Moving On – St. Michael’s and Southward
A couple days after my friend Christine’s visit, we said a reluctant goodbye to Annapolis and turned Gratitude southeast toward St. Michael’s, MD. We left a day later than we had planned, resigning ourselves to a new route that did not include the Potomac. We’d really wanted to venture up and anchor in front of Mt. Vernon, George Washington’s home/museum. But that route required more days than we could give it. On the plus side, our revised plan would allow us a little more leisurely pace, which meant more days at anchor to enjoy the stops we made.
Our first stop was in St. Michael’s, MD, and what a beautiful place to kick around! We’d read that the anchorage was typically crowded, but I think that must apply to spring and summer, because in mid-October we were one of maybe five boats in the harbor. The weather was absolutely gorgeous, so once we anchored we launched the dinghy to go exploring ashore.
I’d read that The Chesapeake Bay Maritime Museum was worth visiting, and that advice held true. I was extremely impressed – I’d call it a “must visit” if you find yourself in this part of the world. There are multiple exhibits that explain life on the Chesapeake across the centuries – from Native American culture to colonization to fishing industry to recreational playground. There’s a screwpile lighthouse relocated from its original home on the water and set up with authentic furnishings, illustrating how the men (and sometimes families) of the Lighthouse Corps lived while stationed out on the water. There’s a smallboat house with every imaginable variation of crabbing and fishing vessels… a mock oyster-processing plant… a crabbing operation… and a whole building devoted to pleasure vessels like sailboats and cabin cruisers. It’s all so interesting! You can really see how life on the Chesapeake has evolved over the centuries.


Other St. Michael’s highlights were exploring Main Street’s shopping and lunch at Foxy’s Bar and Grill. Some cruising friends had told us, “Oh, this Foxy’s was built to look just like the original!” To which we say, “Well, sort of.” There IS an outdoor gazebo that does somewhat remind you of the one at Foxy’s on Jost van Dyke… but we missed the grass-hut roof, and the sand floor, and the college football flags and license plates nailed to the rafters, and the boat stickers and graffiti scrawled on every possible surface from travelers passing through. Nevertheless, we raised a glass in honor of the Foxy’s we hope to return to once this pandemic is good and DONE.
Also, Maryland Crabs! You can’t not eat them when in Maryland.




From St. Michael’s we motored south to Tilghman Island and docked at a little mom-and-pop marina that doesn’t host many catamarans. They were a very friendly outfit, but we were visiting in the off-season and there wasn’t much to see or do. Also, the weather turned cold and blustery, raining one full day during our visit, so we mostly hung out on the boat and watched the Braves both defeat and be defeated by the LA Dodgers in the 2020 National League Championship Series.

Then we sailed back to Harrington Harbor South for one night so that we could pick up our final guest for this Chesapeake hurricane season – my friend and personal trainer, Shane Bonilla. I first met Shane 7 years ago, when our son Clint (inexplicably and miraculously) convinced me to try a new gym starting up down the street. To everyone’s surprise, I loved it – and have been working out with Shane ever since. I love his whole family, and had hoped that both he and his wife Lauri could come see us in the Caribbean. When that plan did not work out, Shane decided that he had to at least see the Chesapeake. Lauri graciously agreed to stay home with the kids and let him fly up for a visit. (Don’t worry – our plan is to make a girls’ trip happen for Lauri in 2021.)

With this new crew member on board, we set out for a week’s journey back to Norfolk, Virginia. I’ll use photos to hit some of the highlights.


One fun stop we made on our way south was upriver to Onancock, VA. We chose it because it gave me and Shane a chance to meet up with a fellow user of our III Nation workout app. Josh Shores met Shane on a Facebook group for Jeep owners, and he joined the III Nation app community, where I met him. Shane reached out to him when he realized this trip down the Chesapeake would be near Josh’s home, and we made a plan to meet for dinner.
But before dinner, of course, we had to workout. And after the workout, Shane decided it was time to jump in the (cold, COLD!) water. And tried out the paddle board for good measure.




Since we couldn’t make a trip up to D.C. work on this trip, we had to make an alternative history visit. So we spent one afternoon and evening at Yorktown, VA, so Shane could visit the awesome history exhibits there.




On our last night in the Chesapeake we needed to deliver the boat to a marina in Norfolk for our delivery captain to pick up over the coming weekend. Coming into the Little Creek inlet we were treated to a Navy exercise with a hovercraft. Check out this bad boy!
Our fall in the Chesapeake thus ended with a bang. We flew home the next day, and Captain Richard Widman delivered Gratitude, over the next 9 days, to Ft. Lauderdale, FL.