What Working for Rick Steves is Really Like

“What’s working for Rick Steves like?” I’ve heard that question many times since I worked as one of his tour guides in Europe. Rick Steves and his partner, Trish, joined me on the Loop Interior Architecture Walking Tour back in 2016. So I thought I’d answer a few of those common questions for our tour guests who use his books for their trip to Europe or religiously watch his PBS show.

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Rick Steves private tour Chicago
Rick was my tour guest on our Loop Interior Architecture Tour.

I know Rick Steves because I worked for his company for over a decade. Before that, I had traveled in Italy and spoke the language. During college, I also held a job as an assistant tour guide in Italy for a different company. Rick’s tour company, which is how his travel empire began, was then called “Europe Through the Back Door.” ETBD hired me as a guide to lead multi-day tours around the country. My background as a freelance journalist led me on a job to work on updating his tour guidebooks about Italy.

The tours are a huge operation managed by an impressive team, but the books are an aspect of the business that Rick personally manages. Rick and I traveled together for four days of training so that I could update his best-selling Italy guidebooks. The tour guides also flew to the Rick Steves headquarters in Edmonds, Washington for an annual week of meetings and social events with Rick and his staff.

So here’s what working for Rick Steves is really like.

Working for Rick Steves is Hard Work

As Rick and I walked around Florence, which is swarming with Americans, people seemed to expect Rick to be waiting around any corner. At the end of interactions with him, they would often say, “Have a great vacation!” Rick Steves is not on vacation. While his television show may suggest otherwise, the man is not sipping wine and nibbling on Spanish churros all day long. He is working really, really hard.

When I worked on the book updates with him, we were practically sprinting around town to see every hotel, restaurant, laundromat, museum, church and train station in the city. We worked from dawn until well past dusk. The day was also long when I worked as a tour guide, since it was full of activities. Being a leader for groups of up to 28 different personalities also had its challenges. To explain that in full would require much more than a blog post.

Rick’s tour company employs 80 full-time employees in the office. They manage the books, television and radio shows, tours and store. On top of that, the European tours employ more than 100 guides, who live around the world. You don’t build a company from the ground up by being on vacation. The man works. All the time.

Rick Steves is Efficient as All Hell


I speak fluent Italian. While training with Rick, he asked me to interpret something for him to a restaurant owner. Rick wanted the restaurant owner to offer a special deal for readers of his book. While Rick said about five words, my interpretation took about five times as long to say. To communicate the phrase as an Italian would, I had to explain the idea and say the same thing in a couple different ways. He flatly expressed to me that he was not at all into the length of my communications.

Rick acquires and checks an enormous mass of information for his books. From working with him, I learned how when you have 50 things to do in a day, if each thing can take half as long, you can accomplish twice as much. As a small business owner, I have to be efficient. I am very grateful to have learned this.

He is a Fun Dude

For his PBS show, Rick has a very chill and friendly persona. Like any television personalities, his real character is not as watered down and wholesome. While he is easygoing, he is still pretty intensely hard-working, as mentioned above. Also, the guy can be pretty funny. You can get a better sense of this if you to one of his public speaking events, like his Ted Talk.

Or you can see Rick Steves dance at one of our tour guide parties a few years ago.

Rick has a great sense of humor. I also know because he laughed at my jokes when he came on our private tour of Chicago’s interiors and the underground Pedway System 🙂

Rick Steves is Not a Total Stoner

working for rick steves marijuana reform

Yes, Rick speaks out about the legalization of marijuana. His advocacy relates to burdens on our criminal justice system and the lost tax revenue that legalization might bring. It’s a no-brainer that the medical uses of it are vast. Rick’s ideas on drug policy reform are very politically motivated.

But no, Rick is not toking a bong every morning before going to manage his huge business. Rick certainly has some hippie roots, but he is not a total stoner.

He Treats His Employees Well

When I began working for Rick Steves’ tour company, I was really impressed how it seemed like almost everyone had been there at least a decade. After I got hired, it took me at least five years before it didn’t seem like I was a newbie. I initially trained as a tour guide with Dave Horelein, who does the awesome maps in the guidebooks, and he’s been working with Rick for 30 years.

Longevity in a company shows that Rick is doing something right. While any business owner has enormous support from his or her employees, it is the leader that establishes a company culture. I would describe the Rick Steves’ company culture as casual, friendly, open, hard-working, liberal and smart.

I may not know him on a really personal basis, but this is what I’ve gathered from working for Rick Steves over the years. It was a great honor to have him take a break from the Chicago Travel and Adventure Show to come explore Chicago with me and on our custom tour.

— Amanda Scotese, Executive Director 


In business since 2010, Chicago Detours is a passionate team of educators, historians and storytellers. We applied a decade of experience as one of Chicago’s top-rated tour companies to become a virtual event company in 2020. We bring curious people to explore, learn and interact about Chicago’s history, architecture and culture through custom tours, content production, and virtual events.


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Private Tour Coordinator and Tour Guide

There is no shortage of things to discover in Chicago—I love being an urban explorer and uncovering its hidden places. I have an MA in Public History from Loyola University Chicago, and I have worked as a museum educator and kindergarten teacher. My desire to learn new things fuels my passion for educating others, which I get to experience every day as a Chicago tour guide. I live in the northern neighborhood of Rogers Park.

“Our guide Ellen was exceptional and gifted with a great personal touch.”


Tour Guide

Whether you are a first-time visitor or a lifelong resident, the vibrant history and modern majesty of Chicago never ceases to amaze. I’m a graduate of Columbia College with an M.A. in Interdisciplinary Art. I’ve worked for many years as an educator at City Colleges of Chicago. As tour guide at Chicago Detours, I integrate my enthusiasm for culture and architecture with my passion as an educator. West Town/Noble Square area is home for me.

“Jen was a perfect storyteller and kept us spellbound for hours.”


Tour Guide

With our Chicago neighborhoods, vibrant cultural institutions and nearly two centuries of larger-than-life stories, there’s never a dull moment here! I’m a fifth generation Chicagoan and a graduate of Washington University in St. Louis. In addition to guiding tours, I’m a creative writer and amateur genealogist. I also enjoy the city’s dynamic theater scene. You can also read overlooked stories from 19th-century newspapers on my “Second Glance History” blog. I live in River North.


Tour Guide

Chicago is unique as it always evolves into the future while holding on to the past. I’m fascinated by how people latch on to old architecture but happily pave over others. My background is in theater and performance and I’ve been a tour guide here for more than 10 years. Currently I’m finishing my Master’s in Public History at Loyola University because I love to teach the history of this scrappy city. I’m in the Edgewater neighborhood.


Operations Coordinator and Tour Guide

Chicago’s history is so fascinating, you could spend a lifetime uncovering its secrets…I’m willing to give it a try! I have an M.A. in US History from the University of Nevada-Las Vegas and then pursued doctoral studies in Urban History at the University of Illinois at Chicago. I love to learn new aspects of Chicago’s rich history and then share my knowledge as a tour guide with Chicago Detours. I live in Ravenswood.

“Marie was a bubbling fountain of information and contagious enthusiasm.”


Operations Coordinator and Tour Guide

As a fourth generation Chicagoan, I have been living and loving Chicago by bike, on foot, public transit or automobile. I am a graduate of UIC where through the College of Urban Planning and Public Affairs, began my eagerness to understand the nature, history and impacts of urban planning and development. It is incredibly rewarding to give back to this wonderful city by helping out in the office of Chicago Detours. I live in the incredibly diverse neighborhood of Albany Park.
“Sonny was extremely knowledgeable about all things Chi-town.”
Wade K


Content Manager and Tour Guide

Chicago has so many neighborhoods, buildings, and by-ways that it’s hard to go long without seeing something new, or something familiar from a new angle. I studied Cinema History for my M.A. from the University of Chicago. I’ve worked as a culture writer for various publications and as an educator of the humanities at the City Colleges of Chicago. I’m thrilled to share my love of this city’s busy past and unique architectural spaces with Chicago Detours. I live in the Chicago neighborhood of Lincoln Park.

“Alex was fascinating to listen to. He clearly knows his history and it shows.”
Katie K

Amanda Scotese

Executive Director and Tour Guide

I’m an interpreter of personal stories from the past and the city’s landscape. I love to imagine what originally happened inside old unmarked buildings, and what forces have shaped their design. I studied Chicago history, architectural history, and anything Chicago-related through my M.A. in the Humanities at the University of Chicago. My love for stories was enriched by my B.A. in Literature from the University of Michigan. I’ve written travel articles for publications like Rick Steves’ Italy best-selling travel guides, the San Francisco Bay Guardian, and The Chicago Food Encyclopedia. I live in the Chicago neighborhood of West Avondale.
“You can TELL Amanda is hyper-passionate about doing the research and getting the story that nobody’s heard before.”
Shelby F

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