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December 3 - Morro Bay - Shoving off for Hawaii


Track Loophole here

(I have had problems viewing the tracker, especially on older browsers.)

Loophole posted up at the Morro Bay Yacht Club in Morro Bay, CA. The plan is to leave for Hawaii from here.

Between MONGO and now Loophole, I have had a lot of light-air struggles on the California coast. Compare this with a couple of potential alternatives, and this doesn't sound so bad. Though I don't plan to use it much when sailing to Hawaii, having an engine was key in making both Monterey and Morro Bay by night fall, if at all. Rolling out of Monterey just before day break on a Tuesday and arriving 35 hours later at sunset on Wedneseday in Morro bay, this leg of the journey was a race against time, set in the slow-motion setting that is Loophole. In very light-air with a lot of swell in the water, light-air sailing - especially downwind - was very slow and challenging, and motoring wasn't much better. I don't know how much I have complained about it in these pages, but Loophole's achilles heel at this point is her 3-bladed fixed prop. I had hoped to remedy this problem before leaving, but that isn't the case so I suppose i'll just deal with it. While we struggled to make just 3 knots average VMG over the course of the trip from Monterey to Morro bay, I can take solace in two things: a) I should have much stronger, more consistent breeze on passage and b) I won't be doing much motoring while on passage.

The Navik wind vane "Jean le Cam" steering Loophole brilliantly well in light air, after a few small repairs in Monterey.

Also on the plus side, Jean le Cam performed brilliantly after the repairs that I made in Monterey, and the boat arrived in Morro Bay ready to throw on final provisions and head back to sea. This leg gained me some valuable experience in sailing the boat dead downwind under main and poled out genoa. This will likely be a very common sail plan on this trip to Hawaii, as it's looking pretty dead downwind for much of the way. The long-term forecast looks pretty good for having enough breeze to make decent average speeds, though i'll have to sail very far south to get that breeze, at a cost of several hundred extra miles and extra days at sea. This passage could likely be the longest that i've ever been at sea, as my current personal record is 23 days while en route from Kauai to Seattle in 2012. With any luck, my next update to these pages will be sometime around Christmas from the Hawaiian Islands. Aloha

-Ronnie Simpson

s/v Loophole

There is likely to be a lot of this on the way to Hawaii... dead downwind sailing

Christmas - Lahaina - Morro Bay to Maui


The 10,023 foot peak of Mount Haleakala emerging from the horizon as the sun slowly dips below it. After nearly three weeks at sea, this was my first sight of land. Behind me, a full moon rose high in the sky as Loophole glided along in warm tradewind breeze. I arrived in Lahaina the following morning, on Christmas Eve. There have been worse moments in life.

20 days out of Morro Bay, California, Loophole has arrived in Lahaina, Maui. We saw 40+ knots of breeze, massive breaking seas from multiple directions and generally the roughest conditions i've ever seen when crossing to Hawaii. When the dust settled however, I arrived in Lahaina literally within hours of my original estimate with virtually no damage to the boat. To say that I am relieved, happy, humbled, grateful... would be an understatement. At thirty years old,  I took off on this passage with very little cash in reserve, no life raft and literally my whole life wrapped up inside of a 29-foot sailboat. If things hadn't gone according to plan, it could have been a very bad situation for me. Fortunately, Loophole performed brilliantly and we arrived in Maui on a very high note.

A full rainbow from horizon to horizon appeared. As the picture shows, the trade winds were extremely strong with breaking seas. My Navik wind vane Jean le Cam steered the entire passage, and Loophole burned a total of 1 gallon of diesel fuel since departing Morro Bay. #winning

More to come soon.

December 29 - Lahaina - passage log


The sunset view on Christmas from Lahaina Harbor. In the back ground is the island of Lanai, and in the fore ground is a crew of surfers on long boards, catching waves until dark. A full moon rose behind me, in perfect view of the surfers in the water. I enjoyed my first-ever few SUP sessions in the surf and also a couple of fun sessions on my 7'6" when a modest SSW swell filled in. After 20 days of looking at the ocean, it was a fitting Christmas present that I was able to play in it for a few days. <3 Lahaina :)

After a couple of brilliant days in one of my favorite places on earth - Lahaina - it has come time for Loophole to move to her new home and complete thie journey. There's no breeze today, but tomorrow a north to northeasterly should fill in and I will set sail for Honolulu with an intended arrival less than 24 hours later on New Year's Eve. Lahaina has been a phenomenal place to relax and recuperate after a long and tiring passage. The weather has been great, a fun little SSW swell rolled in and I was able to catch up with my Maui 'ohana' and enjoy this little paradise that is Lahaina.

Morro Bay, California to Lahaina, Maui vital statistics

20 days

Average speed 5.04 knots

Passage length - 2,418 nautical miles

Slowest 24-hour run- 101 nautical miles

Fastest 24- hour run - 133 nautical miles

Total diesel fuel burned: approximately 1 gallon


Loophole Hawaii log


Dec 3 - 1930 - Departed dock at Morro Bay Yacht Club


35* 19 N, 120* 52 W - 651 to waypoint 


Dec 4 - 1345 - 40 miles west of Point Conception


34* 20 N, 121* 15 W, sog 5 kts, cog 190, 592.8 to waypoint


Last night was a memorable beginning to an ocean crossing. Memorable in it’s spontaneity, as I made an almost instantaneous decision to change my plan and leave in the dark on Thursday night, instead of departing on Friday morning as originally planned. I had come to Morro Bay to wait out a front, complete final provisioning, and then set sail for Hawaii. So when I saw the potential for all of those goals being accomplished and had an opportunity to sneak out even earlier than planned and make additional miles, I jumped on it, and that meant changing plans. 

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January 2, 2016 - Honolulu - Loophole is home


The mighty Cal 29 'Loophole' leaving Lahaina in her wake on December 30. Thanks for the memories, Maui! Departing in a SW sea breeze, we genoa-reached northwest before hitting a light-air transition zone and motoring for a few minutes. Stiff NE trades quickly built and 'Loophole' was off to the races heading west under headsail alone. After a light spot and some motoring 5 miles south of Kaunakakai, Moloka'i we were back under sail and cruised all the way until an early morning arrival at Waikiki. About 15 hours from Lahaina to Honolulu and a half gallon of fuel burned, avergaing more than 5 knofs. A perfect first island passage with a lot of wild life as well!

5 weeks, 4 ports, 2,700 miles and 6 gallons of diesel fuel since leaving San Francisco, s/v 'Loophole' has arrived in her new home port of Honolulu. It was a bit dodgy at times, but the boat is in better shape than when I left San Francisco. Incredibly happy to be here. Out of season south swells have been creating fun surf in Waikiki, and New Year's Day brought a surf/ sail combo with a great afternoon surf and a Friday night Beer Can race trimming head sails on the J/120 "Malia Kai".