So Long, Chesapeake

We’ve been in the Chesapeake for over six weeks and it’s been great, but it’s time to bid it adieu. We’ve loved the sailing here, and we’ve loved Annapolis. We could probably spend many, many summers here and never explore all the rivers, anchorages and towns. But it’s not like each bay has its own dialect and delicacy. Actually, there are a few themes that are found repeatedly. You’ve got your quiet anchorages which will either be surrounded by farm fields or summer homes. Then you’ve got your quaint towns. Each has its own maritime museum, a couple restaurants and a marina or two. The sameness of it is part of why we didn’t do more side trips while stationed in Annapolis. But we will miss the Chesapeake.

Here’s a few things that struck us the most about the Chesapeake:

The sailing here is excellent. If you like the adrenaline that comes from suddenly realizing you’re in a race with a few boats on the same tack, you’re in luck. Here, there are always multiple boats on the same tack as you! They’ve all got to round the same buoys as you to work their way into or out of the same river you’re navigating. So, you get to continue your race through multiple tacks. It’s great fun!

Spartan at sail.

No one swims here. For such a big body of brackish water, I was surprised to find no one swimming in pretty much any part of the Chesapeake – even when it was 37 degrees here! In much of it, the water is quite turbid and unappealing. But there are a few other things that keep would-be bathers out of the water. Sea nettles, for example. These creatures look just like jellyfish and sting just like jellyfish. I don’t know why they are not jellyfish, but apparently, they are not. Also, there is some sort of flesh eating bacteria in the warmer waters of Chesapeake. And while it might not be rampant, it probably needs a better PR team to spin “flesh eating” into a positive.

You can’t get to a road from most anchorages. This seems weird to me. You’re in a quiet anchorage, with many roads nearby and you want to stretch your legs. But you can’t get there from here. In Canada, I just can’t imagine having to go too far before coming across a park, some crown land or some field that might be owned by someone who couldn’t care less about you using it as a way to get to a road. But here, every speck of the shore is privately owned, landscaped to the extreme and guarded zealously. There are signs everywhere discouraging you from attempting to come ashore. Your exercise routine will not include a cardio element.

A no trespassing sign.
Apparently, the word “posted” is the most important part of these signs found all over the Chesapeake. I don’t get it. Seems clear to me

I hope you like crabs. Go into any restaurant on the Chesapeake. Ask them what they are famous for. The answer will be crab cakes. Every single restaurant is famous for the exact same crab cake. It’s astounding. They’re never famous for their chowder. Never for steamed crab. Never for their crab tortellini, salad, sushi or soup. The star of the menu is always a crab cake, and it’s always with Old Bay seasoning.

A Chesapeake Crab Cake

The Chesapeake is forgiving. Although it has shoals, the Chesapeake is far more forgiving than Georgian Bay. Instead of rocks, the bottom is almost entirely mud. This makes grounding far less dangerous. Essentially, it’s as if the entire bay is lined with a great big fender.

Every port is 5 miles out of your way. After sailing down the main bay, you can usually count on 3-5 miles of additional travel before you can reach a port or anchorage. Large shoals guard each river. So while there are many, many rivers to choose from, most will require an hour or so to reach. This is particularly noteworthy when the days are short as each resting stop cuts into your daylit travel time.

Okay, that’s it for the Chesapeake. Tomorrow we will travel through the Dismal Swamp!


  1. Hello Thom and Kath,
    Great Blog entry! I feel I know more about the Chesapeak now. Formerly my knowledge of that area came from reading James Michener’s novel of the same name…it was one of my favorites. I will be interested to learn about the Dismal Swamp in your next posting. Happy and safe sailing.


  2. Hi Kath (and Thom, who I have not met, but am getting to know through this blog) I once bicycled around Chesapeake Bay, and loved it. It took about a week, of 30-50 miles per day.
    I am currently in Thailand, heading to Bhutan on Saturday and may resurrect my own blog now that yours has inspired me!


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