See it larger.
A guy in a motorboat towed several sailboats past Castle Island from the direction of the harbor islands towards the inner harbor yesterday.
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Tows them out there at the beginning of the regatta.
and my maritime hallucinations, or is there another person hanging out in the caboose boat?
There was somebody in the last boat. You can get a slightly better view by clicking on the "See it larger" link above.
It's harder to tow a line of boats without someone in the last boat. Kid of like the firefighter in the little booth in back who steers the rear wheels of a long ladder truck.
On a boat or hook and ladder firetruck, it's the tillerman.
a person who operates the tiller of a boat or other vehicle, such as the rear of a fire engine.
passing by Peddocks Island near Nut Island.
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