Rolex Big Boat Series: A Regatta 50 Years in the Making

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There are many reasons to love the Rolex Big Boat Series, which celebrated its 50th Anniversary this year.

The caliber of sailors and boats, the array of classes, the sheer beauty of sails against San Francisco’s landmark backdrops; it’s a regatta not to be missed.


Farr 40s approaching the Golden Gate Bridge in a bit of San Francisco fog, photo by: Sail Couture


Farr 40s Groovederci, Enfant Terrible and Plenty racing by Alcatraz, photo by: Rolex / Daniel Forster


The Farr 40 Class racing past the San Francisco city front, photo by: Rolex / Daniel Forster


Getting a sense for the immenseness of Tom Siebel’s Mod 70 Orion when next to Shadow, Peter Stoneberg’s ProSail40… photo by: Rolex / Daniel Forster

The diversity of boats, with everything from 23’ J/70s to the massive 70’ Mod70 Orion multihull, has something to interest everyone. You really haven’t lived until you’ve seen the Orion in action, coming at you full throttle.


Andy Costello’s winning J/70 team, photo by: Rolex / Daniel Forster

As the West Coast’s premiere sailing regatta it attracts many world-class sailors, including Paul Cayard, who sailed on Any Costello’s J/70 Double Trouble and Terry Hutchinson, who sailed on Alex Roepers’ Farr 40 Plenty. Not too surprisingly both boats took first place in their class.


The Farr 40 fleet, photo by Sail Couture

This year the Farr 40 class was particularly robust, boasting a 15-strong international fleet. Their World Championship is here next month and many did the Rolex Big Boat Series in preparation.


Groovederci’s Deneen and John Demourkas with Zephyr and Mistral, photo by Sail Couture

A personal favorite is Deneen and John Demourkas’ Groovederci Racing. This team has style, from their moves on the course, to their lipstick kiss spinnaker, to their “Groovederci Style” Tumblr – full of gorgeous sailing, fashion and wine images.

It was a shared passion for sailing that brought Deneen and John together and has continued through their marriage.

What does Deneen do when not sailing? “Planning for the next race,” she replied. That planning pays off. Groovederci got third in their class.


Farr 40 Voodoo Chile (Corinthian), photo by: Rolex / Daniel Forster

There is a lot of passion in the Farr 40s. A similar sentiment was echoed by David Chapman of Voodoo Chile, an Australian entry, he replied when not sailing he’s “thinking about it.”


Voodoo Chile’s David Chapman and Phil Armstrong. David is professional sailor/tactician and Phil trimmer and full time accountant, photo by: Sail Couture

David, who is a professional sailor, divides his time between Sydney and the Isle of Wight. It was his first time sailing San Francisco and he’s a fan now, at least for the wind, maybe not as much the tides he said.


Aeolus and Madmen, photo by: Rolex / Daniel Forster

Locally, the J/111 Madmen made splash their first outing in the Big Boat Series, securing a second in their class. Only one point separated the winner, Rob Theis’ Aeolus.


Madmen and her iconic martini spinnaker, photo by: Sail Couture

The iconic Madmen kite, or spinnaker, and the boat name, well, works so well on so many levels for sailors, doesn’t it?


J/111 Madmen skipper Dorian McKelvy, photo by: Sail Couture

The very fast J/105 Blackhawk returned to the Big Boat Series and was rewarded with a second in the class. Unlike some other classes, which allow one or more professionals aboard, the J/105 fleet allows only amateurs to race.

This year owner Scooter Simmons’ son Ryan skippered and he recruited friends to crew. Jon Rosen is one of those friends who joined Blackhawk this year, and what a year they’ve had.


Jon Rosen has enjoyed his first year on J/105 Blackhawk, photo by: Sail Couture

“It’s been lovely sailing with friends and doing well. Gosh, we’ve had fun!” said Jon.


J/105 Team Walloping Swede, left to right: Alex Kent, Theresa Brandner-Allen (skipper), Michael Irish, Patti Johnson, Andrea Peiro, and Jeannet Daroosh, photo by: Sail Couture

Another J/105 having fun is the female-skippered Walloping Swede. Teresa Brandner-Allen has been sailing 10 years, first in partnerships. Always assigned to the bow and wanting to move back, she realized she’d need to buy a boat to drive – so she did. Teresa enjoys challenging perceptions.


J/105 Walloping Swede skipper Theresa Brandner-Allen, photo by: Sail Couture

With a high-pressure career, Teresa races for relaxation and actually raced until she was 8 ½ months pregnant.

“I want to pass on a long a legacy of the woman racer model to my daughter,” Teresa said. She’s started an Optimist Dinghy fund for her daughter and it’s off to a nice start with two 20 pound notes from English friends.


The Melges 24 Posse crew, left to right: Rajat Dutta, Ana Ferriera, Anna Alderkamp and Sallie Lang and Jan Crosbie-Taylor, co-skippers, photo by: Sail Couture

While Theresa’s crew is half male, half female, the other female-skippered boat in the regatta has just one man. Posse, co-skippered by Sallie Lang and Jan Crosbie-Taylor had a particularly eventful regatta. Their Melges 24, was dismasted the first day.

With some quick action and some help from a fleet member who had a spare mast, they started working on the boat early on Friday and were good to go by Race 2.

Sallie and Jan actually live across the street from one another, which makes the partnership much easier and actually inspired the boat’s name. It’s Posse after the block party dinners the neighbors enjoy so much.

Isn’t that what the sailing lifestyle is about? Enjoying life on and off the water.

The lifestyle extends beyond the racers of course, support is key too. While taking a break from the water, I met some especially charming Chance supporters on the St. Francis Yacht Club Observation Deck. Later, I ran into the team as well. Chance got a second in the J/120 division.


Chance supporters on the St. Francis YC Observation Deck, left to right: Skylee and Hadley Gingo and Kate Ross, photo by: Sail Couture


Some of Team Chance left to right: Aaron Elder, Sean Ross, David Krausz, Michael Redmond, and Matt Gingo – all of whom have been racing on Chance for more ten years, photo by: Sail Couture


Barry Lewis’ J/120 Chance, photo by: Rolex / Daniel Forster

Looking forward to the next 50 years of the Rolex Big Boat Series!

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