The Strange Life of Delivery Captains and Crew

The Strange Life of Delivery Captains and Crew

What To Do-VI Glenn HarmanI’m always at a bit of a loss when people ask what I do for a living, or whether I travel for business or pleasure. Basically, I get paid to move other people’s boats around for them. Sometimes it’s fun and sometimes it is the worst job in the world.

If you think that a little knowledge of sailing gives you the ability to deliver boats, let me tell you, it’s more complicated than harnessing the wind for propulsion. Beyond challenging conditions and the constant upkeep and repair all boats need, the littlest things can become a Gordian knot.

Haircuts in Foreign Countries

If you travel long enough, eventually, you need a haircut. After about a month, I find it is time to start looking around and weighing options. It is a disconcerting when you have no idea how to say, “a little above the ears, please,” in a foreign language.

What To Do-VI Haircut
Glenn’s crewmate in need of a haircut

I thought I was in the clear in the French islands; I have a working knowledge of French. Imagine my surprise to learn the person cutting hair was from the Dominican Republic and did not speak French or English! Luckily a trilingual patron was able to translate for me. They had a poster on the wall of all the different styles they could cut, but none of them looked even remotely like what my hair was like.

I got a cut on St. Lucia after a three-week crossing from the Canaries. I felt like a sheep in need of shearing. In the hot climate, it was just too much. At a Friday night fish fry, I saw a house with a sign for haircuts and the barber was still inside cutting. I decided to give it a try. Taking a hint from all the other patrons, I crossed the street and got a beer to enjoy while I waited my turn.

What To Do-VI Haircut
Bad hair day

When my turn came and he put me in the chair with a good view of the street festivities. In fact, the barber shop was the cornerstone of the party and the barber seems to also be a bartender. In any case, he decided not to mess around with those scissors things, which was just fine with me since I had lost count of how many beers the barber had while I waited. Instead, he used the electrics and despite my asking for, “ a trim just a little above the ears,” I was shorn like the sheep I was.

My friends coming to rescue me did not recognize me at first. They said I resembled Lance Armstrong. (While he was still riding..) Fortunately for me, the only difference between a good haircut and a bad one is about two weeks!


Traveling a lot also means that various things expire while you are overseas. During a particularly long summer in the Mediterranean, my USCG license expired. I had been responsible for a large sailboat in Greece that was getting ready to be hauled out for the winter.

What To Do-VI PaperworkPart of the procedure was to sign the responsibility for the boat over to the marina and that involved the Greek customs authorities. This was the start of Greece’s first economic crisis and anyone in the government felt especially sensitive about justifying their jobs. For me, this meant I got to stand in a huge line at the local office to pay an import tax.

Then, with hours to spare before my flight, I had to get a customs stamp on our cruising paperwork. This also involved paperwork from the marina, copies of the boat insurance, and proof of ownership of the boat. The last piece of the puzzle was a notarized letter from the owner and my…USCG license!

Glenn Harman What To Do-VIThe agent asked for each piece of paper in turn and carefully studied it to make sure each was genuine. He even ran his finger over the raised notary seal. When it came time for my license he was a little bit at a loss as he had never seen is USCG license.

At the time they were quite fancy and looked like a diploma that you might frame and put on the wall. But down in the corner, there was the date and it was clear that it had expired a few months ago.

Just as he started to scan it, I explained that it was a US license and was even signed by President Obama! At the mention of this name, there was a chorus of officials repeating the one word in English they knew. The officer, at that point, offered if I had any extra money, they could use some in Greece. We all had a good laugh about it and then he asked for the next document.

Whew, professional crisis averted, and I made my escape…

Land, Sea, Air, Repeat

Glenn Harman What To Do-VI SailingOne of my first boat gigs was a minor refit in England. Once the installation was complete, I was to sail with the owners to Spain. When we finally got to Barcelona, I booked a flight back to the US through Germany.

I changed planes and there was an immigration check prior to boarding the US flight. The agent spent some time looking at my collection of stamps in my passport and eventually asked how I had gotten to Germany.

I pointed over my shoulder and said I had taken a plane from Barcelona. He then asked how I had gotten to Barcelona. I replied that I had sailed there from England. He then explained that I had overstayed my allowed time in Europe.

After some further thought, he looked over his shoulder at the gate where my plane was boarding and the ticket in front of him. I did my best to smile. To my immense relief, he decided to send me on my way.

This turned out to be one of my better results with immigration and visa issues. Now I am a bit of an expert on the word “Schengen” but I still get in trouble when traveling outside of Europe. (Don’t even ask about being denied boarding for a flight to Brazil… That’s a whole new story.)

A Normal Life

After one particularly challenging gig with an owner who was really a type ‘A’ personality, I complained to a friend that I just wanted to work for someone who was more normal. She replied that normal people don’t own the kind of boats I worked on!

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Glenn Harman

Glenn HarmanGlenn Harman is a USCG and RYA licensed boat captain who has been sailing in the Caribbean for the past 15 years. He is now a resident of St John and the author of the book “Captain Glenn’s Guide to the BVI’s”. It is available on Amazon and at

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