Enjoying Middle Maryland, Post 25-28
- Jimmy Lee
- Jul 13
- 4 min read
Updated: 4 days ago
Thursday July 3 through Wednesday July 10
From Annapolis Maryland to St. Michaels Maryland
26 NM (30 miles)
Our first morning in Annapolis we dinghied from our mooring to a convenient dinghy dock and went on a long walk to pick up some Amazon packages at the UPS Store. It was a great orientation walk through some nice neighborhoods along some trails to get to our destination.

After we got back to the boat we went on another walk to get some materials for our water maker in Eastport across Spa Creek. That evening, we went out for dinner and drinks with our friends Cam and Denise on Quest II.
As a side note, Annapolis is one, of if not the most cruiser friendly areas we have been too. There are so many free dinghy docks to land your dinghy and due to the fact that the city is so water-centric, you can get close to your destination via dinghy wherever you might want to go.
Friday was July 4th, so we were really excited to see all the festivities in Annapolis. We ended up deciding to spend the evening on Quest II, so we ended up going to the grocery store in the morning and then doing some food preparation before going to their boat and cooking a wonderful meal of fajitas. The Whitlock's invited Baxter over so we brought the cat over so he wouldn’t be alone on our boat during the fireworks. We then had a front row seat of the fireworks set off on a barge in the harbor. There is something special about watching fireworks from your own boat.
4th of July in Annapolis
The evening ended with a comedy of errors when transporting ourselves and Baxter back to Utopia, he got a little excited to get back on the boat and he ended up going into the water. I in turn jumped in to retrieve him with both mine and Sondra’s phones in my pockets. Later Sondra jumped in to retrieve my hat, so all of us went for a night swim. All was well with Baxter and the phones, but he was not particularly happy about going for a swim.
Baxter over the 4th of July in Annapolis
Saturday through Monday were somewhat down days with cleaning and maintenance done on the boat. I stayed on the boat on Sunday afternoon while Sondra went shopping with our friends and we ended up going to see the F1 movie on Monday. Good flick!
Tuesday morning, we slipped the lines of our mooring ball and set out for St. Michaels, Maryland. It was a slight backtrack to the south and the trip took about 5 hours with some sailing near the beginning and motor sailing for a couple of extra hours. So far, the wind in Chesapeake has been light with a lot of motoring which is typical for summer in this area (especially the northern portion of the bay). Also, it has been pretty hot also so it is nice that we have booked three nights in St. Michaels Marina so we can run our AC for a few days. Our friends are also here at the marina, and we are docked right next to them. After we checked in, we spent the afternoon at the marina pool.
St. Michaels Claim to Fame
St. Michaels is a quintessential colonial town with an interesting history:
“St. Michaels, Maryland, is widely known as "The Town That Fooled The British" for its role in the War of 1812. Local legend says residents dimmed the town lights and hung lanterns in the trees to trick British attackers into firing over the town during an attack in 1813. While the story is debated, the town embraced the nickname, and it remains a central part of its identity. Beyond the "fooling" legend, St. Michaels is also known for its rich maritime history, particularly its shipbuilding industry and its role as a center for oystering and crabbing. -NPS.GOV “

Wednesday, we went with our friends to the Chesapeake Bay Maritime Museum in St. Michaels. This was an awesome museum that goes over the history of Chesapeake Bay with an emphasis of the Underground Railway for people escaping slavery. You can read more about the museum here. After we went to lunch at a local spot and then ran errands in the afternoon ending with some pool time and dinner on the boat.
Thursday, we had an enjoyable day and visitor from our hiking days of the Appalachian Trail last year. Our friend Sully drove 2.5 hours from the DC area and visited us on Utopia. We spent the day going out to lunch and catching up on what has been going on since the trail. We had hiked with Sully off and on from New York to New Hampshire. We have kept in touch over the months, and it worked our great that he came for a visit.
Fun in St. Michaels, Maryland
Tomorrow, we plan on heading back to Annapolis for a couple of days before we continue north towards Long Island Sound.

St. Michaels Marina
Just a small kudos to St. Michaels Marina. This was a great spot and a very accommodating marina, albeit a bit pricy. The staff were very attentive, and they took a few drone pictures of our boat. They have two restaurants on site and a nice pool to cool off in. Also, it is right downtown. We would stay again.
This is post 25-28. Last week's block post about Solomons, MD and the post following this one, about leaving the Chesapeake area are available below under "Related Posts"
Video of random of sights between Wrightsville & Beaufort NC:
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