Ulladh - Please look at the PM that I sent you.
All - Thanks for your encouraging words and good advice.
We've been to Winters a couple of times as suggested here, and the Catalina 250 that Jim mentioned there is a real possibility. In fact, I think we were on that very boat at the same time Ulladh posted his message yesterday.
We were planning to head to the Annapolis/Mayo/Deale brokerages in the near future, but wanted to stay closer to home yesterday, so we limited ourselves to Havre de Grace and Georgetown.
Jim - "Based on your followup posts it sounds like daysailing with your family close to home pretty much sums up what you want to do." You are absolutely correct, it summarizes what I
want to do (but not necessarily "the boss"). The C250 is like a "daysailer on steroids." The cockpit is very roomy for a boat that size (almost as good as a daysailer), but still has enough of a cabin to change clothes, retreat from the sun, etc., especially with the pop-top cover installed. Just not enough room or facilities to spend more than one night in it. The issue here is that Lori (my wife) does not yet completely agree with the "sailing close to home" concept. She has a pretty strong bias against the Delaware River - one which some here clearly agree with, and some others don't. And the problem is that she has a funny way of being right.
I'm concerned that we may not use a boat enough to make it worth it unless we keep it very close. It's just the nature of our lives where we cannot go away for a whole day because of some little 1 hour commitment at noon on a Saturday (to cite a common example). That's enough to blow away any chance to travel down to the Chesapeake for the day, but we could easily get down to Essington to get a nice afternoon sail in. I also don't want to deal with the frustration of driving 3 hours round trip and find out there's lousy wind. It's a lot less frustrating if we've only driven a short way to find that out. She's not one for "hanging out on the boat" - I know from our experience on our prior boats that if we're not sailing she'll want to go home right away.
But I'm still open to keeping a boat on the Bay or its upper tributaries, especially if I cannot convince Lori otherwise. Havre de Grace, Port Deposit, Northeast, Georgetown, Bohemia are all just 60-75 minutes away if the traffic is good. Rock Hall, for all its benefits, is about 2 hours, which makes it a real hike. But if I were to keep it that far and take it out into the Chesapeake, I would probably go larger than 25 feet.
This whole process is part of the fun (I keep telling myself). Still open to more comments.