Tall Ship Windy Chicago : Unique Sailing on Lake Michigan

Chicago is famous for beautiful city skyline from the Lake Michigan. Breathtaking views of our Chicago skyline is equally enjoyed and appreciated by locals and visitors the same way.

Tall Ship Windy has been serving since 1996 from Navy Pier, making sure that sailors enjoy the best possible views of the Windy City from the Lake Michigan.

This majestic, four-masted schooner provides visitors with a chance to experience Chicago from the water at its best.

In my opinion, whether you’re a history lover, a sailing enthusiast, or simply looking for a unique adventure, a journey aboard Tall Ship Windy is an unforgettable experience.

Tall Ship Windy is a true icon of the Chicago waterfront. This traditional Tall Ship Windy was built in 1996, modeled after classic Great Lakes trading ship from the 19th century.

Tall Ship Windy is inspired by the past, Windy is constructed with modern craftsmanship and safety features, making it look like a blend version of old-world charm and contemporary engineering.

The ship is a U.S. Coast Guard-certified passenger vessel and has been a proud part of Navy Pier’s attractions for many years.

It was originally commissioned by Captain Bruce Randall, an experienced mariner and storyteller who envisioned creating a vessel that would not only be a beautiful sailing ship but also an educational platform.

Since it started operation in 1996, till date Windy has hosted thousands of sailors during summer season.

On the ship visitors has a great opportunity to learn about the maritime history, the art of sailing, and the significance of Lake Michigan in shaping Chicago’s identity.

Quick Tips: You may also like list of boat tours in Chicago.

What to Expect on a Tall Ship Windy Cruise

Aboard Tall Ship Windy, passengers are assured to enjoy the great sailing experience. Unlike modern motorized tours, Windy relies on wind power to navigate the waters, offering a truly authentic sailing adventure. Here’s what you can expect when you set sail on this majestic vessel:

Spectacular Views of Chicago’s Skyline

One of the most breathtaking aspects of a cruise on Windy is the world famous view of the Chicago skyline.

As the ship sail away from Navy Pier, passengers will get to see the views of some of the city’s most iconic landmarks, including Willis Tower, John Hancock Center, and the Aon Center.

In my opinion, seeing these architectural wonders from the lake provides a unique experience, especially during sunset sails when the city lights begin to shimmer against the evening sky.

Types of Tall Ship Windy Tours

Tall Ship Windy offers a variety of tours that provide unique experiences on Lake Michigan. Here are some of the types of tours they offer:  

• Chicago Skyline Sail: This is a classic tour that offers stunning views of the city’s iconic skyline. It’s a great way to see Chicago from a different angle from Lake Michigan and get some amazing photos.  
• Educational Sail: Tall Ship Discovery Sail: This tour is perfect for families with young children. It’s an educational adventure where you’ll learn about the history of the Tall Ship Windy and the maritime history of Chicago.  
• Chicago Sunset Cruise: This romantic tour is perfect for couples or anyone who wants to enjoy a beautiful sunset over Lake Michigan. I highly recommend this cruise to enjoy the views of the city skyline at sunset are simply breathtaking. Make sure to check weather because on cloudy day this cruise is not fun.
• Fireworks Cruise: This special tour is offered on select nights throughout the summer. You’ll get to see the city’s fireworks display from the Lake Michigan.
• Concert Sails: These special events feature live music performances while you sail on Lake Michigan. It’s a fun and festive way to enjoy the city’s music scene.  For example, Chicago Blues concert sail.

In addition to these public tours, Tall Ship Windy also offers private charters for events such as weddings, corporate outings, and family reunions.

Why Tall Ship Windy is a Must-Do in Chicago

There are plenty of boat tours available in Chicago, but Tall Ship Windy stands out for several reasons:

1. Authentic Sailing Experience

Windy offers a sailing experience unlike any other in Chicago. The running on wind power, the creaking of wooden decks, and the flapping of sails all contribute to an authentic maritime adventure. In my opinion, it’s not just a boat ride but it’s a stepping back in time.

2. Family-Friendly and Educational

Windy provides an experience that is both fun and informative for all ages. The combination of storytelling, history, and interactive activities ensures that everyone onboard remains engaged and entertained.

3. Breathtaking Photo Opportunities

Photographers and social media enthusiasts will love the stunning views from the Windy. Visitors will have great opportunities to capture the ship’s sails billowing in the wind, the sun setting over the skyline, or the reflections of the city lights on the water. Yes, all kinds of picture-perfect moments.

4. Connection to Chicago’s Maritime Heritage

Chicago’s history is deeply tied to its waterways, and Windy serves as a living example of this heritage. For those who want to get deeper into the city’s past, sailing on Windy provides an opportunity to connect with the stories of early traders, explorers, and sailors who shaped the region.

Tips for Enjoying Your Tall Ship Windy Cruise

To make the most of your Tall Ship Windy cruise, keep these tips in mind:

• Book in Advance: Especially during peak summer tourist seasons, tickets for Windy can sell out quickly. Booking online ahead of time ensures you secure your spot.
• Dress for the Weather: Chicago weather can get extreme, especially Lake Michigan’s winds can be unpredictable. Even in the summer, bringing a light jacket is a good idea.
• Arrive Early: Plan to arrive at Navy Pier at least 30 minutes before departure to allow for boarding and any pre-sail instructions.
• Bring a Camera: These days everyone has cameras in phone, but if you are looking to capture professional quality photos, then do not forget to bring a camera. The views from Windy are spectacular, so be sure to capture the experience.
• Engage with the Crew: The crew members are knowledgeable and passionate about sailing. Don’t hesitate to ask questions and participate in hands-on activities.

Whether you’re a local looking for a fresh way to see your city or a visitor seeking a unique adventure, sailing on Windy provides a unique experience to enjoy Chicago. I would say one of the best things to do in Chicago.

So next time you find yourself at Navy Pier, step aboard this magnificent schooner and let the winds of Lake Michigan carry you on a voyage of discovery and wonder.