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

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.

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.

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.

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.

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.”

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.

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.

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

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.

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

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.

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.

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.

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