The Windsong Experience – Spectacular Sailing in Cape Charles

Cape Charles is known as a hidden gem of sorts.  Its history is intertwined with the Chesapeake Bay waters that border it. It’s no wonder that more people are finding their way to this idyllic town and calling it home—with picturesque streets lined with colorful historic homes, and a great friendly, ‘small town vibe’ that’s equal parts historic and hip, rugged and refined.

Cape Charles is sometimes called a storybook town. Maybe that’s why it’s the launching point for so many new adventures.  Corey Roy and Bronwyn Comer understand the allure and romance of the sea and the Chesapeake Bay waters as well as anyone. Owners of Windsong, a 47-foot schooner built in 1954, the husband-and-wife crew have taken their passion for sailing and set out on a journey to share it with others.

Docked in Cape Charles, Windsong is an absolute beauty. Captain Corey and First Mate, Bronwyn offer adventure, escape, and sheer wonder to the guests who sail with them on Windsong. Bronwyn explains their excursions: “We have a Cape Charles Day Sail where guests can experience the natural beauty and history of Cape Charles and the Bay. They can also take a hands-on approach and help us set sails and helm the boat! We also have a Cape Charles Sunset Sail — it’s an incredibly stunning experience out on the water. Cape Charles is one of the only places on the East Coast where you can watch a sunset over the western horizon. A perfect ending to the perfect day.”

Windsong is also available for bespoke excursions, accommodating special events and full-day sails. “Sometimes guests will bring charcuterie boards or box lunches…and we can help set them up with some of the local catering shops in town to make that happen. Some guests bring spirits and we’re happy to do bottle service,” says Bronwyn.

No sail is quite the same. “We often see dolphins, which are always majestic. Sometimes we’re just out sailing, and we talk about all the historical points of the town, the lighthouses, and anything from facts about the bridge construction to water depth in the Chesapeake Bay,” she says. “Every sail is its own new adventure.”

Lovers of the Water

Corey and Bronwyn’s thriving business evolved naturally out of their interest in sailing.

“I’ve always loved boats, and I have a history in raft guiding and kayaking,” says Bronwyn. “I didn’t start sailing until I met Corey about six years ago. I loved sailing because it was the next step that could take me places. You can only go so far in a kayak, but sailing can take you around the world,” she smiles.

“Corey grew up in the high desert in Oregon, so he’s a mountain kid. But he always had a fascination with the ocean,” says Bronwyn. “Corey joined the Navy and then found his love of sailing through living and working on boats.” “Corey and I met on a sailboat while crossing the bay over to Cape Charles in 2018,” recalls Bronwyn, “so this town has a little bit of a special place in our hearts.”

Charting A New Course

It was 2020. Corey and Bronwyn had been thinking about acquiring a boat for quite some time. “We were always keeping an eye out for the right boat… casually schooner shopping,” Bronwyn laughs. “And then one day, we saw an ad and thought, this is the one. We put a deposit on it that weekend.”

Living in Norfolk at the time, they took on the ocean-sized work of meticulously restoring the craft, which they would christen ‘Windsong’. The dashingly beautiful schooner was sea- and praise-worthy. When some friends from Cape Charles Community Sailing invited the couple to run a summer camp with Windsong, things got interesting. The camp was a huge success. Never ones to stay at anchor, Bronwyn and Corey decided to try offering some sunset sails in the evenings after camp hours. They sold out the entire week.  Then, another week, and another.

“We thought, ‘OK, this is where we need to be’,” says Bronwyn. The next year, they brought the boat over to Cape Charles and what they thought was going to be ‘a weekend thing’ blossomed into an exciting new business.

They now offer sunset sails and education-oriented trips tailored to their guests’ unique preferences.  Each voyage offers stunning views of Cape Charles’ coastline and often, dolphin sightings. Beyond leisure cruises, the Windsong is committed to environmental stewardship, partnering with the Vessel Disposal and Reuse Foundation which is a local nonprofit in the Hampton Roads area dedicated to cleaning up the waterways. They also enjoy participating in events in support of the Chesapeake Bay Foundation. For those interested in learning, Windsong offers sailing lessons taught by Corey, who is a certified instructor.

Keep A Weather Eye

Windsong guests experience a feeling of exhilaration on the water that stays with them long after they return to port. But besides the Bay breeze and sea spray, it’s the joy of the unexpected that takes folks by surprise.  

“We saw a sea turtle last year,” says Bronwyn. “That was a first for me. She was large, floating just beneath the surface alongside us. As sailors, we often see dolphins, too. They’re the best over on the Eastern Shore. Later in the season—August or September—we’ll see large groups of dolphins.  They love to swim around the boat, jump the bow…they’re very playful.”  “These sails are also really fun for locals and visitors…they get to see things from the water, looking back at the beach and the town,” explains Bronwyn. “That’s a perspective that most people don’t get to see.”

A new perspective is just what Windsong promises. Cape Charles is a place where adventurous souls seem to gather. It’s a fitting home, then, for Windsong, whose sleek, yet unassuming deck and billowing sails ferry the adventurers, the merrymakers, the nature lovers, and the dreamers toward the far horizon and back home again.

We invite you to discover Windsong and embark on an experience you’ll remember for a lifetime.

About Windsong

Schooner Windsong is a 47-foot Tancook Schooner designed by Ray Stevens of Nova Scotia.  She was built by Guy H. Asbury between 1954 and 1960 in Yarmouth, Nova Scotia. Much of her life was spent in New York; both around Long Island, and on Lake Ontario. Throughout her life she has been named Pleiades, Dream, John A. Noble, Chasseur, and Sara B. Schooner Windsong is now based out of Cape Charles, Virginia, offering sailing charters for up to 6 people on the waters of the Chesapeake Bay. Sail in style with full-service charters or put hands-on with the crew!

Schooner Windwong
11 Marina Road
Cape Charles, VA 
757-912-9270
schoonerwindwong.com