You might look at a folding trimaran - Although not exactly an ideal cruiser
a Corsair F-31 is trailable and easily rigged. I think they also have a
smaller model. Quite seaworthy too and can go into very shallow bays! But
not exactly cheap.

If you want a monohull in the 26-30 ft range (about max for trailering, you
will need a FS SUV or truck for towing. You will need something with drop
keel, keel-centerboard or maybe just shoal draft. They do exist - do a
search on the Yachtworld or Soundings sites.

There of course many power boats that might do the job, but.........

Good Luck

"tt" wrote in message
oups.com...
I was forced to give up my live aboard lifestyle when hurricanes and
condominiums destroyed or replaced affordable Marinas. I moved away
from central Florida and live about 1 hour from the coast in South
Carolina. I never imagined how much I would miss the boaters
lifestyle. I don't think I will ever be able to live aboard again but
would like to spend extended periods on the water, mostly Carribien
and Intercoastal cruising. My question , Is there a trailerable( I
never want to be at the mercy of a marina again) sailboat that is
suited to long distance cruising and extended periods of living? By
the way I am retired and not a rich man.