Private Lake Michigan Sailing Charter and Sightseeing Chicago Skyline Cruise

We’ll depart from the north side of Monroe Harbor at our dedicated pick-up/drop-off spot. 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 the day, will depend mostly on wind the 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 sail on Lake Michigan during which you will sail in close proximity to some or all of the landmarks listed in the itinerary below.

Our charter begins with a quick motor passed a part of Monroe Harbor named in honor of a visit by Queen Elizabeth II. On July 6, 1959, a small barge ferried Her Majesty from 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.

Another building which cannot be ignored as we depart from Monroe Harbor is the Shedd Aquarium which sits prominently at the south end of Monroe Harbor. Completed in 1930, the Shedd Aquarium’s mission is “Sparking compassion, curiosity and conservation for the aquatic animal world”. The large dark windows facing the lake house the Abbott Oceanarium exhibit. Added in 1991, the Oceanarium features Pacific white-sided dolphins and beluga whales.

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. As we head out into 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.

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.

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!

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.