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 - withe the beautiful Chicago skyline as your sunset backdrop. You can't do better than Salty Dog Sailing Co.! read more

I highly recommend chartering with Salty Dog. Captain Kirk () was very professional. I was a little 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! read more

Captain Kirk was so knowledgeable, talented, and down to earth. This was our first time sailing and we will absolutely be coming back for more! read more

The Salty Dog Sailing Co. - Boat Charters Near Me - Chicago, Illinois

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Went out on a sail with my girlfriend her nephew and myself. What a great sail team. When arrived we found the dock easy to find and sail boat was very clean and well maintained. The Captain offered us sunscreen and a baseball cap for her nephew that was visiting and wanted to go sailing at the last minute. What an amazing day to go sailing. Couldn't have asked for a better day with Salty Dog Sailing Company!! Thank you Captain Kirk and Woody. Will definitely be going again soon. read more

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Captain Kirt was awesome! This was such a great way to see the city. Seeing all the other boats go by with dozens of people, we were so happy we opted for a private sail. 5 stars! read more

We did a two hour tour with Captain Kirk. The boat is absolutely beautiful and handles amazing on the lake. He could not have been any kinder and was a great host. It was a perfect day on the lake and highly recommend to anyone considering booking a voyage! read more

Had a blast with Captain Kirk and Woody on our two-hour couples charter. We just moved to the area, and it was our first time on a sail boat. We learned a ton about both sailing and Chicago. Everything was well-beyond our expectations. We really could not have asked for more. We will definitely be back! read more

Salty Dog Sailing was laid back and fun. Kirk was skillful, knowledgeable, and had a great playlist! He took us on a great ride and his dog Woody was a chill co-captain. Yelp! Is encouraging me to say more, but what more is there to say? Great captain, great ride, awesome tunes, and felt safe the whole time. Highly recommended! read more

This was the first sailboat charter in Chicago that I have taken, and it was exactly what I was hoping it would be - and more! Captain Kirk was friendly, knowledgeable, laid back and made for great company. Woody, the darling mini doodle, was absolutely precious and set this charter apart from others. He was so well behaved, too. The boat ride itself was amazing - relaxing and smooth, with fantastic views of the city. read more

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I highly recommend Salty Dog if you're looking for a wonderful and mellow sailing experience on a real sailboat. I surprised my husband on a "date-day" and he loved it! The 2- hour voyage was the perfect amount of time to feel the sunshine, light wind and be on the water! Captain Kirk and his mate Woody were so kind, knowledgeable and hospitable. They are a super-chill duo and Woody is the ultimate "Dood." Captain Kirk is officially in my "rolodex"---I will be back and will also refer my family and friends. Thank you Captain Kirk and Woody for a wonderful Saturday! We couldn't have asked for anything more... read more

Captain Kirk and his co-captain Woody the dog were awesome on our anniversary sail! We were able to easily find the harbor and slip, and enjoyed a stress free ride on a beautiful night. He picked a prime location for us to watch the fireworks and had us back to the harbor quickly but without feeling rushed. This was a wonderful private sailing experience! Go! We will definitely be back. read more

Awesome experience, took us out for a nice sail. Very knowledgeable as well. Boat was nice and can move quick - lots of fun read more

We had a blast!!!! Captain Kirk and his dog Woody were true pros. It was a perfect day on the water and a perfect day with a friend. Captain knew just how to take care of us and make sure we felt ok the whole ride, even out past the breakpoint! His boat is a beautiful boat with character. I will call him again next time I'm in town and go again. I've never enjoyed a sail or boat ride as much as I did this trip. read more

The Salty Dog Sailing Co. - Woody! - Boat Charters Near Me - Chicago, Illinois

The sail of a lifetime! Where do I begin? My Mom and I had the enormous pleasure of spending a memorable evening with Captain Kirk and his mate Woody on beautiful Lake Michigan. The boat is incredible and exudes power and grace. Captain Kirk is skilled at both sailing and making his guests feel like old friends. And Woody is the perfect pooch - a real salty dog who will snuggle with you if you like, but will respect your space if snuggling is not your thing. (side note - i highly recommend Woody snuggles) Just DO this - you will be so glad you did!! read more

The Salty Dog Sailing Co. - Boat Charters Near Me - Chicago, Illinois

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An absolute wonderful experience. If you're in Chicago, do not hesitate to reach out to Captain Kirk. We will definitely book a sailing trip again on our next visit! read more

Parents and 2 teenage boys had a great evening Fireworks sail on a Wednesday night in mid August. Captain Kirk checked in throughout the day to keep us posted about the weather. read more

The Salty Dog Sailing Co. - Wed night with Salty Dog Sailing - Boat Charters Near Me - Chicago, Illinois

Taking this trip with Captain Kirk + Woody was a highlight of my trip to Chicago. I felt as though I had escaped a big city for a few hours and was somewhere far away at sea. Being someone who also loves to understand how things "work", Captain Kirk was generous with sharing his knowledge, both of the boat and of the city of Chicago. I am so looking forward to booking my next adventure with him next summer, hopefully a 72 hour excursion across the lake to explore the shores of the neighboring states. Cheers, Cap and thank you! read more

My friends and I sailed with The Salty Dog on 8/21/15 from 9:30pm-12am and it was AWESOME! Rob laughed with us the entire night and made us feel very safe. The boat itself had enough room for everyone to feel comfortable and had enough room for all of the food and drinks we brought with us. The only thing I was sad about was that their dog Woody was too tired to sail with us. Next time Woody, next time! read more

We had originally scheduled our sail for a day that ended up being stormy, and Captain Kirk gave us a heads up that the weather was looking bad, so we rescheduled easily on the website. The sail was lovely and the captain was friendly and chatty. He even provided some pressure point wristbands for a couple folks who were feeling a little nauseated. Thanks for a fun day! read more

Just went out with my cousin and some friends with Captain Kirk on Saturday! He is hands down the best most knowledgeable sailboat captain you'll find in Chicago! Not to mention his dog Woody is the perfect addition to a nice day out on Lake Michigan! Can't wait to go sailing again with this crew!!!! If your looking for a fun day out on the Lake contact Captain Kirk! read more

Great sail with Captain Kirk! Boat is beautifully maintained, Woody is a total sweetheart, and Kirk was knowledgeable, fun, and super professional. I had originally been sad when the sailboat connection I've relied upon for years fell through with guests coming into town, but I'm glad to now have another "go to"! read more

We had family in town from Mpls. and this was a fabulous time on the water! Captain Kirk is the best. He made the morning sail perfect! We will for sure book another trip on the Salty Dog with the Captain! read more

I found Salty Dog on Groupon, but Salty Dog had the same deal on their own website so I just signed up that way. Captain Kirk was very entertaining and clearly excited to teach us about sailing, since most of us had never gone before. He let my dad steer for a while, which was great since it was a birthday gift for my dad. I had concerns about the weather since everything I saw was calling for storms right when we were supposed to go. However, Captain Kirk was confident we'd be okay and he was correct. The weather ended up being great for sailing. So if that happens to you and he tells you it'll be fine, listen to him. Overall, we had a lot of fun and recommend giving it a try. read more

Amazing experience! Proposed to my girlfriend on this sailing trip!! Captain Kirk is great and took fantastic photos! Cannot say enough good things about this company! Getting married in a few weeks, and the engagement all started on this sailboat! read more

The Salty Dog Sailing Co. - Boat Charters Near Me - Chicago, Illinois

My friends and I sailed with Salty Dog on 9/19/15 and it was a perfect experience. Kirk is completely transparent and extremely accommodating when it comes to the whole sailing experience and what is going to happen out on the water. My friends and I felt completely safe during the trip. I have already recommended this charter company to several friends/family who asked what charter they should take in Chicago. It was a great deal and a great time with friends. I would highly recommend Salty Dog for any of your sailing adventures! read more

We had a great night with Captain Rob - very informative, helpful, and fun!

Surprise birthday gift on a private charter from my husband, one of the best gifts I've ever received! Thanks to Captain Kirk for facilitating an evening of fun on Lake Michigan. Cannot wait to come back before the season ends with our best friends and daughter. Tell Woody the sea pup we'll be back! Thanks again from the Alexander's! read more

We took my husband out for his birthday today! Our whole family had lots of fun on the boat! Our children got to help steer the boat and the sails. There was a lot of room for our family and and of course Woody, captain Kirk's dog! The whole ride felt very safe and it was all enjoyable. Although we had a little fog in the beginning it cleared up. It was lots of fun, and I hope that you will get a chance to go sailing with Captain Kirk and his dog Woody! read more