How This Wisconsin Sailor Is Spending Her Summer Without Olympics

Stephanie Roble is looking forward to setting sail in Tokyo next summer.


Stephanie Roble’s passion for sailing started at an early age on the waters of tiny Lake Beulah in Walworth County.

But the U.S. Olympic sailing team member encountered choppy conditions at first when her father, a casual weekend sailor, signed up her and her brother for lessons.

“At first, I was pretty scared and intimidated by the sport,” Roble said.   

She credited the Lake Beulah Yacht Club for creating an atmosphere that eased her initial fears of being on the water. 

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“Sailing school was such a fun thing for me and so was being on the water with my friends growing up,” Roble said.

The East Troy Native began sailboat racing at age 7. 

“We had these weekend races on the lake, and I figured out a young age that I really liked competing,” Roble said. 

By the time she became a teenager, Roble started racing in national and international competitions.

“I just loved the challenge of racing and becoming a better sailor and a better athlete,” she said. “That’s led me to where I am today.” 

Those early days on the lake with her family and friends set Roble on a course for a destination few ever reach. In February, in the face of intense competition, Roble and her sailing partner, Chicago native Maggie Shea, together earned spots on the U.S. Olympic team that is scheduled to compete in Tokyo in 2021.  

“We will be representing Team USA at the Olympics next summer,” Roble said, excitedly, during a recent interview from Lake Garda in northern Italy, where she and Shea have temporarily settled to train under the direction of their Italian coach, Giulia Conti. 

They arrived in Italy in July and had to endure a two-week quarantine before returning to the water. They received a special invitation from the Italian Sailing team to join them for training, which is key since there is a ban on U.S. travel to Europe. 

“Being in Europe is a really important part of our season because there are so many teams that are over here,” Roble said. “There is racing happening here in August and September, so for us to be able to come over here and participate in that is really huge for our team.”

Photo courtesy of Stephanie Roble

They plan to remain in Europe until mid-September and have been undergoing weekly COVID-19 testing.

Roble arrived in Italy after a month of intense training in Miami, where she and her fiance, Taylor Canfield, a professional sailor from the U.S. Virgin Islands, make their home.

Although uncertainty remains around the Olympics due to the pandemic, one thing is for sure – Roble and Shea have secured their spot in next summer’s Games. 

Earning a trip to Tokyo came with immense challenges. 

Roble and Shea won the medal race at the 49erFX world championships in Geelong, Australia, in February. With the victory, they captured a bronze medal in the world championships and an all-important spot on the 2020 U.S. Olympic Team.

Roble and Shea trailed two-time Olympian Anna Tobias and her partner, 2016 Olympian Paris Henken, by four spots entering the world championships. The victory in the medal race pulled Roble and Shea into a tie with Tobias and Henken in the U.S. Olympic selection trial process. Roble and Shea earned the berth based on a tiebreaker. 

“The team we were up against was incredibly experienced and talented. Both of them had been to an Olympic Games and one of them has a gold medal,” Roble said.

Securing a spot in the Olympics game down to the last race in the regatta, which was worth double points. 

“Mentally and physically, it was full on,” Roble said. “I’m getting chills just reliving it.”

Photo courtesy of Stephanie Roble

Even after crossing the finish line, Roble wasn’t sure she’d be bound for Tokyo. 

“It took a couple minutes to figure out the results,” Roble said. “The first news we received was that we won a bronze medal at the worlds, which was really exciting.”

Then came the official word that Roble and Shea would be representing the United States at the Olympics. 

“I just instantly started crying tears of joy,” Roble said. “I was overcome with a little bit of relief and so much joy. I was really proud of our team for the performance that we had.”

There are 10 different classes of sailing in the Olympics. Roble and Shea compete in a class known as 49erFX, where it’s just the two of them on a high-performance skiff.

“It’s the fastest boat that women sail in the Olympics,” Roble explained. “Our boat is super fun. It’s really fast. It’s built for high performance. The better athlete you become and the stronger and more agile and more fit that you become, the harder you can sail the boat and push yourself on the racecourse.”

Roble chuckled when she mentioned that the casual fan doesn’t realize what it takes to compete at the highest level in sailing.

“A lot of people traditionally think of sailing as a cruising sport, where you have a glass of wine in one hand and with the other hand, you’re steering the boat,” Roble said. “By no means is that what we are doing.”

In addition to the training on the water, Roble spends countless hours in the gym building strength and overall physical fitness. Mental toughness is also crucial.

“We have to be really sharp in order be successful on a race day,” Roble said. “The speeds we are hitting require us to be really sharp, precise and accurate. Communication is really important. If I do something and Maggie isn’t ready, I can dunk her in the water.”

Shortly after securing their spot on the Olympic Team, the coronavirus pandemic put an immediate halt to training. 

“There were three months where we weren’t able to be on the water at all. That was pretty hard,” Roble said. “Not even having access to a gym for a large portion of that time was pretty frustrating, too. But if there’s one thing that sailing has taught us is there are a lot of things we can’t control. We can’t control the wind, waves or the boats around us. That’s something we’ve been able to bring forward into the whole COVID situation.”

Shea moved to Miami in mid-June to join Roble for training. 

Roble has lived in Miami for about seven years. 

“It’s a good training hub,” she said. “The endless summer conditions are pretty hard to beat and it allows us to maximize time on the water.” 

Roble and Shea have made several trips to the Olympic sailing venue, located in the small town of Enoshima, southwest of Tokyo. 

“It’s a pretty cool little setup because the sailing venue itself is out on an island,” Roble said. “It’s a unique and beautiful venue and it’s known by the locals as a surf town. It almost has like a Hawaii or SoCal feel to it.”

Roble is hopeful that the Tokyo Games will be carried out, in some form, after a year-long postponement.

Photo courtesy of Stephanie Roble

“I’m confident in it. I’m not sure it will look like the games we are all used to seeing,” she said. “Maybe there’s a limit on fans or maybe no fans at all. Our team is going full steam ahead planning as if we are going to Tokyo next July.”

Postponing the Olympics gives Roble and Shea additional time to train, but the delay comes at a huge financial burden to the team. 

“It’s about $340,000 for us to run our campaign for another year, because we pay for all of our own coaching, logistics, flights, housing, everything,” Roble said. “We’re very lucky to have a big network of supporters and sponsors who help us afford this.” 

Roble’s and Shea’s primary sponsor is Kilroy Realty, a Los Angeles-based real estate firm. Support also comes from the Lake Beulah Yacht Club and the Chicago Yacht Club, Shea’s home club.

“I’m really grateful for the support I’ve received from Wisconsin, especially the Lake Beulah community and my family there,” Roble said. 

Roble’s family continues to call Southeast Wisconsin home. Her parents, Nancy and Dale, sill live in the same house where Roble grew up.  

An intense training schedule, along with travel restrictions stemming from the coronavirus pandemic, have limited Roble’s trips back to her hometown. 

“I absolutely love being up there in the summer. With this whole COVID situation, it’s been really hard,” Roble said. “I was really looking forward to going home for the Fourth of July, but that didn’t happen.”

Roble was quick to conjure up memories of her childhood on Lake Beulah.

“It’s a small lake, so the people there are my family,” she said. “I grew up at the Yacht Club with my friends’ parents watching me and my friends running around the club and jumping off the dock into the lake. That’s really where my heart lies and where I fell in love with the sport of sailing.”

Her brother, Brad, lives in Chicago, but returns to Lake Beulah to sail. 

“He’s really good,” Roble said. “He crushes the races there.”

Another area sailor, Sally Barkow, a native of Nashotah who grew up on Pine Lake and competed in the 2008 Summer Olympics in Beijing, is an inspiration for Roble. 

“She was a real trailblazer for women in sailing and still is,” Roble said.

Like Barkow, Roble attended Old Dominion University in Norfolk, Virginia, where she became a three-time All-American sailor.

Joe Skotarzak, 53, is commodore-president of the Lake Beulah Yacht Club. He first became aware of Roble when she was a youngster just making a name for herself in the local sailing community.

“She’s been a rock star since she was a little kid,” Skotarzak said.  

The two formally met about 10 years ago and have sailed together a few times since.

“One of the best days of sailing I’ve ever had is when she and friend crewed for me,” Skotarzak said. “We sailed really hard and just laughed the whole time. It was just a great day.”

Roble’s tenacity as a sailor has impressed Skotarzak. 

“There’s nothing physically imposing about here, yet she’s a frickin’ force of nature,” he said. “When she puts her mind to something, there is no stopping her.”

Photo courtesy of Stephanie Roble

In a community of sailors, Roble has always stood out, Skotarzak said. 

“Clearly, she’s an extraordinary talent,” he said. “The other thing that has always impressed me about Stephanie is that she’s a real person. If you were to happen upon her sitting at a coffee shop and she was sitting at the next table, she’d strike up a conversation with you. She’s the nicest person you’ll ever meet.”

Roble serves as an excellent, and willing, role model for young girls, too, he said.

“When she and I first met I had a daughter who was young,” Skotarzak said. “It’s magical to watch her talk to kids, telling them how to tack their opti.”

Roble’s successful quest to become an Olympian has left Skotarzak with an array of emotions.

“After having paid close attention all these years, it’s a culmination for her and wasn’t even a surprise,” Skotarzak said. “On the other hand, it brings a tear to your eye. It couldn’t happen to a nicer person. As much as she’s achieved, she’s worked hard to give back to the Lake Beulah Yacht Club and the Lake Beulah Sailing School. This is just one corner of her life but there is just no end to how she stays connected. She’s so untouched by all of the success she’s had on the international stage.”



Rich Rovito is a freelance writer for Milwaukee Magazine.