Tall Ship Windy: Lakeside Architecture Sail

The Lakeside Architecture Sail tour is the single most popular tour regularly offered on the Tall Ship Windy—a charming topsail schooner measuring roughly 150-foot-long in size. This 75-minute guided tour departs from Chicago’s one-of-a-kind Navy Pier, and takes you out into the midst of lovely Lake Michigan. There you’ll be able to enjoy unique, spectacular views of downtown Chicago while learning all about the history of its world-famous skyline. In particular, the Lakeside Architecture Sail tour highlights the stories of the men and women who made Chicago into the city it is today, making it an informative and scenic excursion.

Money Saving Tip! This tour is included in the Go Chicago Card as well as the Chicago Explorer Pass. Both Chicago Tourist Passes can save you a lot of money if you are going to multiple Chicago attractions.

Lakeside Architecture Sail Tour Details

Tall Ship Windy’s Lakeside Architecture Sail is offered two times each day—at 11:00am and 5:00pm—with tickets costing about $30 for adults and $10 for kids. Available seasonally, the Lakeside Architecture Sail usually operates daily between June and October—though of course you’ll want to check their website in advance of your visit for the most up-to-date schedule. All visitors are required to arrive at least 30 minutes prior to their tour’s scheduled departure time. The tour itself typically runs around 75 minutes, and most often takes place regardless of the weather, including rain or shine. The Lakeside Architecture Sail departs from Chicago’s beloved Navy Pier, then cruises out into gorgeous Lake Michigan where your crew and guide will point out many of Chicago’s iconic buildings while sharing fascinating stories and anecdotes about how this remarkable skyline came into existence over the past 150 years.

Lakeside Architecture Sail Major Highlights

Navy Pier: Your Tall Ship Windy Lakeside Architecture Sail tour leaves from Chicago’s Navy Pier. First opened in 1916, today Navy Pier remains the longest public pier in the world. It hosts millions of visitors each year, and is home to a number of restaurants, bars, and shops,  as well as popular attractions like the Centennial Wheel, Chicago Children’s Museum, and the Chicago Shakespeare Theater.

Lake Michigan: The only one of the five Great Lakes situated completely within borders of the United States, Lake Michigan is an aquatic treasure loved and celebrated by water enthusiasts of all backgrounds. Experiencing Lake Michigan from the decks of the Tall Ship Windy as part of the Lakeside Architecture Sail tour makes for an unforgettable afternoon.

Chicago Skyline: Many people consider Chicago’s skyline to be one of the absolute most beautiful skylines found anywhere in the world, but it’s not every day you get to experience it from Lake Michigan. The Lakeside Architecture Sail tour will grant you the special opportunity to encounter this wonderful city from a whole new perspective.

Tall Ship Windy: Even as you enjoy the sights and sounds of Lake Michigan and downtown Chicago, you’ll want to take some time to explore your cruising vessel itself, the good Tall Ship Windy! This 148-foot-long boat, designed to resemble a classic sail ship, was built in 1996. In addition to its beautiful sails, it contains a 300-horsepower diesel engine, internal pressurized plumbing, a full-service bar complete with snacks, and a small gift shop.

Is the Lakeside Architecture Sail Tour for You?

This leisurely cruise is perfect for those visitors who’ve long dreamed of viewing Chicago’s unrivalled skyline from Lake Michigan. You’ll learn more details about Chicago’s architecture and history during this tour than you would on other Lake Michigan sailing outings. However, if you want to see and experience Chicago’s acclaimed architecture up close and personal, you might want to consider one of the Chicago Architecture Center’s renowned offerings. Likewise, if you’re visiting Chicago as part of a group and/or family traveling with small children, you might consider one of Tall Ship Windy’s Skyline Sail with Tales of Real Pirates of the Inland Seas tours. Those tours feature remarkable views punctuated by a series of swashbuckling stories told and performed by the ship’s own cast of pirates. Still, if you’re looking for a detailed narration that’ll share with you plenty of key facts about Chicago’s famed architecture alongside the chance to snap some breathtaking photos, this is a good option.

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