Look at a
Pearson 365 cutter or
sloop. Lots of room, some nice design features for actually
living aboard, and
shallow draft. Not great sailors but adequate and you're cruising anyway.
A good windlass is priceless,
canvas awnings to cover the
deck do away with the need for
air conditioning. Being at
anchor keeps air flowing through the boat and cuts way down on expenses. If you need A/C to
cruise you aren't cruising. You shouldn't need a
watermaker if you rig the
canvas to catch water. Some areas like
Baja, CA and other desert locations do need watermakers. A ham
radio is way cheaper than
Marine SSB and the knowledge gained getting the
license is very beneficial. A couple of
solar panels and/or
wind generator should supply all the power you need.
Refrigeration is a pain in the butt to keep running and an energy hog. You not only need to have the tools and expertise to maintain
refrigeration but the generating power to keep it running. Try eating
food at room temp. Really amazing how much better it tastes. In any case, food will keep a couple of days without refrigeration and mayonaisse doesn't need refrigeration at all. Do get a
windvane. Being a slave to the
helm is PITA. Autopilots are nice but electrickery is just a failure waiting to happen.
With your job skills, bet you could leave and never come back. People with expertise in Restaurant/hotel management are in great demand anywhere there are tourists. Work permits may not be easy but you probably could hire out as a consultant to skirt the labor laws.
We went when we were in our early 30's. The best times of our lives and something we've never regretted doing. Just wish we'd stayed out longer. We knew a number of couples on very small boats with small children. Having the parents around 24/7 seemed to do the kids a world of good. It will be a challenge, howver, as that mobile age between 1 and 2 without reason is interesting.
Aloha
Peter O.