How Charter Sailing Started
Special to the KCSA Bulletin
In retirement, Kingsmill resident Bill O’Donovan has pursued a charter boat business to share the joy of sailing. It all started on the beach of Kingsmill years ago when Bill and Bonnie Tully met. “He took me out one afternoon on a 14-foot Sunfish, and we sailed all the way out to the Idle Fleet and over to Hog Island. I became quite taken with sailing, and him.”
Before long the couple upgraded to a 16-foot sailboat that they kept at the Kingsmill docks for a decade. The boat was named Wendin for their young daughters Robin and Wendy. They enjoyed many an afternoon sailing the James River from Kingsmill Marina.
Later he began taking newspaper clients from The Virginia Gazette out for “schmooze sailing.” He said, “Everyone enjoyed the unique surroundings of the water while getting to run the boat and meet new people. It was an ideal setting, and someday I thought it would make a viable business model.”
With Bonnie’s support, he completed rigorous regulatory and compliance hurdles to earn a U.S. Coast Guard captain’s license and form Let’s Go Sail under Wendin LLC.
Five years later, he is living the dream by taking out hundreds of tourists and locals on three-hour cruises from early spring through Thanksgiving. Capt. Bill switched rivers and now sails the York on a 32-foot Hunter at a marina in Gloucester Point. He offers a narrative from the water’s perspective on the 1781 Battle of the Capes and the Siege of Yorktown. He gives informal lessons as well. His Boatbuyer Cruise discourages buying in favor of renting, which comes as a pleasant surprise to wives. Each cruise runs three hours, which many people recall from “Gilligan’s Island.”
As a newspaper man, Bill learned Internet marketing early on and now exploits social media to get leads. He’s written more than 700 blogs to boost that effort. “If you google the words Let’s Go Sail, I come up eight times on the first page. That reflects the impact of social media.”
Years later the girls commissioned an oil painting depicting the origins of the sailing family at Kingsmill.
His most notable customer? “Dean Sheridan served as a rescue paramedic in every American war after Grenada. He made 18 combat jumps to save injured and captured Americans, including Jessica Lynch in Iraq. On the day he and his wife sailed with me, I noticed he was limping. Doctors removed the last of shrapnel from his hip. Dean won two Bronze Stars, the Distinguished Service Cross and seven Purple Hearts.”
One peculiar niche for Capt. Bill is house guests.
“Some of them evidently stay too long,” he said. “I get most of the house guests from another gated community. The homeowners suggest they take a nice sailing trip—without them. Who knew?”
He’s done engagements, weddings and burials at sea. “Ashes only,” he clarified. “My first wedding produced a dozen dolphins jumping out of the water as if celebrating the couple. For engagements, I give the fellow a fake ring in case he drops it off the bow.”
What’s next? “I take many couples out sailing from Kingsmill and the Resort. I’d love to set up a second boat at the Kingsmill Marina, where we began.”
Let’s Go Sail
Check rates and pick a day for a sailboat charter. See reviews on Trip Advisor.
How Charter Sailing Started
The origin of Williamsburg Charter Sails dates to the early 1980s when a couple met on Kingsmill Beach along the James River.
Capt. Bill O'Donovan
Williamsburg Charter Sails