Chicago, Illinois Boat Rentals & Yacht Charters

Chicago Reviews

1. RK

   Rish

   Diversey Harbor Gorgeous 48' Sea Ray Luxury Yacht

   I proposed to my girlfriend on the Sea Ray boat, and it was an unforgettable experience. Kevin was fantastic to work with—he coordinated everything seamlessly and responded very quickly to all my questions. Captain Evan was also great. They both went above and beyond to make the proposal and our evening truly special and memorable.

2. AD

   Alejandro

   Charter a 31' Pearson Cruising Sloop, Chicago

   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.

3. SV

   Sabrina

   Charter a 31' Pearson Cruising Sloop, Chicago

   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!

4. 

   Anthony

   Charter a 31' Pearson Cruising Sloop, Chicago

   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!

5. AM

   Andrew

   Charter a 31' Pearson Cruising Sloop, Chicago

   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.

6. LK

   Linda

   Charter a 31' Pearson Cruising Sloop, Chicago

   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!