I used to have a Morgan 35 for a number of years, and took the kids cruising for a week or 10 days at a time in the Maine islands. But that got too expensive, so I traded it in for a 26-footer with a swing keel that let me get into shallow water. But that got too expensive, so I sold it and abandoned the sailing cruises for picnics in a small powerboat. But that got too expensive . . . .
So it goes.
I’m not sure if I’d recommend the sail cruising life unless you’ve grown up with it. Emergencies happen very suddenly, sometimes—squalls, thunderstorms, reefs, fog, and so on—and you need to know what to do, sometimes without time to think about it.
Sounds like every fantastic stage suited your life, well done!!
I don’t recommend this 30’er gambit casually. It’s for a young man (as defined) who really wants a change, wants adventure, wants mobility, and isn’t afraid to get sweaty and dirty for a few months.
For him, it’s an amazing chance. If I get a few emails in coming years from new sailors, I’ll be gratified. And your description of your boating life also fills me with happiness at the idea of your joy.