CAMBRIDGE — Walking up to the enormous and breathtaking Pride of Baltimore II, it was like being transported to a scene from Pirates of the Caribbean. All that was missing was Jack Sparrow and the icy blue Caribbean water.
The impressive deck crew and Capt. Jeff Crosby made guests feel comfortable and at home as they arrived onto the vessel and during the sail. Views of Oxford, the gorgeous Choptank River and Cambridge were enjoyed by all.
Crosby grew up sailing on the Great Lakes starting out in small 420 sailboats and began progressing to larger boats. He shifted to more traditional sailing in his early 20’s and joined the Pride of Baltimore II in 2008 as a deckhand. He returned in 2016 and was promoted to Captain in 2020.
“I mean, Pride has a lot of really wonderful things to offer but really, the thing that I enjoy the most is just its super performance,†Crosby said. “She’s a fabulous sailor and the builders did a really good job.â€
Many of the Pride’s deckhands like Brenna DeAngelis said one of their favorite things about working on this boat is working with Crosby.
“You will never see him being unnecessary in any sort of fashion. Calm, cool, collected, concise, all the time,†DeAngelis said. “He’s even laughing and cracking jokes under a lot of stress, and it’s so relieving.â€
It is evident as soon as you step on board that the crew work well together. Even when deckhands are suspended a hundred feet in the to air let down a sail, fellow crew members listen intently for instructions. Crosby guided the Pride out of the dock and redocked the vessel, but while the sail was underway, deckhand Grace Cloherty manned the helm as Crosby observed and gave direction when necessary.
Cloherty’s late father, Tom Cloherty, also worked on the Pride of Baltimore II. She said she feels grateful to be able to carry on the legacy and honored when Crosby trusts her with the helm. Cloherty has been a part of the Pride crew for three weeks and said she’s been able to steer the ship three times now under Crosby’s guidance.
Candace and Scott Taylor have lived in Cambridge for 20 years but are originally from Baltimore. They lucked out on having a shared day off of work and took the opportunity to sail on the Pride for the first time.
“I’ve always wanted to go sailing, and, of course, being from Baltimore, you know, we love the Pride of Baltimore, and we just wanted to see it,†Candace Taylor said.
Scott said he remembers the original Pride of Baltimore from the 1980s but never had the opportunity to go on it.
“I’m from Baltimore originally, and I’ve always wanted to go on the ship, so this was just perfect timing,†he said.
The Pride is no joke of a vessel. According to boatswain Kai Joswig, the sailboat has traveled overseas over 40 times and the farthest expedition was to Shanghai, China.
“She’s a very hard boat. She’s very heavy, and she’s also rigged traditionally,†he said. “So, this rigged design and this vestal design is from the War of 1812 period.
The Pride of Baltimore will be docked at Long Wharf Park until Tuesday, and tickets are available at its website.

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