Boat Rentals Near You

Local Reviews

1. RJ

   Robert

   August, 2023

   Set Sail with 36' Sailing Boat in Downtown, Chicago

   Ray and Cassidy were great! We didn't have a planned route or destination so Ray chose his own and it was incredible! The views were amazing and we had the best seats in the house to the Air and Water show! Ray and Cassidy were both friendly and knowledgeable through the whole experience. We couldn't have asked for a better crew! The boat was beautiful and a couple of us even had a chance to steer it. All around amazing.

2. BG

   Bradley

   September, 2022

   Set Sail with 36' Sailing Boat in Downtown, Chicago

   Ray and Cassidy were very friendly, and allowed us to help sail the vessel as we requested. Ray is very qualified and enjoys sailing. I'm sure we could have laid back and relaxed as they did all of the work, but I think our experience was much better for having been more involved. Thanks, and we'll definitely use Ray again if we are back in the area and have the chance!

3. 

   Beth

   June, 2022

   Set Sail with 36' Sailing Boat in Downtown, Chicago

   I can’t say enough for how great my experience was with Captain Ray, Captain Dawn and Captain Ted. From the initial booking all the way through the actual sailing, they were responsive, accommodating and amazing to work with. My fiancé and I did our engagement photos aboard Siren Song and the experience and photos exceeded everything I dreamed this day and these photos could be. Highly recommend!

4. LG

   Leigh

   June, 2022

   Set Sail with 36' Sailing Boat in Downtown, Chicago

   Ray and Dawn were excellent, professional captains. We departed around 6pm and took a lovely sunset trip around the harbor. Unfortunately the winds were a bit too high to sail further out onto the lake, but we all appreciated the safe and relaxing trip. Highly recommend!

5. BS

   Bree

   June, 2022

   Set Sail with 36' Sailing Boat in Downtown, Chicago

   Ray and Dawn were excellent captains and hosts to our group. The boat was very cozy and we had a fun time being right in the action of the sails. If you book with Ray absolutely make sure you get your sail time in! Even if you're heading to the playpen, take the long route so you can enjoy the peace and quiet of Lake Michigan.

6. CB

   Courtney

   May, 2022

   Set Sail with 36' Sailing Boat in Downtown, Chicago

   WOW could not have had a better sailing experience with Captain Ray!! He was so quick to communicate with and everything went so smoothly. He was on time and ready to go so we could have as much time out on the water as needed. Such a pleasant time out on the water and he is down to take your group on a little cruise, go to the playpen, or station up so you can jump in the water! His crewmate Cassidy was so good at making sure we always had drinks in hand or helping us get the perfect group picture! Can’t wait to go sailing with him again!