Reservations Specialist

Milwaukee Food & City Tours

For the past 14 years at Milwaukee Food & City Tours, we've been offering delicious walking and bus tours exploring neighborhoods of Milwaukee originally settled by Italian, Irish, Polish and German immigrants. Recently we acquired Chicago Food Tours, a nearly identical company exploring Chicago's neighborhood cuisines. On all of our tours, our guides provide historical commentary and point out architectural highlights and cultural hotspots, while allowing our guests to sample flavors from restaurants along the way. Please visit our websites for more in-depth details about the many tours that we offer to locals and tourists alike.

Position Details

Reservations Specialist
Southeast Wisconsin
Milwaukee, WI

Ideal candiate should be an organized and detail-oriented person who is able to work independently on multiple projects at one time. To succeed in this position, the candidate must be proficient in Microsoft Excel to manage our reservation process. This person will be an integral teammate in taking our company to a new level of growth. This position offers a unique insight into the great cities of Milwaukee and Chicago. As a small business, we take pride in the experiences and tours that we offer to our guests. Therefore, as the person who takes the lead on making restaurant and attraction reservations in Milwaukee and Chicago, this position can be quick-paced and demanding. The tasks of this job give our tour guides the tools to lead successful and seamless tours, and enhance our tour guests to have happy memories and celebrational events such as birthday parties, bachelorette parties, family reunions and corporate team outings. At the end of the day, we focus on getting the job done over position titles!

We are in search of a Reservations Specialist to coordinate tours for Milwaukee Food & City Tours and Chicago Food Tours. Key responsibilities in this position are the facilitation of proposing and planning itineraries, and seeing them through to completion.

To do so, key responsibilities include:


  • Must be able to use time management skills to plan and always be working ahead several weeks or months to book restaurant reservations
  • Utilize databases daily to process payments, make reservations and collect participant contact information for marketing purposes. 


  • Make restaurant reservations on a weekly basis via phone and email, and document all of your communications in Google Sheets
  • Report final head counts and itineraries to restaurants, tour guides and bus drivers  
  • Respond to customer service emails promptly, taking care to note all food allergy / vegetarian requests and documenting all conversations to ensure excellent tour implementation. 
  • Must have access to transportation and be comfortable traveling for occasional meetings in Chicago to build strong relationships with new restaurant partners (gas stipend provided)
  • Poses a calm demeanor in order to execute up to 25 tours / events a day at a time. 
  • Run tour errands regularly throughout the downtown Milwaukee area, dropping off supplies to tour guides, stocking buses with items, meeting with hotels / restaurants, and picking up supplies from vendors. 
  • Assist with gift card sales and redemptions
  • Answer guest questions regarding tour routes and options
  • Maintain professionalism when meeting with vendors and/or guests in the community


  • Our candidate will be an expert in Excel and able to work in a high-pressure situation - this is non-negotiable and must be a skill currently in practice with candidate
  • Ideal candidate can take on a non-traditional schedule, primarily from home. Staff person will work Tuesday - Saturday (Sunday / Monday off; can swap Saturday dates with other staff as needed).
  • Must have an ability to stay extremely organized, timely in communications and document all conversations in master reservation system
  • Must have at least 2 years experience in an administrative assistant, event planner or non-profit capacity. Worked in the tourism field already? That's even better.
  • Must have an ability to work independently - once you are trained, this is a work-from-home position
  • Must have an ability to receive direct feedback from guests on an ongoing basis
  • Must have an ability to quickly understand our tour offerings and promote that to guests
  • This is an hourly position at $18 an hour. Please do not apply if this is not acceptable to you. 
  • We do not offer a health care plan. 
  • We do offer 1 week paid vacation, but you are welcome to take additional unpaid vacations and we are flexible to the quantity of the amount of time taken. 
  • Once trained, this is a work-from-home position - we provide a laptop and cell phone, and we do compensate for mileage. 

This is honestly an amazing job, but you must be able to think fast, work hard, manage a lot of questions and calls. You must be able to handle the pressure of delivering flawless tours to guests with high expectations. As we grow, if desired, there will be growth and travel opportunities for the candidate that is the right fit.

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