What a FUN TIME we had! My niece had a tight budget for her wedding. She reached out to Greg and…read morehis co-captain to have her wedding on his boat in September 2018! EVERYONE HAD A BLAST! He even acted as the wedding officiant for the ceremony since we did not have anyone. My friend and I went a few hours ahead to decorate the boat. Greg was totally willing to help and the wedding was a success!! This was a great budget friendly decision :) Bathroom - Bluetooth - lighted boat and more!.SO MUCH FUN!! THANK YOU :)

Our boat day with Captain Greg was easily the best day of summer 2022! We had the most amazing time…read moreand the entire experience from booking to the trip couldn't have been better. The communication was wonderful, planning was so easy, and the boat was exactly what we were hoping for and more. Highly recommend a boat day with Captain Greg! We will definitely be booking again in the future. THANK YOU SO MUCH!

They were Awsome! Our boat trip on the Chicago River was so fun and interesting. Chicago Boat…read moreRentals were perfect. They were so nice and set us up where we were completely comfortable driving this boat!! Also - a must do - is the take our "on the river" with Taco place ... QR code at boat hut where you check in.

My friends and I booked a private pontoon ride with Chicago Boat Rentals for a Monday night at…read more7:30, and it was the perfect way to soak up a Chicago summer evening on the water! The crew made everything easy -- they showed us how to drive the boat ourselves, and we got to bring our own food and drinks onboard. Such a fun, laid-back way to see the skyline. Highly recommend!

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!

Our experience last summer was fantastic! This team was amazing and professional! Unforgettable…read moreexperience! Fun in the Sun went above and beyond to make sure every detail was perfect. From start to finish, everything was truly amazing. The yacht itself was stunning, and the crew The captains were professional and knowledgeable, making the trip feel safe yet exciting. They couldn't do enough for us from serving us our food and drinks to taking some amazing photos. The whole team has a good dynamics and they all know how to treat their clients properly. They were like a really close friends to us! Wonderful people and service. Thank you guys and will definitely avail your service again next time!

Fun in the Sun was absolutely amazing. Our experience last summer was fantastic! The whole team…read morewere friendly and personable they made us feel like we were family. Our boat was ready to go when we were, was clean, and in good condition. I can still remember how amazing our last summer is because of this team! We learned so much about boat traffic and we had a chance to drive the boat. Their Team Captain was the best, high energy, very positive, and super patience! Very professional and attentive service! When it comes to their prices, everything was fair and great. We rented for an incredible day price. I cannot recommend this place enough. We will definitely be coming back. I am completely amazed how much fun we had! Amazing experience thank you so very much!

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.

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 have been with this program since the early days and have never been happier. The company…read morecontinues to expand and become ingrained into the Chicago boating culture. Respectful, professional, and charitable, Pinnacle as a family has been a pleasure to be apart of. All the boats are kept spotless and well maintained. The program is really put together well from the training to picking your calendar, it runs like a well oiled machine. We started on their 37ft sail boat and now moved up to bigger and better. They welcome even the most novice to the saltiest of sailors and power boaters. I highly recommend experiencing what it's like to have the feeling of owning your own boat but without the boat yard hassle and or $$$ our of your pocket.

The boats were clean, maintenance was on point, and the staff overall are super responsive. Tech…read moresupport is always especially helpful and enjoyable to work with.

What a fantastic boat and crew! We had such a beautiful evening cruising along the shoreline with…read morethe impressive Chicago backdrop. The crew was very professional and working with Kerbi and Samantha was a pleasure. They were extremely proficient with all of the event planning and were very easy to work with. We had a 70 year old on board with us who was recovering from a minor surgery. We were a bit concerned about the ride for him but he was extremely comfortable in the lovely saloon. I highly recommend this company for any event and will be back again soon!

We had some concerns about renting a yacht sight unseen -- but we were completely amazed! Kirby was…read moreso helpful arranging a beautiful five star dinner down the Chicago river for our small group. Captain Brian is hysterical and kept us laughing through the night!!Our friends weren't from the area and really enjoyed the delicious meals and seeing Chicago. Every member of the crew we interacted with was polite, attentive and greeted us with warmth and kindness. Would highly recommend this yacht trip to anyone seeking a unique group experience! Five stars!! Sea stars!