'LOOPHOLE' sailing upwind on San Francisco Bay during shakedown sailing for her voyage to Hawaii. After 10 or so trips across the Bay, a 20-mile jaunt to Half Moon Bay and a 100-mile offshore route back, LOOPHOLE is almost ready to tackle the Pacific. Photo Brian Boschma/ sv Red Sky
I’m about to do something that sailors always tell other sailors not to do. When asked, it's one of the first pieces of advice that I give out. Never sail on a schedule. One thing led to another this year, and i’ve got to be in Hawaii to begin school in January. It’s nearly December, my boat’s only 29 feet long and my projected routing looks shit. Simple math says I need to get out of dodge, as I may have a long, difficult journey ahead of me and time is of the essence. On 'Black Friday', the day after Thanksgiving, I plan to un-tie LOOPHOLE's dock lines and depart San Francsco Bay, bound for Hawaii. First, I will sail to Monterey to finish up a few chores, perform final checks and provision for the trip. After waiting out an expected front, I plan to jump on the next window to get south of Point Conception and head south and then west to Hawaii, with ducking into Morro Bay or Santa Barbara as my most likely bail out options. Once south of Point Conception, my prospects for sailing to Hawaii improve dramatically.
LOOPHOLE's new look Looking flash with her custom name decals and Navik wind vane 'Jean le Cam'. #feelthebern
The story of this rather impromptu passage to Hawaii began in New Zealand back in February... I was turning 30 and had been cruising my simple, engineless boat, MONGO, in the South Pacific. I was moon-lighting as a yacht racing journalist and falling back on general boat skills by teaching sailing, working on a charter fishing boat and doing the odd delivery here and there. Life was easy and it was good. I was in a beautiful place and enjoying life, surrounded by a good crew of friends. Honestly, had I had a bigger and/ or better boat, a bit more residual income or the right woman, I probably wouldn’t have come back just yet. But ‘voyage of MONGO’ was always intended to be a one year journey, and it had been about a year. No need to mess with success.