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!

Knock Out Charters are the best! Captain Chris and Brook did an amazing job in helping my family…read morearrange an outing in honor and memory of our loved ones. It was a solemn occasion, and they met us with the utmost sensitivity and respect. Thank you Chris, Brook, and Knock Out Charters, and we hope to see you again for a happy celebration too!

Captain Chris & the entire crew made our day! We booked a…read moresunday pregame cruise for the Bears vs Cowboys on september 21st. We were able to board & sail around tailgate style for a couple hours before getting dropped off at soldier field. After the game we go picked up & had a nice 20 minute ride back to DuSable harbor. The vessel is awesome & they provided staff to bartend, etc. Awesome day! I highly recommend KnockOut Charters & will definitely book again in the future.

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.

What a fantastic party on the beautiful Free Spirit cruise...my husband was thrilled with his…read moresurprise party! First of Angela the owner is wonderful to work with, she is great with emails. The entire crew were sweet and hospitable to our guests. We had a blast with the open bar, food and dancing. The only glitch is the parking... we need to figure that out way in advance. Will be trouble if there is a game at solider field. Cannot wait to host another party soon!

We had the after party for our wedding on the gypsy spirit and it was beyond our expectations. The…read morecaptain and crew were so kind and accommodating. The boat is also in great condition. Our guests enjoyed every minute. We cannot recommend them more!

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!

I booked the boat through Boat Bound but next time I would contact Offshore 312 directly to save…read more10%. The boat was spacious and large enough for 10 guests plus captain and crew member. 312 suggested a list of captains. We went with Captain Dan and he was awesome and super helpful, knowledgeable and accommodating. I would rent from 312 again and recommend them to others.

I would not recommend this boat to anyone looking for a premium boat experience. The boat was…read moreancient and not kept up well, it smelled, was dirty (think hair everywhere), and the stereo system did not work. The price of this boat does not include the captain, so you're not getting a good deal. I would pay a little more for a better experience. If you do decide to use this company, do not use Captian Larry, he seemed very knowledgeable and friendly over the phone, but he did not know anything about the architecture in the city and things he said could provide proved to be all talk. Very disappointed with the entire experience. On top of this, the weather was nasty on the particular day of the charter, and they did not cancel. I know the weather is not their fault, but the safety of the passengers should always be the first priority, and I believe money is theirs.

I always have the best experience with CE boating I've used them for my annual boat experience for…read more3 years in a row they always come through! The boats are very nice and fit a decent amount of people ! 10/10!

From the owner: We are closed for the 2025 Season and will return for the 2026 Season. We will welcome you back…read moresoon to book your private boat rental with CE Boating in Chicago. Cruise Lake Michigan, pop bottles, relax, and celebrate. Limited spots.

So fun! Highly recommend this company. They take the time to call you beforehand to make sure all…read moreyour questions are answered. My family and I got captain Larry and he was so kind and told us fun facts about buildings that we passed by. I will for sure be doing another boat tour with them!!

Excellent time on Lake Michigan. We had to reschedule our first appointment due to bad weather and…read morewere so happy we made it back to Chicago just for this trip. We got lucky to have good wind and had a true sailing experience. Captain Conway knew what he was doing and we always felt safe and in good hands. We would certainly recommend this charter to anyone looking for a sailing trip while in Chicago. We will be back!

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.