Trolley Driver / Tour Guide- Key West in Key West, FL at Historic Tours of America, Inc

Date Posted: 9/14/2022

Job Snapshot

Job Description


Have fun driving the Old Town Trolley and the Conch Tour Train while sharing the history of our region.
Entertain visitors while educating them about historic Key West!

  • $20/hr Base Pay PLUS Gratuities*
  • Paid Training at $18/hr.
  • FT employees earn 2 weeks of paid vacation time and 5 days of sick leave each year!
  • Choice of HRA or Traditional Healthcare Plan
    • Employer pays the majority of the premium for employee only coverage
  • Teladoc - 24 hr. access to doctor by phone or computer for employee and their dependents.
    • Employer pays 100%
  • 401K Plan 
  • Fun & Supportive Environment
  • 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!

Already having a CDL is a plus, but not required because we'll train you and prepare you to test for one!

Our ideal Tour Conductors have a passion for helping people and making their vacation experience a memorable one. A sincere love of history and the culture of our city is ideal.

Most tours are approximately 1-2 hours in duration and Tour Conductors narrate several tours during each shift.


Job Requirements

Required Knowledge, Skills and Abilities

  • Tour Guides must be able to drive a non-air-conditioned vehicle, on a busy public street 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
  • 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.


  • Must be at least 21 years old
  • Must pass a DOT physical upon employment
  • Must have a valid Driver’s License with an acceptable and verifiable driving record of at least three years

Successful candidate must undergo a drug test and a background search


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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