Sailing Story: Claire DeDeckere

Claire’s first year of sailing doesn’t look like that of many first time sailors. In one sailing season in the Virgin Islands, she had racked up more hours on a sailboat than some hobby sailors do in a lifetime. 

“I was just kind of blown away,” Claire said. “The amount of stuff we can pack in with the guests is crazy.”

Claire spent the 2025 sailing season as first mate for her boyfriend, Captain Jalil, with Go Sail Virgin Islands. 

“Those first couple weeks it was pretty impressive realizing how much I was retaining,” she said. “By the end of the season I had students commenting– you’ve only been doing this since November?! It seems like you know so much!”

And she was just as impressed with the students as they were with her. 

“I don’t know what it is about Go Sail customers. Everyone who comes aboard the boat is ready to learn, cordial and kind to each other,” Claire said. “By the end of the charter people are exchanging phone numbers and want to go sailing with each other again.”

Her love of sailing grew along with the students and now, Claire is excited to continue her sailing journey into the Bahamas. In December, she will be joining a crew of all-women sailors in the Abaco Islands with Go Sail. While Claire loved sailing with all of Go Sail’s ASA students in the Virgin Islands, she is excited to see how different sailing with an all-female sailing crew may feel. 

Over the course of her first sailing season, Claire noticed that “men tend to focus a bit more on boosting their own skill set whereas women tend to be a bit more community-oriented.”

She imagines the all-women’s trip being a collaborative experience where all the trip participants really work to build each other up. She noticed confidence can be something women struggle with when learning to sail. 

“Especially for the women who come aboard they are almost always with their husband and some you can tell they have been dragged along,” she laughed. “[Then] they get behind the helm and they are like, ‘oh I think I really can do this!’”

Claire says her advice to anyone who feels imposter syndrome, like she did, when they first step aboard a sailboat is to know that feeling will fade with time. 

“I think it’s the same with anything new— it’s going to feel scary until it isn’t,” she said.  “There is a first time for everything, you have to get past the first time to get to a second and third. The more you do it, the easier it is.”