Stew Whitney Fair used to drink. Living in the art and entertainment scene in New York and Los Angeles, partying was a big part of her life.
When she got into yachting a few years ago, she fit right in, always ready for a night out with her mates.
One night camping in Utah with her best friend, they decided to ride bicycles across the United States. Never mind that neither one of them owned a bike or that her friend, Promise, had never even learned how to ride one.
“It was nothing more than beers at a campfire and my friend said let’s do this,” said Fair, a tall, slender woman with bright eyes and a quick smile. “I didn’t put a whole lot of thought into it. It wasn’t ‘why?’; it was ‘why not?’.”
Then in October of 2011, freshly 30 and with this adventure looming in her future, she stopped drinking.
“With my free time, I was always going out,” she said. “It wasn’t fun anymore, drinking, cutting loose. I needed a lifestyle change.”
In yachting just a year, she left the 88-foot Westport M/Y Seas the Moment and flew to Las Vegas the following May. Two weeks of training with Promise and they flew to Oregon to begin a summer on two wheels, riding the TransAmerica Bicycle Trail from Astoria, Ore., to Yorktown, Va., 4,233 miles. It took them 90 days.
Fair said she faced a lot of resistance from family and friends. Though her parents supported the ride, others told her she was crazy. “You’re not a cyclist,” they’d say. “You’re not an athlete. What makes you think you can do this?”
“I kept thinking ‘I’m going to do this; you’re just adding fuel to the fire’,” she said. “It might take us five or six months, but we’re going to do it.”
Finally, she asked a guy in her bike shop in New York if he thought she was crazy.
“Absolutely not,” he told her. “Anyone can do it. Maybe you only ride 20 miles or 40 miles a day, but you can do it.”
After that, the trip was a go.
“I’m an extremist,” Fair admitted. “If I’m going to ride my bike, I’m not going to do it across one state, I’m going across the country. Either I drink or I don’t drink.
“Sometimes I wish I had more balance, but if I did, I wouldn’t have done some amazing things.”
While the extreme bike-riding adventure fits her personality, having done it has given her back much more than it cost in blisters and sores.
“This trip changed my life,” she said, tears welling in her eyes. “I proved to myself that I can do anything I set my mind to. … Why waste time thinking about it? If you have a goal, put it in your mind, visualize it and make it happen. It’s just that simple.”
And coupled with her decision to stop drinking, it’s also powerful stuff.
“I don’t think I would have done this trip if I hadn’t stopped drinking.”
Fair kept a detailed journal of her trip, complete with photos and videos. She shared her funny, often irreverent blog posts with family and friends at MyFirstSoberSummer.com. She has recently made her posts live, sharing one a day with followers of the CrazyGuyOnABike.com site, where it is the featured blog this week.
Back in yachting now and solo stew on the 90-foot Burger M/Y Current Issue in the Yacht & Brokerage Show, she’s not sure what the future holds. And she likes it that way.
“I’ve had a storage unit in New York for the past 10 years while I’ve been traveling,” she said. “People say how can you do that? But to me, I see them and say how can you do that?”
She plans to visit Australia and wants to hike the Appalachian Trail. This fall, she hopes to take acting classes in New York, improv and comedy. Her dream in life is to work on Saturday Night Live.
“Why not?” she said with a smile. “Every palm reader and psychic and fortune teller I’ve ever talked to told me I’ll probably figure it out later in life, but that’s OK because I’m really enjoying the ride.”
Lucy Chabot Reed is editor of The Triton. Comments are welcome at