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Sail the City: Become an Urban Skipper—All the Cool Kids Are Doing It!

September 17, 2015

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.

Sunset over Alcatraz (Photo: iStock/Thinkstock)

My goal: to be a safe and serious sailor. My dream: to be ripping along on a beam reach at seven knots on a starboard tack, get into a traffic situation with an approaching boat, have all eyes turn to me for instructions, and then say calmly, “Hold your course. We are the stand-on vessel, but if they don’t tack in 10 seconds let’s go ahead and bear away.” I grew up watching my dad roll like that, and I want that. (And if that sounds like Greek to you, don’t worry, it did to me at first, too.)

A month into my training at OCSC, I haven’t reached my father’s level of badassery just yet, but I’m getting there. Like a zen koan, the process has its own rewards — not to mention being out-and-out fun. Whether sailing certification is your goal, or you just want to get out on San Francisco Bay for the day, there’s nothing quite like the satisfaction you’ll feel harnessing the wind to explore obvious (though awe-inspiring) landmarks like the Golden Gate Bridge as well as more hidden local treasures like Angel Island, Sausalito, and Clipper Cove. Being on a boat means experiencing a city in a way few get to, and damn if it isn’t addicting.

If you’ve got the itch, too, here’s where to raise anchor across America, where big cities offer sailors of all abilities big-time urban sailing adventures.

A new perspective on New York City (Photo: iStock/Thinkstock)


San Francisco

Olympic Circle Sailing Club: Servicing San Francisco’s next wave of sailors since 1979.


Offshore Adventures: Captain Rick’s latest passion is racing, so you can speed past Chicago’s skyline or enjoy it leisurely at sunset.

New York City

Manhattan Sailing School: NYC’s largest sailing school gets you up close and personal with Lady Liberty in lessons off downtown Manhattan.

Washington, D.C.

Mariner Sailing School: Belle Haven’s mostly quiet, calm waters are especially suited for newbies

Los Angeles

South Bay Sailing: Charters include champagne cruises and jaunts to Catalina Island. 


Windworks Sailing: Plying the waters of Puget Sound, just six miles north of Seattle, since 1992.

Dave George is Director of Talent Communications at Yahoo. He lives in San Francisco where he sails, surfs, makes videos, and performs stand up comedy.