Great Loop: St. Michaels, MD

Days 118-119: May 15-16, 2023

The halfway point of our May voyages took us to St. Michaels, Maryland. It was a bit windy and rocky. We opted to go to the San Domingo Creek side of town as it was a much closer. As we got near, the area was more protected and the wind calmed, and it turned into a wonderful day.

Once settled into the anchorage, it was time to check out the town. A short dinghy ride and a quarter mile walk took us to the edge of town. Tonia had scoped out some options and there just so happens to be a distillery and winery (or two) there. Hmmm. Ok, we have to check them out. We started in The Old Mill District with the Lyon Rum & Windon Distilling Company. It’s two distilleries in one. Their labels are Lyon Rums and Gray Wolf Spirits. After their free sampling and picking up a few bottles, the winery was next up. Lo and behold, St. Michaels Winery was right next door. Must stop!

The St. Michaels Winery has a Gollywobbler wine that’s pretty tasty, plus shirts that say “get wobbly” so Tonia splurged. Fun fact: A gollywobbler is a sail used by the old ships. We were the only people in the tasting room and I’m sure the lady thought we were nuts, but it was a great time for us.

What’s next? There was a brewery literally next door, but the group was still in the mood for wine. We walked a few blocks down to the Bordeleau Winery tasting room. Now we’re talking! While the St. Michaels Winery had some nice fruit wines, the Bordeleau had some really nice reds. I liked their Cab Sauv.

After our fill of wine and spirits, it was time to get some dinner. At every stop we asked for recommendations and the two responses were Foxy’s Harbor Grille and Ava’s Pizzeria. We decided Foxy’s and headed that way. And while the random house with a “Happy Hour Starts Now” placard wasn’t hopping, we finally found Foxy’s.

We had eaten so early that we now had time to walk around town a bit. We strolled thru the Chesapeake Bay Maritime Museum and checked out sites. Hey, I see another screw-pile lighthouse. The town was quite pleasant to check out with lots of character.

The coolest little free library in the shape of a screw-pile lighthouse!

We made our way back to the dinghy and, go figure, found an ice cream shop on the way.

The next morning Tonia and I got out the kayaks and went up an inlet near the boats.

After that, we popped back into town to meet up with some fellow Loopers at Ava’s.

And, you’ll never guess… more ice cream!

Day 118 Trip Details (May 15):
Harbor Island Marina, Solomons, US to St. Michaels, US
Time 4 h 31 m (09:25 to 13:56)
Distance: 34.52 nm

Leave a comment