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60 Trolley Jobs Hiring Near You

Trolley Hospitality Companies

Server

Norfolk, VA · On-site

$12 - $19/hr

Trolley Eats is the corporate dining division of Trolley Hospitality Companies, a Richmond-based hospitality group serving the greater Richmond and Hampton Roads regions. We specialize in tailored ...

Unioncollege

Trolley Driver - On Call

Schenectady, NY

$19/hr

Varies Trolley Driver - On Call Pay Status and Classification: Temporary, Non-Exempt, Part-time. Supervisor: Transportation Manager Position Purpose: Provides transportation of Union College students ...

Union College

Trolley Driver - On Call

Schenectady, NY · On-site

$19/hr

Varies Trolley Driver - On Call Pay Status and Classification: Temporary, Non-Exempt, Part-time. Supervisor: Transportation Manager Position Purpose: Provides transportation of Union College students ...

Trolley Hospitality Companies

Catering Cook

Henrico, VA · On-site

$18 - $21/hr

Groovin' Gourmets is the catering division of Trolley Hospitality Companies, a Richmond-based hospitality group serving the greater Richmond and Hampton Roads regions. We specialize in delivering ...

Philadelphia Trolley Works

Be Seen First

Mechanic

Philadelphia, PA · On-site

$20 - $40/hr

Philadelphia Trolley Works/The Big Bus Company is Philadelphia's largest provider of Sightseeing Tours and Specialty Transportation in the Philadelphia region. The company has grown to become an ...

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Trolley Jobs Information

Infographic showing various job openings at Trolley in the United States as of August 2026, with employment types broken down into 100% Part Time. Highlights an 100% Physical job distribution.

Trolley Driver/Tour Guide

Historic Tours of America

Key West, FL • On-site

$23/hr

Full-time

Medical, Retirement, PTO

Re-posted 28 days ago

Job description

Trolley Driver/Tour Guide

This position must have a good sense of fun, a desire to entertain and excellent driving skills as they drive a trolley on busy public streets while narrating a sightseeing tour multiple times a work shift and drive a Conch Tour Train when needed. Tour Conductors bring to life the history of America and all the positive things it represents. 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.

Employee Benefits

  • Competitive pay: $23 per hour plus gratuities --> $3,000 Sign On Bonus*
  • Paid Training: $20 per hour
  • All FT Employees are eligible for paid vacation time, as well as company sponsored health and wellness plans
  • 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



Requirements:

Essential Functions

  • Drive in a safe, competent manner a non-air-conditioned trolley on busy public streets wile entertaining guests by narrating a scripted sightseeing tour up to 4 to 5 times daily
  • Meet and deal with the general public and diverse company in a prompt 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

  • 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 to apply - we hire for personality. We will put you through our paid CDL training course and prepare you for the CDL Testing.
  • Ability to learn and memorize scripted tours and routes as assigned.
  • Ability to work independently over long periods of time within the scope of established rules and regulations while performing tours and satisfy the needs of our guests.
  • Ability to deal with unpleasant, angry, or discourteous people in a calm and pleasant manner
  • Ability to read, write, and speak clear English in order to communicate with co-workers, general public, law enforcement, and emergency personnel and to complete required paperwork correctly.
  • Ability to learn new duties, policies, and procedures and adjust to new situations encountered on the job within a reasonable amount of time.

Qualifications

  • Must be at least 21 years old
  • Valid Florida Class C or higher CDL with passenger endorsement (will train to acquire CDL. Must obtain a CDL in the first month of employment)
  • Acceptable driving record for the past 3 years.

Other Requirements

  • Must pass pre-employment MVR/background check and substance abuse testing
  • Must pass annual Motor Vehicle Reports (MVR) checks as required by the Department of Transportation (DOT).
  • Valid DOT physical required
  • TWIC Pass, Federal background check, Key West Port Pass required
  • Have a passion for helping people and making their Key West experience a memorable one.