Private Sailing Experience: Chicago Lakefront Views

Experience a private sunset sail on Lake Michigan with stunning Chicago skyline views. Customize your adventure for an unforgettable evening.

Duration: 2 hours
Cancellation: 24 hours
Highlights
  • Come Sailing, Inc. - 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 will depend mostly on wind the direction. However, being that this is a private…
What's Included
  • Use of Bluetooth speakers
  • Professional captain licensed by the US Coast Guard
  • All applicable taxes
What's Not Included
  • Gratuities
  • Food and drinks (you may bring your own)
  • Parking
Additional Information

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…

Location
East Monroe Street & South Lake Shore Drive
From the northeast corner of Lake Shore Dr. and Monroe St. follow the lakefront trail to the north and continue along the harbor’s edge as the trail bends to the east. Our boat will meet you along the Monroe Harbor wall east of the cement pier (aka the pump out dock). Our boat’s name is BERNARD.
Cancellation Policy

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

Customer Ratings
5.0
(24 Ratings)
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Elizabethscott_n
Sep 23, 2024
Beautiful Sailing, Pleasant Company - We had a beautiful sunset said with Captain Mike. Wonderful city views, pleasant conversation about sailing, the City of Chicago, and our lives, with milk and chocolate chip cookies to celebrate our Dad's 80th birthday with a memorable experience for us all. Highly Recommended!
Review provided by Viator
Patricia_m
Aug 18, 2024
Captain Mike was awesome!... - Captain Mike was awesome! We really enjoyed the trip. It was beautiful and definitely unforgettable.
Review provided by Viator
Daniel_k
Jul 3, 2024
Best idea ever - We went for a birthday celebration, myself and 4 other friends, and it truly was the greatest time I have ever had with my closes friends. Captain Mike was easy to talk to and made you feel safe but also knew that we wanted to experience this great time together on the front oh his boat. He let us eat and play music. I couldn’t ask for anything better.
Review provided by Viator
Rene_a
Aug 29, 2023
Great sailing!! - Capt Rich was an excellent tour guide and helped us have a great experience. Beautiful evening on a beautiful boat.
Review provided by Viator
Christine_w
Aug 20, 2023
Gorgeous Views! Perfect! - Capt. Mike was phenomenal! The sunset cruise was gorgeous and perfect! We got day views…. Sunset views…AND night view! So special! Thank You! ♥️
Review provided by Viator
Curtis_a
Jun 20, 2023
Abrams' Birthday/Juneteenth Celebration - The ENTIRE experience was WONDERFUL!!! Including the very accomodating Captain Mike. Thank you all for EVERYTHING!!
Review provided by Viator
V9504psjanej
Jun 12, 2023
Beyond expectations - This sailing experience was worth it! The sunset views were unparalleled. Will definitely be doing it again
Review provided by Tripadvisor
Tlippert78
Jun 11, 2023
Nice evening on the lake - Nice evening on Lake Michigan. The weather didn’t cooperate for a sunset, but we had a great boat ride and the temperatures were perfect. The views of the City were amazing and our captain was very informative.
Review provided by Tripadvisor
Ernest_a
Sep 25, 2022
Lake Michigan Moment - There is nothing like seeing Chicago from the lake. And there’s nothing more beautiful than being on the lake and experiencing the sky above. The beautiful color of the waters that surround you. A perfect family moment, great place to pop the question or just to sit in awe.
Review provided by Viator
563shayb
Sep 10, 2022
A must do sailing adventure! - The sunset sail was positively amazing! Captain Mike made the sail even better! We will definitely do again.
Review provided by Tripadvisor