Historyteller at the Old Jail

Historic Tours of America
Saint Augustine, FL

Old Town Trolley tours of St. Augustine voted BEST EMPLOYER!

Named one of the Top 3 Employers and Best Leadership in St. Augustine. Proud winner of the Chamber Member of the Year and Florida’s First Coast Tourism Impact Award. Join the team everyone's talking about!

Position Summary

This position must have a good sense of fun and desire to entertain. Our guests judge our company and all of our other employees by the way you handle your duties. The stories shared at the Old Jail are an important part of St. Augustine's history. It is the Historyteller's job to bring this history to life in a respectful, accurate, and engaging way.

Employee Benefits

  • Competitive pay and paid training: $15 per hour
  • All FT Employees are eligible for 2 weeks of 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, Charleston 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

  • Present historically accurate information in an entertaining manner in costume both indoors and outdoors in various weather conditions, several times a work shift, in a loud, audible voice without amplification for an audience of up to 65 people.
  • Portray costumed historical characters, either based upon real persons or composites of real persons to teach or interpret local history.
  • Study and rehearse roles from scripts in order to interpret, learn, and memorize lines and cues as directed.
  • Learn about characters in scripts and their relationships to each other to develop role interpretations.
  • Capability to fill the roles for host, historical characters, and switch roles with ease when required during a work shift.

Required Knowledge, Skills, and Abilities

  • Ability to work independently over long periods of time or as part of a team within the scope of established rules and regulations
  • Ability to read, write, and speak clear English communicate with coworkers and the general public.
  • Ability to learn stage direction and memorize details provided in scripted story and relay scripted story in an entertaining manner.
  • Ability to be heard in a loud, audible voice.
  • Ability to give the scripted story in the time allowed

Qualifications

  • High school graduate or equivalent preferred
  • Strong interest in St. Augustine history is a desirable
  • Prior performance or interpretation experience preferred

Other Requirements

  • Must pass pre-employment background check and substance abuse testing
  • Have a passion for helping people and making their St. Augustine experience a memorable one
Posted 2026-08-03

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