The Chesapeake. Doesn’t the mention of it bring to mind sailing with the wind through your hair, watermen tending their crab pots, seagulls, beach grass and sunshine?
Our broadbrush plan had us cruising the Chesapeake in October, when the heat and humidity are gone and hurricane season is winding down. We ended up entering the Chesapeake on October 16, a little later than planned, due to spending time in other places on the way south, mostly due to weather.
We entered the Chesapeake via the C&D (Chesapeake & Delaware) Canal right where Maryland and Delaware come together at the north end of the bay. We left Delaware City, on one end of the canal, quite early in the morning and were through the canal and officially in the Chesapeake a couple of hours later.
And what was one of the first sights we saw? Seagulls flying close behind the boat in the sunshine. Just as imagined!

We anchored the first night in a quiet anchorage off the bay. There are lots and lots of spots to anchor throughout the Chesapeake, wherever a creek or river enter the bay. Where the bigger rivers enter the bay, there are towns, but there are opportunities to find an anchorage up river, if the water is deep enough.
This anchorage, Still Pond Anchorage, was where Still Pond Creek entered the bay. There were a few private docks and some very shallow water to get there. We have intel on where the anchorages are through apps we use: Navionics and Waterway Guide. There is a little symbol of an anchorage on the electronic chart and when you click through, there is more information including reviews of people who have stayed there.
This particular anchorage gave very specific information on where to hug the side of the waterway and when to turn left to get into water deep enough to not run aground. Many of the reviews are written by sailboaters who require several feet more draft than we do, so if a sailboat can get it, we certainly can. This anchorage was specifically recommeded to us by a local harbor host. He was right on the money.

When we turned off the main shipping channel into the side of the bay to get to the anchorage, we immediately ran into a maze of crab pots. We had to carefully make our way through the minefield, with two sets of eyes looking for the bouys.
We have found that anytime we are out of the main shipping channel, there are crab pots, so we stay in the channel, carefully hopping out when a ship comes by. In the Chesapeake, there is plenty of water depth outside the channel for a boat our size, it is just that the crab pots are everywhere.
After the night at anchor, we made our way over to Baltimore.
On the way in to Baltimore Harbor, you pass by Fort McHenry, where Francis Scott Key was inspired to write the Star Spangled Banner. It seems that there was a fort on almost every spit of land going into the various harbors.

We passed under some linemen working high on a power line, suspended from a HELICOPTER! We marvelled at the skill of both the helicopter pilot and the linemen.


The harbor host had recommended Anchorage Marina, so we took his advice. It was very nice, with a grocery store and a West Marine within walking distance. Baltimore Inner Harbor was a couple of miles away, so we took a Lyft and walked around there for a while. It was fun to see it.




The next day we travelled down the bay to Annapolis crossing under the Bay Bridge.
We took a mooring ball on the “Front Forty”, the 40 balls out in front of the Naval Academy, right next to what they call “Ego Alley”. Ego Alley is a short waterway in downtown Annapolis, where all the pedestrians in the square can look at the boats tied up there.

We arrived shortly after the boat show, so the alley was not open for boats to moor until later that night. It is quite spendy to stay there, although it is very convenient to everything in downtown Annapolis. And, our boat isn’t one that is generally held to be beautiful by boating standards, so we opted for the mooring field.
There is a water taxi that runs throughout the mooring fields, so we took it in to Annapolis on the two days we were there. “This is mooring ball 17 requesting a ride.” The water taxi pulls right up to the boat and you scramble over the side onto the taxi boat. From where we were, it ws $4 per person per ride.






On the second day, we took a guided tour of the Naval Academy. It was a very good tour and we are so glad we went.





After the tour we went to a highly rated deli restaurant for a lunch of their signature crab cakes. It was 1/2 pound crab cake, so quite large. And delicious. And we can say we’ve had a Maryland crab cake in Annapolis.
After we returned to the boat around 2:30, the waves and wakes were very rolly poly. We aren’t sure if it was the wind or passing boats, but the rocking did not stop the rest of the day and went on through much of the night. It wasn’t safe to walk around the boat without holding on tightly.
Friday, the day we left Annapolis, had originally been forecast for good winds for making our way further down the bay. As we got closer to Friday, the forecast was not quite as good, but early in the day still looked good. We knew we could not stand another day on the rocking and rolling mooring ball.
We were bound for Solomons Island, a five and a half hour cruise away. A local harbor host from Solomons had reached out to us about an opportunity to stay at the Solomon Islands Yacht Club for a reasonable price and we had made a reservation there.
As we started out early in the morning, we could see there was a small craft advisory slated for noon and beyond. We had some biggish waves starting out, but soon found a good speed and direction for minimizing them. When we had to leave the channel for a ship to pass, we discovered some calmer water closer to land and spent a couple hours making good time there. (Always keeping an eye out for crab pots.)
As it got to the last two hours of our trip, as we got closer to the mouth of the Potomoc and Pauxetant Rivers and as the tide turned against the prevailing wind, the waves got larger. We slowed down and Lance put all his head knowledge about driving in big waves into practice.
Our track of that day shows some zigging and zagging. That was to keep us at a favorable 45 degrees to the waves. We had some four footers, I’m sure. They count from the top of the wave to the bottom of the trough. The bell on our boat would CLANG when we had a particularly deep one trough go through. This was the first time we’ve been in waves that produced a clang.

When we went downstairs, we found lots of things on the floor. Our Brita pitcher was a goner, but that was about the only casualty.
Once we turned up the Pauxatent River toward Solomons Island and got behind a spit of land, it was immediately calmer and as we went upriver, the water was smooth and sparkly once again.
One reason we wanted to get out of Annapolis and down to Solomons Island is because there were big winds forecasted for the weekend. We were able to extend our time at the yacht club to wait out the winds. There were several other boats doing the same thing.
We were very grateful to be tied to a sturdy dock for the winds!







Inside the church.