Rolex Big Boat Series 2016: Big Boats, Big Fleets, Big Fun

The West Coast’s premier sailing event serves up a big helping of the best of the sailing lifestyle.

The Rolex Big Boat Series hosted by the St. Francis Yacht Club is the West Coast’s premiere yachting event—on and off the water. The 2016 edition boasted the largest fleet ever: 120 boats in 11 classes including a Mod 70 trimaran, a brand new Pac52, and fast-growing J/70 fleet tuning up for their upcoming World Championships.

rolex big boat series spinnaker parade 2016.

Donkey Jack leaving the way to the finish in the J/105 Class. Photo: Rolex/Daniel Forster.

scott kokka's beautiful audacity, rolex big boat series 2016.

Scott Kokka’s stunning Morris Yachts M52 Audacity. Photo: Kara Hugglestone/Sail Couture.

At Sail Couture, this is one of our favorite regattas of the year because it epitomizes the sailing lifestyle highlighting the gorgeous yachts, skilled sailors, and fabulous parties all against a stunning backdrop that make the San Francisco Bay such an amazing place to live and play.

Big boats and big fleets

There was much anticipation to see how Fox, the first of the new Pac52 class, would perform in her debut event. The Pac52 is similar to the TP52, except that it’s lighter, faster, and boasts more sail area.

victor wilds' pac 52 fax, rolex big boat series 2016.

Victor Wild’s Fox races past the Golden Gate Bridge. Photo: Rolex/Daniel Forster.

pac 52 fox racing in the rolex big boat series 2016.

Pac 52 Fox sailing to Alcatraz. Photo: Rolex/Daniel Forster.

victor wild helms his pac 52 fox in the rolex big boat series 2016.

Owner/skipper Victor Wild helms his Pac 52 Fox. Photo: Kara Hugglestone/Sail Couture.

Skippered by owner Victor Wild of San Diego Fox did not disappoint, handily winning the regatta’s grand prize, the St. Francis Perpetual Trophy, with four firsts in the ORR A class. Three new Pac52s are currently in build and more of boats expected to appear at next year’s RBBS.

tom siebel's mod 70 orion, rolex big boat series 2016.

Tom Siebel’s magnificent Mod 70 Orion. Photo: Rolex/Daniel Forster.

Tom Siebel’s Mod 70 Orion was the biggest boat in one of the largest multihull fleets in recent memory. From the water or from shore, you never forget seeing a Mod 70 in action. “It’s really closer to flying than sailing,” said Tom. And fly she does, reaching speeds of 40 knots. San Francisco is a rather confined pasture for a space-loving thoroughbred like the Mod 70; her crew generally has to tack an average of every five minutes on the course.

j70 class downward leg, rolex big boat series 2016.

Nearly 40 J70s racing downwind. Photo: Rolex/Daniel Forster.

j/70 fleet, rolex big boat series 2016.

The J/70 fleet nearing the finish. Photo: Kara Hugglestone/Sail Couture.

With the Alcatel J/70 World Championships starting this week at StFYC, the J/70s were the biggest little fleet in town with almost 40 boats participating (more than 80 are registered for Worlds). For the top teams, it would be the final test in their run-up to Worlds; for the new boats, it would be their taste of what it’s like to be on an 80-boat line.

On the water

From the first race to the last, it was very much Breeze On. While there were short postponements as the race committee and the fleet waited for the wind to fill in, once it did, it was San Francisco Bay sailing at its best. Saturday was the breeziest with average wind speeds building into the mid-20s and some boats reporting puffs into the 30-knot range. Even on Sunday, which started with dockside and then on-the-water postponements, the breeze filled into the low 20s by the time the last boats were finishing.

melges 32 kuai, rolex big boat series 2016

Team Kaui, right to left: Daniel Thielman (Skipper) Jennifer Canestra (Bow) Mike Wolfs (Tactician), David Lee (Mid Bow) Terre Layton (Pit) Chelsea Simms (Main Trim) being shy, Chad Howard (Mast / Trim), Auric Horneman (Trim) – not pictured.

“What could be better than spending four action packed days on the water with your best friends?” said Jen Canestra, owner of Whitecaps Marine Outfitters, the official green sponsor of the event. Jen raced on the Daniel Thielman’s Melges 32 Kuai.

In typical RBBS style, there was a course list of some 80 possible courses starting from three different race areas using permanent and dropped marks east and west of the Golden Gate. The fleets were given a variety of windward/leeward courses and reaching legs, with most of the boats finishing downwind in front of the clubhouse to the delight of those on shore each afternoon.

“I love the level of competition, the great parties, and the intensity of four days of racing. Although some don’t like the long Bay cruise-style races, it’s a nice change from the simple windward/leewards one normally races in one-design regattas,” said Jay Palace, main trimmer and tactician on David Bailey’s J/105 Akula.

While the race committee, as always, did its best to spread the fleets out, it was crowded on the Bay. Fleets converged as they do upwind and downwind, at mark roundings, and in the finish area. It makes for a sometimes interesting and sometimes frustrating additional dimension of sailboat racing.

farr 40s twisted and blade race in the the rolex big boat series 2016.

Farr 40s Twisted and Blade II race along the San Francisco city front. Photo: Rolex/Daniel Forster.

tony pohl's farr 40 twisted, rolex big boat series 2016.

Tony Pohl’s Farr 40 Twisted tacking. Photo: Rolex/Daniel Forster.

farr 40s twisted and coquille race in the rolex big boat series 2016.

Twisted and Coquille heading to the Golden Gate. Photo: Kara Hugglestone/Sail Couture.

The Farr 40 (known as California 40s in this regatta) Twisted was forced to duck the J/120 Twist at a particularly in opportune time, sending them out of the current relief. (Sail Couture writer and contributor to this piece Jenn Virskus was the spinnaker trimmer on Twisted for this regatta.)

Later that same race, Twisted found themselves mixed up at the upwind mark with three other boats—another J/120, an Express 37, and the Morris 52 Audacity—all of which were different sizes, with different spinnaker setups, trying to sail vastly different courses toward different marks or finishes.

In another more notorious event, as the Farr 40 fleet was rounding Blackaller, an oft-used mark just to the east of Fort Point, they looked up to see the Mod 70 Orion screaming in to make the same rounding. It was an incredibly exciting moment that was caught on video, although the footage shared on social media doesn’t do it justice. From the perspective on Twisted, Orion was so close that it appeared to have actually hit Blade II and narrowly missed Coquille as they were forced to tack in a port/starboard situation.


No doubt every boat out there, save for the J/70s who were kept apart in their own race area in the Berkeley Circle, have similar stories to tell. But while the congestion on the Bay is not always advantageous, it is fun to glance up occasionally from one’s upside down hiking position on the rail to check out how friends are doing in the other fleets.

When the wind came up on Saturday afternoon, the Farr 40s were given a course that included two trips out the gate to Point Diablo. With puffs up to 25 knots swirling around the South Tower, the Twisted crew worked hard to keep their focus on their own boat as other boats rounded up nearby, struck by the infamous South Tower Demon. But when everyone gets back to the dock in the afternoon, the boat’s cleaned up, and they’ve finished their debriefing, it’s a perfect time to grab a beer or a rum drink and talk to all the sailors on all the other boats, friends and foes, to get their take on the day.

j/105 wonder racing in the rolex big boat series 2016,

J/105s Wonder and Moonshine in a downwind duel. Photo: Rolex/Daniel Forster.

“It’s been awesome—fun, fast, windy. It’s everything I expected and more,” said Lori Shink of Port Huron, MI, who joined the J/105 Wonder crew for her first but certainly not last RBBS. “Will definitely be back next year, I love sailing in the Bay!”

“I’ve probably done every Big Boat Series since 1995, with the exception of 2003 when I was at J/World Annapolis,” said Jay, who divides his time between mountain and sea spending winters in Avon, CO, where he teaches skiing at Beaver Creek and Vail, and summer living on his boat in Sausalito where he runs his company Group Experiential Learning (GEL) organizing executive leadership retreats focused on teambuilding though sailing.

“I keep coming back to RBBS because it is the premier sailing event on the West Coast, and I really enjoy that it brings international sailors and friends like Lori from the Midwest to my home waters. It’s great to reconnect with people I’ve sailed with over the years, like America’s Cup sailor Mark Strube [who was sailing on the Custom Farr 52 Zamazaan],” Jay added.

The parties

It just wouldn’t be the Rolex Big Boat Series without the Big Boat parties. Whether it’s fresh cold cups of beer served on the docks, the beautifully catered Rolex Party, or the Mount Gay Rum lawn party, regatta chair Susan Ruhne and her team worked hard to make sure just as much fun was had on land.

rolex big boat series party 2016

Fun, food, fashion at the Rolex Big Boat Series party.

“Rolex and the St. Francis Yacht Club do an amazing job with the event—the sailing is always top notch and the after parties are even better, often being an opportunity to catch up with people that you haven’t seen since the prior RBBS!” said Jen Canestra.

mount gay rum party, rolex big boat series.

Rolex Big Boat Series is also about seeing old and new friends. America’s Cup filmmaker P.J. Panzica greets old friend Jack Palace. Photo: Kara Hugglestone/Sail Couture.

mount gay rum party, rolex big boat series 2016.

Some of the great drink choices at the Mount Gay Rum party. Photo: Kara Hugglestone/Sail Couture

racers lori shink and jay palace, rolex big boat series mount gay rum party.

Lori Shink with sailing buddy Jay Palace. Photo: Kara Hugglestone/Sail Couture.

The Mount Gay party is rather legendary. Guests enjoyed a choice of three signature cocktails, each of which was a themed update to an old standby. The Black and Stormy was made with Mount Gay Black Barrel and ginger beer, the Big Boat Series Classic was Mount Gay Black Barrel Rum and tonic, and the One Two Punch was Mount Gay Rum, simple syrup, lemonade, and fresh Lime Juice.

The Steel Drum Band kept the party swinging and a selection of food trucks provided an assortment of goodies from bacon cheeseburger and pulled pork sliders with a side of bacon-wrapped mac and cheese to wood-fired pizzas. The food truck lines were long, but as many sailors said, “You have to stand somewhere to drink your rum drink!”

Saturday was the official crew dinner night upstairs in the club dining room. That was, incidentally, also the busiest afternoon in the ladies’ showers with the regatta’s hard-working sailor women transforming (after a three-minute shower) into much more polished versions of themselves. The phrase, “Wow! You clean up nice!” was on repeat in the club’s foyer as crewmembers waited for dinner to start.

Upstairs, the St. Francis served Cesar salad, grilled steak and veggies, and a fabulous fruit tarte with fresh ice cream. Now that the Farr 40 and J/105 crews had passed their weigh-ins, everyone was happy to indulge.

The podium

To win Rolex Big Boat Series takes boat speed in all possible conditions and a seasoned crew that’s able to change gears as quickly as the wind shifts (which, okay, may or may not be that quick depending on the year, but you get the idea), not to mention the endurance to give 100% over four grueling days of racing.

J/120 peregrine, rolex big boat series 2016.

David Halliwill’s Peregrine, winner of the J/120 Class.

j/120 peregrine crew, rolex big boat series 2016.

Team Peregrine: Bottom row, left to right: Mark Maymar (Squirrel), Lauren Savett (Assistant squirrel), Randy Smith (Tactician), Greg Felton (Trimmer/ Grinder). Second row: Mike O’Callaghan (Helm), Michael Thornton (Mid Bow), Victor Piltch (forward mid bow), John Verdoia (Spin Trimmer), Chris Davison (Bow). Back row (in line with mast wearing red hats): Tad The Commodore Lacey (Main Trimmer), EJ Rowland (Pit and Crew Boss). Not pictured is owner David Halliwill who is on the East Coast and did not race. Photo: Kara Hugglestone/Sail Couture.

Excellent teamwork was on display throughout the series, particularly amongst the crew of David Halliwill’s J/120 Peregrine, which snapped up their third RBBS win in as many years with five bullets and two seconds in the seven-race series. Hailing from New York City, David is a board member of Oakcliff, the prestigious performance sailing school.

Michael O’Callahan attributes Peregrine’s success to a long sailing partnership—many of them have been sailing together since their teens. “Tad Lacy who knows how to make a boat go fast and [crew boss] E.J. Roland put together the team and all the tools I need to put the boat on course,” said Michael, who’s been at the helm of Peregrine for the past three years.

In the multihull class, Orion took the top prize finishing every race in the top three, including four firsts. Jerome Ternynck’s Extreme 40 Smart Recruiters was second.

c7c 30 extreme2, rolex big boat series 2016.

C&C 30 Extreme2 fighting the chop. Photo: Rolex/Daniel Forster.

c7c 30 etreme2, rolex big boat series 2016.

Extreme2 leading the C&C 30 fleet. Photo: Rolex/Daniel Forster.

Other notable wins, with multiple 1sts include Dan Cheresh of Saugatuk, MI, who in the C&C 30 class with Extreme2 posted six firsts and one second for a 10-point win over Steve Stroub’s Tiburon.

express 37 golden moon, rolex big boat series 2016.

Teamwork aboard Kame Richard’s Express 37 Golden Moon. Photo: Rolex/Daniel Forster.

Kame Richard’s (Alameda, CA) Express 37 Golden Moon easily topped their class with six firsts. Having wrapped up the regatta, he sat out the final race, which allowed Jack Peurach’s Elan to score a race win. Richards, who has raced the regatta more than 30 times said, “My secret is that I’m scared to death of failure; don’t screw it up.”

soto 30 gentoo, winner of the sportboat class, rolex big boat series 2016.

Paul Dorsey’s Soto 30 Gentoo and her iconic penguin spinnaker. Photo: Rolex/Daniel Forster.

Paul Dorsey’s (San Francisco, Calif.) aptly named Soto 30 Gentoo (a type of penguin that is also the fastest diving bird; it can reach speeds up to 22 mph) won the PHRF Sportboat class with four consecutive firsts in the final races over Kuai.

godot leads the j/105 fleet against the san francisco skyline, rolex big boat series 2016.

Godot leading the J105 Fleet with San Francisco Skyline as backdrop. Photo: Rolex/Daniel Forster.

Julian Fernandez Neckelmann’s J/70  Flojito Y Cooperando took first in the largest class and Phillip Laby’s Godot (Oakland, Calif.) won the the J/105 Class, the second largest in the regatta, just one point over Ryan Simmon’s Blackhawk.

rolex big boat series prize giving, including rolex stainless steel submariner date watches

The prizes! Photo: Rolex/Daniel Forster.

rolex big boat series 2016 winners

The Winners’ Circle with their new Rolex Stainless Steel Submariners. Left to right: Victor Wild (Pac 52 Fox in ORR A); Tim Fuller (J/125 Resolute in ORR B); Philip Laby (J/105 Godot); Julian Fernandez Neckelmann (J/70 Flojito y Cooperando); Michael Shlens (California 40 Blade II); and Scott Kokka (Morris 52 Audacity in ORR C). Photo: Rolex/Daniel Forster.

The memories

With RBBS 2016 all packed up for the year, we’re taken back to a few of our favorite memories: Topsy Turvy’s playful smiley face spinner spinnaker emerging from the San Francisco fog on day one, sipping a Big Boat Classic while meeting old and new friends at the Mount Gay party, the Orion mixing it up with just about every fleet on the water, and of course the dramatic spinnaker finish each day against the backdrop of the Golden Gate.

topsy turvy's spinnaker always makes us smile, rolex big boat series 2016.

Topsy Turvy’s smiling spinnaker emerging from the San Francisco fog. Photo: Kara Hugglestone/Sail Couture.

mod 70 orion mixing it up with other boats, rolex big boat series 2016.

Mod 70 Orion cutting through the fleet. Photos: far left Kara Hugglestone/Sail Couture, all others Rolex/Daniel Forster.

the j/105 fleet, rolex big boat series 2016.

A dramatic finish for the J/105 fleet. Photo: Rolex/Daniel Forster.

There is majesty to the whole experience whether as a participant, race committee volunteer or spectator, a regatta not to be missed. The 2017 edition of the Rolex Big Boat Series is tentatively scheduled for September 13–16—we’ll look forward to seeing you there!

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