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Reading Group Guide 

  • What do you think of the itinerary Jefferson drew up? If you could add another location to his itinerary, where would it be and why?

  • Discuss the key points of interest in Jefferson’s Hints. Which did you find most interesting? Did you find ways of exploring his points of interest in your own life?

  • Derek finds himself stuck-in-place at the beginning of his journey. Have you ever found yourself in a similar situation? If so, what did you do to get out of the rut?

  • Jefferson is most widely known as the author of the Declaration of Independence and as the third president of the United States, but what was the most surprising thing you learned about him from this book?

  • Of all the trips Derek and his family took in pursuit of Jefferson, which one would you most like to go on?

  • It’s difficult to reconcile Jefferson as an influential Founding Father as well as a slave owner. Did your vision of him change by the end of the book?

  • How did enslaved people at Monticello find paths to freedom? For those who could not escape, how did they preserve their culture in the context of a cruel institution?

  • Sharing his experiences with family and friends makes Derek’s travels more meaningful. What do you think are the benefits of traveling with others?

  • When facing adversity—in the form of a global pandemic—Derek finds a way to celebrate Jefferson’s lessons with his family while staying safe at home. What are ways you can apply these principles to your everyday life?

  • In what ways has travel changed since Jefferson wrote Hints? In what ways has it stayed the same?

Printable copy of this guide

* I would love to speak to your book club via Zoom or, in some cases, in person. Let's talk Jefferson, travel, and writing. Drop me a line to my email

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