Embark on a private Lake Michigan sailing tour. Customize your adventure and enjoy Chicago’s skyline with a licensed captain. Book your unforgettable experience today.
Embark on a private Lake Michigan sailing tour. Customize your adventure and enjoy Chicago’s skyline with a licensed captain. Book your unforgettable experience today.
- Come Sailing, Inc. - Departing from Navy Pier Marina on the north side of Navy Pier, the journey begins after a safety briefing and securing all dock lines. The sailing route is primarily determined by the wind direction, but as this is a private charter, the itinerary is highly flexible and can be tailored to your preferences. If there’s a…
- Come Sailing, Inc. - Departing from Navy Pier Marina on the north side of Navy Pier, the journey begins after a safety briefing and securing all dock lines. The sailing route is primarily determined by the wind direction, but as this is a private charter, the itinerary is highly flexible and can be tailored to your preferences. If there’s a specific landmark you wish to see or a particular route you want to sail, simply inform the captain, who will gladly accommodate your request. Alternatively, if you prefer to leave the decisions to the captain, they will ensure a delightful sunset sail on Lake Michigan, passing by some or all of the landmarks listed below.
- Navy Pier - A prominent landmark along Chicago’s lakefront, Navy Pier is a top tourist destination in Chicago. Sailing past the east end offers a fantastic view of the Grand Ballroom, perfect for selfies or capturing stunning architectural photos. Opened in 1916, Navy Pier has served various roles, including a significant one during WWII. This iconic piece of Chicago is much more than just a photo opportunity!
- Chicago Skyline - Renowned as one of the most beautiful waterfront cities globally, Chicago’s stunning skyline is best admired from the water. The city boasts numerous stories about its remarkable architecture, landmarks, and engineering achievements. Which stories you hear is entirely up to you. As this is your private charter, you set the tone for the trip. Whether you wish to socialize with friends and family or enjoy a guided tour, our captains are ready to serve as both captain and guide. Come Sailing and let us showcase the city we adore.
- Adler Planetarium - Located on the northeast corner of Northerly Island, the iconic dome of the Adler Planetarium, built in 1930, is a picturesque public museum dedicated to astronomy and astrophysics. It’s a popular spot for wedding photos. From the lake, you can view a side of this magnificent structure that most visitors overlook: the lakeside! Here, you’ll find the Doane Observatory, which houses a large telescope available to the public.
- Soldier Field - Opened in 1924, Soldier Field, now home to the Chicago Bears, has hosted numerous significant and historical events. Despite the stadium’s extensive renovations over the years, the original colonnades remain visible from our vantage point on the water.
- Buckingham Fountain - On July 6, 1959, a small barge transported Queen Elizabeth II from the HMY Britannia anchored outside Monroe Harbor to the aptly named Queen’s Landing for a 13-hour royal visit. As we pass this historic site, Buckingham Fountain comes into view. (Pro Tip: this is an excellent photo opportunity.) Buckingham Fountain, one of the world’s largest, was designed as a focal point for Grant Park. According to the Chicago Park District website, John Philips Souza conducted his band in playing “Pomp and Circumstance” before an audience of 50,000 during the fountain’s dedication in August 1927. Contrary to popular belief, Buckingham Fountain is not associated with Buckingham Palace or the Royal Family. It was donated by Chicago art patron and philanthropist Kate Buckingham in memory of her brother Clarence Buckingham.

- Use of Bluetooth speakers
- Navy Pier Facility Fee
- All taxes
- Professional US Coast Guard licensed captain
- Use of Bluetooth speakers
- Navy Pier Facility Fee
- All taxes
- Professional US Coast Guard licensed captain
- Gratuities
- Food and Drinks
- Parking
- Gratuities
- Food and Drinks
- Parking
Indulge in a private two-hour sailing adventure for up to six guests along the stunning Chicago lakefront. Sit back, unwind, and let a US Coast Guard licensed captain guide you through breathtaking views of Chicago’s magnificent skyline. Tailor the experience to your preferences. The flexibility of a private charter allows you to customize nearly every…
Indulge in a private two-hour sailing adventure for up to six guests along the stunning Chicago lakefront. Sit back, unwind, and let a US Coast Guard licensed captain guide you through breathtaking views of Chicago’s magnificent skyline. Tailor the experience to your preferences. The flexibility of a private charter allows you to customize nearly every aspect of the sailing journey, from the guest list to music choices and sailing route. Three departure times are available daily. While this experience is not designed as an in-depth guided tour, our captain is more than willing to highlight interesting sights with engaging stories and historical insights. Simply ask the captain. For a sunset sail, explore our other product listing “Come Sailing with us at Navy Pier - Sunset Sail on Lake Michigan.” If you wish to enjoy the Navy Pier Fireworks from a private sailing charter, check out our other product listing “Come Sailing with us at Navy Pier - Saturday Fireworks Sail.” Please note that all charters are NON-SMOKING experiences.
- NO SMOKING - All charters are NON-SMOKING. Use of any tobacco products, cigars, pipes, cigarettes, e-cigarettes, vapor devices, etc. are strictly prohibited. Use of any of these products may result in a non-refundable, early termination of your charter and the assessment of a cleaning fee.
- CONSUMPTION OF ALCOHOL - Customers and guests may bring and consume reasonable amounts of alcoholic beverages within the bounds of Illinois State law.
- NO GLASS ON BOARD - Glass containers are prohibited. Please do not bring them. Wine and Champagne bottle are permitted as long as they remain secure in a protective container during charter. Please bring plastic cups for drinking.
- CUSTOMER/GUEST BEHAVIOR - Customers and guests are expected to conduct themselves in an appropriate manner. Inappropriate behavior will not be tolerated. Any behavior determined by the captain to be inappropriate (lewd, offensive, unsafe, etc.) may result in a non-refundable, early termination of your charter.
- WEAPONS ARE STRICTLY PROHIBITED - Weapons on any kind are strictly prohibited! Guns, knives, or weapons of any kind are NOT allowed on board our vessels at any time. Bringing any of these prohibited items aboard may result in a non-refundable, early termination of your charter.
- ANIMALS ARE PROHIBITED - Unfortunately, we cannot accommodate animals of any type.
- SWIMMING MAY BE PERMITTED - Swimming may be permitted on charters of 3 hours or longer. Swimming is not guaranteed and is at the captain’s discretion. If swimming is deemed permissible by the captain, every passenger on board will be required to sign a waiver & release prior to swimming. Swimming will not be allowed after the departure time of our Sunset Sail scheduled for that same day. SWIMMING IS AT YOUR OWN RISK!
- FOOD AND BEVERAGE - Food and beverages may be consumed on deck. Please clean up any spilled food or beverage and take your garbage with you. A cleaning fee may be assessed for excessive spillage.
- SEASICKNESS/MOTION SICKNESS - Any person that experiences seasickness must remain on deck. The cabin area below deck is NOT an appropriate place for any person to deal with seasickness. A cleaning fee will be assessed for any person vomiting anywhere in the below deck cabin area of the sailboat, including the “head”/bathroom.
- GALLEY STOVE AND SINK - The galley stove onboard our sailboat is NOT for use by customers. The sinks on board our boats drain directly into the lake and are NOT intended for food prep nor for disposing of unwanted items. None of the sinks have garbage disposals. Please do NOT treat our sinks like you treat your kitchen sink. They are NOT the same.
- CLEANING FEES - Cleaning fees, if applicable, will be equivalent to the standard, full price of your charter.
- TERMINATION OF CHARTER - The captain reserves the right to cancel a charter at any time for reasons of weather, mechanical failure, or safety. Charters will be rescheduled at the customer’s convenience. A refund will be offered if rescheduling cannot be agreed upon.
- LATE ARRIVALS - The late arrival of customers and guests may result in a shortened charter sail without refund nor adjustment to price.
- BOOKING ERRORS - We reserve the right to cancel reservations that are the result of incorrect pricing/availability due to malicious acts or software/website errors.
- CONSENT TO BE FILMED/PHOTOGRAPHED - Boarding our sailboats is your implied consent to be filmed, photographed, and recorded. Furthermore, by boarding any of our sailboats you are granting our company, its agents, successors, assignees and affiliates, and their respective employees, officers, directors, shareholders, and representatives the right and permission to use such film, photographs, and recordings of your voice, image, and likeness for the purpose of promoting our company and its related services. You further agree that you will not receive any financial compensation or cash payment for the rights or permissions granted by you. In such case that you are the parent or guardian of any minor child that has accompanied you aboard our sailboat, you further consent to the foregoing on behalf of that minor child.
For a full refund, cancel at least 24 hours before the scheduled departure time.
For a full refund, cancel at least 24 hours before the scheduled departure time.