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Sail Chicago's Lakefront on a Yacht

Chicago, United States

Experience hosted by Greg

2 hoursHosted in English
Committed to safety
This host committed to Airbnb’s COVID-19 safety guidelines.
Up to 6 people
Includes drinks and equipment

What you'll do

Our sailing experience begins at Monroe Harbor right in downtown Chicago. Guests will enjoy a captained cruise on our luxury class sailing yacht, a Jeanneau Sun Odyssey 37. We will cast off and motor out to Lake Michigan where we will set sail to a favorable course. Bring your favorite food and drinks, listen to music, relax, and take in the views of our city’s iconic buildings from the lakefront. The courageous can try their hand at the helm and rigging the sails-Captain Greg is a volunteer sailing instructor for a local non-profit and enjoys sharing his knowledge. On hot days be sure to bring a bathing suit to swim in the lake to cool off. Please feel free to inquire about custom bookings. We have hosted engagements, bachelorette parties, corporate outings and many more memorable events!
Other things to note
New friends will join your booking unless you reserve the entire boat. We only wait 15 minutes for a late guest out of courtesy for timely guests. We only cancel for lightning and will refund everyone. If you tend to get motion/seasick, or have a hangover, take motion medication 30 minutes prior.
Our sailing experience begins at Monroe Harbor right in downtown Chicago. Guests will enjoy a captained cruise on our luxury class sailing yacht, a Jeanneau Sun Odyssey 37. We will cast off and motor out to Lake Michigan where we will set sail to a favorable course. Bring your favorite food and drinks, listen to music, relax, and take in the views of our city’s iconic buildings from the lakefront. The courageous can try their hand at the helm an…

What's included

  • Drinks
    water, soft drinks
  • Equipment
    lifejackets, towels, sunscreen, bug spray, cups, plates, wine glasses, bott...

Meet your host, Greg

Host on Airbnb since 2013
  • 197 Reviews
  • Identity verified
We are avid sailors and enjoy sharing our passion for sailing with travelers and locals! For us, sailing offers adventure, relaxation, and the discovery of new places and people. There is no better place in the world to combine the thrill of sailing with views of a world class skyline. Greg holds a Master Captain’s license from the US Coast Guard, and Cait is a local architect focused in skyscraper design. Our boat is fully licensed as a commercial passenger vessel and operates under the highest safety standards as monitored by the US Coast Guard.
We are avid sailors and enjoy sharing our passion for sailing with travelers and locals! For us, sailing offers adventure, relaxation, and the discovery of new places and people. There is no better place in the world to combine the thrill of sailing with views of a world class skyline. Greg holds a Master Captain’s license from the US Coast Guard, and Cait is a local architect focused in skyscraper design. Our boat is fully licensed as a commercial passenger vessel and operates under the highest…
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From $209
/ person
No dates available

Where you'll be

Your experience takes place on our boat! We will meet at the Monroe Harbor North Harbor Public Dock. There is a taxi drop off cul-de-sac at 400 E. Monroe on the east side of Lake Shore Drive. From there it is a quick walk north along the lake front trail just past the Chicago yacht club docks. Our dock is by itself, made of concrete with wood pylons, and runs north-south. We will send a map on the day of the experience.

Rated 4.96 out of 5 from 197 reviews.

Rita
October 2020
We booked a private tour for 4. We had a great time! The Chicago architecture and skyline from the lake was gorgeous. Greg was very welcoming and easy to talk with.
Elisabeth
October 2020
Firstly, Greg is an absolute sweetheart and took great care of us! Greg and Cait are super quick and helpful with their communications. The experience itself is great because of the Chicago skyline. The boat is lovely and I wish them all the best with their next trip 🥰
Firstly, Greg is an absolute sweetheart and took great care of us! Greg and Cait are super quick and helpful with their communications. The experience itself is great because of th…
Ali
October 2020
Sailing was my girlfriends idea, I was a bit afraid to say the least. Greg explained the safety precautions before sailing and 5 minutes later I was thrilled. His an expert at showing spectacular views of the skyline. Hands down the in the books for one the greatest experience ever!
Sailing was my girlfriends idea, I was a bit afraid to say the least. Greg explained the safety precautions before sailing and 5 minutes later I was thrilled. His an expert at show…
Julia
October 2019
We highly recommend this experience. Greg was friendly and very knowledgeable, and even after living in the city for a few years, we'd never seen it from these angles. Greg took some amazing photos for us on my camera and had snacks, drinks, blankets, and Dramamine available. We would do it again.
We highly recommend this experience. Greg was friendly and very knowledgeable, and even after living in the city for a few years, we'd never seen it from these angles. Greg took so…
Natalie
October 2019
Has a great time with Gregg. He was kind and very knowledgeable. Was a great way to spend my first day in Chicago!
Sydney
September 2019
Such an amazing experience! Cait and Greg were so accommodating from the drinks and snacks to the level of comfort they gave it all. We unfortunately were not able to meet Cait on our trip but Greg alone did a wonderful job. He seemed so knowledgeable about sailing. On top of that we lucked out with the best weather. We will forever remember our sailing trip on Lake Michigan!
Such an amazing experience! Cait and Greg were so accommodating from the drinks and snacks to the level of comfort they gave it all. We unfortunately were not able to meet Cait on…

Activity advisory

Expert industry partners
Every adventure follows industry guidelines. We partnered with the Adventure Travel Trade Association, expert leaders in adventure travel, to define best practices and standards for safety.
Know your comfort level
Please note outdoor activities carry risks, and you may be exposed to dangerous situations as part of this experience. Make sure you can participate safely given your abilities and the conditions (such as location, weather, and equipment).

Things to know

Cancellation policy

Any experience can be cancelled and fully refunded within 24 hours of purchase, or at least 7 days before the experience starts.

Guest requirements

Up to 6 guests ages 5 and up can attend.

What to bring

Sun glasses or hat

Rain coat or jacket