Join Date: Mar 2006
Location: Kirkland, Washington
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I liked the O'Day Daysailor that my father had before he got his "Big Boat" for his circumnavigation. Reasonably fast, stable, and easy to set up. I liked the cuddy cabin forward. He and my brother cruised it for a week in the North Channel islands of Lake Huron for a week, and if worked for that (They camped ashore)
Flying Scot is a boat with a great reputation as well.
I don't know what kind of shape you are in, but it seems to me that if you intend to trailer sail the boat, you should make sure that you are comfortable rigging, especially stepping the mast before you decide on a boat.
If you're uncomfortable setting the boat up, you're unlikely to sail much. A larger boat would increase your sailing season.
I wonder if it is possible for you to find mast up dry storage for your boat, which, at least in Michigan, was much cheaper than a slip. This worked out real well for us, as it greatly reduced the hassle of setting up the boat.
To further confuse the issue, I wonder if you might be better off with a keel boat, like a Shark, or a swing keel boat, like a Catalina 22. You wouldn't want to trailer sail the Shark, and would wind up needing a slip for it, but it would greatly extend your sailing season, since the risk of capsize is extremely low.
You'd be in trouble relatively quickly in a cold water capsize, and would quite rightly limit your sailing to months when the water was reasonably warm in a smaller boat.
1987 CS 36 Merlin "Kyrie"
"They drove a dump truck full of money up to my house. I'm not made of stone!" -Krusty the Clown