Captains & Crew

Captain Jan Miles

Pasadena, Maryland

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.

Jeff Crosby

Chief Mate
Duluth, Minnesota

Jeff sailed aboard Pride II from 2008 to 2010 and was the ship’s carpenter for the 2017 winter maintenance period. He has a degree in boat building from The Landing School. One of Jeff’s goals this year is to find the line between not enough coffee and too many cups of coffee.

Halee Grimes

Second Mate
Lakeland, Florida

Back for another round, Halee is returning to Pride II as Second Mate. She sailed aboard Pride II for the 2014 season. Halee brings experience from a number of other ships including Robert C. Seamans, Kalmar Nyckel, Gazela, Bounty, and schooner Freedom. She likes to knit and crochet, and if it has cheese on it, she will eat it. Don’t forget to ask her about her Chaco sandal tan lines.

Kelsey Mullin

Philadelphia, Pennsylvania

In addition to being on the winter crew in 2014 and 2017, Kelsey has spent a number of years in her hometown of Philadelphia aboard Gazela. Other ships she has worked on include, Moshulu, A.J. Meerwald, Soundwaters, and Oliver Hazard Perry. Kelsey majored in linguistics, enjoys climbing things, and reading books.

Charles Reynolds

Seward, Alaska

Charles returns to Pride II after being aboard for the second half of 2016 as engineer. He has worked aboard a number of traditional sailing vessels including Lady Washington, Picton Castle, and Kwai. In his spare time Charles is a recreational hypnotist & is in the process publishing a thesis regarding the role of the munchkins in The Wizard of Oz.

Phil Keenan

Hawley, Massachusetts

Phil returns to Pride II for his second year as cook. With past experience in the galley aboard Black Dog Tall Ships, Shenandoah and Alabama, Phil is a natural. A big fan of NPR, Phil is the ship's unofficial political correspondent and when he isn’t cooking, he can be found trying to get on air with Diane Rehm or mingling with visitors. We are happy to have Phil back and look forward to all his tasty treats!

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 or Captain Jordan Smith: or

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.

Brandi Poort

Norfolk, Virginia

Brandi started her sailing career aboard Denis Sullivan in 2015 and has since worked aboard Pride II, Lynx, Lady Maryland, and Virginia. Brandi has a passion for lobster rolls and sailing fast. She contends that she is the preppiest tall ship sailor in the fleet.

Chris Peterson

Raleigh, North Carolina

After performing maintenance work on Pride II in the winter of 2017, Chris will continue on as a deckhand for the sailing season. Chris has spent time sailing aboard Gazela, Irving Johnson, and has experience racing dinghies. When Chris isn’t sailing he likes to rock climb and play with his dog. One of his favorite pastimes is mopping large hardwood floors. Chris loves a quality white t-shirt with a lay-flat collar.

Darcy Cogswell

Glastonbury, Connecticut

A new addition to the crew, Darcy joins Pride II having sailed aboard Mystic Whaler, Brilliant, Corwith Cramer, and Soundwaters. Darcy loves the outdoors, hiking, backpacking, and canoeing. She has hiked “rim to rim to rim” in the Grand Canyon.

Jennifer Roberts

Southampton, New Jersey

Joining the crew for the 2017 season, Jennifer has sailing experience on the Dutch schooner Oosterschelde. Jennifer grew up on a small apple farm, went to elementary school with Johnny Appleseed, and said he is a brat. She once ran with a mob of kangaroos and her favorite day of the week is taco Tuesday.

Justin Mayer

Broken Arrow, Oklahoma

This is Justin’s first season working aboard a tall ship, joining the sailing crew after working on winter maintenance. Justin is a professional jazz pianist and stagehand. He is also a dual citizen of the U.S. and Austria and considers himself a “massive nerd.” Fun fact: a number of Simon and Garfunkel songs were inspired by Justin.