'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.


The transofrmation has begun! While the name on the back still says "Sleepy II", (though that will change very soon), Cal 2-29 #744 has officially become 'Loophole' at heart. From grandpa's weekend condo to performance racer/ cruiser, I have converted the boat from wheel to tiller steering, assembled an inventory of sails and have pulled the mast and fully re-rigged the boat to reflect her new ambitions. With any luck, I will sail my house in her first beer can race this week in Oakland and possibly do a 27-mile in-the-Bay race with a few friends next week. After anoter re-fit in September, the boat should be fully ready for our first big adventure: cruising Southern California and the Channel Islands for the winter and chasing surf. 

First off, I have spent way more at this point than I initially planned. Having said that, I have ended up doing a lot more than I originally planned on and feel that all of the money was well spent, so i'm generally pretty stoked. Just very broke. When I entered this re-rig, I wanted to achieve a few major things: get rid of the stock wooden spreaders, install all new standing rigging, internalize my halyards, and generally bring the rig up to date (new VHF antenna, tri-color light, etc). In typical me fashion, I didn't really come up with a super thorough game plan, I just pulled the rig out of the boat and tackled things one by one until I felt it was ready to step. Having dismasted boats is a pain in the ass and having a mast or a boat in a boat yard is equally a pain in the ass, so time was of the essence.

'Loophole' dismasted. My Cal 2-29 dismasting was much smoother than my Cal 2-27 dismasting :)

Step 1: Chop the top of the rig off with a large and powerful saw. No, seriously.

 When I went into this project, one of my main goals was to make the halyards run internal in the mast. My mast was the ultra-stock shitty cruising version which was equipped with just two wire-to-rope external halyards


Cal 2-29 #744 'Loophole', (ex-Sleepy II) sailing in Alaemda, CA April 2015.

It's been six weeks since i've been home, and five weeks since i've written in the blog... Geez, has it really been that long? What can I say, time flies when you're having fun! San Francisco sailing is truly world class and I am beyond thrilled to be back here for a while. I've been sailing a lot, racing a lot, working on some other boats and generally getting back into the scene, while 'Loophole' has begun it's transformation from 1970's weekend condo to bluewater cruiser and possibly ocean racer. I'm still transitioning back to life after my journey across the Pacific on 'MONGO' and getting re-established in California, yet I am already getting itchy feet as I live on, and love, my cool little Cal 2-29 'Loophole'. 

Birds of a feather.... 'Loophole' and the turbo Volvo 70 'Maserati' rafted up together in Oakland before 'Maserati' goes out to smash the SF - Shanghai record. Thanks to 'Timo' for the hospitality and boat tour!

In between idyllic day sails in the Alameda estuary, cocktail parties and entertaining friends on board and beginning a re-fit, I have found myself perving on Google Maps at night and planning a journey. It's my nature, and part of the reason I live on sailboats. The route looks something like a gentleman's run at the 2016 Singlehanded Transpac and then quick cruise to Asia and back or a longer cruise to Mexico, central America, then French Polynesia, South Pacific, New Zealand and onto Asia and back. Or Mexico, Central America, Panama Canal, Carribbean, East Coast and over to Europe. I digress.... While my brain, empowered by ownership of another fine Lapworth-designed sloop, has begun to conjure up vivid dreams of knocking out tradewind miles to distant lands, I have become a bit more focused in my goal to do this year's Baja Ha-Ha.


As soon as one chapter closes, another one opens.... Truly the end of an era, but my beloved s/v MONGO has been sold in Opua, New Zealand and I have flown back to California and purchased the Cal 2-29 "Sleepy II", which is to be renamed. Total transition time? 2 weeks from final sale of MONGO in Opua to signing of papers on Sleepy II in Alameda. Had a killer four months in New Zealand, but ultra-stoked to be back in the Bay and pursuing all that life has to offer on the left coast. Stay tuned, a lot more to come as I prepare this Cal for it's first journey to Mexico this fall and update the blog with more from my time in New Zealand, the Moth Worlds in Australia in January and upcoming adventures including this summer's "TransAtlantic Race", another Hawaii return delivery, September's Big Boat Series and probably the Baja Ha-Ha in October. Much more soon.

The new whip - Another fine Bill Lapworth-design built by Cal Yachts. 1975 Cal 2-29 "Sleepy II", lying Alameda, CA. Lovingly owned by the same couple since she was nearly new, Sleepy II has spent most of her life under a full cover, only seeing the light of day on weekend sails. As a result, she looks almost like new inside and out and runs like new with her low-hour Universal 3-cylinder diesel. Once again, California provides and i've scooped up another clean small cruising boat well capable of going places. This little boat has absolutely no idea what is about to happen to it...


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