I've taken quite a few boat rides over the years. Small boats, large boats, and a few in between…read more So when a friend invited me to join a few people for a ride with this charter service, I was happy to go. I really didn't have any expectations beyond what I already understood a boat trip to be. I figured we'd cruise up and down the waterfront, enjoy the scenery, and eventually make our way back to the pier, just like I've done plenty of times before. Well, I'm not above admitting when I'm wrong. This was an amazing experience. It wasn't because we stopped at an amazing restaurant. It wasn't because we traveled up and down the Chicago River. Those things certainly made the day special, but what really made the experience memorable was the captain and his wife. Before we even stepped onto the boat, we had to change our reservation a few times because of Chicago's bipolar summer weather. The captain was extremely responsive throughout the entire process. He explained why we needed to reschedule, stayed in communication with us, and made sure he personally took care of us when we were finally able to get out on the water. Once aboard, he and his wife were simply wonderful. They made the entire experience feel personal, comfortable, and genuinely enjoyable. All in all, this wasn't just an amazing boat rental. It was an amazing experience because of the people behind it. I would happily take another trip with this team again and again.

This is by far my favorite boating experience!!! I have used their services a few times. They will…read morehelp execute your vision and the customer service is TOP NOTCH!! They take pride in their boat and in making sure the passengers are safe while having a good time! This was an awesome and romantic way to spend my birthday on the water. Thank you Pier Pressure!! Not only will I be back, I'm telling everyone I know!

This was the first time my friends and I have booked a rental for an afternoon at The Playpen…read more Quinn quickly corresponded with us from the very start and answered any questions we had leading up to the day. Her instructions via payment, booking, and arrival (via welcome email) were extremely clear, leaving out no details. Upon arrival, she greeted us and gave a quick tour of the boat. She provided water for us and ensured all of our questions were answered before embarking. The boat was as described, included a great Bluetooth speaker/subwoofer, and everyone had a great time. Captain T was a professional and ensured everyone was safe the entire time. We would definitely book with Pier Pressure again.

We used Adeline's Sea Moose for a private corporate event (approximately 30 people), and it was an…read moreexcellent experience from planning through execution. The team was extremely responsive and accommodating, helping us build an event with a variety of food. On the day of the eventt, everyone was extremely hospitable, and we found it to be an unexpected nice touch that they regularly checked if we needed beverages, collected our garbage frequently, and passed out the apps to ensure people received food. Would absolutely recommend, and definitely plan to use this crew again. Thanks for a great time!

Responsive | Personable | Flexible |…read more Responsive - The crew at ASM was very flexible. Their website is well laid out with a chat service that answers most of your questions. Chelsea, the administrative assistant and scheduler answers emails in 24 hour or less and is very helpful with answering questions and providing examples to help customize the perfect charter for your group. Personable - the entire crew Flexible - The crew at ASM was very flexible throughout the process of securing the charter and the day of. There was a thunderstorm in chicago 30 minutes prior to Pro Tip: The Captain smokes, so if you have a sensitivity to smoking, just make sure you let Chelsea know that your group is sensitive to smoking. Pro Tip: Call the crew 5 minutes before you show, because they have to come out to a gate to get you. We were in the middle of a rain storm and had to wait 5 minutes at the gate before getting on the boat. Therefore, our group was soaked on our way on. It really affected our group because it set a bad tone. But, once everyone was warm we had a great time.

My friends and I chartered the catamaran in August 2021 and it was the highlight of our summer! It…read morewas such a great way to enjoy the Chicago skyline and swim in the lake. The boat was spacious and comfortable. Can't wait to go again this year!

We reserved a private Monohull charter Memorial Day weekend. The pre-charter communication was easy…read moreand awesome! It was so easy to use the mind body app. The dock was easy to find and right in the heart of downtown. We were warmly welcomed by Captain Scott and Skipper Jao and immediately felt like old pals. We felt safe, comfortable, and had a ton of fun the entire charter. They were totally flexible with our sailing route and also willing to recommend the best route due to the current conditions. They even let us help sail! Would definitely recommend and do this again!

SO MUCH FUN!! How it…read moreworks: You charter a boat along with the captain and crew. The boats are owned by the company. We chartered a boat on Labor Day, with Bill and Nancy. We departed from Montrose Beach. We were able to bring our own drinks and snacks for the sail. There were 7 of us total at ~$100/person. We specifically selected this company because they had a money back guarantee in the event of inclement weather - most other boating companies do not offer this! HUGE PLUS. Fun Fact: All of their boats mean "Lost" in different language, but not to be confused with lost at sea!

We had an excellent charter experience with Captain Bill on a speedboat. Booking the boat was quite…read moreeasy through the website, then you can contact the captain yourself to see who is available (company gives names/contact info). I would definitely rent from CSC again. Prices were also pretty average compared to other companies! Definitely recommend.

We got married on the Sophisticated Lady at the end of September 2025 with just our respective kids…read more(his 4, my 2) and siblings/spouses on board...a total of 17 people...most from out of state. I contacted Taylor for all the arrangements early summer and my fiance and I went to the city overnight to see the boat. (We live in Western Suburbs) My kids have always loved our overnights in Chicago and a sunset cruise the second time around seemed like the perfect wedding. We prayed the weather would cooperate! Booking was easy, selecting food options and drink packages was not necessarily cheap but they had a great selection with the premium beverage package that was good for all. The 3 person crew were great...they went with the flow. We got married on Lake Michigan (bartender said it was the first wedding they'd ever had ON the boat.) We are bikers so most of our kids dressed accordingly (as did we). The Captain stopped the boat in a protected harbor for the 20 minute ceremony so no one would get pitched over. Everyone had a fantastic cruise and the sunset did NOT disappoint! We absolutely LOVED this unique wedding experience!

Sophisticated lady is a gorgeous boat, I really like the myriad of spaces where you can sit down…read moreand talk or dance or just take in the view. The food on the boat is excellent and the crew is very attentive. Overall, highly recommended.

I found this boat charter on Yelp! Spoke with Paul and the process to book was so seamless! He…read moreanswered all my questions promptly when wondering how to tip and if we needed to bring coolers. They supplied ice for our trip which was great! At the end of our time we were already trying to book with them again! With the new adjustment we were able to have 30 with proof of vaccines! Highly recommend them!

Captain Paul and team was AMAZING! We had a post graduation cruise for my daughter and best friend,…read morecruising into the sunset. The most memorable trip for my daughter, friends and family. Captain Paul was extremely flexible in making the most beautiful experience. We cruised on both the river, and saw the sunset on Lake Michigan. The experience of a private yacht for my daughter's celebration was priceless. Thank you Captain Paul for your hospitality!

I wanted to find an affordable private boat tour for a bachelorette party, and this fit the bill…read more Dan was very accommodating and made sure everything went smoothly for the day. When we decided to bring food onto the water, he met us by the harbor and provided a cart for us to place all the bags of food onto it. He let us choose if we wanted to spend more time at The Playpen or sailing on the open waters. Floaties were also available. Communication was great, the weather was great, the music was great, and the people were great. Thank you for an authentic and fun boating experience!