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Sail Boston Parade of Sail, courtesy of Craig Linehan.

Captain’s Log: Reflecting on Sail250

Date: July 19, 2025

I am writing shortly after the last formal Tall Ship Festival Port celebrating America’s 250th Birthday. Boston this last weekend.

The planning for Tall Ship Festivals marking America’s 250th Birthday was long. Years in the making.

The actual execution by Pride of Baltimore II spanned five and a half weeks. Five ports. Richmond. Norfolk. Baltimore. New York. Boston. 1,115 nautical miles. Four tall ship parades of sail. Nineteen deck-tour days. 36,128 visitors.

Getting Pride II ready was led by Captain Jeff Crosby throughout last winter. Including replacing engines and transmissions. The new auxiliary power is now by Cummins. We are enjoying quieter, actually smaller size motors, yet increased power. While also more efficient. Burning less fuel for similar performance. And running somewhat cleaner. So, not just maintenance of rigging and spars and hull and deck cosmetics.

This year’s crew have performed admirably. All enjoyed the spectacle of gathered together tall ships from around the world. All are tired. Now looking forward to a slower pace.

Captain Crosby is back aboard now. He and I split the Tall Ship Festival ports. He sailed the first two before Baltimore’s own Tall Ship Festival. I sailed the second two after Baltimore. Monday (July 20), Pride sails onward to the ports of Portland, Maine; Salem, Massachusetts; Lunenburg, Nova Scotia; thence back to Boston around mid-August, where I am scheduled to come back aboard for the ports of Rockland, Maine; Greenport, New York; thence return to Chesapeake Bay, Havre de Grace. And Captain Crosby returns aboard. (Additional rotations through end of October are being considered.)

How has Pride been received? Reviewing media it is clear she was a major feature in all of the ports.

Perhaps more important than media coverage were the conversations aboard. Tens of thousands came aboard Pride. Many with little previous knowledge of Baltimore Clippers. Or privateering. Or the Chesapeake’s role in the War of 1812. A deck tour becomes an opportunity to explain why Baltimore mattered. Why Maryland mattered. And why that history remains relevant.

Pride was not simply another visiting tall ship. She represented Baltimore. She represented Maryland. She represented the city whose shipbuilders produced vessels that altered the course of maritime history during the War of 1812. That story was welcomed in every port.

The extra appreciation we experienced is her representation of Baltimore’s role during the War of 1812. The final act in the long effort toward full American independence. And the beginning of America’s large presence upon the world scene. I enjoyed sharing with the Governor of Massachusetts and the Mayor of Boston that Pride was honored to pay respects to the city that started the Revolution, coming from a city that helped conclude it.

The Tall Ship Festivals are now behind us. The Semi quincentennial itself is not. Pride continues north. More ports. More visitors. More opportunities to remind people that history is best understood not only by reading books, but also by walking the decks of a ship built in the traditions of those who lived it.

Signed,
Jan C. Miles
Senior Captain & Executive Director