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 lake views of our city’s iconic buildings from the lakefront. Certain tours catch the sunset or Navy Pier Fireworks- every Wednesday and Saturday evenings Memorial through Labor Day. 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!
Greg And Cait
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.
water, soft drinks
fridge, bathroom onboard lifejackets, towels, sunscreen, bug spray, cups, plates, wine glasses, bottle opener and blankets…
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.
Keep these in mind
Any experience can be canceled and fully refunded within 24 hours of purchase.
Always communicate through Airbnb. To protect your payment, never transfer money or communicate outside of the Airbnb website or app.
Up to 6 guests ages 5 and up can attend.
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.
Sail Chicago's Lakefront on a Yacht