Chicago, IL, United States 4.5/5 stars 15 reviews


With Captain
Up to 6



The Boat

Model: Pearson 31 Pearson
Type: Sail
Year: 1987
Length: 31 ft.
Passenger Capacity: Up to 6
Sleeps: 6
Rooms: 0
Fuel Capacity: 20
Horsepower: 17


Depth Finder
Vhf Radio

Boat Rules



Cancellation Policy

Free cancellation up to 5 days from trip start and 50% refund for cancellations within 2-5 days from trip start. Cancellations within 2 days of trip start date are non-refundable.
+ service fees

You won't be charged yet


- or -
Captain Info
If requested, the owner can provide a list of available captains for bareboat charter or the renter can use their own qualified captain. If the boat is being time chartered, the owner will provide the Captain.

Meet Joey

Aboard since 2017
Response Rate
< 12 hours
Response Time


4.5/5 stars
  • 5/5 stars (5/5)
    Sep. 21st

    Joey was a fun captain. He showed us a great time. His boat is nice, enough room for us, the route he took was scenic, gave us a lot of opportunities to take great pictures of the Chicago sky line. It was worth every penny. Will definitely ride with him again at another occasion.

  • 5/5 stars (5/5)
    Aug. 25th


  • 5/5 stars (5/5)
    Aug. 10th

    Joey was kind and funny! Boat had ample room and we had a blast. Only caveat is no water toys - so either bring your own or make sure you can swim ;)

  • 5/5 stars (5/5)
    Jul. 26th

    Joey is a great captain. He really knows his stuff and provided us a great bachelor party experience all around. Would recommend

  • 5/5 stars (5/5)
    Jul. 27th

    Joey was so kind and considerate. It really added to the experience which just made it a wonderful time! Would def recommend!

  • 2/5 stars (2/5)
    Jul. 20th

    Small older boat. Cramped for even 4 ppl. Captain Joey a little too in your face. I wouldn’t have been so harsh but the cost is too high for this type of experience.

  • 5/5 stars (5/5)
    Aug. 03rd

    We had a great time with Joey. Boat in top shape condition, a very pleasant skipper, very knowledgeable about sailing and the area.
    We recommend him totally!

  • 4/5 stars (4/5)
    Jul. 29th

    He was amazing :-)

  • 2/5 stars (2/5)
    Jul. 06th

    Overall, we did have a good time. However, it felt like Joey didn’t want to be friendly to us. We are a group of 6 very successful professionals and Joey did not respond nicely to us. He kept telling us what to do and didn’t let us enjoy the boat.. even though we paid money for... he expected gratuity and felt like he wanted to control everything. We tried to go to a familiar place on the lake and he decided for himself without asking our opinion. I would recommend AGAINST captain Joey.

  • 5/5 stars (5/5)
    May. 31st

    Joey was great! Took 6 friends out and we had a wonderful time.

  • 5/5 stars (5/5)
    Aug. 30th

    Worth every penny. Captain Joey's personality was just the icing on the cake. Thanks for the lessons too.

  • 5/5 stars (5/5)
    Aug. 24th

    Although the weather didn’t cooperate on our boat day, my family and I enjoyed our trip with captain Joey. The boat is beautiful and enough room for 6 people! We had a great time and would do it again.

  • 5/5 stars (5/5)
    Jul. 21st

    Captain Joey’s excellence as sailor and personality as captain were essential in capping what became an immensely successful bachelor party I had thrown my best, life-long friend. Our embarkment from the Chicago Yacht club was coordinated was surprising ease as we began voyage of Lake Michigan. Due to adverse sailing conditions, we were unfortunately kept close to shore. Sympathetic, Captain Joey extended courtesy by allowing us to stay a half hour past our contracted time so that we may watch Saturday’s Navy Pier fireworks display from harbor. Professional service. Great conversationalist. Highly recommend.

  • 4/5 stars (4/5)
    Jul. 20th

    We had a great experience with Captain Joey. While the weather wasn't perfect, we relied on Joey's experience and had a great time. Safety was paramount to Captain Joey and we appreciated that. The ship was great for our group of 5. We would certainly recommend Captain Joey and hope to get back out on the water with him.

  • 5/5 stars (5/5)
    Jul. 04th

    Ton of fun! Highly recommend Joey and this boat for a cruise on Lake Michigan with 6 people and some beers

Boat Location - Chicago, IL, United States}