Sail Chicago's Lakefront on a Yacht

Chicago, United States

Experience hosted by Greg

2 hours, Hosted in English
Committed to safety
This host committed to Airbnb’s COVID-19 safety guidelines.
Up to 6 people
Includes food, 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

  • Food
    Assortment of chips and bagged snacks
  • Drinks
    An assortment of pop, seltzer waters, beer and wine
  • Equipment
    fridge and bathroom onboard
    lifejackets, towels, sunscreen, bug spray,...

Meet your host, Greg

Host on Airbnb since 2013
  • 249 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 $150
/ person
$150 per person
Join 2 other guests
$150 per person
$150 per person
Join 4 other guests
$150 per person
$150 per person
$150 per person

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 4.97 out of 5 from 249 reviews.

Mike
September 2021
Greg has put together a great experience with a mix of beautiful scenery paired with Chicago history and fun facts, sailing lessons, and great personal storytelling - overall a fantastic day out on the water. Highly recommend!
Ana
September 2021
I recommend this to anyone who want to quiet down a bit their Chicago visit and enjoy the sound of the wind and waves. It’s a stunning view of the skyline of the water. And Greg is a wonderful and kind host.
Brett
September 2021
The sunset sailing excursion is such a spectacular experience, and the only way to see the city by water - the epitome of relaxation and beauty. Greg’s hospitality was unparalleled, and went above and beyond to ensure our experience was enjoyable and memorable. We can easily say it was a highlight of our trip and would highly recommend to all future travelers.
Jessie
September 2021
Wonderful evening on the water with Greg! Such a magical experience with beautiful people in a fantastic location, couldn’t ask for more! Greg is a seasoned sailor with great stories. He knows quite a bit about the lake, it’s history, and the city. Hope to do it again someday!!
Mallory
September 2021
We had a wonderful time on this experience! Greg was a great captain with tons of experience sailing. The boat was beautiful, the weather was great, and he even provided wine and snacks. Would highly recommend!
Bashir
September 2021
Greg was awesome, we had an amazing time on his yacht, it was very relaxing being on the blue water. Some folks got a chance to dip in and go for a swim. We'll 100% do it again if we are in Chicago

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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 canceled 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.

Alcohol

This experience includes alcohol. Only guests who meet the legal drinking age will be served alcoholic beverages.

What to bring

Sun glasses or hat

Rain coat or jacket