I was looking at Craigslist the other day and there were a surprising number of boats available with a full range of prices and conditions. Not a bad place to start.
With a 20'er you'll be looking at boats with an outboard motor
(at least that is what I would want). You will want a reliable motor
so it could turn out to be the single
largest expense - discount or add as appropriate (you may want to check out your local marine
store for 5-20hp motor prices --- and weights). The dingy could be the second big expense. After that it will just be a matter of picking though the boats. Most 20's don't put a lot of strain on the rigging
. The lines might be old but they can be replaced fairly cheaply and easily. You'll want to have a look at the sails
for condtion but again, not a huge expense to replace or add --- you might even find someone with some used sails
. I suggest hank-on sails for a small boat
vice roller furling
...this will give you more sail options. There shouldn't be too many thru-hulls, if any, and that is a good thing - that is what will sink a small boat
. Basic wiring
for a depth sounder
, VHF radio
, and a single
12 volt battery
to power the GPS
, CD player and occasional interior
lights at night will be plenty. I wouldn't get too wrapped up about the paint/gelcoat - this is where you can put some elbow
grease in to clean it up and practice your skills. Boats ALWAYS need a buff and bottom - with a trailer
boat you might as well do it yourself rather than pay the past owner - IMO.
Keep it simple and you will sail more, and maintain less.
After you see 1/2 dozen boats or so, you will have a very good idea of what has been maintained and what hasn't, and what it is going to cost you.