Hello friends! It’s been a minute since we last posted. Part of that is because we’ve been busy sailing, seeing, and doing. Another part of it was a feeling, on our part, like we didn’t have all that much to write about. As I started reviewing photos, however, I realized just how wrong we were! We’ve had enough adventures for at least 2 posts! So here’s Part 1, covering our September in the Chesapeake Bay.
We left Beaufort, NC on September 5, expecting a little bit of bounce and an 24-hour sail up to Rudee’s Inlet, VA (just south of Virginia Beach). This journey would take us around Cape Hatteras, which is notorious in the sailing community. Long-time East Coast sailors all seem to have a Hatteras story, and we took that seriously. However, most of our research indicated that sailing north around this cape was not as big a deal as sailing south around it. So we plotted a course, watched the weather, and decided we could do a day plus an overnight and arrive in Virginia on the morning of September 6.
About 6 hours into the trip, however, we realized we had seriously misjudged the distance, and the weather. For one thing, it took a lot longer to get out of Beaufort because there is a HUGE shoal around Cape Lookout; this meant we had to go south for quite a while before we could turn northeast.
And once we turned – holy COW! – the seas and the wind were on our nose! We started bashing into the waves pretty steadily, which makes for a very uncomfortable ride. You accept a certain amount of bashing, as a sailor, but after several hours it really begins to wear on you. For one thing, you feel like you are in a washing machine. For another, everything that’s not nailed down seems to crash land in the cabins – water bottles, dishes you forgot to put away, knives, bottles of rum… 😜 Finally, fighting the seas in this manner really slows your speed. We went from a good 7.4 knots coming out of Beaufort to maybe 3.5 knots once we turned north. That blew up our schedule, for sure.
Around the aforementioned 6 hour mark, we had a serious discussion about whether we should turn back and wait for better conditions, or press on. (There is no good place for a sailboat our size/height to enter or anchor along the Atlantic coast of the Outer Banks. You have to get almost all the way to the Chesapeake before there’s an opening with no bridge or shallows obstructing the passage.) Andy’s vote was to turn around, but I could not stand the thought of giving up the progress we’d already made. We agreed to press on.
And things did get some better as the day wore on. We kept bashing, but with reduced violence, and our speed picked up to between 4 and 5 knots. We finally reached Rudee’s Inlet about 6 pm on the 6th, almost 36 hours after our departure from NC. It’s located just south of Virginia Beach and offers two possible anchorages. Only the one to the south is accessible to tall-masted boats like ours.
We weren’t sure what to expect at this anchorage, however, because it was in a small lake surrounded by private homes, and our Active Captain charts indicated that there wouldn’t be room for more than one or two boats. Indeed, when we turned into the lake, we saw a lot of boats already camped out. But most were small pleasurecraft, and we spotted a place that gave us enough room, as long as we didn’t let out too much chain. We did so cautiously; it’s always dicey to anchor in a place that feels like someone’s backyard.
Turns out we needn’t have worried. Once the anchor set and we started prepping our dinner, a nice powerboat cruised by carrying 3 locals – a married couple and one of their buddies. They asked us where we came from and welcomed us to their neighborhood. Sometimes other boaters can be territorial, even abrasive, but we were blown away by the friendliness of these people. We learned that everyone who lived on this lake was a boater and was very cool with transients like us spending a night or two. They also gave us restaurant recommendations and ideas for things to do. It was so nice, coming in tired and hungry and stressed, to encounter a warm welcome!
We ended up staying two nights on Lake Wesley, both to rest and to do a bit of exploring. It was Labor Day weekend, after all, so the break felt appropriate. But we still had a few hours of sailing ahead to make it to our ultimate goal, the Chesapeake Bay. And we were eager to reach that milestone.
The morning after Labor Day we pulled up the anchor and headed out and around the Virginia Beach area towards the Bay. It was pretty thrilling to catch sight of the Chesapeake Bridge-Tunnel and realize we were entering historic waters. This was, after all, where Captain John Smith sailed with the colonists who started what would become the U.S. of A.
History aside, it’s also cool to view that Bridge-Tunnel from the water. In order to accommodate both car and boat traffic, the engineers who created this marvel built a bridge that soars over the water, then plunges into a tunnel, not once but twice! Cars on this bridge go over and under the Bay; ships and sailboats navigate a channel crossing the water over the tunnel. It’s an impressive feat of engineering.

Yorktown, Jamestown, and a Visit with Polaskis
When we arrived at the York River Yacht Haven, two wonderful things happened. First, one of our neighbors came out to catch a line and help us tie up to the dock. This turned out to be a fortuitous meeting. Andy started talking about the difficult passage we had just had, and Capt. Don, aboard Cat’s Meow, was a wealth of information about weather routing and information. He spent quite a bit of time explaining his approach, the resources and software he uses, and his general experience.
Second, we discovered that the YRYH was also home to an oyster bar! Some marina restaurants leave a lot to be desired, but we ate ate this one almost every day, after enjoying this on our first evening:

We also spent our time doing a good bit of sightseeing. Yorktown, VA is right across the river from the YRYH, and is the site of Cornwallis’ surrender to George Washington that brought Americans our hard-won independence. The whole area is a treasure trove of museums, rebuilt fortifications, monuments, and attractions. And another 30 minutes away is Jamestown, the first successful English colony in the New World.




Back at the marina, we also enjoyed a visit with my friends Don and Sandra Polaski, who drove to see us from their home in Richmond. They have spent almost all of 2020 at home because of the pandemic, so we were especially honored that they took the risk of coming out for an evening on Gratitude. We ordered seafood from the Oyster House and opened a bottle (or two!) of wine. It was a delightful evening, capped off after dark when Andy got to show us all his recent discovery of bioluminescence in the York River!

FU all the time!
From Yorktown, we spent a few more nights making our way up to Annapolis, stopping at small towns along the eastern coasts of Virginia and Maryland. We anchored in a secluded spot near Reedville, VA, then again right outside a tiki bar on Solomons Island, MD. (The bar was advertising live music by The Amish Outlaws, which we were TOTALLY down to see, but alas, the show was rained out. Think of the memories that were not made!)
Our final stop before Annapolis was at Harrington Harbor South marina. THIS was such a nice place! Reasonable docking rates, beautiful scenery, a nature walk, two on-site restaurants, a pool, and walking distance to a quaint little town with more places to see and eat. We spent almost a week here. Fellow cruisers, we highly recommend it. I regret not taking any photos here, but I did take a couple from the boat on the trip up.


Next up – adventures in Annapolis!
This was fun to read! I grew up in MD. My father went to the Naval Academy in Annapolis, and then taught Naval History there before attending law school. My mom lives in Bowie, MD still. Enjoy your travels! So good that you are writing about it!
Thanks for reading, Kristen! We LOVED Annapolis. So boater friendly! Easy to walk or dinghy around. We wanted to tour the Naval Academy but it’s closed to visitors this year, of course. Happy Thanksgiving to you and your family!
It was such a great visit! Next time we’ll show y’all more of the lay of the land (cemeteries and wineries, basically) 😉
Hahahaha! We would enjoy BOTH! Next time, Lord willing, we won’t have to work around a pandemic. Much love to y’all, and hope you have a good Christmas!