Jacksonville, Fl, Vero Beach, St Augustine, Stuart would seem like good places to look. Oriental, NC., Savannah, Ga. Annapolis, Md. Most of these places have some sort of transportation system. many marinas also have a courtesy car of some kind.
Good stuff Xort...lots to choose from - (didn't know Jacksonville was that hoppin - I've heard some negatives about it) ... had no idea about the courtesy car (neat stuff - I bet some are doing this zip car thing too since it's taken off)...
Clear Lake/Houston TX will fit a bill as well. Very nice marinas with pools, WiFi, near all. Occasional hurricane and insufferable heat and humidity are a downside.
There are plenty of cheap boats, it seems like the place absorbs old boats. Most marinas run auctions of abounded boats once or twice a year where you can get older 27-30 footer for a song.
Interesting - and I didn't know about auctions (it's so hard to know what auctions are legit and what are scams these days ...imagine calling a bunch of marinas would probably be the best bet)
Just make sure you can stand up in the boat.
Get a dehumidifier into boat to keep your bedsheets and laptop dry.
There are sometimes boats with keel damage that make them unsafe to sail any distance - these are perfect liveaboards, so ask the docks for those.
That's going to be a tough one for me Emagin - I'm 6'2 ... I don't think there are going to be ANY sailboats that work for me (no matter what the price) ..so I already figured I'd be knockin' my head about here and there ... the thing with the unsafe to sail variety is - I actually WANT to sail
(that's another reason I'm thinking gulf or east coast - I want to do the Carribean someday) ...thanks though...
Check out Baltimore. All of the inner harbor marinas meet your criteria for central location and transportation. Reasonable air transportation from BWI to most anywhere. Inner Harbor :: Baltimore.org
I lived aboard for close to 20 years at a marina in Solomons, MD which met most of if not all of your requirements. Plus it was a lot cheaper than Annapolis. I actually sailed more while living aboard than I do now. One other benefit of living aboard is the world cruisers that you get to know.
Baltimore/MD guys - I actually lived there for a few years! (that's what got me turned onto all this) ...another long story - but have to focus on North of MD and South of Virginia (in other words - can't do Mid-Atlantic) ...Baltimore is pretty ideal though in terms of the basics I listed... agreed though Lance - I want to sail - not JUST live aboard. To me this isn't just a form of housing - but it's killing 2 birds with one stone - my love of anything "marine" and also - a nice way of NOT having to deal with being tied down to one location for a year or more.
Hey thanks to all ...lotsa' great stuff here....