I am Amanda Scotese, founder and Executive Director of Chicago Detours, a tour company for the curious, Ask Me Anything!

Chicago Detours
May 16, 2018

I launched Chicago Detours in July 2010 after spending close to a decade in Italy as a Tour Guide and Guidebook Researcher with Rick Steves’ Europe. I decided to bring my travel expertise back home to Chicago with tour experiences that are fun, educational, and truly make us feel connected to our grand city. Chicago Detours brings curious people to explore stories and places locals don’t even know through guided walking and bus tours of architecture, history, and culture to public and private groups. 


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How interested are you personally in learning about the history of the place?
May 20, 12:41PM EDT0
When does it get really busy? What's the tourist season like?
May 19, 6:57PM EDT0
Do you recall a funny incident during any of your tour that you can share? Why was it funny and what was it all about?
May 19, 1:52PM EDT0
What's the most famous package or tour you see people buying in Chicago Tours?
May 18, 8:49PM EDT0

Hi did you mean what tour is most popular with my company, Chicago Detours, or did you mean to ask generally what is the most popular Chicago tour for any company? 

May 19, 1:48PM EDT0
What does a guidebook researcher do? Can you tell more about this experience?
May 17, 8:38AM EDT0

From my understanding, guidebook researchers for most publications just send an email every couple years to the business owners and update from there. 

However, Rick Steves has a very impressive approach. To my knowledge, his books are the only travel guidebooks that are checked in-person. When I did the guidebook updates, I had to visit every single hotel, restaurant, tourist site, and even landromat's to check on open hours, management, ambience, cleanliness, etc. Also, when we saw people holding the Rick Steves guidebooks, we would talk to customers to make sure they were happy and see if they had any suggestions. 

By the way, people think it's a dream job, but it was grueling! Imagine checking every guesthouse in the little towns in the Cinque Terre, which are two to three flights up, doing that all day long! There wasn't time to stop and smell the roses. It was a lot of work!

May 17, 3:41PM EDT0

Go through your naming process. The site name is A+

May 16, 8:58PM EDT0

Why thank you Vince! I knew I wanted to denote something off-the-beaten path. I like something involving the word "alley" but it ended up sounding too grungy. I didn't want to literally use the words "off the beaten path" because that is a little overused as well. And I wanted to express that we are a tour company that is doing something different! 

People say that imitation is the best form of flattery, and regarding our name we have had some issues in that regard in fact!

Last edited @ May 17, 4:01PM EDT.
May 17, 3:43PM EDT0
How did you design the tours you offer in Chicago? What did you want to highlight in them?
May 16, 8:30PM EDT0

First of all, I looked at what other tour companies were offering. When making new products, in this case tours, you have to do a combination of understanding what people want through what others are successfully doing as well as differentiating yourself with new kinds of products. 

So I basically from there come up with a concept. Then I think very geographically as to what we can feasibly do via our mode of transport (foot or bus). Then we start digging into the research (see question below on details). 

We want to highlight both sites that are spectacular and everyday as well as the famous and the forgotten figures of history.  

On our Big Shoulders Historic Bar and Food Bus Tours, for example, we tell the story of Johnny O, who sold hot dogs in the neighborhood from the age of eight until he passed away at 85. I got to explore the neighborhood with Johnny, and he shared his own personal stories. He told me about an "uppity bar owner" who let them drink underage but then when make them listen to her ramble about living in New York. Or his buddy "Lefty" who had a funny ditty he would sing about the smells in their formerly industrial neighborhood. Here's a picture of Johhny, he's on the left: 

Last edited @ May 17, 3:59PM EDT.
May 17, 3:50PM EDT0
What inspired you to start Chicago Tours? What do you enjoy most about what you do?
May 16, 7:07PM EDT0

Hi Nour, 

I'd like to clarify that the name of my company is Chicago Detours. I had worked in travel for years and I knew that I loved it. But I also have always been inspired by finding the beauty in the everyday things around us. I love that every place has a reason for existing and a story to tell. That's why I designed a tour company to "explore stories and places that locals don't even know."

What do I enjoy most? Meeting people and sharing new ideas with them. See question below regarding what we find most rewarding. 

May 17, 3:46PM EDT0
What kind of research do you do when you decide on new destinations?
May 16, 4:30PM EDT0

To design new tours, we do a ton of research. We look at scholarly articles, books on the topic, archival materials (like diaries, pamphlets, etc), historic photographs and film. We use this variety of sources to come up with unique stories that no one could just google. 

May 17, 3:47PM EDT0
How do you schedule the tour of the clients? Also, how can you handle frustrated customers?
May 16, 10:05AM EDT1

People register as individuals for regularly scheduled public walking tours. For private groups, we schedule the tours for them, depending on our availability. We really don't get many frustrated customers. Usually the issue lies in that they have their own expectations of the tour based on some other experience they've had, and then are thereby disappointed since our tours are not so standard. My philosophy is to listen to them and thank them for their feedback, and then internally we assess to what degree we need to modify the experience or our marketing content. 

Last edited @ May 16, 12:02PM EDT.
May 16, 11:27AM EDT0
What key improvements would you like to see in Chicago's Tourism?
May 16, 10:05AM EDT0

Great question! First of all, I think that the city needs to partner with airlines to give people an incentive to do a one- or two-night layover in Chicago. So many people just transfer in O'Hare airport and never get a sense of all the incredible culinary, historic, architectural and sports attractions we have to offer. 

Secondly, I notice that tourists - especially the international ones - want to explore our diverse neighborhoods. However, they often don't know where to begin. A neighborhood tour like the ones we offer can be an excellent introduction to a neighborhood and provide a basis for exploring outside downtown. I think more should be done to promote tourism in neighborhoods and help tourists plan their time there. 

Last edited @ May 16, 12:05PM EDT.
May 16, 11:30AM EDT0
Have you ever booked a tour package through a travel company yourself? How has been your experience?
May 16, 8:14AM EDT0

So first of all, we do city tours, so all our tours are 1.5-4.0 hours in length. We don't do multi-day packages. 

I have never registered for a tour package myself, but I used to lead multi-day tours of Italy through Rick Steves. As someone who began travelling with Lonely Planet guides, I was a fiercely independent traveler and frowned about packaged group tours. However, through group travel with Rick Steves I found that a person can have an even more enriching experience from the incredible perspectives of a tour guide. Also the tours got us access to wineries, historical sites, and restaurants that a regular tourist would likely not find on their own. And lastly, another incredible value of a group tour like that is that all the planning is done for you. You don't have to waste time reconfirming your hotels or figuring out the train schedules, etc. 

May 16, 11:34AM EDT0
How was your experience working in Italy? Where did you give your tours?
May 16, 7:38AM EDT0

I very much love Italy. It was a dream job. I got to talk to people about history and architecture as well as my own experiences as an American in Italy. The tours I led were all over, from north to south. We covered the big tourist stops - like Venice, Florence and Rome - however my specialty is really the South. I've spent most of my time in Rome, Naples, Amalfi Coast, Matera and several cities of Sicily. 

Last edited @ May 16, 5:16PM EDT.
May 16, 11:35AM EDT0
How do you plan to attract the customers of all ages towards the tour plans of your company?
May 15, 7:50AM EDT0

What's interesting about our target market is that the demographics are not so delineated for what people are calling the "cultural traveler." We create tours that appeal to curious people who want to learn, and age is not really a factor. Physical mobility can be a challenge in some cases for older travelers, but otherwise we let the tours speak for themselves as far as reaching people of different ages. We also have a very interactive dynamic, and some of our tours can appeal to children as well. Interactive dynamic on a tour

Last edited @ May 16, 5:11PM EDT.
May 16, 11:37AM EDT0
Have you visited another country with friends or family?
May 15, 5:56AM EDT0

I worked as a tour guide in Italy for 10 years with the Rick Steves tour company. I took groups of Americans around the country, and my speciality was in the South - Rome, Naples, and Sicily, too. I have also traveled around Southeast Asia, around Europe, and spent a good amount of time in Mexico. 

May 15, 5:57PM EDT0
What is the most rewarding part of starting tour company?
May 15, 12:03AM EDT0

The most rewarding part is experiencing people's excitement around seeing the world around them in a new way. We discuss the complexities of historical perspectives, the psychological effects of interior space, the origins of music genres, and a whole host of topics that explain why things are the way they are. I love sharing new ideas with people, and also witnessing the care at which our entire team shares in this excitement. We all find it rewarding to enrich other people's lives. 

Last edited @ May 16, 12:11PM EDT.
May 16, 11:39AM EDT0
What goes into developing a new adventure. When you’re building a new vacation, what do you look for?
May 14, 4:07PM EDT0

Ok so the tours aren't really "vacations." But in regards to developing new city tours, we look at what our competition isn't doing, and we look at what kinds of stories of Chicago we feel are important and need to be told. 

May 16, 11:41AM EDT0
Why should a discerning tourist choose a fully-guided tour over independent travel?
May 14, 10:21AM EDT0

When you say "fully guided", do you mean like a multi-day tour or just a city tour, which is what we do? 

May 15, 5:59PM EDT0
What’s your favorite thing about travel for you?
May 14, 8:08AM EDT0

Favorite thing about travel is connecting with people. Human connection can be surprising at times, even when there are language and cultural barriers. 

May 16, 11:41AM EDT0
What is your advice for someone wishing to set up similar small-scale, cultural tours in another city/country on how to avoid common pitfalls?
May 14, 7:41AM EDT0

Excellent question! I would advise to properly prepare a business plan first. Study your competition to understand how you will differentiate yourself. And also, imagine that there will be much more overhead than anyone would imagine regarding operating a business and marketing. 

May 16, 11:42AM EDT0
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