SAN FRANCISCO—Anytime Paul Cayard gets homesick for sailing a Volvo 70 on the edge in the Southern Ocean he can step out for a similar rush on an 18-foot skiff on his hometown San Francisco Bay.

“I actually did sail one of these here back in ’79 or ’80,” Cayard said as he chatted with competitors on Crissy Field after Day 2 of the 18′ Skiff International Regatta. “It was wild.”

Cayard stopped by at the prodding of his son Danny, 16, currently a youth sailor who like most competitors his age is more attracted to the wild side of sailing than to the sedate Star keelboats his father has sailed most of his life.

That’s the direction a teenage peer, Samuel (Shark) Kahn, 17, has taken, not only with his Olympic aspirations in the 49er skiff but early success in the 18s, where he swapped first-place finishes with veteran Howard Hamlin Wednesday on another blustery day on the Bay.

Hamlin, from Long Beach, Calif., won the first race and followed Kahn in the second race for a 1-2 day that moved him past Australia’s John Winning (2-3) into first place overall with four races remaining. Hamlin has eight points, Winning nine, and Kahn is right there with 10 after discarding an earlier fifth place when the first of two discards kicked in Thursday.

Friday’s action includes the 6 o’clock Bridge to Bridge classic—five miles from the Golden Gate to the Bay Bridge, with a flock of windsurfers and kite boarders joining the fun. The 18s will tune up with one of their usual nine-mile buoy races at 4 p.m., three times around a 1 1/2-mile long windward-leeward course along the bay front.

Two boats will be sailing with their 10-foot-long bowsprits repaired or replaced. Grant Rollerson’s DeLonghi and Peter Barton’s West Marine both limped back to the beach during the second race after their extensions snapped.

If the brisk winds continue—during Thursday’s racing it peaked at 32 knots near Angel Island on the north side of the course and 24 at the leeward mark—the Bridge to Bridge should be a spectacle.

Kahn’s Pegasus Black craft had capsized three times in the first two days but Paul Allen, Kahn’s forward crew, figured they’ve now found the secret to success.

“Keeping this big black stick in the air,” he said, referring to the mast. “Once you get in the lead, if you stay upright you usually stay there.”

Kahn followed Hamlin and Winning in the first race but blew off the starting line in the second, soon tacked to cross the fleet on port tack and never looked back. Allen, who trims the spinnaker, played a key role.

“Downwind you really feel the pressure of the spinnaker,” he said. “You’re the throttle guy. If it gets scary I pull the kite in to stall it and that slows the boat down a little bit. It feels like your arms have been pulled off by the end of the day, but I like being up front. It’s a good view from up there.”

Hamlin had his own “18 moment.” After running away to finish 2 minutes 12 seconds ahead of Winning in the first race, he had to scramble for second place in the second race.

“We had a nuclear puff on the second [downwind] run and just blew by people,” he said. I was doing something I’d never done before: holding the tiller with two hands.”

Almost like the Southern Ocean.

This is one of the class’s three major events each year, along with the JJ Giltinan World Trophy Championship in Sydney and the European champion held last June on Lake Garda in Italy.