Re: Chartering in the Caribbean or Europe?
So, just to be sure we understand, you are thinking of starting a charter business in a foreign country and running it yourself, without hiring nationals or legal residents of that country to do the work? Did you have a particular prospective host country in mind?
Each country makes its own rules, and many are interested in protecting jobs as well as receiving income from the business and enforcing safety and licensing requirements. In addition, you will need to meet the requirements of whichever insurance company might be interested in covering your business.
The basic issues are
business permitting for a foreign-owned business
professional licensure (captain's license)
boat inspection/licensure, safety equipment and requirements
permit to work in a country as a foreigner
tax regulations, banking, insurance, hurricane preparation/contingency planning, advertising/marketing, importation of parts
distinguishing your operation from well-established, experienced charter captains and companies -- cuisine, service, equipment, customizing trips for special interest groups, etc.
To be sure, there are probably some gray or black-market charter operations ... but the penalty for getting caught could be very steep... especially if your boat is your home.
Putting a boat in charter with an established charter operation is easy by comparison, assuming your boat is a model and vintage/condition of interest to charter companies.