Sail the City: Become an Urban Skipper—All the Cool Kids Are Doing It!
Riding the winds of San Francisco Bay (Photo: iStock/Thinkstock)
When you think about visiting America’s big cities — San Francisco, New York City, Chicago — you think skyscrapers, not sailing. But our most populous cities were established around deep-water ports, and sailing schools and charter businesses continue to thrive.
Imagine this scene: rafting up with 10 other boats 100 yards from AT&T Park while the San Francisco Giants play ball. That was enough to get me setting a course straight for the water.
My goal was not just to charter a boat with a licensed skipper but to get certified to “bareboat charter” (take a boat out on my own with my own crew). Given San Francisco Bay has some of the most exciting yet challenging sailing conditions in the world — consistently strong winds, big waves, fierce currents, rocky shores, 1000-foot-long freighters, and plenty of fog — I would need some serious training.
Exciting — yet challenging — conditions for urban sailing (Photo: iStock/Thinkstock)
My first stop was Olympic Circle Sailing Club in Berkeley, just a short drive across the Bay Bridge. Around since 1979 it’s widely regarded as one of the best sailing schools in the country, offering yacht charters (bareboat or skippered) and a wide array of social events, from their popular Wednesday night sails to free monthly barbecues. OCSC makes it easy — and safe — to experience the Bay’s challenging waters whether you’re an old salt or a complete lubber who doesn’t know a halyard from a sheet.
For me, I was somewhere in between. My father was the paragon of the quiet, confident U.S. Navy-trained seaman, and we grew up sailing off the East Coast on his 40-foot Island Packet. But by “we” I mean “he” — I spent most of my time underway either goofing off or fighting with four brothers and a sister, my experience relegated to turning the wheel and pulling the line until he told me to stop. Hardly the training I needed to skipper a boat around the rocky hazards of Alcatraz Island where a smooth-as-a-lake, light-winded day can turn into a serious blow in an instant.
So at 44, I was ready to learn. OCSC’s 50-boat fleet is manned by 40 instructors who have a reputation for being fun, friendly, and absolutely willing to put in the time until you feel competent and safe — and absolutely unwilling to sign off on your training until they are sure you are, too.