American Offshore Solo Sailors at the Annapolis Sailboat Show 2026
"Working together to beat each other!"
At the age of 16, Brian Gray sold his motorcycle and bought a Snipe dinghy. He also read the book “Dove,” about a young man who sailed around the world on his 24-foot sloop. Gray decided that’s what he would do someday.
“I had great parents,” he said. “If you told them your dream, they’d say, ‘That’s cool. How are you going to do that?’ They were always supportive.”
When he met his wife in graduate school at Georgetown, he told her he’d sail around the world one day. She knew what she was getting into.
Fifty years since that first sailboat and a few “almost-ready” moments later, Gray now pours all of his energy into the upcoming Global Solo Challenge, departing in October 2027 from Vigo, Spain. The Annapolis solo sailor will compete in his Class 40 Kawan, now undergoing a major refit in Kiel, Germany.
SpinSheet readers may remember Gray’s bright green Classe Mini 6.50 and its fun graphic of the name Trouble, No Trouble, in which he competed in the Annapolis Bermuda Ocean Race (2016) and several Bermuda 1-2 Races. He raced in all of them single- or doublehanded.
When he was raising his kids, Gray says that “family was first; sailing was second.” Although he continued to windsurf and charter with his family in the islands, he didn’t focus seriously on shorthanded sailing until his kids went to college 15 years ago. That’s when Trouble, No Trouble came into his life.
“It was a great boat,” he said. “It jumped up and ripped through the water.”
For a SpinSheet article in 2019 about the Bermuda 1-2, Gray said, “I’m a thrill seeker. You have these challenges you have to figure out yourself. Working out solutions to problems is the best part… Every time is a learning experience.” (Find it at spinsheet.com/thrills.)
Gray had hoped to do a 2017 Global Race, but he wasn’t ready. 2020 was his next chance, and we all know what happened there. He was close, yet still not ready in 2023, the year that Cole Brauer put the event on the map. Now, he feels confident that he has the right boat (the Class 40, the “Checker cab of this race,” he says) and the right team outfitting it for the challenge. After hopefully spending time in Antigua, he intends to sail Kawan to Annapolis in the spring of 2027 and have her back on European docks by the end of summer for the start.
Global Solo Challenge competitors will gather on the docks at the Annapolis Sailboat Show (October 15-18), including Gray, Tim Kent, and Ronnie Simpson. Wanting some unity as the American entries in the challenge, they formed a group called American Offshore Solo.
Gray says, “Our motto is ‘Working together to beat each other.’” Anyone at the show who’d like to discuss solo sailing is welcome to join the conversation on Dock K, where Kent’s and Simpson’s boats will be on display.
