The Delivery Skipper’s Delivery Skipper

This sailor is the go-to guy for racing and post racing sailing up and down the west coast. in From Herb's Blog for May 20, 2008.

Herb Hippie 368

Herb McCormick

They call him “the Hippie,” and it’s not hard to see why. Jon Shampain is one of the West Coast racing scene’s most ubiquitous, well-known figures, a fellow who knocks off miles and miles to Mexico, Hawaii, and other Pacific Ocean ports-of-call almost every year. He’s a traveler, all right, but with his long, gray ponytail and beard to boot, it’s obvious there’s one spot Shampain has not visited in quite some time: the barber’s chair.

Before last month, the last time I saw Shampain was in the summer of 2005, somewhere near Antioch, Calif., in the latter stages of the annual Delta Ditch Run from San Francisco Bay to Stockton. He was, unfortunately, in rather dire straights; the mast of his Hobie 33 was buckled over and he was in the midst of gathering the debris. I hollered over to see if he needed assistance though it was abundantly clear he and his crew were on top of the situation. His thumb went up, and he bent back down to his labors as we sailed on.

When I caught up with him again in April, at the end of the recent Corona del Mar-Cabo San Lucas Race, he laughed when I reminded him about the dismasting. “It was too bad,” he said. “There was an Olson 30 that was the boat to beat that year if you wanted to win it, and we really had them put away. They were so far behind us we almost had the mast back on deck when they finally went by.”


Shampain has sailed a lot of ocean races, but his reputation as a stellar seaman was earned not just in the heat of competition, but also in its aftermath. For over the years, he’s been the go-to guy for countless owners who were more than happy to race to Hawaii or Mexico, but less intrigued about addressing the long slog back. And that’s where Shampain comes in: He’s been delivering boats home after Transpacs and Mexican contests for three decades now. Now 54, though he admits to slowing down a bit, he’s still plying his trade.

“I’ve been really lucky,” he said in Cabo, while readying the Santa Cruz 50 Horizon for the delivery back to Southern California after racing the boat down to Mexico. “I’ve had a lot of great opportunities, a lot of really good owners, and a lot of really great boats.”

This past year, Shampain hit a serious milestone, knocking off his 200,000th mile at sea. “It just adds up,” he said. “I’m getting close to 40 Mexican races, both ways, coming and going. It’s the same with those Hawaii runs. Some years I’ve done two Hawaii deliveries (back to California), plus the race over.”


A native of South Florida, Shampain grew up surfing and originally landed in Southern California for the waves. He hadn’t done much sailing at all when he bought his first boat, a 33-foot wood sloop built in Holland in 1955, with the goal of searching out isolated surf breaks. From his base in Oceanside, just north of San Diego–where he’s now lived aboard for close to 35 years, though he now calls a Grand Banks trawler home–he cut his sailing teeth wandering south of the border and started picking up boat work, varnishing and painting, between cruises. He got into buoy racing with some pals aboard their classic 6- and 8-Meters. Before long, he graduated into ocean racing and never looked back.

Ask Shampain about some of his favorite boats and passages and he’s quick to invoke names like High Five and Mongoose, the latter of which he crewed aboard for a couple of Transpacs and enjoyed one of his more memorable runs home, an 11-day, 3-hour trip. When he’s in full delivery mode, he usually brings his boards along, and that was the case last winter when he brought the Perry 56 Free Range Chicken back to the mainland from remote Fanning Island via Hawaii. Shampain got slammed in “the worst ocean I’ve ever been in” in reinforced tradewinds on the way up to the Kona Coast, but it was worth it for the rides he rocked on Fanning.

“The place is amazing, it’s out in the middle of absolutely nowhere,” he said. “It’s got like two really good waves, one’s a Northern Hemisphere spot, the other is a Southern Hemisphere spot. So it seems like there’s always something going on. Both spots are (situated in) offshore tradewinds, so as long as there’s some trades blowing you can surf literally all day long.”


These days, as far as deliveries are concerned, Shampain says that he deals exclusively with race boats. “Many, many cruising boats just aren’t that well prepared,” he said. “The only thing the ocean knows is that it wants to kill you. If you’re not prepared for it, you’re going to get beat to death. That’s one of the things I bring to the table. I’ve had a couple of bad problems over the years: a couple of dismastings, a lost rudder coming home from Hawaii. But all the years of racing, cruising, and living aboard gave me the experience to deal with those things.”

As far as sailing aspirations go, Shampain feels pretty comfortable with where he’s been and what’s he’s seen. “To be honest, I’m ramping down a bit,” he said. “I’d still like to do an Atlantic crossing. But I’m okay with what I’ve done. I’ve met some of the real sailing legends. I don’t have too many more sailing goals.”

That’s not to say Shampain is done pursuing the life of a waterman, a life that’s taken him far and wide over the ocean he loves. “Oh, I’m not ready to hang it all up,” he laughed. “As far as I’m concerned, I’ve only lived the first half of my life.”


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