Tom Carmichael is more than just a tour guide—he's an expert on Chicago architecture. If Tom is a teacher, a boat in the windy city is his classroom. The First Lady is one of four boats in the fleet visitors can take to enjoy city via the Chicago River. The highly trained docents, like Tom, go through months of training and are all volunteers.

The tour gives you a look at the windy city you can't get by driving or walking. All you have to do is look up at some buildings dating back to the 1870s.

“Usually, what you hear is ‘Wow’ and ‘Ohh, gosh’ and ‘Isn't it beautiful?’ because it really is a gorgeous vista along the Chicago River,” says Tom.

The 90 minute tour takes you past some of Chicago's most famous buildings, such as the Trump Tower, Chicago Sun Times, the impressive Aqua, and that unusual round building seen in Ferris Bueller's Day Off. Of the 10 tallest buildings in North America, six of them are in Chicago.

While most of the sights are hundreds of feet high, others are just inches above your head. There are more than 50 bridges in Chicago and the First Lady goes under 27 on the tour. All of them raise and lower for the larger boats.

Not only is it a tour for those who love architecture, but there are also some pop culture tidbits, such as sites where The Dark Knight were filmed.

You may be wondering when the best time of day to actually take one of these river cruises is, and it really depends on what you’re after. If you want to take photos, the best time to go is the first one of the day at 10:00 am. Otherwise anytime works.

Below deck guests can enjoy drinks and the boat can even be privately chartered for parties or receptions.

Captain Bob Agra owns the fleet, and despite touring the city countless times, he still spots things he hasn't seen before.

“You get to see the different eras in architecture, the different styles in architecture, little bit about the history of the city,” says Captain Bob.

“People come off the boat from all over the world and they say ‘Chicago is a beautiful city! I didn't realize what a beautiful city it is,’ and that's really true and the river is the best way to see that,” says Tom.

For more information on the times and prices of the river boat cruises, click here.