Tales of a delivery skipper

Profession: delivery skipper. It sounds like a dream job; getting hired to sail boats to exotic locations all over the globe, and it really is a great way to see new places, meet all manner of people and spend a lot of time out at sea.

But ask any captain who has done a few yacht deliveries and they will tell you that the business is not necessarily all that it promises to be.

Yacht deliveries are inherently frustrating, not because of the boats but due to the owners. Anyone who owns a vessel capable of crossing the seas but chooses to hire someone else to do that for them is a little bit sketchy. In the delivery world there are three main types of owners.

First, there are those who have commitments with family or work and are therefore unable to sail their boat to the desired destination. Then there are those who want to cruise the far reaches of the globe but for some reason cannot bring themselves to brave the open ocean. And far more common than one might think are the owners that had a dream to sail the world but decided after the first ocean crossing that it wasn’t their cup of tea and that they would rather hire someone else to sail their boat home.

I got my first taste of dealing with bizarre owners on my second offshore delivery. Four others had sailed Ragtime, a 65-foot race boat, from New Zealand to Hawaii, and I jumped aboard on the final leg of the passage from Honolulu to L.A. We had a mostly uneventful crossing, and were motoring the last few miles into port after 17 days at sea when a Zodiac roared up alongside and deposited an obese, red-faced man aboard. This was the owner. After 7,000 miles of upwind sailing from New Zealand, he had to pilot the last mile into port, Sydney Hobart flag triumphantly hoisted and blonde girl at his side as if he had just made the voyage himself.

We arrived to find we were just in time for a huge party at the yacht club, the kind with rich yacht owners in fresh-pressed suits sampling fine champagne and cocktails. We must have been quite a sight for this crowd, having not bathed in almost three weeks and still wearing our mismatched foul weather gear and sea boots. Someone handed me a beer, and we enthusiastically jumped into the festivities.

Unfortunately, after a brief time in which we downed a very sailoresque amount of alcohol, we were pulled away from the yacht club by the owner and put in a van to take us to our hotel for the night. At this point we were exhausted from the delivery and very drunk.

After assuring us that we had reservations made for our stay, the van passed through the most ghetto part of L.A. and dropped us off next to what looked like a rundown mosque that could have housed the prophet himself. This was the Ali Baba Motel, which was run by Koreans who had a very limited understanding of English. It turned out that reservations had not been made, which was a significant problem, seeing that none of us had any money yet and we weren’t in the part of town one would want to spend the night outside with the street crowd.

In the end we were able to secure two rooms for the night after many hours of intoxicated negotiating on the part of my crew member Patrick. All I remember of the night is lots of shouting, becoming acquainted with a gangster who was on his way to bash someone in with a metal pipe, meeting a kind hobo who brought us food from Taco Bell and listening to the near murder of a prostitute in the room next door. Through all of this, the boat owner didn’t answer his phone once. Eventually, the money was wired and the problems taken care of but never did the owner apologize for the situation.

The next time I had to deal with a frustrating owner was more than a year later when once again I joined the delivery of a boat from Hawaii to California. The owner, a high-ranking member of the U.S. Central Intelligence Agency, was a balding, overweight man in his mid-60s who spent most of his time reading the New York Times and indulging in his favorite food, chow fun.

Immediately after departure we had to return to port due to a leaking fuel tank. Somehow, a local shipwright convinced the owner that he had to replace it with an invincible titanium tank that would cost ten times as much, take weeks to deliver and install, and that archeologists would find at the bottom of the ocean in pristine condition in 10,000 years.

And so we spent the next six weeks waiting at the marina for the custom tank to be ordered, built, shipped from China and finally assembled and installed in the boat. The owner refused to consider a temporary plastic tank that would take a few days to install. All this time, the risks involved with the passage increased as the fall approached and the huge low pressure systems plow across the North Pacific, and rough weather becomes almost inevitable. The owner passed the time by downing bowl after bowl of chow fun and boring anyone who would listen with endless stories of his time in Afghanistan.

I’m sharing this with you today because I’m currently negotiating delivery terms with an owner that is in, of all places, a small village in the mountains of Peru. He is trying to wire money for the delivery to the States but it is taking longer than expected, likely because the money has to travel on the back of a llama and go through the same mail service from the time of the Incan Empire. And it somehow has to get past dozens of greedy officials. Ah, the joys of working in the yacht delivery industry!

The very best place to sail, in my opinion, isn’t all the cruise ship-infested ports in the Caribbean or the delightfully polluted waters of the Mediterranean, but right here at home. In the Pacific Northwest we have miles and miles of cruising grounds filled with beautiful fjords, thousands of unpopulated islands, protected waterways teeming with fish and untamed wilderness where the trees are as big as 30 feet around, all close to vibrant, modern cities like Seattle and Vancouver.

It is the ultimate cruisers’ paradise, and you don’t have to hire someone like me to sail your boat there!


4 Responses to Tales of a delivery skipper

  1. Ray Hardy June 5, 2017 at 8:51 am #

    I seen your post on Cruisers forum. I am looking for a delivery skipper so decided to google your name and found this. Sounds like you have had some bad experiences, but calling your potential customers sketchy…….

  2. Kris Amundson August 15, 2012 at 4:49 am #

    Hey Ryan,

    Sounds like you have a good start to your delivery skipper career and have some good stories to tell.

    Some advise though, insulting your clients publically, along with naming boat names and professions, is no way to build a reputation as a delivery skipper people want to hire.

    I understand that there are a lot of arrogant, wealthy a-hole yacht owners out there who treat you like taxi driver (maxi driver? 🙂 but insulting them publically is just bad business in the long run.

    If I had a situation where I needed some help getting a boat back from a singlehanded transpac, or was able to sail a race to Hawaii but couldn’t take the time off work for the return journey, I would indeed look to possibly hiring a delivery skipper to help out. I would not choose one who might spin it negatively, complaining about an owners habits, methods, gear selection, or how they might need to hit the gym.

  3. Elena Leonard May 7, 2012 at 10:34 am #

    I agree about the world-class sailing here. My family and I chartered in Greece 2 falls ago. When we came home and went sailing on Puget Sound we realized how much more beauty and fine, fine sailing there is here! (although I do love an occasional ocean crossing)

  4. Rick Dettinger May 4, 2012 at 10:12 pm #

    Another concern for international deliveries is smuggling. The owner hides the drugs onboard without the knowledge of the delivery skipper and collects them after the skipper clears customs. This happened to a well known world cruiser and writer.


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