I Passed the Impossible Test! Now I’m a Certified NYC Sightseeing Guide

Chris Dolan

8/22/20243 min read

body of water near trees and high rise buildings during daytime
body of water near trees and high rise buildings during daytime

Fifteen years ago, we moved to New York City, and from day one, I fell in love with its vast history, incredible infrastructure projects, unique cultural experiences, and the endless list of attractions. No matter how much time we've spent here, the city continues to reveal new, unexplored corners that surprise and delight us. There’s always something around the corner I haven’t seen yet, and I’m determined to explore it all.

Over the years, my passion for learning quirky, fun facts about the city became a hobby. Whether sharing stories with friends or entertaining visitors, I’ve always loved providing a glimpse into NYC’s rich history. Friends started suggesting that I should give tours professionally. I’ve even led a few informal tours for colleagues visiting on business trips. But something always held me back: becoming an official guide in NYC requires passing a certification exam, and the mere thought of that test was daunting.

The Test Seemed Impossible

Yes, that’s right—you need to be certified to give tours in New York City. The test for certification is notorious for covering an exhaustive range of topics. While I’m no stranger to NYC trivia, the idea of being tested on everything from the city’s history to obscure transportation regulations was intimidating.

I’ve never been a fan of tests in general, and this one seemed especially tough. The study materials provided by the certifying agency are vast, and it felt impossible for one person to master them all. It covers so much—dates, names, buildings, architecture, boroughs, and even rules related to tour buses. NYC is more than just Manhattan; there are five boroughs, each with its own history, culture, and hidden gems. It felt overwhelming, to say the least.

Where Do You Even Begin?

After a bit of Googling and chatting with other certified guides, I discovered the go-to study tool: flashcards. Several sets are available, created by those who’ve already passed the test, and they cover a broad array of topics. From the history of iconic buildings to ethnic foods and obscure facts about the outer boroughs, the flashcards seemed like the best way to prepare.

Much to my surprise, I knew more than two-thirds of the answers right away! For the rest, I had at least some familiarity with the topics, so it felt manageable. The test is only 150 questions, but between all the flashcards I studied, I reviewed over 300 potential questions. While no flashcard set can cover everything, I started feeling more confident.

The Nature of the Test: Why You Don’t Need to Know Everything

As I dove deeper into the material, it bothered me at first that I was relying on flashcards to pass a test about the city I love. But I came to understand the purpose of the exam. It’s not about memorizing every last detail; it’s about ensuring a baseline of knowledge. NYC’s history is too deep and rich for any one person to know it all, but the test serves as a foundation.

What I learned through this process is that most successful guides specialize. No one can be an expert in everything about New York City, so guides often focus on one specific topic, like the Revolutionary War or the city’s connection to the Titanic. (Yes, there’s actually quite a lot of Titanic-related history here!)

So, How Did I Do?

I passed! Not only that, but I scored quite well on my first attempt. The flashcards helped alleviate some of the pressure, and while I think I might have passed without them, they made the whole experience much less nerve-wracking. Knowing I had prepared gave me the confidence to take the test without stressing too much.

What’s Next?

Now that I’m officially certified, I’m planning to launch my own tour company. I want to create experiences that offer a fresh, engaging take on the city, drawing on my love of history and random fun facts.

Keep an eye out for updates on my upcoming tours! If you’re planning to visit NYC soon, feel free to reach out—I’d love to create a personalized tour just for you.

Stay curious, and I’ll see you in the city!