Cruising the Chesapeake, Part 1

When we last spoke, we had just arrived at the southern end of the Chesapeake after a slow, and wonderful, trip north up the east coast from Florida. Our plans were to spend a couple of months at York River Yacht Haven and then do some exploring. Yep, done did that! Following is a recap of some of the highlights of our Chesapeake Cruise, Summer 2020. Sorry, it’s a bit longer than my usual posts, so if you’re determined to read this entire blog post in a single seating, you might want to get a fresh drink and perhaps take a bathroom break before you continue. Consider yourself warned.

Leaving York River Behind

After a couple of months in York River Yacht Haven, we were ready to do some exploring. There is so much to see in the Chesapeake and even though we’d miss hanging with our Covid safe friends, in early August we realized it was time to get moving. The first part of our tour of the bay would include places on the eastern shore that we’d never been to before, then we were going to spend some time in Annapolis and Baltimore, and finally we planned to make a run up the Potomac River to visit Washington DC. If that seems ambitious, it was, but off we went.

Cape Charles

Our first stop was Cape Charles, located just across the Chesapeake on the southern end of the Eastern Shore. CC is a cool little tourist town complete with beach bungalows along quiet streets lined with beautiful trees. The marina is right downtown. There’s a hardware store, malt shop/drug store, a few restaurants, and of course there are plenty of tourist shops. Unfortunately, we found that many of the shops and restaurants were closed due to Covid, but that didn’t stop us from getting our bikes off the boat and riding up and down every street and peering in the shop windows. One of the few (only?) restaurants open was on the marina property and got rave reviews, so we were excited that we could get a reservation to eat outside, but 10 minutes before our seating, the heavens opened up and it rained nearly all night. Ah well, on our next visit…


About 40 miles north of Cape Charles is a small waterfront town that was recommended to us by our friends Bart & Julia Hedges the former owners of the N55, Vamos! We had a perfect ride up the coast (ZERO wind) and arrived at Onacock late in the afternoon. Getting up the Onacock River is a bit tedious, but the town is well worth the effort. We anchored right outside the city marina and took the dinghy in to look around. The town is very small and I don’t remember even seeing a grocery, but we enjoyed a nice long walk through several waterfront neighborhoods.

The folks at the marina told us that a fishing tournament was scheduled for the next day and warned us that it might get a little noisy early in the morning. I was up early to watch the start of the tournament and after a 1 hour delay for weather, it was “On Your Marks…” and 75 or so boats blasted out of the marina, past us and out in to the bay. By early afternoon, the boats had returned with their catches, winners were announced, and the partying began. There were boats floating all around us, partying. After months of isolation and deprivation, it was odd to see such disregard for Covid. We stayed on our boat and watched with awe and envy.


We were headed to St. Michaels, but we got a late start from Onacock and decided to stop in Solomons so that I could pick up a part at the West Marine. We’ve been here before and have enjoyed the town immensely, but this time around it was strictly business, though I did get a nice picture of Roam at anchor just after sunset!

Annapolis and Baltimore

We stopped for groceries and to spend more money at West Marine and Home Depot (yawn), but we ate at a real restaurant — in doors! And it was spectacular!!! And we didn’t feel guilty at all. In fact, we had lunch the next day at a taco bar and we survived. Man we really miss people!!! Speaking of which, it was time to head to Baltimore to pick up Michelle’s sister, Lana and their friend Cheryl.

Lana and Cheryl were flying in to BWI airport, so we moved Roam up to Baltimore’s Inner Harbor so it would be easier to pick them up. When we lived in Annapolis in the late 80’s I dreamed of anchoring in the Inner Harbor on my own boat. It took a few years, but we got it done!

We had a great weekend with Lana and Cheryl, showing them around the town we lived in in the 80’s. Annapolis has hardly changed at all and we still love spending time there.

Sassafras River

After we dropped Lana and Cheryl off in Baltimore, we headed up to the Sassafras River for a few days of rest. We anchored at the Turner Creek Park and unplugged! We had spent so much time in each other’s quiet company, our systems were in shock from all the recent human activity. It turns out we needed to ease back in to the human race…

Back to Annapolis

Fully recovered, we headed back to Annapolis for an extended stay. We stayed on a mooring ball up Back Creek for a week, then figured out we could anchor right in the middle of the Creek for free, so we moved! On our first anchor attempt, we picked up a group of cables that had been laid across the river bed and I had to jump in the water and reach down through 3 feet of mud to tie a line on the back of the anchor to pull it free of the cables. I came up looking like the swamp monster from Black Lagoon! Attempt #2 put us in the perfect spot in the creek — dead center, like a highway median. This was our home for the next three weeks.

Annapolis is the only seaside town that I’ve been to where every street that ends at the water is a city park and includes a dinghy dock for visiting sailors to get to shore. We pulled our bikes out and left them in a bike rack at the nearest park and used them daily for runs to the store and for touring the area. We discovered that the old Baltimore Annapolis Rail Road had been turned in to a fantastic bike/hike trail and we enjoyed riding along the well shaded path. Our electric bikes have around a 30 mile range, which, it turns out, is enough power to get out to Severna Park, where our old house is, so we were able to look at the old homestead.

After three weeks on anchor, we moved in to a marina less than 100 yards from our anchorage. Michelle flew to spend a few days with family, and I stayed behind to take care of the dogs and do some maintenance on Roam. I had to work in long pants, a sweater and SHOES and SOCKS! Brrrr…I forgot that fall begins to set in by the end of September and it can get quite cold! When we lived here in the 80’s I remember working the Annapolis Boat Show and having to wear a heavy coat and gloves.

Saint Mary’s

We left Annapolis and headed back to the Eastern Shore. First stop: St. Mary’s College. By the end of September, most cruisers are headed south or have started preparing their boat for winter, leaving Michelle and me alone in the anchorage. The land around the college played a significant role in the history of Maryland. Colonized by the English in the 1634, led by a member of the Calvert family. They named the new settlement Saint Mary’s. The small community prospered and for 61 years was actually the capital of Maryland. The college of Saint Mary’s opened as a seminary for women in the early 1800’s and today is a well regarded liberal arts school.

The campus was open when we were there, with many classes being held on the beautiful school grounds. Michelle and I enjoyed walking the dogs and exploring the campus and the ruins of the old settlement. Most of the old town’s buildings are gone, but the architectural society has rebuilt several and there is an excellent self guided walking tour of the town.

It feels like this post is never going to I’ll call this Cruising the Chesapeake, Part 1 and continue in another post shortly. In the meantime, let us know what we missed because we’ll passing through the Chesapeake again in 2021. If you want to come visit us, reach out. We love it when our friends come cruising with us and now that Covid is finally behind us, we’re especially anxious for company!

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One Reply to “Cruising the Chesapeake, Part 1”

  1. Thanks for your continued updates. So glad you are continuing to explore and enjoy your travels at sea. Glad you were able to the medical help you needed. Continued safety, health, and joy for you!

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