R
A relaxing morning sail on Lake Michigan
Captain Ulysses was great. Fun, friendly, and very responsible. Good communication leading up to the trip. A beautiful way to see the Chicago skyline.
Private Sailing on Beautiful Lake Michigan - Navy Pier, Chicago
+3 photos
At a glance
- Duration
- 2 hours
- Price from
- $567 / person
- Rating
- 5.0 / 5 · 73 reviews
- Languages
- EN
- Group
- Private
- Cancellation
- Free cancellation
- Meeting point
- 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.
- Confirmation
- Instant
Prices checked on Sep 11, 2026Things to do in Chicago
Description
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. Three departure times offered daily. 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 a sunset sail, see our other product listing "Come Sailing with us at Navy Pier - Sunset Sail on 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.
Tour Options
Itinerary
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.
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.
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.
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.
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.
Highlights
Use of Bluetooth speakers
Navy Pier Facility Fee
All taxes
Professional US Coast Guard licensed captain
What's included
Included
Use of Bluetooth speakers
Navy Pier Facility Fee
All taxes
Professional US Coast Guard licensed captain
Not included
Gratuities
Food and Drinks
Parking
Traveller Ratings
5.0
73 reviews
Important Information
- Public transportation options are available nearby
- Suitable for all physical fitness levels
- 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.
Frequently asked questions
How long does this tour take?
Private Sailing on Beautiful Lake Michigan - Navy Pier, Chicago lasts about 2 hours. The itinerary has 6 stops.
How much does this tour cost?
Prices start at $567 per person for this Chicago experience, booked through Viator with the price shown before checkout. There is 1 booking option, so the final price depends on the option you choose.
Can I cancel this tour for free?
Yes. Cancel at least 1 day before the start for a full refund. Later cancellations are non-refundable.
Where does the tour start?
The meeting point is 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.. Hotel pickup is not part of this experience.
What languages is this tour offered in?
The experience is available in EN.
Is this a private or a group tour?
It is a private experience: only your party takes part. Up to 15 travellers can book together.
Is the tour suitable for children?
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.
Will my booking be confirmed immediately?
Yes, bookings are confirmed instantly.
Reviews(73)
J
A+! We loved every minute.
We LOVED our sailing excursion with Captain Ulysses! 6 of us went during a girls weekend, and it was the absolute highlight of our trip. Captain Mike and Captain Ulysses got us on board right on time, and we enjoyed two hours of sailing with great wind and a ton of excitement. If you’re considering booking, DO IT. As a group of moms, we tend to spend our girls trips catching up and reminiscing, and not always making NEW fun memories together. This was exactly what we needed, and we’ll remember this outing forever. We were begging to buy out the next hour, but someone already had it booked. We’d absolutely do it again! Thank you for a great time!
E
Wonderful Chicago boat tour! 5 star!
Wonderful Chicago excursion! Our guide was so personable and accommodating! Great way to see the Chicago skyline and enjoy some relaxation. Highly recommend!
L
The Perfect Afternoon
My husband and I had a wonderful cruise during our trip to Chicago. Seeing the city from the water was a unique twist on the typical tours and absolutely beautiful. The sailboat was pristine and our captain was incredibly engaging, answering our endless questions both about the city’s history and sailing. This was a perfect way to spend an afternoon. I would absolutely recommend this tour!
P
Fantastic voyage
Wonderful way to experience the Chicago skyline Captain Mike was awesome, time flew by and we want to do it again.
S
A great time out on the...
A great time out on the lake. Our captain was very capable and informative. I would recommend for just a fun experience or for a special occasion.
O
Great time on the Lake
We had a wonderful time sailing on Lake Michigan with Captain Mike! The views of the city are amazing, and the chance to get out on the lake and experience Chicago from the water was just what our group needed. He is a gentleman and had a very sweet manner with our group. Would definitely recommend to folks visiting Chicago and wanting a Lake Michigan experience.
C
Wonderful sailing trip
My son picked going sailing for his birthday adventure. We did a Saturday morning trip & the weather was 75 & sunny. Beautiful and relaxing sailing! Great captain took care of us. Highlight was when the engines shut down & the sails went up! We got to move to the front of the boat & just enjoy, best seat on the boat! Would recommend!
M
Best way to experience Lake Michigan
Great experience. I would have been on there all day if I could! It was a wonderful way and intimate experience to be on Lake Michigan in a sailboat and not with a lot of other people.
J
A beautiful day on the lake!
We 5 ladies enjoyed a beautiful afternoon sailing! The boat was clean and comfortable. Captain Mike was knowledgeable and friendly. The afternoon was perfect!
Compare similar tours in Chicago
| Tour | Duration | Rating | Price | |
|---|---|---|---|---|
| Private Sailing on Beautiful Lake Michigan - Navy Pier, Chicago | 2 hours | 5.0 (73) | $567 | |
 Chicago Architecture Center River Cruise aboard First Lady | 1h 30min | 4.9 (7,026) | $57 | View |
 Chicago Architecture River Cruise | 1h–1h 30min | 4.8 (16,969) | $39 | View |
 Chicago River 90-Minute Architecture Tour | 1h 30min | 4.7 (10,918) | $45 | View |
 Chicago Sightseeing River and Lake Cruise | 1h 30min | 4.7 (722) | $46 | View |
 Chicago River 45-Minute Architecture Tour from Magnificent Mile | 45 min | 4.7 (3,577) | $28 | View |
 Chicago By Night River and Lake Cruise | 1h 30min | 4.5 (432) | $50 | View |