Captains & Crew

Captain Jan Miles

Pasadena, MD
Captain Miles is a licensed ship's master who has been with the Pride of Baltimore organization since 1981, when he joined as one of three rotating captains on the original Pride of Baltimore. He is a tall ship master with more than 35 years of experience as a professional sailor. His voyages have included five Atlantic Ocean crossings, as well as three Pacific voyages of 5,000 miles, each taking about 25 days. He has traversed the Saint Lawrence Seaway more than a dozen times. Captain Miles holds a USCG 500 Ocean Master License for Power and Sail, as well as numerous other certifications. Prior to joining Pride, Inc., Captain Miles served as master or mate aboard 15 vessels, including Lady Maryland, Californian, Bill of Rights, New Way, Alexandria, Brilliant and Clearwater. Along the way he also helped develop model sailing programs for youth at risk. His accomplishments and contributions to the tall ship sailing profession have been recognized both within and outside of the maritime community. In February 2013 Captain Miles was recognized with the Lifetime Achievement Award by Tall Ships America.

Interested in becoming crew aboard Pride of Baltimore II?


All interested applicants must be U.S Citizens and either be prepared to prove being drug free, as per USCG regulations, or meet the regulations for being qualified as drug free. Prior traditional working sail vessel experience is required. USCG certification required for 1st Mate (at least 100 GRT Auxiliary Sail). All applicants are requested to provide by email a Cover Letter and Resume plus References. In the Cover Letter please describe what you would bring to the ship and her mission, as well what you would gain by being a crew member.

Email your application and cover letter to Captain Jan C. Miles:

Katelinn Shaw

Second Mate

Charles Reynolds


Charles comes to us from Seward, Alaska. He has been an engineer on the following vessels: Lady Washington, Picton Castle, Kwai, and Lady Washington

His credentials include: STCW basic safety training, Advanced Fire Fighting, Tankerman Assist, Vessel Personnel with Designated Security Duties, and is a qualified member of the Engineering Department (Oiler)

In his spare time, Charles is a recreational hypotist. He claims to have evidence that the munchkins from Frank Baum's world of Oz painstakingly orchestrated the kidnap of Dorothy so that Toto could fulfill a prophecy revealed to them on a burnt piece of toast and often wonders if the world would experience deeply meaningless change if Sara Lee started making bacon horseradish cheese cake.

Sarah Newman


Nicknamed “Squirrel,” Sarah hails from Arlington, Texas. Her past sailing experience has found her aboard Elissa, Irving and Exy Johnson, Oliver Hazard Perry, and Mystic. Her first time as a crew member of Pride II was just last year.

She is USCG-certified in STCW (Standards of Training, Certification and Watchkeeping) Basic Safety Training, and proficient in Survival Craft. She is also licensed as a basic scuba diver.

She jokingly admits that she “fits into most overhead storage compartments.” Despite her small stature, her thirst for knowledge and experience is unmatched. She has degrees in both marine biology and creative writing. Back at her land-based home, she has a cat named Maggie, who keeps her returning from sea!

Will Lankford


Philip Charles Keenan


Philip, or “Phil,” is the master cook who keeps our crew fed and happy, especially after long days and nights at sea. Thanks to his efforts, the crew is always ready to take on the day. His past experience cooking aboard a vessel includes time with SV Shenandoah and SV Alabama.

Phil is actually a big nerd at heart. He has spent years lecturing at Amherst College on the subject of “Improvisation.” He’s been a Selectman for almost twenty-five years, which is an elected official of the government of New England towns

Captain Jordan Smith

Annapolis, Maryland

Captain Smith comes to Pride of Baltimore, Inc., as a licensed ship’s master with a lifetime on the water and a unique blend of performance racing, ocean cruising, and traditional sail experience. Immediately prior to joining Pride Inc., Jordan served as master rigger for the re-rig of the historic sailing warship USS Constellation. His tall ship command experience includes the schooners Appledore V, Appledore IV, Appledore II, and Edith M. Becker, as well as a tour aboard the square-rigger Hawaiian Chieftain along the west coast. On these vessels, Jordan has logged thousands of miles on both coasts of North America, the Great Lakes, and the St. Lawrence Seaway.

Before concentrating on tall ship command, Jordan worked as a rigger, sail maker, and professional racing sailor, primarily out of Annapolis, MD. He has been part of winning teams at some of the most prestigious racing events in the world, including Block Island Race Week, the Annapolis to Bermuda Race, the Annapolis to Newport, Miami to Jamaica, Key West Race Week, and many others. This has also included many events in the ultra competitive Etchells class.

On occasion, before he merged his wandering urge with his profession, Jordan would fit out and go voyaging in his own cruising boats, primarily to the Caribbean and South America. When not on Pride II, he lives aboard his cruising boat in Annapolis.

He attended St. Mary’s College, where he was a member and team captain of the Offshore Sailing Team. Jordan began sailing with his family on the south shore of Long Island well before he was old enough to remember it.

Chad Lossing

First Mate

Chad hails from Big Rapids, Michigan – our second Michigan native this season. His sailing experience has found him aboard Nordlys, Hindu, and Tres Hombres. He was also a sailmaker’s apprentice at the Bierig Sail Loft. With experience as a mate, a lead rigger, bosun, and deckineer Chad brings a wealth of expertise to the ship.

Chad has a soft spot in his heart for Dances with Wolves and The Sound of Music, his two favorite movies when he was a kid. Just looking at his side passions, you’d think Chad was training for the circus — he used to spin fire and he is currently learning how to juggle.

Krista Swedberg


Carolyn Corbin


Carolyn, a native Marylander, has sailed on multiple vessels. Her sailing history has brought her aboard Niagara, Lynx, Corwith Cramer, Maryland Dove, and Mystic Water. This is her second time aboard Pride II, but first time sailing her.

Carolyn is an avid rugby fan. When she leaves Pride II at the end of the season, she’ll spend the winter months mushing sled dogs.

Will Cutshall


James Fitzgerald


Gray Meyer