CHAPTER 1

Whose Idea Was This Anyway?

So what drives a person to even consider buying and living on a boat? Two words:midlife crisis.

That's right. Muscle cars and dating high schoolers are so passé. If you'rereally serious about regaining your youth, you buy a boat! I kid, sort of.Boaters are more likely to be middle-aged though (which means between 40 and 90years old these days). By then they've had time to accumulate enough money tobuy a boat, maintain it, and eat and do fun things too—in that order.Whatever your age, you'll want to ensure that you have the strength and energyto do manual yachty things for whatever length of time you want to sail.

Potential boaters might be on sabbatical or enjoying early retirement. "Kids"(under 40) might want to get their wanderlust out of the way before they settledown and start a family. Seniors who have been sailing only on weekends orvacations can finally take off for good. You may even run across a few blokeswho live and breathe the sea and have figured out how to make a living being onthe water. Lest you think that boating is just for couples or men, you'd besurprised how many families you'll see out there with infants to teenagers and,yes, a few hardy solo women ply the seas as well. Folks of all sorts decide thatthey've done what they were supposed to do—they had jobs, earnedpensions/401(k)s/retirement savings, and raised their kids, and so can now runfree. Dogs? Cats? Yep, they're out there too. There's a mishmash of people inthe sailing world, which is what makes it so much fun.

Nothing personifies the idea of freedom more than boating. Just about everyonewe've ever talked to about our experiences says the same thing, "Boy, I wish Icould do that." I don't think they really mean boating—it ain't quite whatthey think it is—but they like the idea of chucking it all and beginninganew. Do any of these people sound like you?

Michael and I were of the midlife crisis variety. We had just turned 40, didn'thave kids, and didn't care about keeping up with the Joneses. We both had great,decent-paying jobs (mine as a technical writer, Michael's as a resort chiefengineer); a small house in a town we loved for many years; and favoriterestaurants, hikes, and TV shows. But we felt dragged down by the monotony oflife. We were sooooo bored! Okay, I was bored. My husband was just fine, but Ineeded something else and didn't have too hard a time convincing Michael that hedid too.

So how did we decide that sailing was the answer?

Well, first and foremost, I was still on my quest for perpetually warm weather.I'd spent my whole life seeking temperatures that only a lizard could love. Ihad grown up in New York City and never liked the cold—ever. College inPennsylvania—brrrr! I dreamt of California, Southern California,and when I finally had the money to do so, I moved there. But 65degrees—not warm enough! Next came Arizona, with summer temps of 110degrees. Perfect—until winter brought frost and sometimes snow. Michaeland I (by then a couple) gave it a valiant attempt, staying there 16 years(Arizona had a lot to like), but eventually the extreme temperatures got to us(Michael's a wimp too). Next?

The Caribbean seemed an obvious place to consider, but how to choose whichisland without seeing several? Even more baffling, how to do that with just twoweeks' vacation? While reading several guides about the Caribbean, I couldn'thelp noticing all those pictures of sailboats anchored in various harbors. Hmm... It dawned on me that buying a boat might be the way to go. We'd be able tosee all the Caribbean islands (and more of the world if we wanted to) withoutworrying about how to get there and where to stay. Even better, we could bringalong our 16-year-old cat, Shaka, while we looked.

I...