The Yacht | DUFOUR 325 | “Peony”

After moving to Chicago six years ago and never having experienced any sailing, we finally decided to try sailing on the beautiful Lake we see every day from our windows. We found Salty Dog Sailing online with many positive reviews. Scheduling the appointment online is very easy, and the website offers a lot of information including very clear directions to the dock at the marina. Captain Kirk is very welcoming (including his trusty four-legged first mate, Woody) and has years of experience which will put the most nervous of passengers at ease. The boat is lovely and comfortable and the two-hour trip flies by. We would highly recommend this pleasureful and relaxing experience and are looking forward to returning for another sail very soon. Thank you Kirk for a memorable afternoon!

My family & I thoroughly enjoyed learning all about sailing and experiencing the expertise first-hand of Captain Kirk! We had a beautiful Sunday morning excursion and loved every minute of it!

Thank you Captain Kirk & Woody for an incredible sailing experience. Your professionalism, knowledge & safety-first handling of the cruise was second to none. We appreciate how thoughtfully you accommodated us and made our cruise so very thrilling and gratifying. We are looking forward to booking you again.

great sunset cruise experience.

Had a great time sailing with Captain Kirk. Lake Michigan was beautiful and seeing the city from the water was peaceful, even during a protest. Make sure to give Woody lots of pets and love!! He is a sweet boy!

Beautiful boat and dog, with an experienced captain.

Captain Kirk was great and made our first time sailing a good experience. He was responsive and flexible with out booking which made our lives a lot easier. Highly recommend booking a charter with this company.

We had a great experience with Capt Kirk and Woody! Capt Kirk was very informative on Lake Michigans weather and water habits and runs his boat very smoothly and safe. Peony (his boat) is very clean and comfortable to ride on and he has years of experience! We will definitely go out again with Kirk and Woody!

We had a great experience with Kirk! He was very experienced and kept his boat very clean. We had a great time and would recommend to anyone!!

Had a wonderful couple hours with friends, capt. Kirk and Woody. Beautiful boat, super professional staff. Really enjoyed it!

5 out of 5 if you are in Chicago I highly recommend booking with the Salty Dog Sailing Co. Captain Kirk was amazing! And Woody was an excellent first mate!

Chartered Salty Dog Sailing for 2 couples on a Wednesday night. Captain Kirk was awesome. Knowledgeable, a great skipper, and generous with his time. He made our evening (our wedding anniversary) a night to remember. He stayed out extra time so we could take in the lakefront fireworks. His first mate, Woody (his mini golden doodle), was a wonderful addition to the crew. When we want another sunset cruise it will definitely be with Salty Dog Sailing. Unqualifiedly recommended. We had our second wonderful experience with Captain Kirk (and First Mate, Woody, the Doodle) last night (08/19/23). We chartered Salty for the fireworks time-slot, and were not disappointed. Kirk is VERY professional, no-nonsense, makes all of his passengers comfortable - regardless as to the amount of time they've spent aboard a boat. His pre-journey communication is excellent - letting first-timers know exactly how and when to get the dock, find him, what to bring (and NOT to bring), and prepare for the experience. Captain Kirk is extremely friendly and personable, and Woody is a devoted crew-member. HIs music selection for fireworks viewing demonstrates canny understanding of what his clients/passengers might appreciate, and he made our time wonderful. Expertly navigating through a myriad of other boats we were parked almost under the fireworks display (which were uncommonly good last night). We've sailed with other captains before, but when we have a choice of who to skipper our Chicago Lakeside cruises, we'll go with Captain Kirk (and Woody) and Salty Dog Cruises EVERY time. Latest Review (9/5/24): Captain Kirk Kessler, a United States Coast Guard - Certified Master Captain, goes all out to give his 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 - with the beautiful Chicago skyline as your sunset backdrop. You can't do better than Salty Dog Sailing Co!

Thank you Kirk and Woody for the best ride ever! My boyfriend proposed to me with the most unique view, and we would 100% go back to sail on Lake Michigan with them and Peony. Kirk was super attentive to the weather and made adjustments so the ride could happen. Truly an unforgettable experience!

Great sail with a skilled, experienced and knowledgeable Captain. It was real pleasurable experience to sail Peony on Lake Michigan with Captain Kirk and Woody. I definitely recommend the Salty Dog sailing experience.

Everything went incredibly smooth, from start to finish. Captain was really attentive with us, couldn't ask for someone better. The music, the knowledge on everything, how clean the sailboat was. Perfect. Will definetly do it again. Thanks Kirk, and of course, woody!

We took a spur-of-the-moment morning sail with Kirk, Woody, and our family of 5, with kids aging from 5-11. Was amazing, easy, peaceful, and a great way to see the city we live in and love in a whole new way. Reservation, parking, payment, and all was super simple. Thanks so much, Captain Kirk! We will definitely be back!

Spent a gorgeous afternoon with my nieces watching the Thunderbirds’ practice runs for the Air and Water Show. Capt. Kirk’s boat is impeccably clean and he is the consummate host; great music and extra dry sense of humor. We had a great time!

Captain Kirk was amazing he was very patient with us and allowed us to get the most amazing pictures for our save the date photos. I would definitely do another sail with him in my future days.

We had an absolutely amazing experience sailing to see the fireworks! We will definitely be back. Captain Kirk and Woody are awesome!

My family celebrated my wife’s birthday aboard the Salty Dog Sailboat. The boat captain, Kirk K. was great. He kept us safe while on Lake Michigan. He provided great music, vibes, sailing education, and more. We highly recommend!

My friends and I had an amazing time sailing with Captain Kirk. It was an amazing experience quite different than a typical - "let's motor out to the 'Play Pen' and drink ourselves into a different day". The boat was well set up and stocked with ice, sunglasses, sunc screen and other items, the website pretty accurately describes what to expect, what to bring, how to get to the boat and food/beverage rules aboard. READ THE FAQs! 🙂 We will certainly be looking to charter again!

Had an awesome time even though we were rained out we still got out for a little bit. The Captain told us to come back up and he'd take us out again. Definitely recommend him and my girlfriend loved the pup too. 5-stars for the captain and his 1st mate.