Your situation sounds very similar to mine (or, where I was two months ago.) I'm 45 and did a fair amount of sailing in college, plus a few week-long charters in my late 20's. But none since. After I got married and had a couple kids, owning a boat just didn't even seem to be in the realm of possibility.
Then in February, due to a couple events that I won't bore you with, I started looking at boats just for fun. I was astounded at what the market is like these days. I was seeing boats for under $10k that would have been in the high twenties in 1996, which was the last time I entertained the idea of buying a boat. I mentioned it to my wife, and to my great surprise she seemed receptive. So if it's not too late to make a long story short, I own a Cal 2-27. I too figure that most of my sailing will be me plus one or two others.
I have two specific ideas to consider:
- Buy a seaworthy but not beautiful boat in the 27-30 foot range for whatever price you can pay with little or no debt, with the understanding that you're on a two-year trial. Based on your estimated crew size, you won't have very many times when everyone wants to go at once. If two years go by and you're still sailing and still married (
), and a few of the kids are still interested, you can trade up for bigger and/or more beautiful. Or sell and get out if otherwise.
- Trial or no trial, a 27-30 footer might be a good compromise between how many you can
carry vs. how many you realistically will
carry on a typical trip.