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!

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.

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.

So the weekend is approaching! It's July! It's Hot! Chicago is surrounded by water, at least on the…read moreEast side. What are your plans? Might I suggest Jet Skiing?! Let me tell you about my 4th of July Adventure....... My plans were to hang out and eat BBQ with a friend, but she wasn't feeling too well and had to cancel our plans. After making sure she was ok, I was on the verge of catching up on a series on MAX. Then it hit me, "It's a BEAUTIFUL holiday, and you are about to watch tv? What are you doing? You said you wanted to go jet skiing before the summer is over. What are you waiting for? Let's Do It!" I called Chicago Water Sport Rentals on 31st and spoke with the owner who assured me that the day was perfect and the water was fine, code for: "No Danger Here". After an exchange of "God Bless You", I hung up the phone, quickly put sunscreen on, gathered my wetsuit and sunglasses and headed out the door toward the lake. When I got to the harbor and my jet ski rental destination, that's where the magic happened. After a thorough tutorial about how to properly use and have fun on the jet ski that I was sitting on, off I went to the high seas, I mean out toward open waters with the rest of the water sports lovers. Once I got past the channel filled with boat lovers, sailers, and jet ski pros, I played around in open-calm waters while the sun and the city were beaming down on me. The views are absolutely spectacular and the experience was exhilarating! I was on that thing for an hour. Yes, an hour. Last time it was 30 minutes. This time I wanted to challenge myself. Once I got into my groove, there was NO STOPPING ME, until my time was up. ‍ Lol. I highly recommend you try something new this weekend. If you have been jet skiing before, try a new venue off the 31st Street Harbor. Then treat yourself to lunch at the restaurant directly next door. This experience will make you feel ALIVE!

We learned a lot about kayaking from the owner, John. He and his staff took their time in…read moreexplaining every detail of the equipment to us. We had a lot of fun paddling in the harbor and checking out all the boats docked there. There was quite a bit of boat traffic this Sunday afternoon so we rolled with the waves as boats come in and out. Some might find that unpleasant but we thought it was a good opportunity to get a taste of what kayaking on the lake could be like. Kayaks and paddle boards stay within the harbor, which is about 9 miles of boat docks. It's quite an different experience from other kayaking locations; it's manmade and urban and the only wildlife is seagulls. There is a parking lot though its $28 for 0-12hrs during the weekends. We chose to park on the other side of the trail and walked to this location. It's a beautiful walk! The best amenity is the private bathroom with shower. We usually don't get wet with kayak but since this is the lake, we were drenched. Highly recommend wearing swimsuit for any water activities. We'll be back to try the jet skis.

I can't speak to the experience on the boat but the captain intentionally drove by my canoe and…read morepartner on a SUP causing a huge wake in the harbor. When I later confronted the captain he said he was "running late," perhaps a sign he doesn't have safety as a top priority.

Highly recommend to celebrate a birthday with tailgate the lake for an evening firework cruise!…read more The dock is easy to find, definitely recommend to Uber to the recommended location shown on their website, it's a short walk to the boat after the drop off. There is a bathroom on board which is great! There is a Bluetooth speaker, so you can jam to whatever you like. There is also a cooler for drinks, table for food and games. You can also swim before sundown. The crew was great, shout out to Steve and Captain Jerry! They were a lot of fun, took us super close to the firework show and out to the lighthouse. It was a blast!! We will definitely be back!

Kirsten (the instructor) was FANTASTIC to work with! Communicative, patient, friendly, flexible…read more(with scheduling, skill level, etc.) - inspiring. We are so grateful we got to meet and learn from her!

Just got back from Chicago stand up paddle boarding and honestly had a really fun time. I went to…read morethe diversity harbor location as most of the beaches continue to be closed due to COVID. The view and paddle boarding towards the city is quite scenic and it is cool to be able to merge the thundering city with being on the water. It is right next to a public park so there are many people walking, biking, and having picnics which is also a nice sight, however, on the other side of the park is a highway so that takes away from some of the scenery. There are not great parking instructions on the website but we managed to find a spot hero nearby which was pretty easy. Booking a same-day reservation was not a hassle and you simply fill out a liability waiver on the phone once you get there. I was not super sure about how clean the rented equipment was which could be a concern for some people right now, otherwise the rental process was easy. Some other concerns I had were that they give you a box to store your belongings in, but the box is just sitting out in the back of a trailer and I am not sure how well guarded they were. There is also a very low bridge that I had to lay down to go under, and while I thought it was a fun little challenge others may think of it as a nuisance. Overall, good way to paddle board near the city.

I was in town and rented a Jetski with these guys. They are very cool and super flexible. They'll…read moregive you a rundown of how to ride the jetski and send you out. I'd definitely recommend them to someone looking to rent a jetski in Chicago!

I had a rather disappointing experience with Captain Larry's boating service. From the start, there…read morewas a noticeable lack of warmth or welcoming vibes. The staff seemed disinterested in providing a pleasant customer experience. When we had questions about the safety procedures and tour details, their responses were curt and lacked empathy. The boat itself was fine, but the overall experience was dampened by the staff's indifferent attitude. Even when we expressed some concerns about the route due to weather conditions, our worries were dismissed without proper consideration. It's unfortunate because the potential for a great boating experience in Chicago is there, but the customer service left a lot to be desired It's interesting that I see a review mentioning discrimination because I couldn't help wondering if the treatment we experienced was related to fact that my partner was with me. We are not ones to display affection in public but our body language is obvious Not recommending this service if you care about equality and not supporting a biased business

I would not return. We were recommended by someone we trust so we had our hearts open. My…read moregirlfriend (who is a strong woman of color) felt patronized and, dare I say, discriminated. We will not recommend Captain Larry services to anyone who values respect