I didn't start sailing til my early 30's.  I started out in Tech dinghies, 
cat-rigged 12 footers.  Dinghies are a great way to learn.  Things happen fast 
in a dinghy.  And since you're the ballast, you really learn to balance the 
boat.  But they require a certain level of fitness and athleticism - 
particularly when you flip them and you have to right them in the water and 
climb back in.  I then moved to 14 foot FJ's, a little more performance 
oriented but basically more of the same.  Then to a J24, which is a completely 
different experience: you're in a cockpit, you have a foredeck, etc.  Honestly, 
if I hadn't graduated to the J24, I might have stopped sailing.  Little bit of 
time in an Etchells 22 around that time as well.  From there I knew I didn't 
want to race so I moved into more cruising-oriented lessons.  Boats were a 22 
foot Soling, then a Pearson 26, an Albin 28, a J29, a Pearson 31, a Pearson 303 
and a Cal 33.  So I've taken starter lessons in both a 12 footer and a 22 
footer.  For an adult, I think you're much better off starting in a 22 foot 
keelboat than a 12 foot dinghy.

My first and only boat has been the C&C 25 Mk1.  I initially looked at 
everything made in any kind of quantity between 21 feet and 28 feet.  I settled 
on the 24-26 foot size.  I wanted something you could overnight in, without the 
complexity of a diesel.  I continued to look hard at everything made in any 
kind of quantity in that size range.  I loved boat donation auctions - a chance 
to see a lot of boats at once without an owner or a broker breathing down your 
neck.  And the best way to identify a well-maintained boat is to see some poor 
ones.  After seeing my first C&C 25, I settled on that make / model.  Looked at 
a few examples, then bought one.  Inexpensive, good condition, my only regret 
being I didn't buy a boat with more upgrades.  I've since converted to jiffy 
reefing, put on a furler, a boom vang, a stern rail, an adjustable traveler, a 
backstay adjuster.  This stuff in total far exceeds what I paid for the boat.

If you sail in any kind of wind, a newbie sailor needs to know how to depower 
the boat and needs the gadgets on the boat that allow him to do so.  Newbie 
sailors tend to sail with friends and family who know nothing about sailing and 
won't be much help when things get exciting.  If the newbie sailor can't 
depower the boat from the cockpit with minimal assistance from "crew" (guests), 
they'll be terrorized and probably won't come back.

Mark 
C&C 25
Dartmouth, MA
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