Tartan 27' owner
Join Date: Jan 2008
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Re: What's funner than a 17' Day Sailer
Tanzer 22 is a reasonable suggestion. Decent sailor that you could actually overnite on with one other person. There is one that races in our club's spinnaker division races (PHRF) and they do quite well against that fleet (fin keel version though, I think).
I had a Lightning 19' for a few years. Similar to a Flying Scot. Fairly large cockpit but it fills up fast as you add bodies making the sailing part more difficult. Fun to sail (nor reef points) and no reason for a motor as .5 knots of wind still made it move. I carried a few paddles for when the wind really died.
The other 19 footer I come up with is the Rhodes/Mariner 19' with centerboard. The smallest big boat you could ever own besides a Montgomery 17' or 15'. The Rhodes 19' had a cuddy cabin that you could sleep in (but was not comfortable) but it fits most of your criteria although most will be on the rather old side now.
If you have $17K to spend look at the Montgomery boats.
"The cure for anything is salt water~ sweat, tears, or the sea." ~Isak Denesen
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