The Rolex Big Boat Series is more than the West Coast’s premiere sailing event. It’s on the water magic with exceptional boats, sailors and experiences. Like the city itself, it attracts the best and the brightest.

“San Francisco’s adventurous, innovative and risk-taking spirit is reflected in the sailing scene at the Rolex regatta,” said Tom Siebel, chairman and CEO of C3 Energy and owner of the amazing Mod 70 trimaran, Orion.

“The Bay is a very exciting place and could be described as the ‘Black Diamond Run’ of sailing venues; it’s challenging with high winds and tricky currents and tides.”

It’s this challenge that attracts boats from around the world, including one of the most famous of all big boats, the 78’ Sparkman and Stephens designed Kialoa III. The yacht accumulated more sailing trophies than just about any other campaign, including an elapsed time record in a downwind Sydney Hobart Race that was held for 21 years.

Kialoa III was recently bought by the K3 Foundation, a syndicate of enthusiasts in Monaco that restored her to revisit many of the races that made the boat so legendary.

TP 52 BUD and Patches, of San Diego and Mexico respectively, and DK 46 Boomerang of Hawaii among others, answered the call this year.

This, the 51^st edition of the Rolex Big Boat Series, also played host to the J/105 North American Championship. Teams came from as far as New York, Texas and even Santiago, Chile, 27 boats in all.

Along with great sailing action there were also moments of sheer beauty. The sport of sailing a perfect match for San Francisco’s natural beauty and iconic landmarks.

The first day of racing was uncharacteristically warm for San Francisco and looked a little ominous with clouds and rainy drizzle but gave way to a lovely afternoon of big breeze and world-class racing.

There was beer après racing and then the Rolex party with yummy nibbles and later a dance band.

Team spirit abounded; the crew from J/111 Bad Dog sported temporary tattoos.

Day two brought more heat and an immense flood tide and fortunately later in the day, a steady a nice 15 knot breeze.

As everyone learned during the 34th America’s Cup here, San Francisco is a natural amphitheatre for sailing. It did not disappoint when viewed from the water, shore, bridge or even Pacific Heights roof deck.

Mount Gay Rum famous party followed, with their equally famous rum punch and yummy gourmet food truck fare, everything from Bacon Bacon to Kara’s Cupcakes.

The wind filled in the afternoon after a long delay on Day 3, Saturday. Three-fourths through the day racers were rewarded with big wind.

It was great to see some of San Francisco’s more iconic boats, sporting some beautiful ‘spinnaker couture.’ The majestic St. Francis Yacht Club is such a perfect location, with boats often finishing on a kite run in front of the club.

There was lots of cool Rolex Big Boat Series gear this year, from Gill and Helly Hansen. Shannon Ryan who is J/105 fleet captain and co-owner/skipper of Donkey Jack modeled several of the selections for us, which can still be ordered through the Coral Reef Sailing Apparel site.

Day 4 proved challenging, with little to no wind. While most hit the bar for the football game or enjoyed an al fresco lunch, the marina was particularly quiet, except for a few. Namely the Melges 24 Looper that did some boat prep and J/105 Perseverance crew who decided to catch some rays.

As the postponement wore on I chatted with the charming Patrick Perigaud, bowman on Express 37 Phat Jack. Patrick said he views the series as a staycation, but a bit of a challenging one this year. It wasn’t just for lack of wind.

“We’re sailing one person short as the mast trimmer twisted his knee the first day and are now 300 lbs. lighter than the limit. It’s frustrating as the boat has new sails and bottom and will never go faster.” But it’s been fun, yes? He laughed, smiled and joked as any serious racer would, “Who cares about fun?”

Since no wind materialized, racing was abandoned and it was time to award the St. Francis Yacht Club’s six historically significant perpetual trophies – and the Rolex Oyster Perpetual Submariner timepieces awarded with them.

Victor Wild of San Diego won the ORR A class and the St. Francis Trophy with his TP 52 BUD. Graciously he said, “I never expected to do this well… This is a place of excellence. The best of the best: venue, club, racers.”

He continued, “Excellence is the rarest thing in the world; we came up here to find it and we did.”

Victor credited the crew with the win, “Most of the crew are amateurs, but loyal and they have gotten better and better. There was a lot of practice – 39 days of practice – and we put together an amazing team and we were very lucky.” The crew enjoyed their RBBS experience.

“San Francisco is an amazing venue. We had the length of the course to have the boat get up and go. It really showed the first day. The TP 62 gets up on a plane and really separates herself from the other boats,” said BUD bowman David George.

Sy Kleinman’s Schumacher 54 Swiftsure, sailing in ORR B lived up to her name besting challenges by the iconic Kialoa III and DK 46 Boomerang. A spry 94-year-old Sy joked that he was in a wheel chair because his doctor had insisted he stop kicking his crew with his foot as he accepted the City of San Francisco Trophy.

Although Sy no longer races aboard Swiftsure II, his passion for the sport and RBBS was obvious. He shared how much he enjoyed watching his “old friend” Kioloa III this year and recalled the days when 80′ and 90′ boats raced the series. Sy said he may bring out the ‘old lady’ next year, ‘Big Blue’ – the original Swiftsure.

Peter Krueger’s J/125 Double Trouble won Atlantic Perpetual Trophy in the HPR Division –  thus his third Rolex. Peter modeled his new watch along with it’s new siblings.

“I’m lucky enough to be able to drive this boat with this crew,” Peter said. Indeed, boat captain Andy McCormick and crew prepared well and it showed.

Jib and spin trimmer Tim Cordrey said, “We took it pretty seriously, training multiple weekends with a coach leading up to the series. Our tactician Jeff Madrigali did great starts and tactics. It’s a good group and it’s always good to win!”

Pleased with the outcome, team Double Trouble is looking forward to an exciting new challenge, the Conch Republic Cup. It’s actually the eighth edition of Quantum Key West Race Week– Cuba Race Week, now including a 90 nautical mile race to Cuba.

The Richard Rheem Pepetual Trophy for the J/120 class went to David Halliwell’s Peregrine for the second year in a row. It was a hard-fought victory though as they won over J/120 Chance by just one point.

“Racing against Chance, my heart was in my throat at every tack,” David said. “They were always right there, and there was never a moment when we weren’t thinking this wasn’t going to happen our way.”

Chance is formidable, recently winning the J/Fest J/120 class here.

Like Peregrine, Rob Theis’ J/111 Aelous also won her second consecutive RBBS and thus the Keefe Kilborne Trophy.

“It’s twice as hard to win twice in a row, it was a tough race out there.” Rob Theis said. “The competition was fierce, we were fortunate to have a good team, that’s what it’s all about… the team, not the individual,” he said.

“It was a light one, beautiful weather, but not what you would expect for San Francisco,” said Ryan Kern, spinnaker trimmer on Aelous. “We knew there was a chance of not getting any races in on Sunday and that we had to make sure that we made every race count.  We wanted to make sure every effort was made to stay consistent.”

Shawn Bennett’s Jose Cuervo won the Commodore’s Cup for the largest one design series, also doubling as the J/105 North Americans this year.

“Winning means a lot to us, because we’ve tried a few times at the North Americans and have fallen short of winning a few times at the Rolex Big Boat Series,” Shawn said. “It’s two things in one: checking boxes that weren’t we successful in checked in the past.” As for winning the Rolex watch for his efforts, “Hands down, it’s the nicest trophy I’ve ever won.”

Five additional victors were named in classes for Melges 24 (Doug Wilhelm, Wilco), Express 37 (Mark Dowdy, Eclipse), PHRF Sportboat (Gary Redelberger, Racer X), Multihull (Randy Miller, Miller Racing) and ORR C (Wayne Koide, Encore).

Kara Hugglestone is a San Francisco-based branding professional, accessory designer, sailor and traveler. When time permits, she also indulges in her passion for things classic: cars, movies, wine and fashion. You can follow her on Twitter and Instagram at @gallerykara.