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Join Our Cast

Old Town Trolley Join Our Cast


Join the ranks of the fun employed!

When you travel to new destinations, it’s always best to have someone you can trust that knows the city inside and out. How would you like to be that person for the thousands that visit San Diego, St. Augustine, Nashville, Washington DC, Boston, Key West, or Savannah every year?

Old Town Trolley Tours has been entertaining visitors in cities across the country for over 35 years. Our company is made up of a diverse, highly motivated team of Castmembers who are ambassadors for the cities that they work in and we are always looking for dependable, enthusiastic people with leadership skills. Being a conductor for the legendary Old Town Trolley Tours is far from your average desk job. One of the seven incredible locations we service would be your office as you wind up and down city streets showing off the very best the area has to offer.

The informal, humorous, and informative way we communicate is our trademark and we’ll teach you to become among the very best tour guides in the country. If you think you fit this description and are looking for an exciting career in any of the cities previously mentioned, we would love to hear from you!

Here are some additional benefits to consider:




Key West


San Diego


Washington DC – Tour Conductors

If you’d like to join our cast and become an ambassador for your city, please click on the button below:


Or call us:

    • Boston: 844-738-6562
    • Key West: 844-838-6562
    • Nashville: 844-887-6553
    • San Diego: 855-738-6562
    • Savannah: 844-387-6553
    • St. Augustine: 855-687-6553
    • Washington DC: 855-338-6562
    • Retail All Cities: 866-538-6562


See yourself in the picture?

  • Family meeting with cast of Old Town Trolley Tours
  • old tow -trolley key west faqs
  • visitors boarding old town trolley key west
  • santa and trolley
  • Cancer awareness trolley
  • old town trolley community service
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