The Headington Family


“I grew up in Greenwich, CT, and so did my husband, Geoff, and it’s just such a totally different lifestyle out here,” Kerry Headington told us as we hung out one windy afternoon at San Francisco’s Crissy Field. “You can’t help but enjoy every day. I remember when I was growing up in Greenwich it would rain a lot, and whenever it wasn’t raining, my mom would always tell us ‘go outside, go outside.’ So when I first moved to CA, I would go outside every day because I had my mom’s voice in my ear. Out here people don’t ask what you do for work, they want to know what sports you’re into, how you’re having fun.”

We’ve known Geoff and Kerry Headington for a long time. Shep and Geoff went to high school together, and their wives did as well. But soon after graduating, they bid farewell to New England and started to make their way out west.

“Kerry went to grad school at Stanford and was living out here,” Geoff told us. “I met up with her at a wedding back in Greenwich and we hit it off. She was living in San Francisco and learning how to windsurf and going skiing in Tahoe, and I thought, ‘That sounds pretty cool, and you’re pretty cool, maybe I’ll go out for a visit.’ I came out on a beautiful weekend in 1998 and I was blown away. Kerry was the catalyst, but after I came out here, I was done. So I moved.”

When Geoff moved out to CA to meet Kerry, he was already a die-hard windsurfer. But it was one afternoon, when he saw a guy kiteboarding out on the Bay, that started to change things for him. “When I moved to San Francisco in 1999 kiting was just starting to get going,” he told us. “I had been big into windsurfing, and kiteboarding is like windsurfing in three dimensions. You have back and forth, but you also have up and down, with massive jumps. That really drew me into it.”

Geoff jumped into kiteboarding with both feet, and soon he and his fellow kiteboarders—many of whom joined us that afternoon at Crissy Field—started to get organized, and get noticed. “We began racing in 2005, and in the summer of 2006 we had these guys from Europe showing up at our beach and they were saying, ‘We want to train with you guys,’ and we were like, ‘Wait, what do you mean, what’s going on?’” Geoff told us with a laugh. “And they told us that we had figured out this new sport, and our racing had excited everyone in Europe. So all of a sudden we had people from all over the globe showing up, and my friends and I started talking and we thought, ‘We need to have a regatta.’”

By this point in time, it wasn’t just the Europeans that were paying attention to Geoff and his friends, the local sailors in San Francisco were interested in getting in on the action, too. “The St. Francis Yacht Club was onto us and they were helping us out with racing,” Geoff told us. “So when we said we wanted to have a regatta, they said ‘You’re using wind, you’re using kites—this is a sailing sport, and we’ll put assets and buoys on the water and we’ll create something here.’ We organized and put on a North American Championship, and people from around the globe showed up—South Americans, Europeans, some Australians. Then the next year we thought, ‘We’ve got to do this again, why don’t we have the Worlds?’ So we hosted the first ever World Championship Kiteboard race competition.” And from there, they were off to the races.

“It might sound surprising, but after 20 years I’m still learning every time I go out on the water,” Geoff told us. “And that’s what keeps me going back.”

“I’m really just trying to keep this going. If we can keep our kids happy, near the beach and on the water, we should be able to keep our active lifestyle going for a long time.”

— Kerry

Now living happily across the Bay in Tiburon with their two young sons, Morgan and Kyle, Geoff and Kerry keep living the Good Life—staying active, getting outside and spending time with their friends and family. “I never really thought about the vineyard vines motto—Every day should feel this good,” Kerry reflected after a day on the water. “I thought, ‘Well, that’s cool for people who can get out there all the time.’ But it’s true. Maybe you can’t get out there all the time, but you need to try and have an appreciation for living life to the fullest. Getting out, being on the water, being outside, experiencing nature. It’s really important.”

“It’s not just that it’s fun to be out there, being in nature and going fast, it’s important to learn something each time. You go back to the parking lot and you talk to someone and you describe what you were feeling and what happened, the timing or what trick you learned that will help you to replicate your last tack or your last jibe. That’s the key to everything, as long as you continue to learn, you’ll keep coming back.” — Geoff
boy manning the wheel of a sailboat
kerry and geoff headington
geoff headington carrying his kiteboard into the water