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.

Captain Brian, Russell, and Ulysses were amazing! We rented both the Catamaran and the Monohull…read moreboats for 3 hours on a sunny Saturday in June and filled the boats with a bachelorette and her friends. I cannot say enough about the experience! So much fun! The Catamaran boat is nicer than I was expecting. There is a bathroom and indoor cabin area to relax if you get too hot in the sun and don't want to cool off with a swim. The captain and crew took care of us the whole time. They have a giant cooler filled with ice and packed the cooler with our goodies so we could relax. They then waited on us, putting on our music, bringing us our drink requests and snacks. That part was so luxurious and absolutely unexpected! We had too many people to fit on one boat so we rented the Monohull as well and the experience was seamless. They made sure the group was together as much as possible. We boarded the boats while the boats were parked next to each other, then both sailed to the playpen and tied up together. We were allowed to hop between the boats so that the whole crew could mingle. It was perfect! The Monohull is also a very nice boat with room for 6 people to sit comfortably in the back or on the front to sunbath. I highly recommend! The only thing I regret is not booking this for a longer time slot.

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!

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.

KnockOut Charters provided such a wonderful and meaningful experience for our family. We booked a…read moreprivate Lake Michigan cruise to scatter my husband Omar's ashes, and the entire experience was handled with kindness, compassion, professionalism, and genuine respect. The captain (Chris) and crew made us feel comfortable and gave us the privacy and peaceful setting we needed to say our final goodbye. They were very accommodating and allowed us to make the ceremony personal to our family. During such a difficult and emotional time, we truly appreciated how thoughtful and caring everyone was. I highly recommend KnockOut Charters to anyone looking for a beautiful, private, and respectful way to honor a loved one. Five stars without hesitation. Thank you, KnockOut Charters, for helping us create such a beautiful final memory for Omar.

Held my Daughter's Bridal Shower on the Nautilus and it was magnificent! Captain Molly skillfully…read moremaneuvered the double decker catamaran through the busy river with ease. The crew was also just amazing - attentive to everyone's wishes. Honestly, a memory both my daughter and I will have forever!! Thanks Chris, Molly and crew!!!

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.

This trip was awesome, we had a wonderful time. Jovahanny M was so helpful, good drinks and…read morepleasant conversation, he made the experience better, the staff is also goos everyone's is so helpful

The boat trip on 'Island Time' was a fantastic evening!…read moreCaptain Rob, contacted me prior to the event to ensure things ran smoothly and his experience shone throughout ensuring we were covered weather wise and we had a great spot to see the fireworks! Amanda our bar tender was superb, she quickly got through our line of 80 people with a smile and was a pleasure to work with! Would highly recommend booking!

It was truly fun day Sunday! Myself self and 10 other…read morelovely ladies embarked on a wonderful 3-hour cruise on Lake Michigan with epic cruise Chicago. I was in charge of this activity and kept in close contact with the captain/owner . I must say out of this experience the customer service was the best part. In my opinion. The captain kept open communication the entire time. Let us know what to expect. Let us know where to park where we can bring. Every detail was ironed out with us. Weather is definitely something that you cannot be in control of, but the captain made sure that the weather was optimal for our cruise that he explained all the safety expectations for us, the news and the don'ts during our journey and everything went off wonderful. The ladies loved it and are still raving about the trip this week. He customized in our cruise where we were able to dock or anchor and the playpen and also get some time to explore and enjoy an area near Grant Park . The boat was spacious. We were able to spread out even use the kitchen area for our snacks and for our drinks and explore the boats and enjoy the wonderful breezes& the picturesque views of the Chicago skyline Definitely want to take part with some specials that he offers, so check out the website in his Instagram page for updates .

Great company. It was a great experience from the beginning of the charter to the end. Safety was a…read morebig priority with this company, The captain was a licensed captain with years of experience. The boat was clean and we left on time. I would highly recommend this company if you are looking to have a great experience,