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Trolley Driver / Tour Guide - Signing Bonus!


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

  • From $20/hr Base Pay PLUS Gratuities*
  • $3,000 Signing Bonus ($1,000 at tour certification, $1,000 90 days after that, and the remaining $1,000 at season's end!)
  • Paid Training at $20/hr.
  • 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

Start your new Career Today!

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) is not required - we hire for personality. We will put you through our paid CDL training course and prepare you for the CDL Testing.
  • 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 upon employment.
  • Must have a valid MA Driver's License with 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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