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Salary
$40k per year
Location
In office (Key West)
Employment
Part-Time

Confirmed on the employer's own hiring board on Nov 5, 2026. First seen by Alion on Oct 22, 2026. Old Town Trolley Tours scores B on the Alion truth index.

Overview
Company
Impact
Profile match
Enjoy Transportainment® with Old Town Trolley, a delightful style of entertainment and transportation that sets our sightseeing tours apart.

Description

JOIN OUR HISTORIC TOURS OF AMERICA FAMILY!

Evening Trolley Driver

The Evening Trolley Driver must have a good sense of fun and a desire to entertain passengers, as well as excellent driving skills as they drive a trolley on busy public streets at night multiple times a work shift. The person in this position must make our guests feel welcome and glad they have chosen our company to entertain them.

Employee Benefits

  • Competitive pay: $20 per hour
  • All FT, PT and Seasonal employees are eligible for: paid sick time, 401K plan with company matching*, fun and upbeat work environment with various award and recognition celebrations throughout the year, First Stop Health - 24 hr. access to doctor by phone or computer for employee and their dependents (Employer pays 100%), discounts in retail stores and free admission to all company attractions

Operating tours, attractions and retail in Boston, Key West, Nashville, San Diego, St. Augustine, Savannah, San Antonio, and Washington, DC since 1980!

Start your new Career with Us Today!

*Eligibility requirements may apply

Shift Times

4:30pm - Midnight

Availability for Monday, Wednesday, Friday, Saturday, and Sunday preferred

Requirements

Essential Functions

  • Drive in a safe, competent manner a non-air-conditioned trolley on busy public streets at night, multiple times a work shift
  • Meet and deal with the general public and diverse company employees in a prompt and courteous manner
  • Handle stressful situations and difficult people both in person and via the radio while maintaining a professional and pleasant composure
  • Maintain radio contact with dispatch during tours
  • Perform an interior and exterior physical inspection of the vehicle daily and accurately complete the departmental documents/forms for inspection

Required Knowledge, Skills and Abilities

  • Ability to drive a non-air-conditioned trolley in a safe, competent manner on busy public streets or driving on company property at night.
  • Ability to work independently over long periods of time within the scope of established rules and regulations.
  • Ability to deal with unpleasant, angry, or discourteous people in a pleasant, calm, courteous manner.
  • Mental attitude required to handle the stress that goes with the job as described.
  • Ability to read, write, and speak clear English to communicate with co-workers, general public, law enforcement/emergency personnel, and to complete required paperwork correctly.

Qualifications

  • Must be at least 21 years old
  • Valid FL Class C or higher CDL with passenger endorsement
  • Acceptable driving record for the past three years.

Other Requirements

  • Must pass pre-employment MVR/background check and substance abuse testing
  • Valid DOT Physical required
  • Have a passion for helping people and making their Key West experience a memorable one.
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