• Old Town Trolley
  • Boston, MA, USA
  • Sep 11, 2021
Full time Transportation

Job Description


Have fun driving an Old Town Trolley and sharing the history of our region.

Entertain visitors while educating them about historic Boston!

  • $20/hr Base Pay PLUS Gratuities*
  • $2,000 Signing Bonus - $1,000 at tour certification & $1,000 90 days post hire
  • Paid Training at $19.50/hr
  • Monthly & Annual $$ Awards for top performers
  • 15% Automatic Gratuity up to $115 for each private chartered tour
  • 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 years.

Employment at Old Town Trolley Tours is contingent on successfully passing drug and background checks. Conductors must have 3 consecutive years of a good driving history and a MA Driver’s License.

*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.

Job Types: Full-time, Part-time

Pay: $20.00 per hour