Ciclismo Classico Bicycle Tour Guide

Working as a guide for Ciclismo Classico is an opportunity to do your best, improve your best–and have fun while you’re doing it!

This job is all about people, and you will have a unique opportunity to meet them and help them create happy memories that will last forever. While it does involve the daily nitty-gritty daily tasks of a service position, you will also have the privilege to be hosts, teachers, and coaches for our guests. They have high expectations for a great experience: your job is to guarantee that all the guests are SAFE, HAPPY, and having the greatest time of their life.

Here’s how you do it at Ciclismo Classico.


  • Be a Team Player . . . you’ll work in a team, share some long workdays with your co-guide, and the quality of your working relationship will affect the spirit of the tour. You’ll have to be communicative, sensitive and adapt to different styles of work and life to find the best balance with your colleague. Remember the goal is not to shine personally, but to run a great trip for our guests.
  • Be Organized . . . Each day you must plan ahead to perform many tasks in the most effective way, and you are in charge of lots of information. You must keep track of all aspects and fill in detailed reports at the end of the trip, therefore we require guides to possess basic computer skills.
  • Be Patient, Flexible, and Creative in solving problems . . . We plan carefully, but eventually something will go wrong, often at a moment’s notice. You should be able to confront obstacles and take a positive plan of action. Even in moments of stress, you must be ready to dive in and calmly deal with the situation.
  • Talk the Local Talk . . . Our tours are not just vacations, they are a quality experience and cultural immersion. You should have knowledge of the local culture and history where your tour is riding. If you’re guiding a tour in a new area, you need to have the research skills to go locate and learn the information before the tour.
  • Walk the Cycling Walk . . . You should possess good bike handling skills, the ability to coach other cyclists ,and be aware of all cyclist’s safety on the road. You should be able to perform basic maintenance and repairs, and to locate and collaborate with the closest professional mechanic for major problems
  • Drive the Cycling Bus . . . You will share driving responsibility with your co-guide, both on ride days and during any required van shuttles. You must have any locally required commercial driver’s license or other documents needed to drive a van with multiple passengers at your tour location. You will be responsible for multiple passenger safety and must be comfortable and confident with that.
  • Be the Savior . . . All tour guides are required to have current certification in both CPR and general first-aid from the Red Cross or other qualified organization.




  • Communicate with customers in advance of the tour to assure they are properly prepared for the trip and familiar with the itinerary.
  • Participate in pre-tour promotional activities including social media postings, zoom meeting with prospects, etc.
  • Make reservations or other advance preparation with local cultural speakers, rental bike vendors, etc.
  • Proactively research guests before trip to creatively help them celebrate on-tour milestones such as birthday, anniversary, biggest climb ever, longest ride ever, etc.

During Tour

  • Greet and welcome customers to the tour.
  • Adapt itinerary during tour to adjust for weather, road closures, and other unexpected situations.
  • Proactively assist guests with pre-ride preparation including pre-tour check of weather forecast and tire pressure, chain lubrication, filling water bottles, assisting in programming and operating navigation devices, etc.
  • Clean guest bikes after foul weather rides.
  • Schedule visits and purchases tickets to museums, galleries, protected parks, and other attractions ahead of time, if required.
  • Proactively plan alternate activities in the event of cancellations, closures, or weather prohibiting scheduled events, routes, or attractions.
  • Handle logistics for and maintain the requisite equipment for each tour, including vehicles, gear, rental bikes, etc.
  • Organize and procure daily ride snacks and hydration with trip to grocery store or another vendor if needed.
  • Use mechanical skills to solve unexpected minor on-road issues (flat tire, adjust shifting, etc.)
  • Be familiar with closest professional mechanical assistance for serious issues (True wheels, purchase and install replacement parts such as broken wheel, etc.)
  • Inform guests about the culture and history of the region or establishments the tour will be visiting.
  • Familiarize customers with each region, establishment, or attraction.
  • Make safety a top priority, including preventing major incidents (check bike condition, watch for traffic or construction hazards, etc.), as well as guest health and wellness (encouraging sunscreen, proper hydration, etc.)
  • Have knowledge of and direct customers to other, non-competing services that might be of interest to them such as museums, hiking routes, gift shops, etc.
  • Communicate regularly with home office to keep management updated about status of tour.
  • Look to future tours–watch for possible interesting new routes, attractions, and establishments that could improve future trips.
  • Be informed of tour budget needs, monitor spending, and retain all receipts for post-tour accounting.
  • Ascertain special needs from guests and use skills creatively to fulfill them without compromising safety or service to other guests.
  • Successfully organize and lead off-bike activities when required such as hikes, kayaking, museum visits, etc.
  • Organize and complete guest luggage transfers successfully and safely when included in itinerary.
  • Use interpersonal skills to interact successfully with all kinds of personalities and viewpoints including guests, vendors, local residents, etc.

Always remember: you are here to help your guests have a positive experience they will remember forever–and that they will want to repeat with you on a future tour. Treat them the way you would want to be treated and make it special for them!


  • If designated, completed post-tour accounting documentation by post-tour deadline.
  • Clean and return any rental equipment including bikes, van, etc.
  • Conduct inventory of tour equipment to identify items for possible repair, replacement, upgrade, guest lost items for return, etc.
  • Assist management in post-tour review, identifying issues and planning proactive solutions for future tours.
  • If photos were taken by guides, complete arrangements for supplying them to guests.

If you have bike tour guiding experience and are interested in leading bicycle tours in the Northeast and/ or Europe*  please e-mail a lively and informative cover letter that tells your story and your specialty bike destinations and your resume to

*European guides must be bilingual in Italian, French or Spanish.