Chicago Private Sailing Tour on Lake Michigan

Enjoy a private two-hour sailing experience for up to six 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.
This experience is not meant to be an in-depth guided tour; however, our captain is always happy to point out interesting sights with anecdotes and historical information. Just ask you captain. Looking for daytime sailing, see our other product listing "Come Sailing with us at Navy Pier - Sail Beautiful Lake Michigan". Looking to watch the Navy Pier Fireworks from a private sailing charter, see our other product listing "Come Sailing with us at Navy Pier - Saturday Fireworks Sail". All charters are NON-SMOKING experiences.

Meeting Point

801 E Grand Ave

801 E Grand Ave, Chicago, IL 60611, USA

We operate from the new Navy Pier Marina located along the north side of Navy Pier. Please gather outside of Navy Pier Marina - Gate D and then text/call us to tell us that you are here. We will welcome you to the marina and escort you to the sailboat.

What's included:

• Use of Bluetooth speakers
• Professional captain licensed by the US Coast Guard
• Navy Pier Facility Fee
• All taxes

Not included:

• Food and drinks (you may bring your own)
• Parking

What to expect:

Duration: 2 hours

Come Sailing, Inc.

400 E Monroe St, Chicago, IL 60603, USA

We will depart from Navy Pier Marina along the north side of Navy Pier. Once the safety briefing is completed and all dock lines have been brought on board, our trip will begin. The itinerary, course/route we are sailing for will depend mostly on the wind direction. However, being that this is a private charter, the itinerary remains very flexible and pretty much at your discretion. So, if you’d like to see a particular landmark or prefer to sail a particular route, just ask our captain and they will be happy to oblige. If, instead, you’d prefer to leave all of the decision up to the captain, no problem. Our captain will be happy to take you for an enjoyable sunset sail on Lake Michigan during which you will sail in close proximity to some, or all, of the landmarks listed in the itinerary below.

2 hours • Admission Ticket Included

Navy Pier

600 E Grand Ave, , Chicago, 60611-3419, Illinois

One of the most recognized landmarks along Chicago’s lakefront, Navy Pier is also one of the most and visited tourist destinations in Chicago. Sailing passed the east end we’ll have a great view of the Grand Ballroom. This would be another perfect time to snap some selfies or capture a stunning architectural photo. Opened to the public in 1916, Navy Pier has played many roles during its lifetime including an important role during WWII. This piece of Chicago is definitely more than just a photo op!

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Chicago Skyline

Chicago, 60601, Illinois

One of the most beautiful waterfront cities in the world, Chicago’s magnificent skyline is best viewed from the water. There are too many stories to be told about the amazing architecture, landmarks, and engineering feats accomplished in Chicago. Which ones you hear are up to you. Again, this is your private charter and you set the tone for the trip. If you prefer to just visit with friends and loved ones, no worries at all. Our captains are happy to the role of captain, guide, or both. Come Sailing and let us show you the city we love.

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Adler Planetarium

1300 S. DuSable Lake Shore Dr., , Chicago, 60605-2489, Illinois

Sitting on the northeast corner of Northerly Island is the iconic dome of the Adler Planetarium. Built in 1930, this picturesque public museum dedicated to the study of astronomy and astrophysics a popular location for wedding photos. From the Lake, we get to see a side of this marvelous structure that most visitors never think to investigate: the lakeside! This is where you will find the Doane Observatory which has a large telescope available to the public.

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Soldier Field

1410 Special Olympics Drive, Chicago, 60605-2902, Illinois

Opened in 1924, Soldier Field, known today as the home of the Chicago Bears, has played host to a variety of interesting and historical events. Even though the stadium has changed drastically over the years, the original colonnades can still be seen from our vantage point on the water.

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Clarence F. Buckingham Fountain

301 S. Columbus Dr, Grant Park, Chicago, 60605, Illinois

On July 6, 1959, a small barge ferried Queen Elizabeth II from the HMY Britannia anchored outside of Monroe Harbor to the aptly named Queen’s Landing for a 13-hour royal visit spectacular. As we pass this historic site Buckingham Fountain comes into view. (Pro Tip: this is a great time for a photo op.) Buckingham Fountain, one of the world’s largest fountains, was designed as a focal centerpiece for Grant Park. According to the Chicago Park District website, John Philips Souza himself conducted his band in the playing of “Pomp and Circumstance” before an audience of 50,000 people during the fountain’s dedication in August 1927. Contrary to conventional wisdom, Buckingham fountain is not related to Buckingham Palace or the Royal Family. The fountain was actually donated by Chicago art patron and philanthropist, Kate Buckingham in memorial honor of her brother Clearance Buckingham.

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