Private Sailing: Chicago Lakefront Views

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.

Duration: 2 hours
Cancellation: 24 hours
Highlights
  • 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…
What's Included
  • Use of Bluetooth speakers
  • Navy Pier Facility Fee
  • All taxes
  • Professional US Coast Guard licensed captain
What's Not Included
  • Gratuities
  • Food and Drinks
  • Parking
Additional Information

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…

Location
801 E Grand Ave
East Grand Avenue
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.
Cancellation Policy

For a full refund, cancel at least 24 hours before the scheduled departure time.

Customer Ratings
5.0
(66 Ratings)
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Carrie
Aug 4, 2025
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!
Review provided by Tripadvisor
Michelle_t
Aug 3, 2025
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.
Review provided by Viator
Jeffrey_f
Jul 12, 2025
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!
Review provided by Viator
Kira_m
Jul 3, 2025
Best Part of Our Trip - We took a two hour sail for our daughter’s 24th birthday. It was fantastic! Everyone in the family felt like it was the best part of our vacation. Captain Mike was awesome and answered all kinds of questions about sailing and some Chicago history. I cannot recommend this enough!
Review provided by Viator
Heidihairston
Jul 1, 2025
Sail with Captain Ulysses! - Amazing time with Captain Ulysses! It was a beautiful day with great company and a great host! The views were incredible and the conversation fun! We had music and drinks and it was a lovely day on the lake!
Review provided by Viator
Samanthara6201hz
Jun 25, 2025
The Best Part of Your Chicago Trip! - I can’t recommend enough that you head out on a charter with Come Sailing; it’ll be the best part of your trip to Chicago! Captain Mike was excellent, he knows what he’s about and he’s very good at it. On top of expertly piloting us around the lake, anything you need, Mike’s already thought of it. There are a pair of Bluetooth speakers onboard you’re welcome to pair to, a cooler of cold water and ice for stashing away snacks, a head onboard if needed, and when one of our party felt a bit seasick, he directed her exactly where to sit on the boat to feel better. He’s also a wealth of cool knowledge about sailing the Great Lakes – be sure to ask him questions! The Bernard is a gorgeous boat, with plenty of places to sit for a picture-perfect view of downtown Chicago. There’s plenty of room to place your bags and shoes while you enjoy the view. We brought a bottle of champagne and a bit of charcuterie to snack on while we took in the skyline. Assume you’ll be sitting outside the whole time (you’re welcome to sit below, but it gets quite hot down there, and the view is much better outside!) so wear sunscreen. Chicago is called the windy city for a reason, so don’t wear any hats you can’t afford to lose. Also, be sure to arrive about fifteen minutes early to give yourself a bit of time to find the correct gate at the pier. If, like us, you stop by the nearby Mariano’s to pick up snacks beforehand, it’s about a 25 minute walk from there to Navy pier. Overall, this is a super fun, safe, thoughtfully-organized and all around incredibly enjoyable activity to round out your Chicago trip!
Review provided by Tripadvisor
Marisa_s
Sep 5, 2024
Highly recommend - Mike was awesome! A beautiful experience on Lake Michigan! Thank you for being a great captain! Would definitely do again.
Review provided by Viator
Shawna
Sep 2, 2024
A fun, relaxing sail on Lake Michigan with an excellent Captain! Thank you Captain Mike for a lovely sail! Will be back! - Fun Safe Family Sailing in a Private Sailboat with. Great Captain. My boys and their friends visiting from out of state had a great time on the lake. Beautiful views and lovely weather and we felt safe the whole time. The boat was extremely clean and well cared for!
Review provided by Tripadvisor
U25qhvictoriap
Aug 18, 2024
Sailing cruise - The views were absolutely amazing! Captain Mike was the best and gave us an excellent sailing experience! Would definitely recommend this!
Review provided by Tripadvisor
Melissa_w
Aug 13, 2024
Great tour, super communication! - Charter Captain was wonderful. Very patient and sensitive to our needs as we were there to put my dad’s ashes in Lake MI. Highly recommend Cpt Michael for any special occasion trip or just a lovely regular sail.
Review provided by Viator
From $508 (Per Boat)
up to 6 guests
1 - Traveler
Cancellation: Free cancellation up to 24 hours before the start of your experience (local time).