@goatsarah @whalecoiner @zoe our first boat was an open 13 foot daysailer with a daggerboard and badly worm out sails, that we didn't know enough to know we're past usefulness. We had a great sail onto Irondequoit Bay and then had to paddle back because she couldn't tack even a little bit upwind. Another time we tried to go out onto Lake Ontario and nearly capsized in the channel out if the bay because we weren't prepared for the sudden change in wind speed - I had to stand up and yank the sail down the mast while Mike leaned out to counterbalance so we didn't flip over.
We had a blast with that $300 boat, and I'm so glad we made our mistakes on a craft small enough to paddle, tow by hand, and probably even tow while swimming if there'd been no other way to get moving. I think I'm done living on boats (not that boat, a boat with an inside) but it'd be fun to have something with a sail that fits on a jet ski trailer again.