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Welcome to Carolina Tailwinds!

So you are interested in becoming a tour leader? After 17 years of guiding tours, we can honestly tell you that this is a very fun and genuinely rewarding job!  It has evolved into a company dedicated to a superior level of customer service, attention to detail, and desire to give our guests one of the best vacations of their lives.

We need individuals who excel in the following areas:

  • Exceptional customer service 
  • Leadership and team work skills 
  • Professional demeanor and appearance 
  • Problem-solving and flexibility in finding solutions 
  • Enthusiasm and positive outlook 
  • Physical ability to meet the demands of the job 
  • Communication and interpersonal skills 
  • Ability to represent Carolina Tailwinds professionally to guests, inn partners, caterers, and the communities through which we travel 
  • Commitment to continuous improvement 
  • Compassion and caring for others 
  • Organizational skills and attention to detail 
  • Strong work ethic and self discipline

Life as a Carolina Tailwinds Tour Leader:

While offering a rewarding lifestyle and career choice, leading tours equally offers unique challenges on a daily basis - mentally, physically, and emotionally. Guides must be extremely organized, master logistics of each tour location, be flexible to respond to both weather challenges and personal conflicts, be able to alternately act as a coach, instructor, motivator, educator, cheerleader and local guide. In short, this means you are "always on". Many people see guiding tours as a "dream job" - riding your bike through beautiful countryside with entertaining people. While partly true, guests do not see all the long hours demanded each day. Mornings usually start around 6 a.m. and your day can last as long as 11 p.m. This requires the ability to maintain balance each day to keep your energy level high and guest interaction fun and fresh.

Frequent Questions:

How will I be compensated?

We offer a very competitive per diem rate which serves as your full compensation regardless of daily hours worked. Carolina Tailwinds does not pay overtime. We will be hiring you as an independent contractor. You will need to consult with your local tax professional to determine the tax impact to you of independent contractor income.

At times, guests will decide to tip you for extraordinary service. These are your responsibility to report to the IRS and local tax agencies.

Should you be hired and work for Carolina Tailwinds through a whole season, Carolina Tailwinds will also outline opportunities for bonuses paid based on customer reviews, repeat business generated from your tours, independent contract renewal for another season, etc.

Carolina Tailwinds will be responsible for all costs associated with lodging, food, and transportation from our home office in Winston-Salem, NC to the tour location. Tour leaders will be responsible for transportation costs to Winston-Salem.

You will be responsible for all costs involving certification or additional training required to meet our skills requirements. Certifications required by us are a minimum of Adult CPR and Standard First Aid. These are courses that can be completed at your local American Red Cross facility.

Additionally, should you feel the need, you may want to attend your local bike shop's Park Tool School or similar training session for additional bike maintenance skills and knowledge.

How many tours and hours can I be expected to work?

This is a part time job.  We need individuals who are willing to work up to 1 - 2 tours per month during our season of March through October. There could be times you would be away from home up to 2 weeks at a time.  Some of our guides only work specific destinations and only work 2 - 4 tours per season.  Others work multiple tour destinations and are able to work 6 or more weeks per season.

There are also opportunities to work more tours per month should your schedule and energy level permit. We anticipate having some local part-time weekly work in Winston-Salem at our office depending upon your skill set and availability.

How many guides are you looking to hire?

We are still assessing our needs for the upcoming season. We anticipate needing 3 - 6 additional guides for our upcoming season. We will be training you on our systems and methods both in the office and "on the job" so that you will be comfortable in a tour leader position interacting with guests.

Still interested?  

Your next step is to complete our application and submit required documents to us via email, or if you prefer, via US Mail.  You may click here to download our application and required document checklist.  We will follow up with you via email to let you know we have received your application and to set up additional contact times that are mutually convenient.  

MS Word Format (able to be edited and saved on your computer):
Carolina Tailwinds Tour Leader Application

Adobe Acrobat Format (able to be printed and completed manually):
ct employment application.pdf

We look forward to hearing from you.  Thank-you for your interest in Carolina Tailwinds!

--  Anne and Greg Fleming

Carolina Tailwinds
P.O. Box 24716
Winston-Salem, NC  27114-4716
Ph: (888) 251-3206
Ph: (336) 794-1054 
Fax: (336) 794-1082


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  Carolina Tailwinds, Inc.  "Carolina Tailwinds" and the Carolina Tailwinds Logo are Service Marks of Carolina Tailwinds, Inc.

Carolina Tailwinds   P.O. Box 24716   Winston-Salem, NC 27114-4716   888.251.3206 or 336.794.1054