Trolley Driver / Tour Guide - Signing Bonus!! in Old Town Trolley Tours at Historic Tours of America, Inc

Date Posted: 9/13/2023

Job Snapshot

Job Description


Have fun driving an Old Town Trolley and sharing the history of our region.
Entertain visitors while educating them about historic Boston!


  • With existing CDL - FROM $23/hr Base Pay PLUS Gratuities*
  • $4,000 Signing Bonus - $1,500 at tour certification, $1,500 90 days post certification, and $1,000 at the end of the Summer Season
  • Holiday Pay (New Year’s Day, Memorial Day, 4th of July, Labor Day)
  • Two weeks' vacation the first year and paid sick leave (5 days)
  • Choice of HRA or Traditional Healthcare Plan:
    • Employer pays 82% of HRA premium of employee**
    • Employer pays 73% of Traditional Healthcare Plan of employee**
  • Teledoc - 24 hr. access to doctor by phone/computer for employee & their dependents
    • Employer pays 100%
  • 401K Plan
  • Fun & Supportive Environment
  • Discounts in retail stores and free admission to all company attractions
  • Flexible Scheduling
  • Established & Financially Stable Company
  • Operating tours, attractions and retail in Boston, Key West, Nashville, San Diego, St. Augustine, Savannah and Washington, DC since 1980

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Job Requirements

Knowledge, Skills and Abilities

  • Our ideal Tour Guides have a passion for helping people and making their vacation experience a memorable one.
  • A Commercial Driver’s license (CDL) with Air Brake & Passenger Endorsements is required.
  • Tour Guides must be able to drive a non-air-conditioned vehicle, on busy public streets in a safe, competent manner while entertaining guests by narrating a scripted sightseeing tour.
  • Must be able to board and exit the trolley and assist guests with boarding and exiting the trolley.
  • Must pass annual Motor Vehicle Reports (MVR) checks as required by the Department of Transportation (DOT).
  • Ability to learn and memorize scripted tours and routes as assigned.
  • Ability to read, write and speak fluent English in order to communicate with fellow employees, the general public, law enforcement and emergency personnel.
  • Ability to sit for long periods of time and tolerate a wide range of temperatures and weather conditions
  • Ability to lift up to 50 pounds


  • Must be at least 21 years old.
  • Must pass a DOT physical.
  • Must have a valid MA CDL with Air Brake & Passenger Endorsements and an acceptable and verifiable driving record of at least three consecutive years.

Successful candidate must undergo a drug test and a background search.


*Gratuities vary with the season, some of our Drivers & Tour Conductors may earn over $100 per day in Gratuities.

**Calculated with employee participating in voluntary wellness program.


Key Words: CDL, Commercial Driver’s License, Tour Guide, Guide, History, Historian, Hospitality, Docent, Guest Service, Storytelling, Reenactor, Fun and Entertainment.



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