What kind of boat is it? My family rented a long one once, the kind that you see cruising along (British) canals and honestly, as cute as it is, I felt super claustrophobic.
I've sailed in the past and I'm quite outdoorsy so cold and crampedness really doesn't bother me.
Doing it on a vacation vs living it every single day are two very very different things... I mean, I absolutely love camping and multi-day back country hiking. But I sure wouldn't want to live in the bush 24/7!