As someone who's managed to survive three category 5 storms at anchor with minimal damage, I'll be the first person to say that the only safe/sane way to deal with a major storm is to be somewhere else when it's happening. Which has a lot to do with always having at least a sketchy plan to make tracks and, if the odds catch up and I wind up losing the boat, to buy a cheap boat elsewhere..
So what sort of boat and where would I look?
During "H" season I keep my eye on a variety of areas. The PNW, Hawaii, Maryland, and France are the places where I know the boat markets and am reasonably certain that I can sort out a boat with minimal bother. They are also places I happen to like and face it, after losing your boat and most of one's earthly possessions, why would I want to go to some red state armpit?
OK, maybe Louisiana because the food and a lot of good people can really make a big difference.
Anyway, about those boats...
I know for a fact that I can live quite comfortably on a 27-foot boat and there are always a lot of them for sale and it's no longer a popular size (too small for most and too big to trailer easily). It's the sweet spot in the affordable cruising boat size range.
These days, everyone considers a 27-foot boat too small but back in the 70/80/90's there were a lot more people doing serious cruising in them than there were in fifty-footers which people keep telling me is the bare minimum for voyaging.
The other day when I was looking at possible boats in France, I counted 39 Sangrias and 19 Fantasias for sale. They were mostly in the less than $5K price bracket which I could board after a flight to Paris and a train ride to get me there.
In Hawaii, there were a couple of Catalina 27s, and a CAL 27 under $5k that would do the trick. Admittedly, while Hawaii is even more expensive than the USVI, it's still a very good place to start out from. I might add that it's been years since I've had a proper spam musubi.
The PNW has a lot of boats for sale in the under $5K zone. As someone who no longer drives, the physical hassle of getting around to sort stuff out except by bike, becomes somewhat problematic.
I'm pretty sure that you could fly just about anywhere and find an affordably priced, 27-foot boat in good condition. They seem to be everywhere and most folk don't want them as they're too expensive to keep in a marina berth. Since marinas continue to gouge and be restrictive, there will be more and more on the market at low prices.
Cruising a 27-foot boat, on the other hand, makes a lot of sense as you can anchor just about anywhere you'd care to go. In the rare exception when you might have to spend a night in a marina, you can afford to since it's a helluva lot cheaper than the fifty footer that the cruising press keeps saying you need.
Lastly, for me at least, the 27 footer would be a temporary solution as I'd either build or buy something a kiss bigger once I'd got back on my feet after losing my boat and most all of my stuff. More than likely the boat I'd build would be a 30ish foot scow or a sharpie. But that's another story entirely...
