How Sailing Charter Started
Special to the KCSA Bulletin
People wonder, How did you start the sailing business?” It started with a few words, Let’s go sail the York River. The object was to let couples sail a serene three hours.
In retirement, Kingsmill resident Bill O’Donovan has pursued a charter boat business to share the joy of sailing. Here’s how charter sailing started. It began 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.”
Kimgsmill MarinaBefore long the couple upgraded to a 16-foot Newport-class sailboat that they kept at the Kingsmill docks for a decade. The boat was named Wendin for their young daughters Robin and Wendy. Bill thought it would be a good bonding experience for the family, and it was. They enjoyed many an afternoon sailing the James River out of Kingsmill Marina. They girls played in the tiny V-berth and enjoyed jumping off the boat into the water. 
After 11 years, when the girls went off to college, the couple upraded to a 25-foot Catalina and moved to York River Yacht Haven in Gloucester Point. The winds were better from the east because of the open proximity to Chesapeake Bay. The Catalina gave way to a  Hunter 29.5 and finally a Hunter 320.

How Charter Sailing Started

Bill 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.”
In 2012 he was laid off by Tribune/Daily Press and took a retirement exit. 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.
Ten years later, he is living the dream by taking out hundreds of tourists and locals from early spring through Thanksgiving. Capt. Bill 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, an iconic term that many people recall from “Gilligan’s Island.” During the Covid pandemic, he billed it as the best Williamsburg tour offering safe “social distance sailing” daily for up to six people.
As a newspaper man, Bill learned Internet marketing early on and now exploits social media to get leads. He wrote nearly 800 extensive 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.” He did it by tying together key words from internet ads to blogs like this one: Extraordinary experience for couples, Leave your worries behind, Experience the thrill of moving with the wind without a care in the world.
Years later the girls commissioned an oil painting depicting the origins of the sailing family at Kingsmill.
How Charter Sailing StartedHis most notable customer? “Dean Sheridan served as a US Air Force 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. That’s because 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. “Most of the house guests come from another gated community Ford’s Colony. The homeowners suggest they take a nice sailing trip—without them. Who knew?”
Weddings on boardHe’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.”
Romance became a key market. By offering a semi-private yachting charter, people were encouraged to go on a romantic sail where they could sit up on the bow for privacy. A unique and intriguing event morphed into an extraordinary anniversary idea. He threw in professional photos for free.
What’s next? “I take many couples out sailing who live in Kingsmill or stay the Resort. I’d love to set up a second boat at the Kingsmill Marina, where we began.”
For now, we celebrate ten years on the water as a thriving business by pursuing the next ten.

Let’s Go Sail                                                                

Scroll down Rates and pick a day for a sailboat charter. Scroll down Reviews on Trip Advisor.  Go back to the Home Page of Williamsburg Charter Sails. 
Let’s go sail the York River, where couples enjoy a serene three hours. Take one of 6 sailing adventures near the Chesapeake Bay for your best vacation excursion: Adventure, Event, Appreciation, History, Lessons, Boat Buying. Sit in the catbird seat or up on the bow. Find happiness and health outdoors near Williamsburg with exciting fun on an anniversary or birthday. Great memories! Learn navigation to become a sailor. See birds, dolphins, maybe a Navy submarine. Bring your dog. The best Williamsburg boat tour offers safe “social distance sailing” daily for up to 6 people. It’s an extraordinary experience for couples. Leave your worries behind. Enjoy the thrill of moving with the wind without a care in the world.

How Sailing Charter Started

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