Creating Your Tour

Guidance and inspiration

You are now embarking upon an exciting mission: crafting the 75-minute architecture tour of your dreams. The task may feel daunting at times, but with these resources and the help of Shoreline coaches and leaders, you will be giving the tour of your dreams in no time.


Start by seeing as many Shoreline Sightseeing tours as possible. Watch different docents, get a feel for our standards and expectations. Watch videos of tours at home on our unlisted YouTube playlist. These videos will be shared with you via email link, follow the link to enjoy! Observe live tours! You can book a complimentary ticket for yourself at any time by emailing the Shoreline Call Center at Let them know you are a new docent and give the date, time, and location of the tour you wish to observe. You could also reach over the phone at (312) 222-9328, extension 1.

After observing as many tours as possible, decide which buildings and landmarks from the tour route that you wish to include on the tour. It is very helpful to make a list of these in order of appearance as you would present them on the tour. Also, decide which Chicago history stories you want to tell. 

Use the CONCEPTS WORKSHEET and STORIES WORKSHEET at this point in your process.

Now’s the time for your creativity and personal point of view to shine. Based on all of the chosen buildings, landmarks, and stories, define what connects them to each other and what connects them to you…this is forming your opening and closing statements! Choosing a main idea for these critical moments should be simple: what’s the biggest takeaway of your tour? If guests were going to remember one big idea about Chicago and its architecture, what would you want it to be?

Use TYING IT ALL TOGETHER WORKSHEET at this point in your process.

Write out your opener and closer, then list your chosen landmarks and stories in order of appearance. Now you have an outline!

You will submit your outline to a coach, who will provide feedback, and make sure your outline is rock solid so that you can build on a strong foundation.


Writing out your tour verbatim is a big task, but it has big benefits in terms of honing and crafting your tour. Decide for yourself if writing it out is the best method for your strengths. A 75-minute tour is about 17 pages single-spaced or 35 pages double-spaced. Remember, it takes about 2 minutes to read one double-spaced page of text. 

It’s not required that you write out your tour transcript, but know that it can be an extremely effective learning tool. Not only does the process of typing out the phrasing help you learn the material faster, you will be more deliberate in your choice of words. The greatest bonus of writing it out is having something written down to refer to while you are committing your tour to memory.

Besides writing out your tour, you have many options for fleshing out the meat of your content. 

You could speak each part of your tour into a voice memo. Play with the order and phrasing until you have a complete tour to listen to and learn.

You could make videos of yourself reciting your desired phrasing and watch them over and over again. 

You could storyboard it, draw it out on a mind map, or create any kind of visual representation that will help you learn your content

Use the BUILDINGS, STYLE, DATA to learn and memorize the facts and figures you plan to discuss on your tour. Make flashcards from this study guide to really hammer down those names and numbers. This data is the building material of your tour. A fascinating, thought-provoking thesis won’t matter if the tour has no quality content. 


Every building or landmark has way more facts and information than we could possibly include in the time allotted on an architecture tour. You are the official editor: you get to decide what goes to print. 

If there is an entire block of marble worth of facts about the Sears Tower, it is your duty to be Michaelangelo and carve out the beautiful David for all to admire.

Some things to think about when choosing facts:

  • Does it answer common questions the passengers might have?
  • Does it answer a question that is posed by the physical appearance of the landmark?
  • Is it interesting to you?
  • Does it make you think?
  • Does it make you laugh or cry?

If you have a fact/story that does not answer yes to any of the above, consider whether it is worth the real estate in such a tightly curated tour.


Once you have the whole movement of your tour mapped out, and you have decided on the content you will cover, it’s time to practice!

Practice your tour. Practice your tour as much as you can. Say it out loud and run a timer. You should have about 65 minutes of content, about ten minutes of the tour will be spent on breaks or photo ops. You can use the DRY RUN VIDEO to guide you, or refer to the timing guide below so you can see how your tour is lining up with the timing of an actual boat ride. 

NOTE: These times are approximate.


Michigan Ave to Wolf Point – 9 minutes
Wolf Point to North Branch Turn – 4 minutes
North Branch Turn – 3 minutes
Wolf Point to South Branch Turn – 16 minutes
South Branch back to Wolf Point – 16 minutes
Wolf Point to Michigan Ave – 8 minutes
Michigan Ave to DSLD – 6 minutes

The length of your spin in the turning basin will depend on the pace of the tour so far!

DLSD to Michigan Ave – 5 minutes


Ogden to DLSD – 5 Minutes
DLSD to Michigan Ave – 6 Minutes
Michigan Ave Bridge to Wolf Point – 7-8 minutes
Wolf Point to South Branch turn – 16 minutes
South Branch Turn to Wolf Point – 16 Minutes
Wolf Point to Michigan Ave – 8 minutes
Michigan Ave to DLSD – 6 minutes

The length of your spin in the turning basin will depend on the pace of the tour so far!

Practice the tour one more time once you think you have practiced it enough, and then alert leadership that you are ready for your 75-minute dry run. 


Below is a compilation of outside resources our docents love and depend on to stay sharp in their knowledge of Chicago and their understanding of architecture. 


  • City of the Century: The Epic of Chicago and the Making of America, by Donald L. Miller
  • The Third Coast: When Chicago Built the American Dream, by Thomas Dyja
  • Terror and Wonder: Architecture in a Tumultuous Age, by Blair Kamin 
  • Why Architecture Matters: Lessons from Chicago, by Blair Kamin
  • The Chicago River: An Illustrated History and Guide to the River and Its Waterways, by David M. Solzman
  • City of Lake and Prairie: Chicago’s Environmental History, by by Kathleen A. Brosnan (Editor), William C. Barnett (Editor), Ann Durkin Keating (Editor)
  • Nature’s Metropolis: Chicago and the Great West, by William Cronin
  • Lakefront: Public Trust and Private Rights in Chicago, by by Joseph D. Kearney (Author), Thomas W. Merrill  (Author)
  • Chicago’s Great Fire, by Carl Smith
  • The Plan of Chicago: Daniel Burnham and the Remaking of the American City, by Carl Smith


Chicago YIMBY

Crain’s Chicago Business

Block Club Chicago

TimeOut Chicago

Chicago Tribune Architecture Columns

Other Websites

Council on Tall Buildings

Skyscraper Forum

Encyclopedia of Chicago

BOMA Chicago


Forgotten Chicago