Why the Chicago Architectural Boat Tour is So Popular

Earlier this summer, TripAdvisor named the Chicago architectural boat tour the single most popular tour in America. That got me to wondering, what is it that makes it so popular?

Sometimes our walking tour guides are hired out to lead a Chicago River boat tour, often on a private yacht charter via Anita Dee Yacht Charters. But the tours from Chicago Detours are mostly either walking tours or cars by bus or sedan. They’re quite popular, but it’s fair to say we’re not number one in the whole country.

So, call it market research or just call it idle musing, but I wanted to think on what, besides discounted prices on Groupon, makes the boat tours so beloved. (By the way, if you’re not in Chicago but want the experience, then reach out to us about the Cruise From Your Couch Virtual Boat Tour.)

We research stories from Chicago history, architecture and culture like this while developing our live virtual tours, in-person private tours, and custom content for corporate events. You can join us to experience Chicago’s stories in-person or online. We can also create custom tours and original content about this Chicago topic and countless others.

chicago yacht charters river boat tour skyline chicago architectural boat tour

#1. The View from the River

The most obviously appealing part of Chicago architectural boat tour is the view. There are few other cities on Earth that can rival the density and size of our skyline. The city includes everything from long-famous landmarks like the Tribune Tower to brand-new wonders like 150 N. Riverside.  From down on the river, the skyscrapers soar hundreds, even thousands of feet into the sky. There’s a pure and simple pleasure in getting to sit back and enjoy such a sight, especially on a gorgeous summer evening.

I think being down on the water itself is part of what makes the view so magical. The streets and sidewalks of Chicago have been raised about 25-30 feet above the natural level of the ground and water. The buildings themselves hug close to the water in downtown. It looks for all the world like you’re passing through a gorge amidst massive mountains of steel, glass, and limestone when you travel down the river. So any spot along the river gives you a dramatic, low-angle view of these soaring, iconic structures clustered into artificial canyons. It’s easy to understand why that’s so popular.

#2. Boat Cruises are Relaxing

There’s a simple, tactile pleasure to feeling a boat steadily pull you along. I always find it very relaxing to step aboard a Chicago architectural boat tour and feel the slight bob and weave of the water. It returns me to the foundation of Chicago. 200 years ago, what would become this modern metropolis was just a swampy stretch of lakeshore with a small river weaving through. The river is one of our last remaining links to the landscape that Joliet, DuSable, Beaubien, or Lincoln would have known. In that slower, older state of mind, I can simply relax and passively watch the city go rolling past me when on a boat tour.

#3. Our World-Class Architectural Heritage

Not to be presumptuous, but I think the buildings themselves are a huge part of the appeal for a Chicago architectural boat tour. This city has become iconic for its architecture in the 146 years since the Great Chicago Fire. That disaster gave architects from all over the world a blank slate when it burned away the old core of Chicago. Into the breach have come some of the most famous names in 19th, 20th, and 21st century architecture: Daniel Burnham. Louis Sullivan. Holabird and Root. Mies van der Rohe. Fazlur Rahman Khan. Helmut Jahn. Jeanne Gang. The names go on and on.

Their physical legacy is the stunning array of buildings strung along the banks of the Chicago River and Lake Michigan. The Chicago architectural boat tour lets you luxuriate in this architectural dreamscape. Oftentimes, the boat guides themselves don’t even need to impress anything onto the guests. The sights themselves do all the talking, really. (It’s nice when you’re on a Chicago architectural boat tour during the fireworks, too). In fact, we notice when guiding tours with Tours and Boats that some of the guests don’t even understand English!

chicago architectural boat tour

#4. The Clever Engineering of Chicago Skyscrapers

That being said, a good Chicago architectural boat tour guide or docent will fill you in on a lot of cool details regarding how everything was built. Maybe it’s just because I’m an architecture nerd, but I love the engineering techniques that go into holding up a skyscraper. Take, for example, Khan’s ingenious design for the Sears Tower. According to the urban legend, he had been asked to design the building and took a smoke break to think about it. When he tapped the pack of cigarettes a bolt of inspiration struck him. Bundling discrete towers together like cigarettes in pack made the building stronger. That internal strength enabled it to be taller. This “bundled tube” design enabled the construction of the landmark tower.

Facts like that fascinate and amuse me. They illustrate the inventiveness that’s required to create a world-class city like Chicago.

#5. What to Do After a Chicago Architectural Boat Tour

Join us for another tour, of course! We always like to say that our walking tours of Chicago are the perfect compliment to the boat tours. Our Downtown Bucket list private tour takes you into some of the city’s famous and overlooked highlights. Stepping into these buildings, and the also the underground Pedway system, after taking a boat tour gives you a more complete sense of the city.

Or of course you can just grab a meal. River Roast is a great option with seating right along the river.

Here’s to seeing you on the water and streets of Chicago soon!

– Alex Bean, Content Manager and Tour Guide


Chicago Detours is a boutique tour company passionate about connecting people to places and each other through the power of storytelling. We bring curious people to explore, learn and interact with Chicago’s history, architecture and culture through in-person private group tourscontent production, and virtual tours.


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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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