Great time on the water at a great price! When I make it back to Chicago, this will be on my to-do list every time. The boat, the captain, and his deckhand (dog) Woody would have made the trip alone. Add to it, sunset and fireworks and it was an evening we wont soon forget. A few simple guidelines on the site to follow that made us well prepared when it got a little chilly.

So, now Ive got a problem. Never, ever having been on a sailboat, visiting Chicago from a landlocked state, this seemed like exactly the right way to take in the full city skyline with a friend. All I wanted was a nice enough afternoon of not falling off the boat and wondering if my ruddy complexion would finally even out in a complimentary shade of seasick green. What actually happened was that I had such a lovely experience that I am feverishly researching sailboats in Tennessee, wondering how to make that a reality on $17, a half acre of sodded weeds and a dream. Yall. We really did have the very best afternoon. The splash of water falling back to the sea, the sound of crisp sail chatting in the wind, the clink of the gears, the expanse of the horizon dancing as you rock on the water -- it rejuvenates a soul. Very worthy. And Kirk is really great: easy going, entertaining and knowledgeable, he is more than happy to share what he knows and engage in good conversation. And his taste in music isnt bad either. A kind of Captain and concierge in one. And dear Woody? Please. He alone is worth the charter. Look at him. Just gorgeous! High five, my friend.

Kirk was phenomenal! An absolute joy to talk to. Full of information, gave lots of detail about sailing and physics. Made it super easy for my now fiancé to propose on the front of the boat! I couldn’t have asked for a better moment and Kirk helped make it happen 😊

Captain Kirk was phenomenal! He worked with me on planning my proposal too!! I highly recommend him

Awesome time on the Lake with Capt Kirk! Gorgeous and powerful sailboat. Can make it whatever you want with Kirk’s easy going and super helpful manner. Wouldn’t hesitate to book if you’re looking for a private charter.

An absolute 10/10 experience - we shot our engagement photos on our sail at sunset, such a beautiful, unbelievable view and an awesome sailboat. Captain Kirk was so helpful and kind - taking us to the best spots for sunlight and calm waters. We will be back again for sure!

We had an AMAZING experience aboard the Salty with Capt Kirk and his sidekick, Woody.Book it. You won’t regret it. We had to reschedule a few times due to weather but Capt Kirk wanted us to have the best experience possible and was really flexible. The boat is a piece of art. The views are incredible. No picture will do it justice. It’s super easy to get to and you park right next to the dock. Capt Kirk is an absolute joy to be around, Woody is the star of the show second only to the scenery. It’s an unforgettable experience.

It was a true sailing experience, with a great performance boat and super professional and super cool Captain Kirk. I would be happy to sail with him again. Woody is the sweetest dog and Chicago skyline from the Lake is unforgettable. Anyhow who loves sailing should do it.

My husband and I had a very relaxing sail with an amazing sunset view of the city after a hectic travel day. It was amazing to see the skyline from the water. Captain Kirk was very friendly and knowledgeable about the city’s history, but the real star of the show is Woody the sailing pup who greeted us at the dock and climbed on my lap when we got on board. Would definitely recommend.

What a wonderful evening on the water. Captain Kirk and his trusty deckhand (Woody) treated us to beautiful views, great conversation, and topped it off with fireworks at the end of the night. It was a very memorable evening we wont forget and was a big highlight of our trip.

Gf surprised me with a sailing date and I had a blast . Captain Kirk was fun to talk to and very knowledgeable about sailing and the city’s history (all history actually). Woody his dog is amazing too. 10/10 would recommend. We will be back in September , skipper 😉

Captain Kirk was great. No frills or hassle when booking like I experienced with other private sailing companies and he was also the best price. The sail was gorgeous and a neat perspective of the city, especially at night. Kirk is down to earth and a laid back, nice guy who’s happy to share his knowledge and make sure your time on the water is enjoyable. Good music and and amazing dog made it that much better.

My wife and I did a night sail and loved it. It was fun to see the city from a unique view. Kirk is a great guy and his dog is a nice addition. You can tell he really loves what he does and is very knowledgeable. Would highly recommend!

This was an amazing time. Kirk went above and beyond to ensure that everything went smoothly. He’s a very kind guy with a great taste in music. Woody the dog is an incredibly gentle and well behaved. I would highly recommend sailing with the Salty Dog.

Thank you so much, Captain Kirk, for a great time sailing on Lake Michigan. My dad and I had a lovely time and I greatly recommend this experience to others who are looking for a fun activity to do in Chicago.

Captain Kirk gave us a great sail to celebrate my daughters 24th birthday. He made it easy to sign up, communicate with prior to the sail, and meet up with him at the harbor during the day of sail. We had a great couple of hours before some rain came in. Kirk was prepared with jackets and vests and made us all feel very comfortable. I would recommend it!

Had a great time sailing with Captain Kirk! Great customer service and we loved learning about sailing. Highly recommended!

Captain Kirk did a great job getting us out to the inland sea with a level we were comfortable sailing. He really knows what he’s doing and we were very pleased with the overall experience.

What a great experience sailing on Lake Michigan. Captain Kirk and Woody were awesome hosts. We had southwest winds at 20+ knots so the sailing was super fun. We will definitely be booking again and recommending this experience to our friends. Thanks again for a great time!

What a fantastic experience yesterday on The Salty Dog cruising around Lake Michigan! Captain Kirk made sure everyone was safe, comfortable and enjoying the ride. From booking to communicating and coordinating the logistics of the day to the charter itself- everything was handled professionally. We’ll definitely book again...especially if Woody dog is on board again!

My fiance and I went on a 2 hour sail on a Saturday afternoon with Captain Kirk. We both enjoyed his stories and education about sailing. It was a great way to get out on Lake Michigan and see the activities but also be more secluded. We would definitely recommend this to others. And wed love to go out, again. Thank you!

I originally had booked a charter with a different company who had cancelled. With just less than 24 hours notice, Captain Kirk was able to book us in his busy schedule.We had a cousin in from overseas, so we did a night sail and watched the Navy Pier fireworks. Captain Kirk was a great conversationalist and Woody was such a good boy. Sailing with these two is going to be our go-to activity for when guests come in from out of town.

Captain Kirk and First Mate Woody were a fantastic host and crew on an unbelievably romantic sail around Chicago! Captain was a true pro sailor. We felt safe and had a lot of fun watching the sun set over the city. Higly recommend booking sooner than later!Mike and Jackie from CO.

Salty Dog Sailing Co. is the real deal for all those who are experienced with sailing or beginning. Whatever your comfort level is Captain Kirk will provide you with the best experience while you are visiting or local here in Chicago. His experience is above the rest! I’ve learned so much from him about Sailing I keep going back for another charter!Best Sailing charter in Chicago. NO DOUBT! Book with him now and see Chicago for the water. What an experience!Enjoy!

Captain Kirk did a great job! We really enjoyed our time sailing with him and his pup Woody. We did a sunset cruise, and the views of the Chicago skyline were incredible. Kirk is on the ball and super accommodating with reservations. We’d highly recommend booking a tour with Kirk!

Wonderful experience. Captain Kirk allowed us to reschedule due to pending rain for our originally scheduled time. Very knowledgeable and showed us a great time on the lake. Highly recommend! Woody, the dog, was a fantastic first mate too.

Enjoyed sailing about Lake Michigan with Capt. Kirk. He provided a sailing experience that was thrilling and fun while making our group of six feel comfortable and safe. I enjoyed the experience and would recommend to anyone who enjoys being on the water, seeing the fantastic Chicago Skyline, and having an adorable golden doodle (Woody) along for the ride.

We had a fantastic evening sailing with Captain Kirk. We booked a very last minute cruise and Captain Kirk was very responsive to our calls and texts with questions. We will be recommending The Salty Dog Sailing Co. to our family and friends when they visit Chicago; it is a beautiful way to experience the city!

Capt. Kirk and his 1st Mate Woody, such an adorable lil pup, were a pleasure to go sailing with. Our group had an awesome time and the views of the Chicago skyline were truly amazing! The group got some really cool pictures. Kirk was an extremely nice Captain and fortunately was willing to share his knowledge of sailing with our inquisitive group. I highly recommend Salty Do Sailing and be prepared for a memorable time out on the water!

I would highly recommend sailing with Kirk and his dog. We had a great time!

It was a really great experience. Kirk was very informative and Woody was the cutest.

The boat is superb, Cap’n Kirk steers a Great Lake Michigan starship, and first mate Woody is very nice.