My first real sailboat was a
Cape Dory 25D. I bought it the second I graduated from law
school, back in 1984, even before I was sure I had a job, because I had motivated myself all the way through by promising myself I would buy a sailboat as a reward. It was used, and I bought it for $28,000, with the owner
financing it for me, with no
money down (he had already bought a bigger sailboat and needed to unload it quick).
I had never sailed anything but Hobies, Sunfish, and other small daysailors before. For three years, I took that
Cape Dory out every weekend and I explored every nook and cranny with three feet of
water in it (and some with less

) in the
Mississippi Sound, and the western
Florida panhandle.
It was such an easy boat to sail that I would usually sail it in and out of its slip (although it had a one cylinder
Yanmar that was absolutely reliable with a
diesel tank that had to filled up once a year) . It was forgiving and with a double reefed main and the
roller furler jib reefed a little bit, would sail in 30 knots of
wind without even being exciting. I put an
Autohelm on the tiller, and it made it a joy to take out
single handed. I spent a lot of days listening to Jimmy Buffett and just watching it sail from the
cabin top.
I had dreams of pitching it all and taking it around the world. I wish I had.
I
sold it when I was transferred to Dallas,
Texas and to this day, it is the one boat I wish I still had. I have a 42'
sloop now, but it is never as much fun as that Cape Dory was to take out.