© Tim Wilkes

Rob Gilliland goes commando on the bow of Chip Schwartz's Viper 640 Timi's Sun. For more photos by Tim Wilkes, click here.

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Rob Gilliland has rediscovered sailing. He and I grew up racing together out of the Cleveland Yachting Club; the highlight of each summer was when we dragged a borrowed Thistle up to the Lake Erie Islands to compete at the Inter-Lake Yachting Association's Junior Bay Week regatta. But the pursuit of higher education took Gilliland inland, where opportunities for racing were few and far between.

The computer-vision engineer struck gold when he moved to Boston earlier this year. Through craigslist, he found a roommate, Mike Hoydis, an experienced small-boat sailor who never passes up the opportunity to race at Boston's Community Boating or in the Marblehead Racing Association's summer series.

Here at the Sperry Top-Sider Marblehead NOOD, Hoydis is racing aboard Fletcher Boland's Viper 640 Business Time; he helped find Gilliland a ride aboard Chip Schwartz's Viper 640 Timi's Sun.

The racing is a little different this time around, says Gilliland. "It's like riding a bike," he says. "Or, it would be like riding a bike if I was sailing the same kind of boat. I have to learn the idiosyncrasies of the Viper, which is not really like a Laser or a Thistle or anything I'd sailed before.

"The boat's set up a lot better [than the Thistle]," continues the 30-year-old. "There's no centerboard trunk in your way, there's no self-bailer cutting up your feet, and when you tack you're not crawling through this small triangle between the centerboard and the vang. When I first sailed the Viper, they were like, 'Pull on the gnav [inverted boom vang],' and I was like, 'Huh?' The asymmetrical is a new thing for me, too. And so is current. I'm not used to sailing on the ocean."

Mike Hoydis (left) has helped his new roommate, Rob Gilliland, plug back into the sport of sailing.

Gilliland has enjoyed an up-close view of the ocean this weekend, since a complication with the bowsprit on Timi's Sun has required the nimble bowman to make frequent trips to the foredeck. This is a dude who barely broke a sweat over three months on the Appalacian Trail, however, so a little seawater's not going to deter him. "It's been fun getting back into sailing," he says. "You get to be out on the water and [points to the view of the Marblehead mooring field from the lawn of Corinthian YC] you get to see nice stuff. Most of the time I'm inland, dealing with traffic and computer screens. So yeah, this is pretty cool."

Moise Solomon's 3 Grins sits atop the 19-boat Viper 640 class with a 3-point lead over Ben Steinberg's Mongoose. For complete results, click here. For photos by Tim Wilkes, click here.