I sailed Lake Huron and Lake Ontario on my own boat back in the 90’s. Raced a little too on a C&C 34. Fond memories of that.
I’ve been chartering with this particular outfit for the past 5 years now. A week out, all in was $3500 for a bare boat charter (no skipper). You supply the food and drinks.
I suppose if you view it as a floating hotel efficiency suite, which it is, it might seem a little steep. But it’s also your daily entertainment, your transportation, and your own private island with 360 water views.
As with most things, size matters. A smaller boat will cost less. Something in the 35 foot range will be closer to $2500 for the same period of time. There are places that are less expensive but their fleet is generally older and a little more worse for wear. I prefer newer and more luxuriously appointed boats. The views, however, are the same no matter what kind of boat you choose.
With the exception of our trailer sailer (a Hunter 23) all of our boats were between 30-37’ and apart from the Fisher motorsailer, I’d have been able to single-hand any of them. I wouldn’t want to, especially close in where my husband is much better at handling a boat than I am.
He always wanted a bigger boat, but I felt like mid-30s was a perfect size. Someday we may charter again, and I expect he’ll want to go big, so who knows? I do know we can probably find any size we want in Annapolis, but not so much down here in Solomons.
I’ve never been fortunate enough to sail upon it but I did read Michener’s book, Chesapeake, years ago. What a rich and fascinating history. I’m envious of anyone that gets to immerse themselves in that setting.
There is a great book called the Gunkholer’s guide to the Chesapeake. It’s helpful guide to the various rivers, nooks and cranies of the Chesapeake for boaters (sail and power). Because the bay is filled with so many shoals, you can only get to some of these spots with a very shallow draft boat - not much more than 1- 2 feet in some cases. That pretty much limits you to a dinghy. But you can get close enough to many places with a boat that draws up to 6 feet.
On one of these shoals on the Chester river (across the mouth of the Corsica river) is a place called Russian Point. It’s called that because as far back as the days before the fall of the USSR, the house (“datcha”) was owned by the Russian government and was one of the perks of being a Russian diplomat or ambassador. The author of the Gunkholer’s guide witnessed an account as follows (paraphrased):
“We watched as two men walked down the lawn from the house. One stripped naked and waded into the water. The other remained clothed until the one in the water, we assume the senior of the two, began to berrate the other until he too reluctantly undressed and cautiously waded in. We can only assume this was some sort of Russian test of manhood because the waters were filled with stinging sea nettles. Every time we venture past this spot, we make sure to observe shore with our binoculars for further displays of Russian bravado.”