I had second job while I was in Cuba as the Supercargo for 2 different shipping companies, one based in Jacksonville and the other in Curacao. All ships were US flagged as required by law. My job consisted of handling any issues on island AND reporting commercial shipping activity to and from the island. In 4 years we had a handful of issues other than the one time a barge got caught in a storm of the Bahama Bank and had to be cut lose from the tug and about 1/3 of the cargo containers disappeared. My role in this was to report it to the Base commander as soon as the shipping company knew it happened and the shipping company flew in a gang of people to take care of it. The rest of the time it was something damaged which consisted of taking some pictures and sending them to Jacksonville.

The other part, monitoring the port for commercial acticvity, was very interesting. It allowed me to enter the port area in my own boat...something that no one else was allowed to do. The industrial area, as it is called, was unfished other than me and anyone who happened to be with me on "official" business. This consisted of taking pictures of any and all commercial boats in the port and sending this information to Jacksonville.

All in I spent about 2 hours a month doing these 2 jobs and was paid $4,000 a month to do so. $4000 of overseas income thus no income or payroll tax. It also afforded me the opportunity to unofficially be the fishing guide for dignitaries and high-level visitors who came to the base. The organization I worked for in my actual 9-5 gig was perfectly fine with me carrying visitors fishing a couple of mornings / evenings a week on my employers dime. Usually these trips were inside the port area because the fishing was better and it as a 5 minute boat ride from my slip. It was LOADED with tarpon and snook and was probably the best bonefish and permit fishing in the Caribbean. Was also the best lobster bullying area around and HUGE cubera snapper, nassau and juvenile goliath grouper on grass flats feeding on lobsters at night. It was a helluva ride...