It would help if you listed your criteria.
For me personally, the criteria for my first boat were simple: Catalina 22 with a trailer, in sailable condition, for under $4K. I looked at 5 boats and bought the best one.
For the second boat the criteria expanded: must have berths for 5, standing headroom, inboard diesel, hot and cold pressure water, real marine head, wheel steering, roller furling, sailable condition, AC / DC electrical system, decent sailing performance. Priced under $20K.
I looked all over long island and southern ct for the right boat. I looked at Catalina 27 (too small), 30 (perfect), S2 9.2A, Islander 30, O'day 28, Irwin 30 and 31, Cal, Ericson, Newport and a few others. I really wanted a Catalina 30 or an S2 9.2A but could not afford the ones I liked. Then, while looking at an S2, I saw a Newport 28. It met all my needs and was affordable. It surveyed fine and I bought it and sailed it home. I spent about 6 months looking before I found the boat.
I sailed that boat for 3 years and it was great for daysails and one night trips, but too small for longer trips. So, the criteria for my next (and current) boat were:
33-36' LOA, with typical accommodations. And it had to include a Swim Platform. I wasn't seriously looking for a boat, but I got a big bonus check at work and I convinced my wife that buying another boat was a good idea. I found an O'day 35 on Yachtworld. The boat was in Newport RI, I am in Selden NY. I called the broker and we chatted about the boat. I told him, look, I want to buy the boat, but I'm not going to bother traveling to see it if it's junk. Long story short, the boat was nice and I bought it for a great price.
As it turns out, my criteria have changed again. My kids are getting older (17, 14, 10) and don't like spending days on the boat. With time being limited, I don't have time for many long trips anyway. So, having a boat with enough space for 5 to spend a week aboard isn't that important anymore. I would rather have a boat that sails much better. I'm not ready to sell my O'day and buy something else, but I can see that happening in a year or so.
Day To Remember, 1986 O'day 35 For Sale
Deep Blue C, 2002 C&C 110 For Sail
Mt. Sinai, NY
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