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Serene Private Sunset Sail on Lake Michigan - Navy Pier, Chicago

Serene Private Sunset Sail on Lake Michigan - Navy Pier, Chicago

Chicago, USA

Serene Private Sunset Sail on Lake Michigan - Navy Pier, Chicago

Recommended by 100% of travelers
Badge of Excellence
Chicago, USA
  • 2 hours (approx.)
  • Mobile ticket
  • Offered in: English

Overview

Soak up unbeatable views of Lake Michigan and the Chicago skyline—and stay on the water long enough to watch the lights come on in the city—on this private, sunset sailing tour. This charter is completely customizable, giving you the chance to choose your music, route, and up to five additional guests. Sail into the sunset with your own drinks and snacks (refrigerator and ice on board) and your family or friends by your side, all led by US Coast Guard–certified captain.
  • Admire views of Lake Michigan and the Chicago skyline most visitors miss
  • Travel on a private sailboat with US Coast Guard–licensed captain
  • Choose your adventure by selecting your route
  • This private tour offers the most personalized sightseeing experience

Cancellation Policy

You can cancel up to 24 hours in advance of the experience for a full refund.

Traveler Photos

Gallery picture 1 (from a traveler's review)
Gallery picture 2 (from a traveler's review)
Gallery picture 3 (from a traveler's review)
Gallery picture 4 (from a traveler's review)
Gallery picture 5 (from a traveler's review)

Reviews

5.0
based on 27 reviews
Total reviews and rating from Viator & Tripadvisor
Sort by: Most insightful

Beautiful sunset sail

Agnes_M, Jul 2025
A fantastic experience - beautiful weather and relaxing atmosphere. Will definitely try again and recommend to others

Awesome and pretty ride

Xander_H, Jun 2025
Mike was a great guide and very friendly!! Nice boat, pretty ride and would 100% book this again. Highly recommend.

Response from Host, Jun 2025

Thank you Xander!

Beautiful Sailing, Pleasant Company

ElizabethScott_N, Sep 2024
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!

Captain Mike was awesome!...

Patricia_M, Aug 2024
Captain Mike was awesome! We really enjoyed the trip. It was beautiful and definitely unforgettable.

Best idea ever

Daniel_K, Jul 2024
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.

Great sailing!!

Rene_A, Aug 2023
Capt Rich was an excellent tour guide and helped us have a great experience. Beautiful evening on a beautiful boat.

Gorgeous Views! Perfect!

Christine_W, Aug 2023
Capt. Mike was phenomenal! The sunset cruise was gorgeous and perfect! We got day views…. Sunset views…AND night view! So special! Thank You! ♥️

Abrams' Birthday/Juneteenth Celebration

Curtis_A, Jun 2023
The ENTIRE experience was WONDERFUL!!! Including the very accomodating Captain Mike. Thank you all for EVERYTHING!!

Lake Michigan Moment

Ernest_A, Sep 2022
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.

Absolutely Amazing

Jody_N, Aug 2021
Highly recommend the sunset cruise. What a great way to view Chicago’s skyline! Friendly, informative Captain helped us decide on must see spots for the rest of our stay. Thank you.

Smoothie sailing

Andrea_M, Jul 2021
Mike was awesome! It was my first time on a private sail with friends. We were comfortable, the sail was smooth and we had a great time. We didn’t want it to end.

Amazing experience!

Rebecca_S, Jul 2021
Great trip! I would recommend going for longer than 2 hours if you are able. We loved every moment and wished we had booked a longer tour.

Response from Host, Jul 2021

Thanks Rebecca! It's really nice to hear that you had such a good time! We are working to make it easier for customers to book longer charters through TripAdvisor/Viator. Thank you! Capt. Mike

I could not stop smiling

Sarah_A, Jun 2021
Captain Mike was awesome! So much fun and very knowledgeable. We had our own playlist playing the whole time and the views..... the best I’ve ever seen. We sipped wine and had the time of our lives. It was worth every penny.

Response from Host, Jul 2021

Thank you so much Sarah_A! I love sailing and it's very rewarding for me to hear that my customers are loving it too! Thanks for sailing with us! - Capt. Mike

Lovely evening

Kim_W, Jul 2020
Perfect weather for a sunset cruise. The views of the skyline were amazing. The captain was informative and pleasant. My only complaint is that we were not informed ahead of time that the hull of the boat was not open due to Covid. That meant we could not use the bathroom. A bit of a problem.

Response from Host, Jul 2020

Hi Kim! Thanks for sailing with us! I'm very glad you enjoyed the sailing but am sorry about the miscommunications regarding restricted access to the cabin below. I will check the product description and update as necessary to be sure people are aware of this COVID-19 related restriction. Thanks for pointing it out. See you on the water! Capt. Mike

Spectacular birthday celebration

Alfredo_V, Jul 2020
It was truly the best choice to do something different, special, and romantic to celebrate my Wife's birthday. We recently moved to Chicago and was the first time we saw the city from the inner lake. The views and sunset were truly spectacular. Captain Mike was quite friendly and professional. We felt quite safe under the circumstances.

Highest level sailboat experience!

Kiley_B, Jul 2020
The captain was ready for us when we arrived. He was very informative. Great experience from beginning to end!

Sunset cruising

Tom_O, May 2019
Cpt. Mike took us out in his boat for sunset, it was fantastic and very relaxed. I would highly recommend him and willl definitely do this again when we have our next visitors to Chicago.

Michael is a magnificent...

RENEFERNANDO_S, Aug 2025
Michael is a magnificent person. He had flexibility and openness to accept a certain tour, answer questions and tell experiences. That plus the magnificent yacht he has and his expertise in sailing in the waves of the lake... made the experience magnificent. I highly recommend it.
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