Wine Trail Ride cycling tours
Be a part of the WindsorEats crew!

WindsorEats, a food and drink guide with a social touch, is currently seeking individuals for positions as Cycle Tour Guide & Storyteller for our cycling tours.

Specifically, we are looking for guides that will specialize in our food and beverage themed cycling tours. These guides will be responsible for leading interactive, theme-based cycling tours and events that will provide attendees with enjoyable, engaging, and in-depth experiences of the neighbourhoods and local businesses of Windsor-Essex as well as provide attendees with in-depth knowledge about food and beverage tasting, industries and history.

Knowledge and a passion for food, beer, wine and/or liquor is a must. Experience with beverage and food pairing is a plus as well as knowledge of the industries, history and culture of the region.

Finally, we believe that the guide is the most important element of our tours so we seek people who are personable, passionate, entertaining, and fun which helps ensure that WindsorEats’ guests have the time of their lives on our tours.

Guides could be used on any of our Wine Trail Rides, Bikes & Beers or Friday Night Lights tours.

Cycling Guide and Storyteller Details

Positions: WindsorEats Cycling Tour Guide/Storyteller
Location: Windsor, ON
Season: May-October (high season), Nov – April (low season)
Hrs/week: Average of 3-6 three hour shifts bi-weekly during high season (May-October)
Rate of pay: $15.00/hr
Hours: Majority of the work is late Friday nights and Saturday mornings and afternoons.


Candidates must:

  • Must have comprehensive knowledge of road and cycling safety, rules and regulations.
  • Must be a capable bike mechanic.
  • Must be a capable of cycling 50+ kilometres at a good pace is needed.
  • Must be knowledgeable about safe riding in both an urban and rural environment.
  • Must be engaging and converse with participants to ensure that they are having the best possible experience.
  • Demonstrate knowledge in one or more of food, beer, wine, or liquor; and one or more of the following:
    • Tour guide experience
    • Acting experience
    • Public speaking experience
    • Food industry expertise.
  • Have experience in interacting with diverse groups of people from a wide range of cultural, racial, and socio-economic backgrounds.
  • Be knowledgeable of and enthusiastic about the history, cultures, and industries of the Windsor-Essex area.
  • Be comfortable with speaking in front of groups of people in a professional manner.
  • Have a positive ‘can-do’ attitude, sense of humour, and friendly personality.
  • Perform well under pressure and demonstrate good judgment and communication skills.
  • Be able to commit to giving at least two tours per month.
  • Exude awesomeness.
  • Bonus points will be given to candidates who:
    • Demonstrate verbal fluency in a language other than English (Preference will be given to French).
    • Are certified in CPR and First Aid.
    • Have special food or beverage related certifications (Sommelier, Cicerone, etc.)


Responsibilities Include:

  • Guide cycling tours for groups of up to 100+ adults.
  • We encourage the guide to bring a cell phone for emergency use.
  • Provide support to the group. Throughout the ride the Guide should make his/her way up and down the trail of riders to ensure that participants are safe.
  • ‘Corking’ with other guides along route to ensure safety of participants.
  • Be responsible for leading the group to each destination and ensuring their safety along the way.
  • A cycle tour leader must also be able to repair bicycles competently, often without bespoke tools.
  • Provide a general check to ensure bikes are in good condition (i.e. tire pressure) as participants arrive.
  • Prior to each ride the Cycling Guide must go through safety tips, cycling signals and what to do in case in need of help.
  • Learn prescribed routes and historic information
  • Facilitate social interaction between guests of varied ages and backgrounds
  • Manage prescribed tour logistics in a safe and responsible way
  • Know the route and manage the journey
  • Function as the appointed health and safety advisor for the trip, and also the medic
  • Give detailed and accurate information to the tour guests
  • Manage the itinerary, which may change to take account of complications


All interested applicants, please e-mail your resume and letter of interest to before March 1, 2015.