Few possessions, I bought a 31' sloop really cheap and took off cruising in thailand and fix it as I go, instead of gazing at the internet and dreaming about 40' bennys!
Anyhow, "love the one your with"?
Wise words and the way to go.
In my case boat size is not the factor, but jobs and days off are.
I have singlehanded prevoius 44' as well as present 33', location of dock
and traffic is more of a factor than the size.
(Busy Fort Lauderdale
with bridge openings and channels and traffic will slow me down more on a 33' than wide open anchorage in, the Bahamas
on a 66'.)
is usually a big factor also as Mr. Surfmachine mentioned:
Go poor, go now and go when it feels good.
A fancy air-conditioned gin-palace named Hylas
won't give adventure but will rather relive boredom...