The Salty Dog Sailing Co. — Local services in Chicago

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...

Headline: Exceptional Boat, Skilled Captain, Unforgettable Experience My friend and I were in Chicago this past weekend for the Air Show. As an avid sailor, I wanted to find a boat that could take us out during the event.

On the morning of our reservation, Captain Kirk reached out to suggest that we arrive 30 minutes earlier for a better view of the Blue Angels. We adjusted our plans accordingly and appreciated the recommendation.

Upon arriving at the dock, Captain Kirk provided detailed instructions on safety and expectations. As someone with years of sailing experience on Tennessee lakes, everything made perfect sense, and I fully understood the importance of his thoroughness. Captain Kirk offers all the essentials—ice, cups, sunscreen, and even seasickness wristbands—so all you need to bring are your drinks. We were so engrossed in the sailing experience that we forgot about the beers we had brought along.

Despite the choppy waters caused by lake traffic, Captain Kirk's boat handled the conditions admirably, making the sailing experience thoroughly enjoyable. Watching the Blue Angels soar overhead was an incredible highlight, but the serene and tranquil sail back to the dock was the perfect reminder of why I love sailing.

If you're seeking a memorable experience on Lake Michigan, I highly recommend booking with Salty Dog.

P.S. - You get a cute little Floof as a co-captain that will make sure you enjoy...

Great time with Captain Kirk and Woody! We booked an afternoon sail aboard Salty, with Captain Kirk expertly sailing his boat for two hours. According to the Captain, the conditions were perfect for a great time. We brought snacks and drinks which were quickly forgotten as we instead enjoyed the sail, and learned a bit about sailing. If I had to make a recommendation, I’d say leave the canned wine and snacks for after the sail and take in the excitement and fun of sailing a smooth, sturdy and FUN boat for your short two hour sail. It goes by way too fast. Captain Kirk is knowledgeable, fun, interesting and loves what he does. His First Mate Woody, a sweet little Golden doodle, was curled up on his little perch and was fun to have aboard. I highly recommend The Salty Dog. If you’re concerned about safety, know that Captain Kirk puts safety first and is incredibly experienced. If you want to have thrills, have him take Salty; however, in the Captain’s words-if you want the charcuterie board choose the Peony: Equally as fun but better for those not looking for quite a thrilling ride. Thank you to Captain Kirk for providing us with a really fun adventure on our...