Looks Good
This date is available.
Cookies & Agreements
By continuing to use this website, you have read and agree to the Terms of Use and agree to the collection and use of your information by cookies and similar technologies, as set forth in our Privacy Policy.
With Captain
Easygoing sailing trips on Lake Michigan with skyline views, a relaxed vibe, and a focus on safe, enjoyable time on the water.
Pearson cruising sloop set up for comfortable day sails on the lake, offering a classic monohull feel for those who want to truly sail.
Responsive, clear with directions, and flexible in planning, this captain is described as friendly, skilled, and focused on safety.
Was this useful?
AI Overview
Owner's Description
Capture in the breathtaking Chicago skyline as we sail out on our Pearson 31' Cruising Monohull sloop. We can accommodate up to 6 passengers on your charter. The minimum charter is 2 hours at $500. My rate for 3 hours or more is $200 per hour. What To Expect On Board: We offer flexible scheduling to accommodate your group when it's most convenient. Our cruises are skippered by Certified Instructors and Crew. If you are interested in learning how to sail, we are happy to let you take a more active role. If not, just sit back and enjoy the cruise and the spectacular views. Bring your favorite food and beverages to enjoy a picnic on the water. We even have a grill on board for your convenience. Don't forget to bring your swimsuit and towel if you'd like to take a dip! Our 31-foot Cruising Monohull boat can accommodate up to 6 people. Boat Specialties: • Private Cruises • Group Outings & Bachelorette Parties • Corporate Team Building Events • Sailing Lessons
Captain Joey
168 total bookings
- Capacity
- 6 guests
- Sailing
- Sloop
Reviews
(38 reviews)
Listing Accuracy
AwesomeDeparture & Return
AwesomeVessel & Equipment
GoodCommunication
AwesomeValue
GoodItinerary & Experience
Awesome
6 photos have been added by reviewers who booked this listing.
CW
Charles
We had a fun experience on Captain Joey’s sailboat during the Air and Water Show. He quickly responds to questions and made sure we had a safe and fun experience.
AD
Alejandro
Great overall experience. I must advice that I had to adjust my plans from what I initially had in mind. I had to get props for the experience on my own, which complicated the planning and fortunately resulted all right. Also, it wasn’t until after booking my experience that I realized that Captain Joey was thinking of going out for a motorboat ride rather than for a sail, which would’ve been a total bummer - I had to talk him into this plan and he kindly agreed to doing so.
Hitesh
Captain Joey was great! Gave very clear directions on how best to meet up with him and is clearly an expert at what he does. Would highly recommend him!
SV
Sabrina
Captain Joey is incredible. He went above and beyond to ensure that my partner and I had perfect wedding portraits. He perfectly mapped out sunset and found us the perfect views. Would not have been possible without out Joey! Cant wait to come back again soon!
Anthony
I contacted Captain Joey back in February of 2022 for a June 2022 engagement charter. Long story short, my partner said YES! Everything about the trip was amazing with the only exception being that I got motion sickness about 20 minutes into the charter (be sure to take CJ’s advice when he talks to you about what to do to prevent this). CJ is a very laid-back, jokster type who really put me at ease while I was: 1. overcoming motion sickness and 2. Preparing to propose to my partner. He is batting 1000 when it comes to engagement charters so I’ve you’re looking to propose on a boat, CJ is your captain!
Captain Joey
168 total bookings
Sailing since 1988. USCG licensed captain. The reason we charter is to make sure your experience is an extraordinary one so you will come join us again and again...
Features & Details
- Preston
- 31
- Capacity: 6 people max
Safety Equipment
Life Jackets (6)
Guest Amenities
Sun Protection
Toilets (1)
Departure Location
You’ll get helpful information for your departure after your booking is confirmed.
Street Address For Arrival
400 East Monroe Street
Chicago, Illinois, 60603
United States
Departure Location
Cancellation Policy
Free cancellation up to 5 days before your trip.
Additional Terms & Information
Children 12 or under must wear life jacket. Cancellation Policies for Private Cruises and Sailing Lessons: • Cancellations/Rescheduling made by you with at least 5 days prior to the day of the trip incur no penalty and may be rescheduled with no additional fees. • Sailing Lesson cancellations made by you with less than 5 days prior, no notice or no-shows will result in loss of lesson time and a $50 rescheduling fee. • Private Cruise cancellations made by you with less than 5 days prior, no notice or no-shows will result in loss of sail with full fee. • Cancellations made by our company incur no penalty and may be rescheduled with no additional fees. • Behavior that is detrimental to the safety and well-being of the vessel, crew or individual, e.g., excessive alcohol consumption, will not be tolerated and may result in a non-refundable, non-credited, early departure from the vessel.
Similar Listings
Top Destinations Nearby
Real reviews from happy Getmyboaters.
4.9 out of 5! 500,000+ reviews
