When I address groups talking about living on a boat...a common question is how would I recommend people get started, to see if this lifestyle is for them.
Maybe a sailing school, although not on a small boat... you will be living on a big boat so learn to sail on a bigger boat. I would avoid sailboat racing of any kind...cruising is toally different.
Assuming you know very little or nothing about life on the water and if you live near the ocean... I would start hanging around the docks and marinas, and if you have friends that are boat owners... ask them to take you sailing one day.
If you are like me, you like to do read up on things. I would suggest reading books and magazines about cruising...Cruising World is my favorite sailing magazine...
Now my kind a cruising, is in the Caribbean, I'm talking what Jimmy Buffett sings about, and the life we lead for eight years... So disregard books on circumnavigation, and articles that refer to 4 to 5 week passages... That doesn't sound like a lot of fun to me... And living on a boat is meant to be fun and low stress.
Crewed chartering, is where you and 3 to 4 other couples, get on a 50 foot sailboat, that has a Capt. and someone to cook all your meals. This intro is especially important if your spouse may not be so enthusiastic about living on a sailboat.
Why the British Virgin Islands? The sailing is very easy, the sails are not very long, lots to do ashore... It is just plain fun too. Do this a couple of times until you are ready to handle the boat by yourself.
You may want to take a crewed charter from say St. Lucia to Grenada, like we did, to get a taste of what open water sailing is all about... I would do the BVI first however.
By this time, you should be familiar enough to know how to, get the sails up and down, basic boat handling underpower.
If you're concerned about anchoring, on my first bareboat charter, I would pay the nightly $15-$20 mooring fee, pick up a mooring ball, and sleep like a baby...you can learn how to anchor properly later...
We bareboated for a week three times... Then to really see if this lifestyle is for us... We rented a boat for three weeks in January 94... We bought our boat four months later... The rest is history.
If I had it to do all over again, I would have purchased the boat already in the Caribbean... Or wherever you want to cruise.
Why? First, no long passage making from the US to the Caribbean... You cannot predict weather reliably for more than 48 hours... We had some very bad weather in the middle of our eight day passage from Marsh Harbour, Bahamas to Jost Van Dyke in the British Virgin Islands...save yourself the agony, cruising is meant to be fun.
Second, the boat should be set up for cruising... You will be guessing about what to buy, relying on uninformed people, if you try to outfit boat in the US. Remember, it is easy and cheap to get work done in the islands... So there you have it, get with it, and enjoy living on a boat.