Yeah, but where do you find the right partner? Lemme guess, you found yours in college, or around that age. I have to go the opposite way: I'm recently divorc

Yeah, but where do you find the right partner? Lemme guess, you found yours in college, or around that age. I have to go the opposite way: I'm recently divorced (I violated your Rule 1), and currently living just a bit too far from a major metro area for women there to want to date me, and there's absolutely zero women around here I have any interest in. So my next move is to move into the metro area, as close to downtown as affordable (considering both rents/CoL and job availability/location), because if I want to have a social life at all, that's where I have to go to find available women in my age range who I would consider dateable. The other problem I see with your plan is that it sounds like you might not have any other friends or family (kinda hard to bring your friends with you on a 5-year sailing trip). I did that with my last wife: I didn't have any friends besides her, and moved around several times with her because of her career, and I think I got tired of her (it didn't help that we had some compatibility issues). Most common advice about marriage seems to include something about having friends outside the marriage. Living in a city gives you better access to that; living on a sailboat virtually guarantees you won't.