Within limits, the ease of handling is more a product of weight of the boat rather than its length. In a general sense, all other things being roughly equal, a 22 footer will be a little heavier and therefore a little harder to handle than a 17 footer, but it will also be a little more seaworthy. In the 1960's there were a lot of small 'overnighters' built. Overnighters usually had a double berth (or cockpit seats designed to serve as berths with a boom tent), a place for a head that often doubled as a place for a small stove, an icebox and in many cases a sink and small water tank.
They ranged from the 18 foot Alberg Typhoon, to the higher performance Oday Mariner (which was a weekender version of the Rhodes 19), on up to the 22 ' Sea Sprite (as pretty a little boat as you will ever see) to the 22' Pearson Electra (which was weekender version of the Pearson Ensign) to the Grampian Classic 22 (which was built right in Ontario. I owned one that I picked up for a couple grand and she was a very nice little boat.These were nicely engineered and offered good performance and ease of handling for its day.) Kenner built the pretty little 23 foot Kittiwake. And so right on up to boats like the 26 foot Pearson Commander, or the ocean capable 26 foot Folkboat for that matter.
These wholesome little boats dropped out of favor in the 1970's to be replaced by more specialized boats; dedicated race boats, dedicated cruising boats, cheap family cruisers, and trailer sailors. This, in many ways, was a shame because there is something nice about a daysailor that has just enough accommodations to spend the night anchored in some quiet little corner of nowhere. And yes you will typically anchor a boat like that in some protected cove, and no that is not a dumb question but it is one that a beginner might reasonably ask.
Good luck to you,
Last edited by Jeff_H; 06-12-2006 at 06:51 PM.