Notes on hiring a delivery team

I had permission from my family to sail to Hawaii from San Francisco, but also sailing back solo was going to be too much time away in the midst of a busy summer, concluding a house remodel, moving towns and relocating my three boys to new schools. What then, to do about the boat?

One choice would have been to sell the boat in Hawaii. Based on my unscientific review of yacht brokerage web sites, my gut says that prices are roughly equivalent between Honolulu and California. I wasn’t really ready to let go of the boat, however, and I knew I would wind up paying for a berth for a number of months while my boat sat unused and gradually degraded. It seemed likely that I would encounter a situation where I felt like the “right thing to do” would be to fly back to Hawaii and attend to some issue during a sale process. I knew such a quick trip would not be well received by my family (despite the charm it held for me). So, I wasn’t going to sell the boat.

Another choice, and one taken by many higher budget racers, would have been to send my sailboat back as cargo on a larger ship. The Pacific Cup and Transpac yacht races help to coordinate such cargos to some degree, but after researching the possibility it seemed like one had to be a participant in the races to take advantage. The group organization helps to simplify the substantial logistical challenges. The process seems to be:

  • Locate a trailer large enough to accept your boat to be hauled by semi-truck, rent it and have it shipped from North America to Hawaii.
  • Once you arrive in Hawaii, get your boat to a boatyard where the boat can be hauled, the mast unstepped and mounted for transit on your boat, and then have the package set down on the trailer you shipped over.
  • Find a guy with a truck to drive the boat from your boatyard onto the big cargo ship.
  • Pay the cargo ship company to bring it back to California.
  • Find another guy with a semi-truck to haul your boat from the dock in Oakland (or Long Beach, those are I think the only California choices) to another expensive coastal boatyard, have the mast stepped, the boat back in the water. Pay somebody to pick up the big trailer you rented and bring it back to its home.

I thought a good case scenario for getting this accomplished would be @$20k. There are people who know the right people and could have coordinated these things for me, but no one works for free (nor should they.)

This left me with finding a team to sail my boat back to California. I reached out to local sailing friends and got a couple of recommendations. I had what felt like a warm lead with one guy – after four weeks of not signing a contract with me, he declined to take my trip as he had secured a much better paying job delivering a hundred-foot motor yacht up the North American coast.

Fair enough, and it highlights the fact that sailing a 32-foot boat the long way home from Hawaii isn’t exactly a plum job. I received delivery resumes from several captains and the number of trans-oceanic deliveries they had completed for boats under 40 feet was minimal. Most people bring bigger boats to cross oceans.

I posted an advertisement on describing my delivery and was contacted by a couple of people. Delivering boats can be a tricky thing. Schedules fluctuate. Boats are in disrepair. John Kretchmer’s books provide some interesting insights about the challenges delivery captains face. One of the groups of people who found my ad was an American couple who were living in Mexico. We had a zoom call and they seemed serious and capable. I liked them. They sent over a contract and we settled on terms, summarized as follows:

  • I would pay a per-day rate (one amount for the captain, a lower amount for the crew) for the delivery. There was also a per-diem rate for food and supplies to be purchased for the trip. An alternative could have been to pay per-mile for the journey, which would yield a known fixed cost. A per-mile scheme also creates an incentive to go fast, which isn’t exactly what I wanted for the delivery. I wanted careful conservative sailing.
  • I paid for flights to Hawaii from North America, and for transportation from the airport to the marina. Once the team arrived I would have the boat ready for them to occupy (else I would have put them up in a hotel).
  • I paid for fuel, oil, etc.
  • The payment terms were something close to 50% up front and 50% when the boat was delivered safely to California.

After we signed a contract, but before I had written a big check, we agreed to meet in Sausalito at my boat so that we could meet, they could sail the boat and we would all have a better idea about the project. We met and had a nice afternoon day sail from Sausalito. I tried to do nothing while we were out sailing and let them demonstrate competency and just answer any questions that came up. They did well, the boat did well, and I think we all felt better.

At the conclusion of the practice sail, I handed over the up-front check and we planned to meet in Hawaii in 7 weeks. As the young couple I met on the internet drove away in a rental car with a four figure check I had written after going sailing for an afternoon, the cynical (pragmatic?) part of me wondered if I was sitting at the poker table unable to identify the mark, being the mark myself. I mean, there was nothing that guaranteed these nice folks would show up in Hawaii when they said they would. But, they had done everything they said they would do, and I had been able to internet-corroborate what they said about themselves, and at some point you have to trust people.

Casey and Amber were fantastic. They gave me good information about their travel schedule (they backpacked in Maui for a week before arriving in Oahu) and showed up just as we agreed. After arriving at the Ala Wai harbor in Honolulu, I hoped to move my boat north twenty or so miles to Ko Olina harbor closer to where my family and I were staying. I planned to let Casey and Amber drive our rented minivan up to the harbor, allowing them time to gather whatever provisions they wanted for the trip. My plan did not work out because the people who run the harbor at Ko’Olina refused to allow me to get a berth for 1-2 days. Frustrating. So, as an alternative, I shuttled Casey and Amber around Honolulu for a couple of hours gathering dry ice, and groceries and some other items they wanted. I was (almost) as interested in their happy success as they were.

I left all of my communications gear (Iridium Go, iPad with PredictWind) on board for their use. We agreed that no news was good news, but a weekly check-in would be appreciated. I also left my Garmin Tracker so I could passively monitor their progress. They did not have an easy trip, (at one point, 34 knots) but then getting to Hawaii is the easy part, getting home is more difficult.

Their arrival in Sausalito was well-timed as to daylight and I caught some photos of their arrival under the Golden Gate. Having spent so much mental energy on this trip over the past two years, there was a certain surreal quality about watching Sure Shot slide across the blue water back to her home port. Here, motoring between Horseshoe Bay and Alcatraz, with only the main up:


While Casey and Amber were sailing back, I received a birthday card from my aunt informing me that Casey’s grandfather was a partner in a Sierra Nevada mountain cabin with my cousin’s husband’s family. We had been “California real estate-related” all along.

They used almost all of the 35 gallons of diesel they had on board. They consumed all of their food and might have been a bit hungry had they not made good use (better use than I did) of the fishing gear I had on board:


The boat was in tip-top shape when they arrived and Casey and Amber took very seriously the cleaning of the boat before handing it back to me. I was extremely pleased with how the delivery worked out. They had family waiting at the dock and received a hero’s welcome. I spent 20 days on the water – they spent 30. They were well paid for a good adventure and I got my boat back in good shape. Good times all around.