Re the route, I would second the suggestions above and offer an option that you might consider if short handed. The Buzzards Bay to Cape May leg is over 200 miles, if memory serves, and in a 30' boat that will take at least two days, maybe three. The alternative would be to use LI Sound to work your way west, passing down the East River (careful of currents) and lay up somewhere like Sandy Hook to wait for a nice 24-36 hour window to make a jump to Cape May of about 110-120nm. (Sailing through NYC is an adventure in itself). After Cape May the route others have suggested (Delaware Bay, C&D Canal, Chesapeake to the ICW in Norfolk) is a good one and it's all day sailing with plenty of places to put in at night to anchor.
You'll want to read up on the trip across the Gulf Stream from Florida because it can be challenging in a small boat. Talk to sailors you'll find in Florida anchorages. I'm sure they will have lots of good info and advice.
Re the age thing.... when considering a trip like this, it's important to be fit regardless of your age (upper body strength is particularily important) , but you've got plenty of time to work on that over the summer. Once you're under way, take it easy at first, and don't try to push too hard, too far each day, especially when you're singlehanding or short handed. (Eight hours is a long day single handing and 12 hrs with two is as well. You know the speed of your boat -- so you can calculate the likely day's run). As someone said above, don't be driven by a fixed schedule.
Take a cell phone, call your wife every night and after a while, she'll relax too.
I wouldn't think you'd need a radar. If the vis. drops, stay put until it gets better.
I would recommend that you have a mechanic you trust give your engine a good going over. You're going to need it. Take lots of spares and as many consumables as you can conveniently stow.
Re the timing of the departure -- the end of the hurricane season makes it somewhat tricky. You're trading off the possibiltiy of having nicer / warmer weather during the northern legs of the route with the risk of a late season hurricane / TS coming up the coast. Don't wait too late -- it can get cold on the Chesapeake in late Oct and Nov, but moving to the Chesapeake in late September and hanging around there for a month or so before moving further south should be considered. There are plenty of good hurricane holes in the Chesapeake, especially for a boat the size of yours. Buy a good chart kit and research the places you might go to hide if a storm came along. The money you've saved on a radar might be well invested in extra ground tackle (e.g. an up-sized Fortress anchor) in the event you did have to hide out for a while well up a Chesapeake creek. There are others who post here who have much better knowledge of the Chesapeake Bay may have suggestions / comments on this strategy.
Good luck and congrats on your decision to start "livin' the dream".
PS. If you're not already a member, join the SSCA (Seven Seas Crusising Association) and stop by their Annapolis "gam" (coincident with the Annapolis Boat Show). You'll meet some nice people, many of whom are probably headed down the path you're following south.
Last edited by billyruffn; 02-21-2008 at 06:32 PM.