WORLD With a special report this month on the tall tales and high times of The Bay Area's Most Enduring Charter Skipper, a father/daughter sailing trip aboard an uncommon sailing craft into the Bahamian Backwaters, plus Charter Notes.
CATE BOSKOFF / RUBY SAILING
You might find 'Ruby' sailing the Bay at any time of day. From sunrise fishing charters to midnight party cruises, she's done it all.
guests more than a few times. Sailing first out of China Basin, and later out of The Ramp restaurant, down toward the southern end of the San Francisco waterfront, Ruby has drawn all sorts of customers over the years, from high-heeled society gals and high-rolling 'suits' from the financial district, to rowdy hookers and hooligans. Somehow, through it all, he's managed to keep his sense of humor. "I've seen it all," says Josh with a chuckle. "It's been crazy at times, but almost always fun." Having grown up as a Southern California 'beach kid' at Malibu, back before the zillionaires took it over, Josh spent many youthful days surfing. It was his grandpa, an accomplished ocean racer named Scrubby Wellman, who introduced young Josh to sailing. When only 14, he started crewing for the old gent in a series of high-profile competitions, including the Chicago to Mackinac Race, two Bermuda Races and even a Transatlantic. Those experiences, combined with his study of cinematography at a San Francisco art school, led Josh to be invited on an around-the-world film-making cruise in 1970. Sadly, the trip turned out to be a scam, so Josh jumped ship in Panama. Not wanting his adventures to end, he bought a well-worn 40-ft wooden yawl which he sailed throughout the Western Caribbean for five years. "I lived on a budget of $110 a month," he recalls with a smile. He had plenty of adventures, including riding out a hurricane. For a while, he bolstered his cruising kitty by purchasing duty-free TVs and watches in Panama and sailing them to Colombia's San Andreas Island in exchange for rum. That, he traded to the Cuna Indians of the San Blas Islands in exchange LATITUDE / JR
25 Years of Joshing: 'Pryor' Experience Not Required For many who try it, crewing on charter boats is a burnout. What initially appears to be a healthy, low pressure gig in the great outdoors, ends up requiring long days of physical exertion, often peppered with stress from demanding — and sometimes clueless — clients. There are some, however, who never seem to tire of charter work. Day in and day out they greet neophyte sailors with a smile and a cool drink, and take great pride in introducing them to the joys of sailing. Here in the Bay Area, no one fits that profile better than Josh Pryor — a guy we think of as 'the godfather of San Francisco daysailing'. Having just completed 25 years of continuous chartering on his custombuilt steel sloop Ruby, Josh has easily logged more hours at the helm than any charter skipper in Bay Area history. If there were such a category in the Guiness Book of World Records, he'd win it, hands down. Averaging roughly 200 days a year on the water, he sometimes hosts as many as four cruises a day. Although burly, weathered and prone to growling like a buccaneer, Josh is actually as gentle as a teddy bear when you treat him right, but he can also hold his own when things get ugly — he's had to wrestle the wheel back from drunken
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for intricately appliquéed molas, which he carried back to Panama — his own version of the famous 'triangle trade'. Five years on a leaky wooden boat set Josh to thinking about building a steel boat capable of cruising anywhere in comfort. Not long after returning to San Francisco in 1976, he took his handdrawn plans to Don and Jeff Millerick, two highly regarded metalworkers, who still work today out of their Cotati shop. At the time, the idea was to complete Ruby, do some chartering to build up a cruising kitty, then eventually take off over the horizon. After eight months of construction, the bare hull was completed in '78. According to Josh, the Millericks did a "superb job." The young sailor spent the next couple of years doing all the finish work himself at a quiet spot on the Petaluma River. He drove a cab at night to earn 'boat money', a sideline he still enjoys today. Josh ran his first legitimate charter in June of 1981. The 'bread and butter' of his charter operation during the early days at China Basin was sedate luncheon cruises — with award-winning food — which attracted well-heeled business people. But he soon expanded his offerings,
The August 2006 issue of the West's premier sailing and marine magazine.