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!

Chicago yachting was an amazing experience ! From great communication to great captain suggestions!…read moreWe used captain dan and he was phenomenal! Can't wait to rent from here again!

We had an awesome time on the boat! Captain was great and super helpful, will use this company…read moreagain in the future

If you're looking to charter a boat in Chicago, this is the place. They have a variety of options…read moreavailable and Captain Russell is fantastic. We did a 5 hour charter for 7 and part of me wishes it was longer. Pack your cooler, get your tunes ready to Bluetooth into the boats sound system and enjoy a nice relaxing day on Lake Michigan.

We had a group of professional women enjoying the day. Everything went perfectly, the boat was…read moreclean and the captain accommodating. We had so much relaxing fun and would like to go again!

Totally loved our experience with sailing with Carlos and Barb! We went out for my husband's 41st…read morebirthday. It was relaxing, good conversation, a very clean boat and great conversation! I highly recommend this company and will for sure be booking more trips with them. I am looking forward to doing the bed and breakfast package for an overnight stay in the harbor when the weather gets warmer!

Barbara and Carlos are the absolute BEST. Did a half day rental with them and they were so…read moreprofessional, incredibly considerate and patient, always made us feel safe during rocky waters. The boat was so clean and had a speaker for us to bluetooth to. They also went above and beyond and blew up one of our floaties that we brought. 10/10 experience can't wait to book another one in the future!!

What a dope experience! My SIL has lived in Chicago for awhile and we went to visit her! She said…read morewe HAD to do this experience because it was so fun. Eating pizza, driving yourself on the boat and site seeing with friends! What more could you want? We rented the boat, it was for 2 hours and they provide 1 frozen pizza for 10 people. I wish it was more.. considering you're paying about $60 bucks per person (taxes, gratuity). Since she's done this before, we bought 3 more pizzas and snacks before we arrived. So cool and since we did it in the evening, it felt so great and was gorgeous. The moon was full, and it was an awesome evening. Getting there/parking was great. They have a huge parking lot. The employees were kind, walked us through the safety and let us on our way. It was an awesome experience, check it out but keep it quiet!

TL;DR: Christina and Rich were awesome and informative, clean boat and easy to operate, grill on…read morethe boat was tricky but it cooked the pizza and the pizza was good, 10/10 would recommend! This was an amazing and much needed experience, especially right now. My friends and I arrived a bit too early, but we didn't have to wait long because Christina was able to check us in and get us on a boat in no time! She was really nice and gave us a quick overview of what to expect before we headed down to the dock. They are limiting it to four people/per boat right now, but honestly that was perfect because we had room to spread out a bit. The boats are sanitized after each group too. Rich thoroughly explained how to operate the boat and our route options. None of us had ever driven a boat before, and he helped us feel comfortable with it before we left the dock. I was one of the drivers (we took turns) and I though it was a lot of fun actually. Also, they have pizza that you grill on the boat and it's pretty good! The grill itself was a bit tricky, but the pizza got cooked, so that's all that really matters haha. 10/10 would recommend!

So fun! Highly recommend this company. They take the time to call you beforehand to make sure all…read moreyour questions are answered. My family and I got captain Larry and he was so kind and told us fun facts about buildings that we passed by. I will for sure be doing another boat tour with them!!

Excellent time on Lake Michigan. We had to reschedule our first appointment due to bad weather and…read morewere so happy we made it back to Chicago just for this trip. We got lucky to have good wind and had a true sailing experience. Captain Conway knew what he was doing and we always felt safe and in good hands. We would certainly recommend this charter to anyone looking for a sailing trip while in Chicago. We will be back!

I had a rather disappointing experience with Captain Larry's boating service. From the start, there…read morewas a noticeable lack of warmth or welcoming vibes. The staff seemed disinterested in providing a pleasant customer experience. When we had questions about the safety procedures and tour details, their responses were curt and lacked empathy. The boat itself was fine, but the overall experience was dampened by the staff's indifferent attitude. Even when we expressed some concerns about the route due to weather conditions, our worries were dismissed without proper consideration. It's unfortunate because the potential for a great boating experience in Chicago is there, but the customer service left a lot to be desired It's interesting that I see a review mentioning discrimination because I couldn't help wondering if the treatment we experienced was related to fact that my partner was with me. We are not ones to display affection in public but our body language is obvious Not recommending this service if you care about equality and not supporting a biased business

I would not return. We were recommended by someone we trust so we had our hearts open. My…read moregirlfriend (who is a strong woman of color) felt patronized and, dare I say, discriminated. We will not recommend Captain Larry services to anyone who values respect

I do not believe this is in business. I left a voicemail last summer and received no response. The…read moreodd part is his voicemail mentions the business name. Go look at the website link which is defunct. I am giving one stars because leaving a business page up on Yelp when it is no longer operational is a waste of customers' time.

It was a very fun experience! My friend and I were in…read moreChicago for the weekend only. Our original day of sail was canceled due to weather, but Captain Sanjay was very accommodating and we were able to go sailing the following day. We had a beautiful day and a great time drinking champagne and enjoying our time on the water. The captain and his first mate (his father) were great company and made us feel very comfortable. Captain Sanjay has a medical background in research and he is an athlete; he shared with us his knowledge about nutrition and sports, as well as the role vitamin supplements play in our daily activities. My friend and I are runners and we are currently training for the MCM marathon, thus his tips and recommendations were very useful to us. Our visit in Chicago ended with the sail and it was the perfect ending to a fun weekend!