Top Chicago Sailing Tours

Cruise down the Chicago River to see the city's famous architecture on this boat tour. With commentary from your onboard guide, watch the spectacular skyline glide by, including more than 40 notable buildings like the Wrigley Building and the John Hancock Building. Cover all three branches of the Chicago River, passing the East Bank Club, the old Post Office Building and the Willis Tower (formerly known as the Sears Tower).

Leave the hustle and bustle behind! Explore Chicago's shores with a leisurely trip around Lake Michigan. Take in the world-famous skyline, enjoy spectacular views, and discover the Windy City from the water. Windy is the Official Ship for the City of Chicago. At 148 feet long, she is one of only a few 4 masted Schooners built in the United States. You will enjoy a relaxing sail around aboard a truly historic vessel. Select from Pirates and Maritime Stories Sail at 1pm, Skyline/Architectural Theme at 3pm and 5pm, and Skyline Sunset Sail at 7pm. This sail is approximately 75 minutes. The ship leaves promptly at the scheduled time, please allow for time to park, off the pier if necessary.

Discover the architectural gems of the Windy City from an ideal vantage point on a cruise down the Chicago River. Offered several times throughout the day, it’s easy to fit the leisurely excursion into your itinerary. Covering more than 130 years of architectural history, the tour is the perfect opportunity to see a huge area of the city without the hassle of taxis and public transit.

A Truly Special Event Sail! During the summer, every Wed & Saturday night, Tall Ship Windy sails from Navy Pier for our guests to enjoy the spectacular night fireworks from the best seat in town. Enjoy the amenities of the 148 foot, four masted Schooner that is the official ship of the City of Chicago. Sail from Navy Pier and see the picturesque Chicago Skyline. Enjoy one of the best summer fireworks displays in the nation aboard a world-class tall ship. Then, get your history fix with a rousing rendition of traditional shipboard working songs against the backdrop of the brilliantly lit Chicago skyline. This is a one of a kind uniquely Chicago experience. The Wednesday Fireworks Boat Tour departs promptly at 8:45pm. The Saturday tour departs promptly at 9:15pm.

The educational sail aboard Chicago's Official Flagship Windy departs at 11am Thursday thru Monday from Navy Pier. Leave the hustle and bustle behind, and enjoy a leisurely Educational Sail aboard Chicago’s Official Tall Ship. Guests will enjoy 75 minute sail where they will learn about sailing and the history of Lake Michigan and Chicago. Ideal for youth groups, children, families and adults.. Chicago's history is forever linked to the history of sailing on Lake Michigan. From these historical maritime roots, guests will be delighted with interesting facts, unique stories, and a healthy dose of whimsy. You will have a chance to help sail Chicago's famous 148' Schooner and you will be rewarded with incredible scenery and photo opportunities of the Windy City. Enjoy your time on the water — the third-largest of the Great Lakes, Lake Michigan is itself a natural wonder. Your guide will provide live audio commentary throughout the journey. This is approximately a 75 Minute sail.

The famous Tall Ship Windy sunset sail is truly famous. Used in many world-renown photos, backdrops for special events, weddings, or just an evening out, the sunset sail aboard one of the only four-mast Schooners still in operation will not disappoint. You will enjoy a sail on Lake Michigan and at just the right moment, S/V Windy will gently turn toward the Chicago skyline for a view of our spectacular sunset. Sit back and relax, enjoy some soothing music, and gently complete your day with this dramatic sunset. ** Please note, tickets purchased for sunset sails on Monday evenings will be upgraded from our traditional 75 minute sail to our Monday Night Blues Summer Concert Series, which departs the dock at 7pm and returns at 9pm. Enjoy live Blues music and 45 extra minutes aboard beautiful Tall Ship Windy!

Soak up unbeatable views of Lake Michigan and the Chicago skyline with this private, sunset sailing tour. This charter is completely customizable, giving you the chance to choose your music, route, and up to 5 additional guests. Sail into the sunset with your own drinks and snacks (refrigerator and ice on board) and your family or friends by your side, all led by US Coast Guard–certified captain.

You will be treated to a morning of relaxation and fun on Lake Michigan on this sailboat charter. You are in charge of the itinerary, guest list, even music choices! There is a fridge and ice aboard if you would like to bring refreshments (no glass please) and if you are feeling adventurous, you can take a turn at the helm.

If you’ve ever dreamed of sailing away on your own private sailboat, this is the perfect excursion for you. You and up to five other invited guests will have the exclusive use of a sailboat, complete with captain and crew for the duration of your tour. Sail on Lake Michigan and enjoy the sights of Chicago’s striking skyline. If you want, you could even take a turn at the helm.

Take in the world-famous skyline of the Windy City from the water, and enjoy a leisurely trip on Lake Michigan aboard Chicago's Famous Pirates Pub. Your ticket includes one complimentary rum punch, domestic beer, soda or water, per person.  Duration: 2 Hours Chicago’s famous Pirates Pub Sail departs every Friday night at 9pm aboard Tall Ship Windy at Navy Pier. This is a two hour charter and returns to Navy Pier at 11:00pm. Your ticket includes one complimentary rum punch, domestic beer, soda or water. Aboard the 148 foot Tall Ship Windy, you will enjoy the merriment of days of yore. You will be able to listen and sing to the traditional songs of the Pirates while enjoying the spectacular scenery that is the Chicago skyline and the wonderment of Lake Michigan. Chicago’s famous Pirates Pub Sail is an event that should not be missed.

Treat yourself to an unforgettable Chicago experience with this private sailboat cruise under the Navy Pier fireworks. Over the course of two hours, you’ll sail along Chicago’s beautiful lakefront with a view of the city skyline. You’ll have the perfect vantage point to enjoy the incredible fireworks from Navy Pier. This customizable experience allows you to choose your own, route, music, and guest list.

Join us for a 2-hour concert sail from 7pm-9pm every Monday this Summer! Chase your Monday BLUES away aboard the 148 foot Tall Ship Windy as you enjoy the breathtaking views of Chicago from the waters of Lake Michigan accompanied by the sweet sounds of the blues. Whether you’re a long-time fan or a newcomer to the blues, you’re sure to be transported by the talent and passion of each amazing artist. With a full bar and a friendly, knowledgeable crew, you’ll be able to relax and enjoy the music in comfort and style. Each concert will bring a unique twist to the blues genre, showcasing the diversity and versatility of this legendary music form. We’ll be joined by music’s greats, including Grammy-elected Michael Charles and his band, Andrew Diehl and Dave Weld & the Imperial Flames. Tall Ship Windy’s Monday Blues is set to become the concert event of the summer! Book now and experience the magic of blues music against the backdrop of one of the world’s most beautiful skylines.

Enjoy a private two and a half hour sailing experience for up to four people along Chicago’s beautiful lakefront. Kick back, relax, and let the US Coast Guard licensed captain treat you to stunning views of Chicago’s spectacular skyline. Make the experience your own. The flexibility of a private charter allows customization of virtually any aspect of the sailing adventure from guest list to music selection to sailing route. All charters are NON-SMOKING experiences.