Sail Magazine put together a short list of trailerable cruisers. They mentioned Seaward Yachts that got their start right here in Stuart, Florida. And, you can't write about trailerable sailboats without mentioning Catalina. I thought I'd throw my own two cents worth in.
Have you ever sold a boat and regretted it later? Years ago we had a Mirage 5.5. They were classified as a pocket cruiser. It was perfect for us, and this area. Our son was about two when we had the Mirage. His favorite sailing position was swinging over the water attached to the jib halyard. We sold the Mirage during a time of financial need. I swear that one day, we'll get another.
We bought an O'Day 23 a few years back. We think it was cursed. We kept it for less than a year. We'd go down to the marina, find stuff that needed to be fixed, spend money and go home. We never took it out of the slip once. On the plus side, it was a very dry boat. Never saw a drop of water in the cabin..........until the buyer showed up. There were three inches of standing water on the floor.
C'est la vie.
Now, we're selling boat stuff. Maybe, one day, we'll sell enough to get that other Mirage 5.5.