Before #boatlife. Before TikTok and Youtube sailors were raking in millions of views. Before the rise of influencers, daily vlogs, brand deals, and giant followings, we were using social media for something other than marketing; we were using it for socializing.
Instagram was still Instagram when Captain Gwendolyn Whitney and I started trading likes on photos posted from our respective boats. I started following her in 2020, and I’m glad I did. Had it been today, the algorithm might have connected us with brands or viral videos instead of each other. Gwen immediately followed back.
Gwen wound up in a boatyard in her home state of Wisconsin after trucking her Cal 40, Squall, to Lake Michigan. She was restoring Squall in the hopes of eventually chartering it. She earned her USCG 100-ton captain’s license working on yachts in Hawaii and on a 65-foot wooden schooner in her home waters. She’s crewed on a 90-foot luxury sailing yacht for a season and delivered countless production boats between the Great Lakes and Bahamas.
While Gwen got her 40-foot Squall seaworthy in the Midwest, I flipped three boats between 26 and 29 feet. We were sharing parallel yet unique experiences, keeping in touch along the way. From the same socioeconomic status, lovesick sea stories, and scrappy school of boat works, Gwen became a yacht captain and I became a yacht broker. It was another level of relatable.
So, when Gwen’s latest captain gig landed her at the helm of a 60-foot classic sailing yacht just 7 miles as the crow flies from my hometown on the East End of Long Island, it was time to make social media real life.
Her tiny stature, golden hair, bright blue eyes, and wide grin greeted me on the sidewalk in Greenport, New York. Within minutes we were arm in arm, laughing and strolling the summer streets like two old friends in a Simon and Garfunkel song. Direct messages and comments became coffee hangs, library meetups, dinghy rides, ferry trips, and yacht sleepovers.
When I introduced Gwen to my father’s best friend, a 75-year-old commercial fisherman from Long Island, his jaw dropped to learn she had captained a 65-foot classic schooner on the Great Lakes and was now the captain of a 60-foot cruising yacht in the Hamptons at the age of 34.
“My first love is the sea,” Gwen said to me as we sat on Squall in an exposed mooring field with no breakwater. “No matter what.”
On an early September charter for a group of affluent passengers (one of whom happened to be actor Neil Patrick Harris), Gwen singlehandedly shoved off, raised and handled all sails, and picked up the mooring in the Hamptons. Her passengers applauded her elegant boathandling skills.
Gwen commands that same respect whether she’s walking in a room or stepping on a boat. She reminds me that you don’t have to be intimidating or aggressive in order to be assertive or effective. Midwest nice is real.
But perhaps one of the most powerful unsung attributes of Gwen’s career is her ability to recognize skills and potential in others. Her friend Kristie followed her from Hawaii to the schooner in Wisconsin, and eventually to Key West; Kristie went on to earn her captain’s license and get her own boat, too.
As for me, I was Gwen’s first mate from Sag Harbor to Newport for the boat show. More yacht deliveries are in our future.