The Life and Times of Captain Charlie

monaco five flag theory

He arrived at the Monaco boat show in style on a 95′ Burger yacht, coming fresh off of a charter in southern Italy. The owner wanted to sell the ship that Charlie had called his home for the past 4 years. He’d been all over, from Australia to Fort Lauderdale, to Monaco and back east to the Cayman Islands.

Captain Charlie got a kick out of working with wealthy yacht owners, most of them couldn’t afford the boats in the first place, and the half that could afford them rarely ever went out on them. Charlie figured out how to see the world, enjoy the ride and get paid for it, and the fact that he had to drive the boat didn’t  matter to him – he would have done it for free had he not been offered a cool 6-figure salary.

Charlie was quite intelligent, despite working what many considered a “blue collar” job at the time. His home country, where he was still a citizen, didn’t tax worldwide income, and he only worked outside of his home country in international waters. His bank accounts were set up in the Isle of Man, a country with superb financial institutions that are known for working with yacht owners and crew.

His salary was basically just money in the bank. As a captain, all of his provisions (food, drinks, etc) were supplied by the ship’s owner, along with his health insurance and any costs that the yacht might endure for repairs and damages.

The Captain was the first person to introduce me to the five flag theory, something he had been living since he got his first gig at age 20.

The way he saw it, the entire world was his playground. His assets were safe in one country, his citizenship allowed travel to nearly all countries worth visiting, and he was always on the move to different places. He could have easily disappeared if he needed to, there wasn’t a single government that had control of his mobility. Instead, he chose to run boats from paradise to paradise, playing with jet skis and experiencing the local culture in his downtime.


To be continued…

Be the first to comment

Leave a Reply

Your email address will not be published.