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.

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 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!

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 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.

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.

We had a group of professional women enjoying the day. Everything went perfectly, the boat was…read moreclean and the captain accommodating. We had so much relaxing fun and would like to go again!

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!

I wanted to find an affordable private boat tour for a bachelorette party, and this fit the bill…read more Dan was very accommodating and made sure everything went smoothly for the day. When we decided to bring food onto the water, he met us by the harbor and provided a cart for us to place all the bags of food onto it. He let us choose if we wanted to spend more time at The Playpen or sailing on the open waters. Floaties were also available. Communication was great, the weather was great, the music was great, and the people were great. Thank you for an authentic and fun boating experience!