If I wanted to charter my British registered boat out, me on board as skipper, in Greece what sort of Greek bureaucracy would I have to deal with? Anyone got an idea on where to even start looking for help?
The law has been changed and in principle you can charter your boat in Greece under British flag. It must have a Greek charter licence, and although I do not have direct experience of getting this, the consensus seems to be that it is much easier to operate through a Greek company and have the boat flagged as Greek. There are many British owned charter boats that operate in this way in Greece.
The procedure is almost exactly the same whether Greek flag or other EU flag. Either way, the commercial activity has to be conducted through a Greek tax registered 'body', whether person or company.
Don't even think of chartering without a licence (skippered or bare) - it's a quick way to lose the boat.