Re: Rookie on a San Juan 21
My first boat was a San Juan 21. Although I didn't have the small boat experience that you had in Wisconsin. The SJ 21 is a nice boat although it is pretty tender for a beginer. It's not unsafe it can just be a little unnerving for a beginer. I am not sure how much you will enjoy staying on it for 2-3 week stretches. It's interior is small for a 21 footer. It makes other boats that are in the 20-22 foot range seem almost cavernous. The headroom is low and the centerboard trunk has a way of always being in the way every time you move around.
On the plus side the boat is a great light air performer and has fine sailing characteristics. I didn't really enjoy the boat while I owned it but that was mostly because I really didn't know what I was doing. Looking back the positives of the boat far outweigh the negetives.
always in decline-never hitting bottom