Get a +/- 30 foot boat that was well taken care of by the previous
owner and is set up for cruising. There are usually a couple of these
for sale in most harbors. Choose an area that is easy to cruise in and
has lots of nice anchorages and port towns, say, Chesapeake Bay, the
Carolinas or coastal New England. Don't make any big hops, just sail
from harbor to harbor during the day. Try to anchor out as much as
possible and use the dinghy. Stay in the harbor if the weather is bad,
in fact, just have fun and hang around in the harbors and wait till the
time is just right to sail on to the next. When you meet other sailors,
always take the opportunity to sail with them and see how they have
their boat set up.

Do this for at least 2 months before you buy a bigger boat. It may be
a little like camping at first, but you will learn a lot, quickly and
any beginner mistakes will be made with a low cost boat.

You can also learn a lot from sailing logs, he

http://cruisenews.net/voyagelogs.html

http://cruisenews.net/shipsatsea.html

henderob wrote:
For as long as I can remember, I've been planning on getting a boat and
taking off, cruising around for a few years. I've read a lot of books
on the subject but up to this point have focused mainly on getting the
$$ to actually be able to do this. I have very limited sailing
experience, consisting of crewing on a large yacht for a couple weeks
when I was younger.

I'm 25 now, and the goal has always been to leave before I was 30.
However, a strange thing happened in the past year - a project of mine
took off, and all the sudden I find myself in a position where I have
the money to go, now. I have somewhere around $200k in the bank. I
could buy a boat and leave, except that I have zero experience and
don't want to die.

So my question is: how do I get to the point where I can realistically
purchase my own boat and take off? I know about the offshore cruising
schools,etc,.. but would it make more sense to look around for a
(probably unpaid) crewing position? And if so, how should I go about
that? Just hang out on the docks at the right time of year?

Also, complicating matters, I will more than likely be bringing my
girlfriend along, who also has no experience sailing.

I would like to be in my own boat cruising within, say, one year. I'm
looking for any and all advice - what to read, what to do, etc etc. .

Thanks very much.
-Bobby