Recently, my good friend Doug, called me and told me he was
buying a sailboat. At first I thought it was a horrible idea. After all,
any boat is a money pit and furthermore, Doug has no clue how to sail.
But as he began to break it down, it all started to make sense and I
encouraged him to go for it. A month later, the guy is sailing three
times a week and loving his new passion. Here's how he did it:

1) Shop around on Craigslist for a deal

Doug went on Craigslist and found a working boat with everything one
needs to sail on San Francisco Bay, for $1200. It's not the sexiest
boat you've ever seen, but it floats, and nothing major was missing.

2) Rally the troops

1200 bucks is cheap for a sailboat, but still quite a bit of money to
flip on a new toy. Having a couple partners helps make it a lot cheaper
and will speed up the general maintenance needed to keep it in good
shape. It would also be a good idea to try to find someone who is a
decent sailor, but in Doug's case, he partnered with good friends who
were equally clueless--adding to the excitement of the first launch.

3) Safety first

Make sure the boat has enough life jackets. (although you would only
have about 6 minutes to live in San Francisco Bay, the coast Guard
hands out steep fines if you're short on the life jackets, so protect
your life and your wallet and make sure you are following all the
regulations.

4) Take the leap (with a friend)

The first launch must have been nerve-racking. One has to consider
tides, currents, and right-of-way rules on SF Bay--not to mention super
tankers that wouldn't even notice if they ran you over. Make sure you
take a friend or two to help out with the rigging.

5) Bring a pro

Although Doug chose to teach himself by just going out for the first
couple sails and using common sense, you'll learn a lot faster if you go
out with someone who knows what the hell they're doing. I went with him
and our other friend Cody, who is a professional sailor, and he was
dropping knowledge on us the whole time. There's a lot to learn in the
sport of sailing and it's a huge boost to the learning process if you
have someone giving your pointers.

All in all, I applaud Doug for his conviction to make this happen.
Sailing is one of the cooler skills to have and it's tough to beat
being out on the Bay for the sunset a couple times a week.