Tour Guide Feature: Jay Arr of Boston by Segway

-This is the first of a two-part series on Boston tour guide Jay Arr.  Today’s article introduces him through the eyes of a trolley tour guide.  In tomorrow’s article Jay Arr will tell us about himself in his own words.

-by Jon Cotton

JR, tour guide, friend, actor

JR has been a tour guide at Boston by Segway for two years.

I first saw Boston tour guide Jay Arr leading his guests single file, like ducklings in a row, down commercial street.  I sidled along, slowly stalking his group (stalking being a habit mentioned previously), I opened the trolley door as I got close, and shouted out, as a stalker might, “Nice Segway!”

He turned, smiling.  He looked at me for a minute, and shouted “Nice trolley.”  I liked him.  Jay Arr embodies the philosophy is founded on – that tour guides form a community, should be friendly with each other when we meet in the field.

“Thank you!” I said waving, titters and guffaws from both our groups.  Later we repeated the performance, and now it’s a regular device to make our people laugh each time we meet.  Eventually he offered me a private tour of Boston by Segway.  “Boston by Segway” is also the name of the company Jay Arr works for.  Boston by Segway is located in the North End (Little Italy) on the corner of Hanover and Commercial Street.

Jay Arr was extremely safety conscious and explained in a brief one-on-one training exercise the proper way to operate and maneuver.  Then we went “gliding” through the  streets of Boston, where Jay Arr showed me how to handle obstacles like ramps, bumps, and traffic.  He even showed me how to go down a small set of steps when I asked if the vehicle could handle it.  Although the total drop was perhaps a foot and a half, I emitted a tiny scream as the vehicle glided me peacefully to the ground while Jay Arr instructed and reassured me of my safety.

It was interesting to see the city from the perspective of a tour guide with a different route from mine and a different method of traveling that route.  He could bring me to the end of the Long Wharf where one stands in open relation to the Sea – an experience we trolley guides can’t give.  In Segways you can enter the waterside sanctum of Rowe’s Wharf, and view John Henry’s yacht, and stand under some of the most expensive condominiums in Boston.  (The wharf is named after John Rowe, who owned one of the Tea Party ships (The Eleanor)).  We glided to Fort Point Channel and explored beneath the bridges that trolleys drive over, and into the back alley where Martin Sheen gets thrown from a window in the movie The Departed.

Jay Arr describes himself as

a Bohemian, a Bostoinian, a huge Art Enthusaist, Writer/Poet, an Entertainer, & Tour Guide.


-Come back tomorrow for Jay Arr’s own words, in which he gives a more complete description of himself on

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