Kent Island to St. Michaels, MD (anchored)
October 21, 2022
After almost 3 months in a marina in Kent Island, it’s time for us to start moving south – it’s starting to get cooler here and we don’t want to get COLD.
John and I had heard so many great things about St. Michaels, so this was our first stop. Today was a great autumn day which made this short hop feel like a good omen for a great trip south.


We departed from Piney Narrows so we could get to the Kent Narrows Bridge for its 10:30 opening.

Lailia has an enclosed cockpit, so even though it was in the low 50s, we were warm in the sunshine today. There was little or no wind so the water was really flat and we motored along at about 6 to 7 knots.

This good timing also extended to our arrival at St. Michaels where we found plenty of room to anchor in the basin. This meant a very short dinghy ride to the docks.

The waterfront has so much history including historic houses and replicas of the shallop that John Smith sailed during his exploration of the Chesapeake.

St. Michaels also has Freedom’s figurehead which was made just before World War II. There’s an amusing story about why she’s on loan to this museum.

John and I toured the replica lighthouse and the maritime museum.



Of course we stopped at Eastern Shore Brewery, which was a short walk in town. We also had some great brick oven pizza before we headed back to Lailia just before sunset.
We won’t always be this lucky with short trips, great weather and calm water and we won’t always anchor in places that embrace boaters the way that St. Michaels does, but this was such a perfect day and a perfect beginning to our southward journey.
We plan to head to Solomons Island tomorrow which will be a bit under 50 nautical miles. That will take most of the day (an hour by car is a day’s ride on Lailia).


Beautiful sunset!! Safe travels! ❤ Dos Capitanas
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Thank you! Hoping Shenanigan is back on the water.
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