1) Who should we call for boat insurance. route is down the ICW to Flordia/Bahamas this fall and winter.
BoatUS for the US portion. Get the tow package just in case. If you have problems, they will probably be in the begining.
2) Health care
insurance providers. I know my dad is a retired doctor but just in case.
We have HSA's (a few grand on cards with MasterCard/Visa logos), plus some high deductable-catasrophy plans. Honestly I think your dad would have a better idea on how to structure something like that.
3) Is it possible to work for several weeks to months at one place and then take off again. I plan on using my marine electrician skills for work while cruising. I am concerned about my girlfriend and father finding work.
However, I don't think my father wants to do medicine anymore thanks to the government.
Yes, although finding something can be a little hit or miss. If you have any connections in advance, I'd do that. You might also want to consdier posting
on craigslist on the town you're headed to next with your resume (or a "looking for work" thing), just to maybe get some leads trickling in.
You guys will probably need to be flexible, depending on how much you need to work. If you guys need cash, regardless of whether your dad wants to work in medicine (as an example), he might need to do it anyway. Sweeping up a boat yard, while not glamorous, is a couple hundred a week that you might not otherwise have.
If you're talking about getting jobs in the exact sector you want to work in, that's a lot harder depending upon sector.
4) Any important advice to give.
It's a lot of work, but that kind of work that you'll be happy to do and is incredibly rewarding. Compare it against a mindless office job where it's not a lot of work, but it's completely unsatisfying and you want to jump out of a window every day.
You're embarking on an adventure that so few people rarely get a chance to experience. Enjoy it, learn from it, and come back and let other sailors gain from your experience and share your insights.
May the wind
be on your beam and the seas on your quarter.