I sail on LI Sound, and went thru the same calculations you are going thru. Family of four, expected mostly daysailing. When all was said and done, I had three main criteria:
1. Big cockpit
2. Head behind a door
3. Less than $10,000
What I found in my search and experience for each:
1. There is no such thing as really big cockpit on boats less than 30 feet long, with a couple of notable exceptions. Most boats are trying to strike a compromise, so if they make the cockpit too big, it takes away from the cabin size, and vice versa. The best I found I could do was to get a cockpit big enough to seat four comfortably, and six in a pinch. Notable exception: the Colgate 26. You can fit eight adults in that thing with no problem. Honorable mention: the Oday Tempest. Perhaps the best looking 23 foot boat I have ever seen. Sweet, traditional lines, very large cockpit, but like the Colgate 26, there is almost no cabin to speak of. Like camping in a very small tent.
2. Head behind a real door? We had a Catalina 22 for a summer, and the Admiral and our friends found it awkward to have to button up the companionway hatchboards every time someone wanted to use the head. Most boats less than 27 feet have the head screened by a bulkhead or behind a curtain under the v berth. The only boats less than 27 feet that I have seen with the head behind an actual door: The Oday 23 and 25, and the Rhodes 22.
3. You can get a nice boat these days for $10,000.
I wound up choosing between an Oday 23 and a Catalina 25. I went with the Oday 23 because it met all three of my must haves, and I liked it better in some other respects than the Catalina. I like the keel/centerboard set up on the Oday better than the Catalina swing keel. I also like the lower fees and maintenance costs of a smaller boat. The one thing I liked better about the Catalina (its "cruisability") has turned out to be a non-issue. No one besides me in my family is really interested in cruising. My wife and daughter love daysailing, but have little interest in spending all day and night on a little boat. My son thinks the whole thing is a waste of time. The smaller boat is perfect for the one or two overnights a year we do, and the weekend daysails as well as my after work quickies. Let us know what you come up with.
Last edited by mstern; 05-04-2009 at 04:58 PM.