In 1926 a 45-foot mahogany classic motor yacht sat brand-new in a ship builder’s lot somewhere in southern New Jersey. Soon thereafter, a man named Walter Bowes, owner of Pitney Bowes (a mailing and shipping company), bought the boat for his own pleasure – to cruise around the inlets and perhaps through the Hudson when he wasn’t preoccupied with work. In addition to cruising, she was also used as a commuter boat by Bowes and future owners. She was restored in the mid-1980s before moving to Annapolis and now cruises the Chesapeake as a boat for charter named Foxglove.

Foxglove Charter

Her new owners, Dorian and Elaine Walker were kind enough to give us a behind the scenes look at it’s like to charter Foxglove. Once I stepped aboard and walked from the wheelhouse to the aft deck, it was like I had stepped back in time! It’s no wonder Annapolis, which boasts 300 years of history, much of it distinctly maritime, was the perfect destination for this classic cruiser. Docked at the Chart House and next to the Water Taxi stop in the Maritime Republic of Eastport, Foxglove waits, eager to take passengers on a journey upon the Chesapeake and also through the gilded age.

Foxglove Charter

On this day, a fleet of small sailors from nearby sailing camps floated by in a line resembling the ducklings following each other on our port side. Comforting clings and clanks of the Eastport Drawbridge raising to let a larger sailboat through found our ears. We set sail and soon found ourselves rounding the US Naval Academy, and quickly approaching 8 knots when owner and captain-for-the-day, Dorain, turns to me and says, “Brace yourself! This boat was built for a time when there weren’t so many waves from pleasure boats.” However, Foxglove elegantly navigated the wake and whitecaps with a confident ease that many of her more modern neighbors just bounced and rocked on top of. She was truly comfortable. 

Foxglove Charter

It’s no secret that Annapolis offers plenty to do and see on land. For history buffs, it’s certainly a museum without walls. But after my cruising experience aboard Foxglove, I highly recommend diving into what the city has to offer on the water. While larger charters like the Schooner Woodwind and Harbor Queen are great options, Foxglove takes the prize for the most intimate, and possibly unique. A party up to six people can choose their destination and travel as far as St. Michael’s. Or, stay local for a morning meander or sunset cocktail cruise. Whatever the choice, it is sure to be a memory you won’t forget. 

John Stefancik

John Stefancik is the Publisher of Chesapeake Bay Media. He spends time on the water aboard his center console powerboat, racing sailboats of all sizes, and cruising between the waterside cities and towns of the Bay. Born and raised into a boating family, John spent summers sharing a berth with his brother while their parents took them sailing for weekends and weeks at a time. “The specialness of the Chesapeake cannot be overstated,” John says, “because one minute one can find themselves floating in a big urban area with city culture, then in the next moment being blissfully alone in one of the richest natural resources in the world!” John lives just outside of Annapolis, on the Severn River, with his wife and three children.