Skip to content
boat ride

Sail Chicago's Lakefront on a Yacht

boat ride

Sail Chicago's Lakefront on a Yacht

190 reviews
Duration
2 hours
Group size
Up to 6 people
Includes
Drinks, Equipment
Hosted in
English
boat ride

Sail Chicago's Lakefront on a Yacht

boat ride

Sail Chicago's Lakefront on a Yacht

190 reviews
Duration
2 hours
Group size
Up to 6 people
Includes
Drinks, Equipment
Hosted in
English

What you'll do

Our sailing experience begins at the Monroe Harbor Public Dock (Google maps). Boarding our 37’ luxury cruising class sailing yacht Dragonfly, a Jeanneau Sun Odyssey, 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. Try your hand at the helm and rigging the sails or let us do the work. On hot days we can anchor near shore and swim in the lake to cool off. Airbnb experiences are social, and up to 6 guests from different parties can join our standard cruise. We also welcome inquiries about private or custom outings. If you do not see a time on our calendar that works well for you, please contact us! Please note we have moved our evening tour featuring the Navy Pier Fireworks to a separate experience called "Fireworks Sailing Cruise on a Yacht."

Your hosts

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
Greg
Cait
Cait

What's included

Drinks
water, soft drinks
Equipment
fridge, bathroom onboard lifejackets, towels, sunscreen, bug spray, cups, plates, wine glasses, bottle opener and blankets…

Guest photos

Guest reviews

Navigation section for review pages

Where you'll be

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. The Lakeside Garage (about $30) off of Columbus Dr., has a southeastern corner pedestrian exit/entrance (follow the sign) at Lake Shore Drive and Monroe.

Guest safety

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 keep in mind

Cancellation policy

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

Communication policy

Always communicate through Airbnb. To protect your payment, never transfer money or communicate outside of the Airbnb website or app.

Guest requirements

Up to 6 guests ages 5 and up can attend. Both our captain and boat are fully licensed, registered and insured through the Coast Guard, State of Illinois and City of Chicago. Please be aware that many charter boats similar to this experience (both on…

More tips

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.

Airbnb Experiences are vetted for quality

Airbnb Experiences are vetted for quality

  • Local experts

    Led by locals who love where they’re from and what they do.

  • Small groups

    With intimate group sizes, you’ll never get lost in the crowd.

  • High standards

    Every experience is reviewed for unique access.

Greg
Sail Chicago's Lakefront on a Yacht
190 reviews
$171/person
190 reviews
$171/person