Thanks for your patience; this follows up the post from two days ago. The port is Boston, the date is November 1960, and the fleet tied up at the T wharf. Luna, pictured below, is still extant; the others . . . I believe are all gone.
Above in the distance and below, that’s Orion.
I have no ID on this gentleman in Orion‘s engine room, or
this gentleman in the wheelhouse of another era.
Allan Seymour went on to a career as a professional photographer, and he sent me these photos.
Here’s how I first saw two of the boats–including Luna–back in 1987. Here’s a report on the historic value of Luna submitted to the Boston Landmarks Commission in March 1985.
Thanks for your guesses, both here and on FB. For the Boston Public Library’s trove of T Wharf photos, click here. And here is the motherlode, at least 150 photos of Boston tugboats from the Digital Commonwealth collection.
tugster: a waterblog 
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April 12, 2019 at 11:25 am
Lee Rust
Luna’s Alden-designed wooden hull and pioneering diesel-electric propulsion system are particularly interesting.
April 12, 2019 at 2:34 pm
Ben Grudinskas Sr.
As “Ship’s Carpenter” I can attest that LUNA is alive and well in Boston. Soon to be shown at Pier #3 adjacent to the US CONSTITUTION.
April 12, 2019 at 6:59 pm
James Gallant
Just a quick note: Boston Towboat Company was based at Lewis Wharf in Boston, not T Wharf. The company was in fact started at T Wharf in the mid 1800’s, but moved away from there in the 1890’s. Boston Towboat DID, however, keep their iconic “T” symbol on their smokestacks as a salute to their corporate heritage….a source of confusion for generations of unenlightened observers of their tugs.
Canadian immigrant Captain Joseph R. Ross took over the old second floor offices of the Boston Towboat Company at the east end of T Wharf, in January of 1900. Arriving there with a fledgling fleet of only two tugs, the IRVING F. ROSS of 1898, and the JOSEPH W. ROSS of 1899, Ross Towboat Company would grow and become second only to Boston Towboat as the largest Boston based towboat fleet. Ross would remain successful for decades, before falling victim to financial problems and a bankruptcy dissolution in the mid 1950’s. At that time, Ross captain Harvey DeVeau and his wife Mary, purchased the remaining assets of the Ross Towboat Company (primarily the tugs SADIE ROSS of 1904, and the BETSY ROSS of 1905, both needing extensive rehab,) and reorganized the company under new management. They moved operations shortly thereafter to a new headquarters at the former Boston Fireboat 44 Firehouse at 18 Northern Avenue, South Boston, at the mouth of the Fort Point Channel. Ross would be the last towboat operators to use old T Wharf, as the wharf was soon condemned and demolished in the 1960’s.
April 12, 2019 at 7:25 pm
tugster
Thx, James….