Lifelong seaman Capt. Jan Miles finds his way home to Pasadena

Jan Miles, captain of Pride of Baltimore II, aboard his Whistler 32 Cat Ketch sailboat.

For 41 years, Jan Miles has skippered the Pride of Baltimore (I and II), replicas of a 19th century Baltimore clipper built to circle the globe and promote both Maryland and maritime history. At 71, Miles has logged more than 250,000 miles aboard the celebrated schooners (the first Pride sank in a storm in 1986). A graduate of Annapolis High, he received a Lifetime Achievement Award from Tall Ships America and lives in Pasadena, a stone’s throw from the Magothy River.

Here are three things you might not know about Miles:


A lifelong seaman, he bought his first craft at age 58.

“In 2009 my wife, Lesley, decided that I should have my own sailboat, because what else would we do in retirement? It’s a two-masted Whistler 32 that we keep in our community’s marina. We’ve sailed as far as Chestertown; I have no ambition to go outside the Chesapeake Bay.


“On this boat, unlike Pride II, I’m doing all of the work — and I get a great sense of accomplishment out of knowing what I’m doing. I don’t have a crew, although — every once in a while — I might want one.”

Even inland, he keeps an eye on Mother Nature.

“Being a sailor, I observe the weather in a way that is pretty uncommon for people onshore. Before going on a drive of two hours or more, I’ll look at radar, maps and wind charts, and may find cause to wait a day or two.

“The idea of flying can be problematic because I have to trust the pilot. Sometimes, on a plane, I have to grab my psyche and focus on something else, so that I don’t drive myself nuts worrying if this guy is going to fly through a thunderstorm. That’s when I need to change the subject in my head.”

He learned to sail a long way from the Chesapeake Bay.

“My father was a foreign service officer, so I grew up mostly overseas. My earliest solo sailing, at [age] 7, was in Malta, an island in the middle of the Mediterranean Sea.”