And dolphins make us happy. Find out more about our cookies policy here.
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. My rate is $200 per hour (minimum of 2 hours). Rates: • 3 hours: $600. • Additional hours: $200 per hour at 5+ hours. 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 If you have any questions, we can answer those through GetMyBoat’s messaging platform before you pay. Just hit, “Request to Book” and send us an inquiry for a custom offer.
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!
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!
I booked this rental for a surprise wedding engagement and Captain Joey did a great job working with me. He helped come up with game plan to pop the question and he was easy to work with even when plans changed. He was also nice enough to play along with the charade before the question was asked to keep it a surprise. I was very happy with how everything turned out and would definitely recommend to others.
We chose Captain Joey for my first sail. There were 4 of us, plus our experienced captain. We had a 2 hour sail and he took us by motor power inside the breakwater and then outside the breakwater for sailing. It was everything I thought it would be - peaceful and a fresh breeze with beautiful views of the Chicago skyline. I would do it again, and I highly recommend it!
Our group of 5 ladies had a wonderful time on Lake Michigan with Captain Joey! The sailboat is beautiful, spacious and well maintained. From the directions to the dock to the actual sailing, Captain Joey knew how to make our trip great experience. The option to bring on drinks and snacks was very nice, and we enjoyed using the “picnic table” on the deck. This is a great way to enjoy the beautiful summer weather outdoors any time, but especially during the pandemic. We felt very safe on this private charter. We highly recommend sailing with Captain Joey!
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...
You’ll get directions to the departure location when you make a booking.
Full refund up to 5 days prior.
Children 12 or under must wear life jacket. 2020 ALL PASSENGERS MUST COME WITH A MASK. 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.