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!

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'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.

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.

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

Sophia was a great host and bartender!!! The boat was very clean and seating was plentiful. Great…read moreviews and vibe was relaxed.

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.

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.

Wow. The ladies, Captain Brian, his crew and the beautiful Sea Moose yacht knocked it out of the…read morepark. My wife's 70th birthday wish was to cruise Lake Michigan with family and friends. So I chartered the Sea Moose thru Chicago Yacht Rentals. Rebecca Huang was my key contact and amazing. Not only did see handle the charter, fantastic catered food and beverage, but she was on board helping the crew deliver a very memorable, unforgettable night for my wife, me and our 40 guests. Topped off by 80 degree weather, clear blue skies, magnificent sunset, smooth waters and a very full moon it was spectacular. I was in the hospitality business for 45 years entertaining groups from 40 to 15,000. So I'm a very critical judge of good quality and delivering what was promised/contracted. Chicago Yacht Charters delivered MORE than what was promised. I highly recommend them and hope to use them for my 80th birthday. Home Run! Ron Officer