Jan Miles, Senior Captain
Pasadena, Maryland
Captain Miles, an Annapolis High School graduate, has been with Pride of Baltimore, Inc. since 1981, when he joined as one of three rotating captains on the original Pride of Baltimore. He was the first to sail the original Pride across the North Atlantic to Europe and was at the helm for Pride of Baltimore II‘s maiden voyage in 1988. He is a tall ship master with more than 50 years of experience as a professional sailor. His voyages have included six 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. He holds a USCG 500 Ocean Master License for Power and Sail, as well as numerous other certifications. Captain Miles has served as master or mate aboard many other vessels, including Lady Maryland, Californian, Bill of Rights, New Way, Alexandria, Brilliant, Clearwater, Elissa, Oliver Hazard Perry, and Tiare Toporo. Along the way, he also helped develop model sailing programs for youth at risk.
His accomplishments and contributions 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. In September 2005, he was the master aboard when Pride of Baltimore II suffered a catastrophic dismasting. As a result of the crew and trainees’ conduct during that event, Sail Training International awarded the ship the Special Seamanship Award. Capt. Miles was named Sail Trainer of the Year by the American Sail Training Association in 2004. He has also been recognized for his efforts to shine a positive light on Maryland, having been named Marylander of the Year by the Maryland Colonial Society in 2001.
Jeffrey Crosby, Captain
Duluth, Minnesota
Jeff first joined our crew as a deckhand in 2008 & returned to Pride as chief mate in 2017 and was promoted to captain in 2022. Jeff grew up sailing on Lake Superior on one-design boats and shifted into the traditional sailing world after graduating from the Landing School with a degree in boat building in 2005. He holds a U.S. Coast Guard 200-ton near coastal master’s license.
Shevawn Innes, Senior Mate
Owosso, Michigan
Shevawn joins PRIDE II as senior mate, bringing a wealth of experience from her time aboard a variety of traditional schooners, including MARY E, APPLEDORE II, HINDU, PIONEER, SPIRIT OF MASSACHUSETTS, HARVEY GAMAGE, and WESTWARD. With a strong background in traditional seamanship, she is excited to be part of PRIDE’s ongoing mission. When ashore, Shevawn enjoys exploring local farmers’ markets and getting to know the communities the ship visits.
Remy Perron, Second Mate
Andover, Massachusetts
Remy brings with him experience sailing aboard Matthew Turner on San Francisco Bay. He also has experience as crew aboard When and If, True Love, and Adventure. For a reason that is still unknown to our staff, Remy is proud to share that he spent Spring Break 2013 driving to Kansas. Remy is an award-winning bartender & loves a good game of rugby. Remy is still seeking a sponsorship from any apparel company that will take him.
Kai Joswig, Bosun
Las Vegas, Nevada
Kai returns to Pride II this season as Bosun, after first sailing with us as a deckhand. His tall ship experience includes Lady Washington, Adventure, J&E Riggin, Ardelle, Isabela and Alabama. While we’re still catching up on everywhere Kai has been since his last time aboard, we’re glad to have him back on deck. In addition to his seamanship, Kai is a lover of film photography and claims he can build “you” a lobster pot.
Mary Walker, Engineer
Kapa’a, Hawaii
We are excited to have Mary rejoin our ranks for another season. In addition to Pride II, Mary brings with her experience sailing aboard Clearwater, Lady Maryland, Gazela, and Argia. Mary is a champion axe thrower. Mary wants you to know that her favorite dinosaur is a Stegosaurus.
Christina Melendez, Cook
Fort Stewart, Georgia
Christina joins the crew as our cook, bringing with her experience from sailing aboard Manitou, Inland Seas, Alliance, Madeline and Champion. She is especially excited to explore Baltimore’s restaurants and museums this season. Christina’s favorite dish to make is curry, and when she’s not in the galley she enjoys reading and lifting things with her big heavy muscles.
David Harrison, Deckhand
Quitman, Texas
David is back! Texas Dave brings with him experience sailing aboard Nao Trinidad as a deckhand. Texas Dave is a Marine veteran, has trained as a gunsmith, & holds an associate degree in applied science. Contrary to the typical Texas archetype, David does not have strong opinions about the presence of beans in chili.
Grace Cloherty, Deckhand
Buffalo, New York
Grace joins Pride II as her very first tall ship, though the vessel is already part of her story—her father, Thomas, crewed aboard Pride II. She comes to the ship with a wide range of talents: she is a boxer, a boxing coach, a volunteer firefighter, and a licensed motorcyclist. Grace has also earned nicknames such as “Gráinne O’Malley, Queen of the Irish Seas,” and describes herself as both “an all-around nice guy” and “pure of heart.” Though she hails from Buffalo, Grace was born in a bathtub in Baltimore and is looking forward to visiting that very spot while back in the city. Since joining the crew, she has especially enjoyed exploring the National Aquarium and Camden Yards.
Benjamin Heyer, Deckhand
Dunkirk, Maryland
New to our crew this season, Ben sailed with Pride II throughout the Great Lakes. He left most of his bio form blank, but he wants you to know he drives a Toyota Tacoma. He has previously sailed aboard Kalmar Nyckel and has worked as crew on a cruise ship. Ben can play the bagpipes and enjoys making sausage.
Sam Springer, Deckhand
Scituate, Massachusetts
Sam has been sailing with Pride II throughout the Great Lakes this season, after first joining the crew earlier in the year. He grew up sailing dinghies in his home waters of Massachusetts and was a member of the sailing club at Virginia Tech. Sam is a member of the Coast Guard Auxiliary and was an intern at USCG Small Boat Station Cape Cod Canal, where he participated in helicopter training. While serving with a unit in Virginia, he also took part in Hurricane Helene relief efforts in southwest Virginia. Sam holds his USCG boat crew certification and is a USCG Auxiliary Operational Auxiliarist. When not sailing, he enjoys skiing and mountain biking, and his goal is to commission as an officer in the Coast Guard. His favorite sandwich is the tuna melt, and he continues to insist that his girlfriend exists—she just happens to work on another ship.
Brenna DeAngelis, Deckhand
Bethlehem, Pennsylvania
Brenna joins Pride II with an impressive range of sailing experience. She has crewed with Portland Schooner Company aboard Wendameen, Bagheera, Timberwind, Hearts Desire and Vela, as well as sailing on Alvei, Niagara, the yacht Columbia and Harvey Gamage. Since arriving in Baltimore, Brenna has become a big fan of the National Aquarium and the Maryland Zoo, and she hopes to take a helicopter tour of the city before the season is out. She is especially excited to bring her parents for a sail on Pride II and has plans to picnic at Fort McHenry with friends.
Katie Moore, Deckhand
Chelsea, Michigan
Katie is back! Katie was an intern with Tall Ships America during the 2022 Tall Ships Challenge Great Lakes. That summer, she also had the opportunity to sail aboard the St. Lawrence II and Nao Trinidad before joining our crew full time. Katie is a graduate of the University of Michigan. She has a twin brother, and it is her lifelong goal to pet every cat in the world.