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.

If you're looking to charter a boat in Chicago, this is the place. They have a variety of options…read moreavailable and Captain Russell is fantastic. We did a 5 hour charter for 7 and part of me wishes it was longer. Pack your cooler, get your tunes ready to Bluetooth into the boats sound system and enjoy a nice relaxing day on Lake Michigan.

As boating season starts in Chicago, I just wanted to let you know that Russell took me, my…read morechildren and their significant others out for my "birthday celebration" and it was thee BEST boating experience this Chicago gal has ever had. Russell took us on the most beautiful route and his boat is beautiful and comfortable for viewing, eating, drinking and laying out if you like. My favorite moment was when we anchored and me and my kiddos did a celebratory jump into the lake as Russell videotaped us. Big Thanks to Russell for the BEST Boating experience in CHI. He is so knowledgable and experienced that I highly recommend 1st Class Charters Chicago!!

We did a daytime private charter on the Chicago Motor Yacht for a bachelorette party and the…read moreexperience was perfect. The staff was very attentive and the yacht amenities were wonderful. I would highly recommend this company! Booking with Chicago Motor Yachts is so seamless and Grace is very helpful.

Wanted to leave a review even though we weren't able to venture out due to inclemate weather. I…read moreappreciated how easy it was to get all the info I needed leading up to the trip with Grace. Also, I had to make some changes to the plans and they were very quick to assist me in transferring the reservation to a delegate. Overall, giving a high rating for the ease of booking, the assistance in answering all my questions, and also the expedient processing of the deposit reimbursement due to poor weather. Hope to actually go on a boat ride on a future visit if the weather cooperates!

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.

Captain Kirk Kessler, a United States Coast Guard - Certified Master Captain, goes all out to give…read morehis passengers a wonderful experience. His boat, the Peony, is equipped in a manner to meet the needs of his guests. His first mate, Woody, a chipper mini Golden Doodle, adds a fun touch to each outing. Kirk is extremely professional, going over his shipboard rules with all his charges before they embark. His rule #1 - "Stay on the boat!" Captain Kirk gets a sense of each of his sets of guests, and how comfortable (or apprehensive) they are on the water. Passengers preferring a sedate, "gentle" excursion will get one (to the extent weather and lake conditions permit); those guests up for a more adventurous outing with 15-30 degrees of heeling will have their wishes fulfilled. As a USCG-certified Master Captain, Kirk knows what he needs to do to trim the sails and change his headings to make his cruises pleasant ones for his passengers and their predilections. A charming host/skipper, Captain Kirk will make your sail/cruise an unforgettable one - withe the beautiful Chicago skyline as your sunset backdrop. You can't do better than Salty Dog Sailing Co.!

I highly recommend chartering with Salty Dog. Captain Kirk () was very professional. I was a…read morelittle nervous, but he set everyone in our party at ease. The boat comfortably fits 4 people, and you can just sit back and relax. Woody is extremely friendly, greeting us on the dock when we arrive, and sleeping next to us the entire trip, except when we turned and he had to flip to the other side! And it's true sailing, we went about 3.5 miles from shore, getting some incredible views of the city. It was a great day, great conversation and an overall awesome time!

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!

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.

I really enjoyed the boat tour! David is wonderful tour guide with lots of funny jokes and…read moreknowledge about the architecture in the city. The boat also has ponchos, snacks, and drinks downstairs. There's also a few intermissions throughout the ride so you can go downstairs to warm up / use the restroom. I highly recommend Summer of George and you can also get a discounted ticket on Groupon as well!

The tour/route and boat were good. But the guide, Hillary ruined the trip for us. She constantly…read morecriticized other architectural boat tours, which we found very unprofessional. First thing she told everyone once we were seated was that talking amongst ourselves during the tour was discouraged. So we all sat quietly, as she asked, then later told us we weren't very responsive, basically seem to talk down to us like school children. Money not well spent. Have been on the Architectural tour run by the actual Architectural Society several times and even though it was much more money, the whole experience, knowledge, and tour guides far exceed this experience.