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Preparing for a Downwind Delivery


It happened as we were nearing the entrance buoys of the Ala Wai Boat Harbor after 16 days and 2,500 miles on delivery from San Diego to Hawaii. We’d already rolled up the jib and were jogging along at just 3-4 knots. A pod of spinner dolphins showed up and began playing around up at the bow as if to escort us in. Eager to visit the friendly dolphins, I grabbed a line, tied a quick bowline to the stern, donned my dive mask and jumped overboard, line in hand. As I towed underwater near the transom, I looked up at the dolphins cavorting at the bow. Suddenly a watery cloud of brown emerged from the back end of one of the dolphins. I tried to dodge it by bodysurfing out of the way, but another cloud emerged from the dolphin swimming next to him…and with that I was in it. I’m not sure if they meant to do it, or whether they were laughing at me, but I try to think of it as a blessing. Sort of a baptism by poo. Either way, it was cool to see, and it didn’t stick.

No matter how you look at being defecated on, the entire trip really was a blessing. What sailor could refuse a delivery like this: a slippery, nearly new 2020 Hanse 458, equipped with a big masthead spinnaker, downwind from San Diego to Hawaii? I’d previously delivered what owner Michael Prescesky said would be his “last sailboat,” a Jeanneau 53, from Hawaii to Vancouver Island, where she was eventually sold. Now, unable to shake his addiction to sailing, Michael wanted to start all over again with a new boat. Michael’s gracious wife, Madeline, who runs the Chinese language program at the University of Hawaii, said the boat should be christened Yo-Lyla, or “here we go again,” in Chinese.

That said, no voyage is without its challenges, even a dream delivery downwind. Ours started early, as the boat was basically stripped. There was no liferaft. No dinghy. No jacklines. Not even any cookware. Barely used, she came pretty much as delivered, with a single water tank, a single diesel tank and single tank of propane. There was minimal solar power. A makeshift portable gasoline generator ran an owner-installed watermaker. The freezer was a tiny slot in the top of the fridge. The cockpit had few handholds, making it a skating rink at sea. Clearly my crew and I would need to put some time in to turn the boat into an ocean-crosser. We had one week.

The crew (from left) Tracy, Donna and Lydia, settled in for the long haul to Hawaii

The crew (from left) Tracy, Donna and Lydia, settled in for the long haul to Hawaii

Arguably just as important as boat prep on passage is the choice of crew. I started with an old hand, Tracy Dixon, a Navy explosive ordnance chief with whom I’ve crossed several oceans. By coincidence, Tracy had actually been through boot camp in San Diego, at nearby Liberty Station, and vastly prefers it as the trendy restaurant zone it has since become. Tracy is methodical, reliable and safe (essential skills when dealing with high explosives, as well as ocean voyaging). Having served in the Middle East, he has seen situations so miserable and dangerous nothing I can get him into at sea bothers him. He takes things in stride, invariably volunteering for the hardest watches and taking on the worst tasks, all the while truly appreciating the amazing experience of it all.

In addition to Tracy, I wanted another two crew in order to keep a 24/7 watch for ships with each crewmember standing a four-hour watch followed by eight hours off. As a skipper, I wouldn’t stand a set watch. Instead, I’d be on call as backup or a second watch-stander both day and night. After a handful of crossings of each of the major oceans as crew and captain, I’ve found this works fairly well. It leaves me available and somewhat rested and ready whenever I need to be on deck for sail changes, dealing with other vessels and the like, while allowing everyone to get some rest on the long trip.

Tracy suggested a friend, a fellow Waikiki Yacht Club member named Donna who sails with club members and checks them out on the use of the club’s fleet of small boats. I hadn’t met Donna, but a lunch of dim sum in Chinatown revealed a chill, diplomatic woman with a quiet demeanor belying many talents in addition to her sailing skills, such as a Ph.D. in economics. The fourth crew would be a friend of Donna’s named Lydia, a fellow economist friend from Tacoma, Washington. According to Donna, she was a dynamic personality who loved to bake and cook. We spoke on the phone, and although the least experienced at sea, she seemed energetic and eager to get involved in getting the boat ready for sea, so I took her on.

We began our preparations by unpacking dozens of boxes delivered to us by Amazon. Owners Michael and Madeline became Jeff Bezos’ best friends, ordering everything from tools to toilet paper. Every day was like Christmas, with dozens of packages waiting to be unpacked and stowed. We also paid a visit to Oceans West Marine Supply in Barrio Logan, where we rented a four-person liferaft with the help of Rosa, the manager there whose crew was also busily refitting a huge 100-man raft for some kind of commercial vessel. Despite the difficulty of shipping the pressurized canister back to San Diego, renting saved us the expense of buying a liferaft for just one trip. Rosa also kindly sent us to Las Quatro Milpas, possibly the best tasting, most authentic Mexican place in San Diego, where we ordered stocked up on fresh tamales, rice, tortillas and beans. Good, I thought, we would need those extra calories offshore.

Of course, issues with systems like the steering or a rig failure can easily double the length of a passage, so I typically count on twice the volume that we really need. This in turn means a good supply of easily prepared canned or preserved food is also essential. Fortunately, San Diego is a great place to over-provision, with plenty of supermarkets and even a nearby Goodwill. As backup for the boat’s water and fuel tanks we brought along a few jerry cans of diesel and gas, along with crates of emergency water.

Another essential job was a sea trial, to learn how the boat sailed and check out the rig and all systems at sea. Sailing out past Point Loma into a light wind and an oily Pacific Ocean swell, we raised the fully battened main and big masthead spinnaker and discovered a nice turn of speed even—a testament to the skill of designers Judel/Vrolijk and Co. Checking all of the leads for chafe, the enemy of any passage, I added chafing gear and changed a few of the leads. A spinnaker halyard, for example, can easily saw its way clear through over the course of 2,500 miles.

Unfortunately, our sea trial also revealed that our newest crew, Lydia, was prone to seasickness. Although she planned to use electronic seasickness bands, I strongly suggested an antihistamine I had brought called Stugeron. Friends who have long experience with bluewater sail training recommend Stugeron as their go-to remedy, because it has few side effects and works well. Although not particularly prone to seasickness, I have tried it myself and found it helped.

We left San Diego on a perfect day as an area of high-pressure forecast provided us with 20-knot north-westerlies as soon as we got clear of calms in the lee of the Channel Islands and Point Conception. As we headed offshore that night we experienced a rollicking beam reach to the south and west, which proved a challenge as the motion was fairly strong, and none of us had our “sea legs” yet. At one point a wave not only made its way into the cockpit but all the way onto the chart table below. Because falling is the most common cause of injury at sea, especially at the beginning of a voyage, I set up some additional makeshift handholds and tethering points. Nonetheless, we all still collected our share of bruises, some fairly painful.

As time went on, the conditions became gradually calmer, until a few days later when we found ourselves in light following winds. We had our sea legs now and settled in for the long downwind crossing. There were days of light winds when the sails slatted and boatspeed stayed low. With limited diesel, we worked to keep the sails drawing, but several cars on the fully battened mainsail snapped. The job of a delivery skipper is, of course, to keep everyone safe. However, it is also to preserve boat and save the sails from damage. We nursed the main and always dropped the spinnaker at night or before squalls.

As alluded to, Lydia turned out to be a dynamo in the galley and regularly fed the crew fresh baked bread and pizza. We also caught plenty of fish. At one point while soaping up on the transom for my daily seawater bath, I looked aft and caught sight of a large mahi-mahi, leaping through the air in a flash of gold and blue. Flying right across our wake he then attacked our lure from above. We eventually succeeded in landing him, and he became dinner, then lunch and dinner again.

One of the greatest recent innovations in offshore safety is AIS, and the boat’s owners had recently installed a new Vesper Marine “Cortex” AIS system that was able to identify and track vessels as far as 60 miles away, all from a dedicated portable handset that also worked as a VHF. I could even track vessels via my cellphone using a Vesper Marine app, which allowed me to look up any vessel traffic that may have been in the area from the comfort of my bunk.

I also attached a personal AIS beacon to each person’s safety harness, which I insisted be tethered to the boat whenever anyone was alone on deck. In an offshore situation, crew overboard can realistically be retrieved in time only by their own boat, and an AIS beacon may be the best and only way to find them. That said, I also told my crew to think as if they were living on a cliff, where a fall would be fatal as the chance of retrieval would be low. It’s nearly impossible to see something as small as a swimmer’s head between the waves, even in moderate seas. When tethered, being dragged alongside a moving boat can be fatal as well. Bottom line: never fall off the boat!

Out for a daysail at the end of the passage

Out for a daysail at the end of the passage

For weather forecasts, we used an Iridium Go! System from Predict Wind, paired with tablets and cellphones. Although it was slow with downloads, the Go! got much better reception with a dedicated marine antenna, which also allowed us to keep the receiver out of the weather. Predict Wind is a great forecasting system, and despite the forecasts being consistently at least 5 knots low, it gave us peace of mind and helped us plan when to jibe or shorten sail. I also used a Garmin InReach to send daily text updates to my wife on shore, who broadcast our news to friends and family. It is possible to text with the Go!, but the minimal fee for unlimited texting through a cellphone interface makes the InReach a no-brainer as a communication tool. In a pinch it can even be used to receive basic weather reports. It’s such a simple and foolproof way to stay in touch, I consider it essential gear.

Rain clouds cleared as we neared the islands, and Tracy won the prize for being the first to sight land as the immense 10,000ft peak of Maui’s Haleakala (House of the Sun) appeared from behind a pair of rain squalls. Lydia wanted to know what Tracy’s prize would be, but Tracy felt just seeing the impossibly high peak materialize the way it did after so many days at sea was prize enough. Another prize was our last night at sea, sailing down the shining path of a full moon through the notoriously rough Ka’iwi Channel between the islands of Molokai and Oahu on uncharacteristically serene seas with 15-knot trade winds. The moon set over Diamond Head as the sun rose in our wake.

We arrived in the Ala Wai Boat Harbor after 16 days, rested and ready for anything. It was sweet to be sailing home, and sweeter still being met by my wife, Kyoko, and Madeline and Michael, fully loaded with leis for the entire crew. An ocean crossing is never easy, but it always seems to provide a unique experience. Many are difficult, others are magical. Some can be both, depending on your perspective. Like being pooed on by dolphins. 

September 2022



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