I had a 23' Bangor Punta O'Day sloop.
The two happiest days were the day I bought it and the day I sold it
(I know that's an old one).
After a number of years, I basically got tired of it. Or tired of sailing it within a day's reach from here.
It was barely trailerable. Towing it and launching it in different waters was a PITA and I discovered it was better to rent a bare boat.
I had a lot of fun with it when I had it, though. It wasn't a fishing boat. The ideal day was with one hand on the tiller, a cold drink in the other hand, some wind in the sails, and half-naked women sunning themselves on the deck.
Notes ♫