Don't give up too quickly on finding an affordable sloop, by far the biggest problem has been... well size lol Most folks around here would be interested in a daysailer or a dock-hugging yacht, one is obv too small and the other is just silly.
Odds are you know this already - but I'll go ahead and rant in case others are on a similar quest
Once yer willing to cross the Mason-Dixon line in the quest for a boat everything changes. Late 70s & early 80s 30ish foot fiberglass sloops - Rangers, Catlainas and others of good name can be had for $5000 - $10,000 and they're usually overbuilt and in fine shape. All the value is in the sails and rigging, many of these boats rarely if ever left the stands let alone the harbor, so if yer careful ya can have a fine boat that just needs topside/hull paint.
There was a
huge but somewhat brief surge in sailing craft purchases during that time period and the market is still flooded. Add to that how overbuilt most fiberglass boats were then and how little your "average" american is interested in anything that doesn't have a screaming V8, cap it off with how fascinated we all are with "new & shiny" and credit debt... Well, ya get my drift. These poor boats are unloved and just waiting for a captain.
Few of these make ebay however - gotta break out the phone and ask about "back lot specials"
A "surprise" expense can be the kicker motor. Outboards are usually trashed and are ungodly expensive to buy new - I'd seek a nice lil diesel inboard. They're far easier to fix, get insane fuel efficiency and are quiet for prolonged running. Very important as you'd have the mast(s) unstepped for most canalways.
Though I'm a woodworker, that's another game entirely. I may be willing to adopt a wooden boat but I dunno if I'd recommend it... it's simply not a level of commitment most would want.
The story of your uncle's cat and the young couple who sailed it off reminds me of so many I met while cruising! I traveled for awhile with a young Canadian couple who were on a 30' ketch with two kids, two dogs and one very confused cat. We'd raft from time to time (tie off alongside one another) so we could have dinner and party on
my lil deck - cause there was more room lol
They didn't have much in the way of experience but they sure as heck made up for it in heart!
However - if you're planning on sticking to the inside mostly than a sailing craft may not be the best choice. Though they're my preferred boat for many reasons it is a bit awkward to deal with a 30'+ pole stickin' up out of yer house heh. Trawlers seem to be the vessel of choice for many retired ICW loopers, unfortunately they're not only expensive - I know little about them. Worth lookin' into though.
Well, I got my rant on for the day heh - hope I didn't presume. I'd love to recommend one of the best and most entertaining books I've ever read on the subject if yer interested, it's a touch dated but is still w/o a doubt worth every page! It was one of the biggest contributing factors in me dropping everythin' and just sailin' off for gawd knows where.
Cruising in Seraffyn by Lin & Larry Pardey:
Cruising in Seraffyn
BTW, it was 4' of water that was breaking
over my decks, not nice gentle 4' swells - tell yer friend not to laugh, you'd be fine with nice lil 4 footers lol
.
