We started Carolina Tailwinds over 22 years ago with the vision of creating a fun and unique vacation experience for our guests. Our desire was to share our passion for touring by bicycle and traveling the geographical areas we know well and love.  It has been a fun and successful ride. Carolina Tailwinds is growing, and we are looking for qualified candidates for our 2024 season.

Please read our requirements for the positions below.  We look forward to hearing from you.

May the Tailwinds be with you,

Anne and Greg Fleming
Co-founders, Carolina Tailwinds

Position:  Bicycle Tour Guide

We are looking for qualified candidates for our upcoming season to serve with us as part-time and seasonal tour leaders. 

  • Do you have the desire to create the best vacation experience for our guests? 
  • Are you committed to putting customer service above your own needs at all times?
  • Do you possess superior people skills and leadership ability? 
  • Do you have strong teamwork and organizational skills, enthusiasm, attention to detail and problem solving skills?
  • Are you physically fit and able to lift bicycles weighing 30 lbs above your head and carry luggage weighing up to 50 lbs?
  • Are you passionate about cycling and love the outdoors? 
  • Do you love sharing that passion with others, exhibit an engaging personality, and have a zest for life?

If you can answer “Yes!” to the above questions, we would love to start the process with you. 

Click Here to Learn More about Joining Our Team