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Old enough to know better
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Thought I'd just reply to my own thread in case it helps anyone digging through the archives in the future.

I did go ahead and buy an O'Day Daysailer towards the end of the 2014 season. I found it very well suited to what I was looking for. It was not at all too much boat for even a rusty sailor to singlehand, although I would not try to launch the spinnaker alone for sure. As far as suitability to the Hudson--the river's strong tides mean you can't really go out if it isn't blowing reasonably well, which meant I did a lot of sailing on pretty gusty days. I usually planned my sail based on returning home with the 5 knot current, or at least not having it on the nose, as fighting back against that even with kindly winds can be very time consuming. Haverstraw Bay is pretty large, but quite shallow, and the water can get very choppy when the wind and current combine. The boat wasn't too much boat to handle in even pretty strong wind, but with only one person aboard an essentially unballasted dinghy, I found even with a reef tied in and hiking straps, I was often unable to keep her as level as I'd like. I nonetheless had a great season sailing it alone. I had a small 3.5hp outboard to negotiate the mooring field, which was useable to get home if the wind totally died and the current wasn't actively against you.

I'll be selling her in the spring, as we now have a 6 month old and I realized that something with just enough of a cabin for Jr. to nap in will really change the way we as a family can relate to sailing... he made it out on the Daysailer towards the end of last season, but the boat is small enough that there really is no room for crew who isn't actively involved in the sailing... so we've stepped up to a 19' Mariner--essentially a Rhodes 19 with a little cabin built on her. Very excited for spring.

Thanks for the input.

Luke
Well good luck with the sale, and child! I am just across the river from you in Haverstraw for the winter, and not sure where I will end up this spring/summer. Will likely be in Viking yard for a while, then further up river or stay in Haverstraw depending on where I am working by then. I am at the other end of the child thing, as my youngest is graduating from high school this year.
 
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