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I'll add that if you plan to race, your focus should be on the Annapolis area unless you want to be hours away from your boat. There doesn't seem to be much racing actvity (Keel boat) around Deale or Solomon's or anywhere between Annapolis and Deltaville. Besides Annapolis, Deltaville, VA and Hampton, VA seem to be were there are active keelboat racing fleets on the Chesapeake. If you're a crusier, Solomons or Deale will suit you fine and might be a tad less expensive than Naptown but not much. Deal is right on the Bay, but Solomons is a couple of miles up the Patuxet from the Bay. Herrington Harbor in Deale will likely be among the nicest marinas you'll find anywhere and since you're used to SF prices it might even seem reasonable. There is an advantage to being on a river off the bay as they often can be a more sheltered place to sail when the Bay gets ugly.

As far as slip availablity, getting straight into your first choice marina might be something of a problem but you can almost certainly find somewhere to keep the boat while you wait. I think your timing might be good as some folks are having to give up their boats in the current economy.

Finally, as others have said, a 6' draft will limit what creeks you can enter, but much of the Bay itself is 25-35 feet and double that in places so the idea that the bay is not sailable is wholly unfounded. There are many anchorages that carry 15' or so of water close to shore so you'd have no problem there, though I assure you some channels will have you sweating a 6' draft. Still, I recently did a race from Annapolis to Hampton, VA (about 120 miles) on a boat with close to 6' draft so you'll have plenty of room to sail. Also, since the bottom of the Bay is mud, you generally don't wreck anything when you do manage to find bottom, which you inevitably will. Tow Boat US unlimited towing is a good investment. Welcome to the East Coast, I think you and your wife will quickly come to enjoy the sailing here.
 
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