour. So early, stores weren’t even open yet. We had breakfast and set to exploring the empty town.

Lots of neat looking buildings
eastern shore
Ghost town

When the stores starting opening, I found a store that offered key lime pie on a stick, covered in chocolate. Yes, this directly and completely goes against my diet, but I’m still pretending I’m in Key West.

st michaels maryland
It tasted like heaven.

We found a farmers market and stocked up on more things that directly violated my diet.

Cheese and ham croissants. Omg, so bad for me
We didn’t get cookies, just admired them.


eastern shore maryland
Obviously, there were cute bikes, it’s a small town!

There’s lots of little stores that sell all sorts of random things with St. Michaels markings. There’s also a heavy emphasis on Old Bay, it must be a requirement to sell Old Bay in Maryland.

Overall, it was fun to walk around, but we check out was noon, so we were soon underway. We spent a night anchored out in Tillman Creek, and then we were headed back to Annapolis!


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