To the Young Beginner w/ Stars in His Eyes
Tool,
How about some context, so we know what the hell we're responding to.
I recently fell into some money…
There's money, and there's money. What kind of money are you talking about? The advice will differ depending on where the decimal point is.
My life plan is to live in a very modest home in an area that is a great for sailing.
Is a "modest home" mean you're planning on buying a house, or renting? If you plan on extended time away, it makes a difference.
How realistic is it to sail around to the small islands in the Carribean?
Quite realistic for somone with 2 pounds of experience. It's a couple of years away from you, at best pace.
Is there a difference between yachts and sailboats?
A yacht is simply a privately owned vessel, as opposed to a vessel of commerce. It can be a sailboat or a motor yacht. Technically, a canoe is a yacht, though the term is typically reserved for a boat with living accommodations. I use it all the time to describe my 30' sloop (one mast, two triangular sails), because I'd like to see the word revived to its proper use, but people do tend to associate it with personal wealth.
What should I figure for an entry level boat?
This depends on what is considered "entry level." My advice: a 14–16ft. used trailerable sailboat you can pull behind a sedan and launch single-handed at the ramp. The advantage of a boat this size are many:
1. economic: small used boats are cheap, and easy to sell again once it's served its purpose
2. logistic (storage is easier in driveway, back yard, or RV storage yard)
3. a dingy (uses a sliding centerboard instead of a ballasted keel) is very responsive to input from its operator (nimble), and will train you in the basics of boat handling very quickly.
Am I being realistic? I just want to start a new life with less stress and more living. Sailing has sang [sic] to me like a siren for years.
You have zero experience, so by definition, you're conception of sailing is romantic instead of realistic. Experience will replace those glossy magazine covers in your mind. But sailing brings its own stresses; many will argue they are preferable to alternative stresses.
Read a good book about "Learning to Sail" that you will buy from Borders or Barnes & Noble. Read it from cover to cover, then go back to the front page and begin to study it. Buy a used dingy in good condition. Sit in the boat and read the book again. When you feel ready, take it out onto sheltered waters in mild weather. Plan on making many mistakes.
After the first season shift your reading to learning about
cruising. Continue to sail the hell out of the dingy through a second season.
Once you outgrow the dingy, you will purchase your first keelboat (has a permanently-attached, weighted keel, either fixed in place or which swings up or down to facilitate launching/recovering with a trailer).
Here, opinion will diverge: some will say a 22-24ft. weekender (has a cabin with sitting headroom, a couple of bunks, maybe a sink & porta-pottie, and an electrical system for lights/radio) is the best next step; others will advise skipping this boat and purchasing a small coastal cruiser of 26–30ft. and 4/5 tons of displacement. Since you're young, and have plenty of time, I think the weekender is a fine learning platform for a couple of more seasons which also allows you to accomplish some micro-cruises to local destinations on a self-sufficient basis: you can practice basic cruising skills on a small scale like provisioning, cooking, planning routes, anchoring, or arriving at a destination and picking up a mooring ball, multi-day weather considerations, use of marine radio, etc. This can be a very fun and fulfilling time for a young intrepid sailor. Maintenance costs are still rather low, and mistakes aren't insanely expensive yet.
Of course, classes are of great value, and I recommend them. You can be reading, taking a class, and practicing in your dinghy all at the same time, and it's great. It all depends on your temperment: many of us are self-taught.