Skip to content
Another Day's end in Chy.The companion way...
Sailboat Paradise in the Windy City - At a Dock!
Sailboat Paradise in the Windy City - At a Dock!
3 guests
2 beds
1 bath
3 guests
2 beds
1 bath
You won’t be charged yet

Ahoy Mate LABOR DAY SPECIALS!Life on the water couldn't be better. From outside to in, this sailboat is it! Boasting spectacular views of the Chicago skyline, and even glimpses of Navy Pier fireworks Wednesday and Saturday nights, for your romantic and or simply fun/leisurely stay. From remodeled stone counter tops in Gally (kitchen land lubbers) to travertine countertops in the Head (bathroom) it's definitely chillin in style. She's got a flat screen and a small fridge and the best view!

The space

Our roomy, well revamped sailboat, boasts up to 6ft standing room while down below. While we have added many upgrades to this 27 ft sailboat, please note that there are a few things she doesn't have. There is no shower. Guests will have access to private boater showers along with land toilets and running water 4 docks away in the boaters facilities (6 min walk). Yes you can use the toliet/head on our boat, but only what comes out of you and 4 sheets of marine tp at a time. This is standard for all boat heads.

Also please note, the sleeping Double V Berth in front can fit 2 adults less than 6 ft tall. If you bigger than that, look elsewhere.

Guest access

Guests will have access to free parking (private boater pass lot) if needed included in price. Street parking is available but after 11pm all cars parked on the street are ticketed. That's why you will have a boater pass for the lot. There is a fee for lost or stolen parking passes.

Interaction with guests

Please contact us via airbnb or via our cell ph(PHONE NUMBER HIDDEN) (Jilly) with any questions or concerns.

Other things to note

Bikes can be rented through Divy located close to boat. One of our host is also a Pilates Instructor and teaches at harbor outdoors by the amazing Lakeside. Inquire for pricing and we will make sure and give a discount since you are airbnb guests!

There is no indoor cooking but we have an electric outdoor grill for your barbecuing desires. We are situated at the end of the dock farthest away from the gate so the actual dock space is wider than normal, providing ample room to sit and enjoy the fresh air and spectacular views!

License or registration number

City registration pending
Learn about this number

Free parking on premise
Family/Kid Friendly
Wireless Internet

Extra people £35 / night after 2 guests
Cleaning Fee £43
Security Deposit £117
Weekly Discount: 10%
Weekend Price £109 / night
Always communicate through Airbnb
To protect your payment, never transfer money or communicate outside of the Airbnb website or app.

Sleeping arrangements
Common spaces
2 sofas

House Rules
No smoking
Not suitable for pets
No parties or events
Not safe or suitable for infants (Under 2 years)
Check-in time is 2PM - 4PM
Check out by 11AM
Self check-in with keypad

Please be respectful of other boaters and keep noise to a minimum. Have a great time but, no raging music well into the night. That's why we have inside speakers. Also no outside guest allowed.


Safety features
Carbon monoxide detector
First aid kit
Safety card
Fire extinguisher

1 night minimum stay

17 Reviews

Check In
Russell User Profile
June 2017
Th place was amazing and was more then I could have hoped. Such an amazing experience living on a boat for a few nights and felt totally free from the outside world (although the wifi kept me connected just enough!) Jumping in the lake in the morning was so refreshing and laying out on the back of the boat sun bathing was a dream. Thanks for the chance to stay!

Bob User Profile
October 2017
You will NOT have an experience like this anywhere else - it was fantastic!!

Nick User Profile
October 2017
Staying in a sailboat on Lake Michigan was incredible. Even though the weather was pretty terrible the sailboat was cozy and accommodating. After experiencing this trip, I'll definitely be apt to staying in more exotic homes in the future. Thanks for everything.

Iulia User Profile
September 2017
This was such an awesome experience!! My dad and I rented this boat for one night and it was probably one of the coolest things we have ever done. We got to drink some beers and relax on the boat and then we went into the city, we walked probably like 40 minutes to get to wriggler field and had dinner in that Neighboorhood. Then we hung out in Millenium park and used the uber to get back to the boat and it was such a peaceful beauitful night. The harbor is pretty north compared to downtown "heart" of the city but with uber it's like $12-$15 into the middle of it all . Awesome awesome experience, clean boat, cool Neighboors , secluded but the city lights are so close and amazing :)

Magda User Profile
September 2017
The host canceled this reservation 16 days before arrival. This is an automated posting.

Brian User Profile
September 2017
What a great unique experience! This was the perfect amount of being close to downtown and yet having a private getaway. The accommodations are very hospital and fitting.

Kelsey User Profile
September 2017
What a fun experience! Robert made check in super easy even in the wee hours of the night after attending a Chicago wedding when it was dark. Very true and accurate to all the height comments and details in the listing. If you're a light sleeper, I wouldn't recommend banking on a sound sleep only because of the natural water and dock sounds you wouldn't normally think about sleeping in a boat, but wouldn't trade it. Very cozy bed. One for the books.

Chicago, Illinois, United StatesJoined in July 2012
Robert User Profile

Originally from the suburbs of Chicago, we are well cultured, extremely busy working individuals, who enjoy sailing Lake Michigan, exquisite homemade food dishes, and living a healthy lifestyle.

Languages: English, Español
Response rate: 100%
Response time: within an hour

The neighbourhood

Similar listings