Before we arrived in the Chesapeake Bay we had done a little research to narrow down the scope of our cruising there. The Chesapeake is HUGE, with more little rivers and creeks and anchorages to explore than one boat could do in just a few weeks. One source we read said that the Chesapeake has more shoreline than the rest of the continental United States, if you separated it out. That’s big.
We knew we wanted to visit Annapolis, and we decided that it would be the farthest north we’d travel. As much as we would have LOVED to anchor in the shadow of the Statue of Liberty or the Washington Monument, 2020’s pandemic required reasonable caution. It didn’t seem like big cities like New York or D.C. or Baltimore were good destinations for this particular year.
Thankfully, however, the Chesapeake has much more to offer. Like Annapolis!
We arrived in “Naptown” the day before our scheduled flight home to Atlanta. Immediately we wished we had built in an extra day or two, but we took comfort in the knowledge that we’d have time to explore upon our return. Annapolis is the very definition of a walkable town. From our berth at Horn Point Harbor we got lunch at the Leeward Market a few blocks away. Thus fortified, we struck out a little further, across the Spa Creek Drawbridge, into downtown Annapolis and… Pusser’s Caribbean Grille! We’d had Painkillers (offered in levels 1 through 4!) at the original location on Tortola, back in March of 2020 before the BVIs shut down. So it was a nice bookend to visit the Annapolis outpost and test the Painkiller once more.


Kyle’s Wedding
The next day we flew home to celebrate the marriage of our son Kyle to our beautiful daughter-in-love, Rachael. They’ve been together for eight years, growing from high-school sweethearts into grown adults with jobs and a new mortgage! When they became engaged in September of 2019, we all anticipated a big and beautiful wedding… but of course 2020 required Kyle and Rach to modify their plans. So a courthouse wedding got the legality taken care of, and we still look forward to the spiritual ceremony and celebration (hopefully in 2021, but we’ll see!). Here are a couple of snaps from the epic day:


Back to Annapolis
Once we landed back in Annapolis we had a few tasks to take care of. One was getting some repairs made to the boat (our water maker was out, AGAIN!). The other was moving Gratitude to a marina on Spa Creek. We had a week-plus reservation secured at Horn Point, but they asked if we would mind moving so they could accommodate a last-minute boat show (they made all the arrangements for us at South Annapolis Yacht Center). This worked fine for us, as it put us right in between downtown Annapolis and historic Eastport – plenty of territory to explore, by walking and by dinghy.

A few of the restaurants we visited (some multiple times!) included the Boatyard, Blackwall Hitch, Davis’ Pub, The Iron Rooster, and Mission BBQ. This last one was a very inspiring place – obviously a tribute to the U.S. Navy (the US Naval Academy is here in Annapolis, after all, and the Navy presence is everywhere). We were surrounded by active and retired military personnel, all enjoying the delicious barbecued pork, beef, and chicken available by the plate or the pound.


A Long-Awaited Reunion
Our final hurrah in Annapolis came with a reunion. As many of you know, I am an avid Crossfitter, and I usually try to visit a gym at least once when traveling. In 2018, Andy and I took a long trip to visit friends in Singapore, stopping off in Tokyo on our way there to break up the flight. In Tokyo, I dropped in at CrossFit Rappongi – my first drop-in at a gym outside the US! It was a little intimidating to navigate the public transit system and find the place, but once there it didn’t take long for me to make a friend. Christine Provost, an American expat who’d been living in Japan for a couple of years, took me under her wing, and we hit it off immediately. I generally trust my instincts about people, and I was really drawn to Christine, so when she invited me and Andy to dinner that evening I jumped at the chance to get to know her better. She and her boyfriend took us to a traditional izakaya, a pub that is often full of young Japanese businessmen. It was a great cultural experience for us, and we’d never have found the place without locals to guide us. (It was located down a narrow alley under the bullet train tracks in Ginza.)
That evening was the start of a good friendship. Christine and I kept in touch through Facebook, and when she learned that I was coming to Annapolis she texted me that she was now living in nearby Baltimore. We couldn’t pass up the chance to reunite, even in a pandemic, so Christine made the drive on a Saturday afternoon to come and hang out with us on Gratitude.

It was a great visit. Andy and I got caught up on Christine’s return to the U.S., and we discovered that she was already up to speed on our adventures as she follows our blog. (Thank you, Christine!) We even talked politics and religion, which with some people can be super awkward, but with Christine was a real pleasure. Although we see some things differently, we found a lot of common ground too. It made me hopeful that our country can find some healing after this contentious year.
Of course we had to get out and see a little of Annapolis, so Christine and I donned our masks, left Andy on Gratitude, and went exploring in the dinghy. One of the great things about Annapolis is that there are dinghy docks EVERYWHERE! It’s a real boater’s town. We motored over to the downtown dock and did some walking. The most memorable sight we found, before settling down for an early dinner, was the Naptown Brass Band – a New Orleans-style street band putting on a show on West Street. Here’s a little sampling:
Next up: St. Michael’s, Onancock, and our return to Norfolk.