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!

Had the best time on the water! We rented the 46' Sea Ray and it was perfect for 12 guests! Captain…read moreDoug was absolutely outstanding from start to finish. We will definitely be renting again in the summer! Highly recommend.

THE Most fun boat rental experience in Chicago! Their Boats are clean, well maintained and fun to…read moreuse year after year. Will be renting regularly!

I rented the 40 ft yacht from this company, making the reservation was really easy Monika is great…read moreI had to change the date and time and she was able to do that without a problem. I rented the yacht for a surprise party the captain contacted me a day before and I was able to explain to him that I wanted to surprise my boyfriend with his family on the yacht and he was able to help me with that, the yacht was very clean. we had a great view of the Saturday night navy pier fireworks, we had an amazing time. I'm renting the same yacht in August again. I definitely recommend renting from them. You won't regret it.

They cancelled and won't give my money back. Lost $1000. They should be ashamed of themselves, how…read moreis this legal??

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!

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!

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.

This is pure BUCKET LIST material ... where else can you feel like the city is literally on your…read moreshoulders - in a cool way! The scenery is unmatched. Add to this the boats (clean & reliable) and the staff ... oh, and the price (divide it among the passengers, and it's the best bang for your hard earned buck!

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.

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.