Boat Sharing Clubs

I came close to joining a club in Deale, MD, while living in Northern Virginia close to where you live. Their model was to sign up/pay for a particular boat, ranging from 27 to 38 feet. You get a fractional membership and are guaranteed at least one weekend day and some number of weekdays. Overnights, multiday access is available. I spoke to one member who said they generally were able to access the boat "enough". Sailing season is early April to late October. They do the maintenance, fuel, dockage, etc.
I'm also aware of another club program somewhere else on the northern Chesapeake, somewhere around Annapolis I think.

IMO its a great way to find a boat or at least a size range you're comfortable and "shop" for a future boat.

chrisknowles said:

The opportunity to learn boat maintenance is huge! Other than working on your own boat, where else can you get that kind of experience?

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I can't tell you how many YouTube videos I watched to learn how to do things during my year long refit.
Don Casey's Complete Illustrated Sailboat Maintenance Manual is a great reference that covers a LOT of ground, starting with inspecting an old boat, then fixing and maintaining it.