I’m wondering why I’ve never read about such arrangements. Could there be insurance issues, or taxes issues ?
Insurance would be a clear cut problem. There would be none for any recreational boat. You need commercial insurance
if you accept money
. If something went wrong this fact would be exposed. This becomes a charter
for hire arrangement. Conducting a charter
business in another country is an issue too but probably off the radar
as far as effecting your actual trip. It's more of a paper problem for them than the insurance is.
Ok, lets assume you accept the risk of no insurance (they may not want to). You are 2 adults and 3 children
. The fact you all have experience sailing makes the idea even thinkable but it's still a handful of people. A circumnavigating
boat is going to be loaded up with supplies (that's what cruisers do that is common to all - lots of stuff!). Fitting you all with your stuff might be a problem.
There are charter organizations that are set up for having hosted charters on private boats. Personally, I think it's the best way to do a crewed charter. It means that they have hosted before and are actually good at it. I found a site for Caribbean
boats. There may be something like that for the areas you might choose too. Having a list might be better since I think many would have a problem with 3 children
It's easier to be a single
person and jump aboard a boat needing help for a passage