Our mission is to offer high-quality, educational and dreamy bicycling itineraries that celebrate the diversity of native people and their landscape.

As a specialized “boutique” tour operator since 1988, we provide the most authentic, unique and exciting vacations in the adventure travel industry. Our well-crafted educational trips in (just to name a few) Italy, France, Spain, Austria, Belgium, New England and beyond are active immersions into local art, language, music and, of course, delicious cuisine. By combining legendary service and rare cultural experiences, our Ciclismo philosophy continues to energize and transform each and every guest.

We warmly embrace our active-travel niche and family-style company culture. Our strengths and excellent reputation lie in our years of active travel expertise, superior and personalized customer service, and multi-talented staff and members of our tour leadership team. Our entire Ciclismo US and Italian base and bilingual guides are passionate about doing things the Ciclismo way-with a sense of fun, creativity and total dedication to quality.

Available Positions

Content & Social Media Manager

The Content & Social Media Manager will lead the content process, create key stories, marketing copy, website content, e-blasts, webinar presentations, blogs, social media posts and other assets and measure their results. Strong writing skills for SEO, an obsession with detail, an established track record managing social media flow from creation to measurement, and exceptional time management, organizational and communication skills are essential. Knowledge, experience and passion for adventure and specialty travel and bicycling is highly preferred.

This role is for someone who thrives in a fast-paced and close-knit, deadline-driven work environment.


  • Build and refine a content creation, delivery and measurement process for each content type: e-blast, blogs, website content, webinar, social media posts and others
  • Develop and drive the company’s annual marketing calendar while keeping it current
  • Manage daily social media marketing including creating posts, managing engagement, promotions and contests on Facebook, Instagram, Twitter and LinkedIn.
  • Suggest content themes and relevant topics based on guest evaluations, guide feedback, and business needs
  • Provide direction to and liaise with external blogger(s)
  • Develop and manage an email marketing automation plan towards results
  • Responsible for managing digital assets (photos, video, art) and photo selection
  • Manage online ad campaigns directly and with vendors
  • Serve as analyst and editor-in-chief of all created content, front-facing social media pages, and measuring engagement through to conversion
  • Assist with other marketing projects as needed



  • 3-6 years experience in content management
  • Proactive problem solving approach with changing priorities in a fast paced environment
  • Mastery of social media platforms (Facebook, Instagram, Twitter, LinkedIn)
  • Top-notch writing skills with an excellent command of the English language
  • Knowledge of writing for SEO; travel and/or bicycle industry plus prior travel to Europe or South America preferred
  • Proven critical thinking and collaborative skills
  • Experience with WordPress CMS, Adobe Suite (Lightroom required), HubSpot highly desirable

This is an office-based position in Arlington, MA.

Please submit cover letter stating why you are the right person for this opportunity, resume and 2 writing samples to

Tour Guide

Hiring window is November to March – see Tour Leader Application Instructions below

US Office Application Instructions

We accept applications on a rolling basis in case a position opens up mid-season. Please send a copy of your resume, a cover letter, and two references to

Tour Leader Application Instructions

Thanks for your interest in Ciclismo Classico! If you are interested in applying for a Tour Leader position for our tours we encourage you to submit your resume and fill the application form. Our normal hiring period for guides is November 1st to February 28th

Tour Leader Requirements
There are a number of qualifications that we look for when we hire tour leaders. We suggest that all applicants review the following list, which will help you decide if you have the necessary skills, personality and experience to join Ciclismo.

The bottom line is that this job is about people: it’s a fun job but it’s not your vacation, it’s a service position. Our guests are special people and it is a privilege to be their hosts, teachers and coaches. They have high expectations for service: your job is to guarantee that all the guests are SAFE, HAPPY, and having the greatest time of their life at all times.

You’ll work in a team, and you’ll share with your co-Leader long hours of work. The quality of your working relationship can affect the spirit of the tour. You’ll need to communicate well, be sensitive to and adapt to different styles of work and life, in order to find the best balance with your co-Leader: remember the goal is not to shine personally, but to run a great trip!

Each day you have to perform many tasks in the most effective way and you are in charge of lots of information; you have to keep track of all aspects and fill in detailed reports at the end of the trip, therefore we require Leaders to possess basic computer skills, like using a word processor and electronic spreadsheets.

While we have planned each day’s events, something will not go as planned: you need to know that things change 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 able ready to dive into an optional plan with zest and confidence, taking a situation and making the best of it.

For hotels, restaurants, grocery stores and the general public. Although we want to do our best to please our customers, don’t forget that we are guests in Italy and Europe, and must respect each country and its culture.

Our tours are not just vacations, they are a quality experience and cultural immersion. You should have a deep knowledge of the culture and the people, and the desire to teach and share this with guests: you are expected to be prepared to answer questions about Italian and European culture, history and art, and to get guests involved in the local culture and history. Being resident in Italy or in the European country that you apply to lead trips in, constitutes preferential requirement.

We require you speak English at a good level, AND Italian or other European language if you apply for our European departures. You should also be comfortable speaking in front of a group.

You should possess good bike riding 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 deal with bike mechanics for major problems.

All Tour Leaders are required to drive a stick shift, 9-seat van and will alternate driving responsibilities with other Tour Leaders. Think seriously if you feel comfortable about driving a van loaded with luggage and bikes on Italian roads.

All Tour Leaders are required to have an updated First Aid certificate.

Guide Training
Every Tour Leader whose application has been selected, will be called by our staff and eventually invited to a spring training camp of a few days, in Italy, where will receive the basic training for our job and, at the same time, will have the chance to show “on the field” his/her skills, for a final selection.
Once assigned to a trip, a new tour leader will do a “pre-tour” of the itinerary, with a senior tour leader that will explain in details all the aspects of the specific trip and of the Tour Leader role at Ciclismo Classico.

If you think you have what it takes to guide for Ciclismo Classico please fill out the form below:

  • Drop files here or
    Accepted file types: pdf, doc, docx, odf.
    Submissions without a Cover Letter will not be considered.