PREPARATION & RULES OF CONDUCT:

  1. THE BOAT WILL NOT TIP OVER. The boat is designed to lean a little to one side (“Heeling”), but will not ‘tip over’.  The keel weighs 2800 lbs and balances the boat.  First time sailors experience this for the first time, and we like them to know what’s happening and why.  It’s normal for a sailboat to lean to one side under sail.
  2. WEATHER: Check the Weather Links in the navigation menu for current and forecast temperatures, wind and wave conditions, wind speed, radar maps, and sunset/moonrise times.  Marine forecast is very accurate.  Winds from the South, West, or Southwest are least wavy lake conditions.  If winds are forecast out of the North and East, the lake will be more wavy if winds exceed 15 kts.  (Please see  “RAINCHECK & CANCELLATION POLICY” for a detailed description of our weather related cancellation/rescheduling/refund policies.)
  3. WHAT TO WEAR: Lake temperatures are 10-15 degrees cooler than land. An extra layer or two – a light jacket or fleece, pants, and non-marking shoes (no black soles, no heels) are recommended. Skirts are not recommended. “Skorts” preferred. Sailing is a water sport.  Please bring a light jacket for protecting from the occasional splash or sprinkle. It is important to remain warm and dry.
  4. SUN PROTECTION and SPRAY-TAN:  The vessel has a sun shade above the cockpit seating area and we provide SPF 50+ sunscreen, hats, visors, and extra sunglasses if you have forgotten yours.  Also, please refrain from joining us with spray tan that can rub off on our decks.  A gracious thank you in advance for your thoughtful consideration of our time and vessel maintenance. 
  5. MAX PASSENGERS: Please remember 6 is the maximum number of passengers in your private group.
  6. TRAFFIC: Plan accordingly. Soldier Field, Museum Campus, and Northerly Island are busy areas during the Summer. Click Here to see Map of Burnham Harbor.  We provide one free parking pass at Burnham Harbor. Please email us about the availability of a second one. A cab, bicycle, or public transit are often better options. If you can to Soldier Field or the Museum Campus, you are within a 5-10 minute walk to Burnham Harbor (Dock N).  You know you are walking to DOCK N when – from the Harbor Master’s Office, Lake Michigan and the boats are on your left as you walk.  DOCK N IS THE 4TH PIER ON THE LEFT FROM THE OFFICE.  Also – there is a Divy Bike station on the far South end of the Harbor where you can park a Divy Bike.
  7. If your are Ubering, you can avoid the “Uber-Adventure” if you make sure the driver is taking you to “Burnham Harbor”.  If you do not see boats when you are dropped off, you have been dropped at the wrong location.  Please use the maps we provide on our “Location” page for specific details on the location.
  8. FOOD AND DRINK: We provide ice, cups (Yeti-tumblers), plastic utensils, plates, napkins, and an ice chest/cooler. Please avoid rolling coolers, large open platters, pizza boxes or shopping bags full of groceries.  If it comes in a bag, a wrapper, or a small cooler, it probably is a terrific choice for a snack.
  9. PLEASE DRINK RESPONSIBLY: The safety of your party, our vessel, and our Captains is our highest priority. — Please no RED WINE or wine bottles.  A champagne bottle is okay (as these are very hard to break).  Please no hard liquor.  We are sailing and ask that you remain in control at all times.
  10. BATHROOM: There is a ‘Head” on board.
  11. MUSIC: There is an iPod/iPhone music hook up for the stereo.
  12. NO GLASS BEER OR WINE BOTTLES. A champagne bottle is okay. (see #9 above again)
  13. NO SMOKING of any kind is permitted during your charter.
  14. NO ILLEGAL DRUGS are permitted on board.
  15. NO FIREARMS are permitted on board.
  16. SWIMMING: Generally not permitted. Only at the sole discretion of the Captain.
  17. ARE CHILDREN ALLOWED? Yes, when accompanied by their parent or legal guardian. You must call or email us in advance to let us know how many children will be joining the charter. Children must be able to stand and balance on their own.
  18. ONBOARD BEHAVIOR POLICY. Passengers are asked to comply with all reasonable requests from the Captain to maintain safety and order on the vessel. Disruptions or damage to the vessel shall terminate the charter without a refund and may result in additional charges to the charter group for such damages.
  19. NO SHOWS. After 30 minutes after the start of any charter time, the charter shall be marked a “No-Show” and are not eligible for a refund or reschedule.
  20. WAIVER: You will be asked to sign a general liability waiver prior to the vessel leaving the dock.
  21. GRATUITY: Yes, it is customary to tip your Captain.
  22. RAINCHECK/CANCELLATION/REFUND POLICY: CLICK HERE
  23. ABOVE ALL: ENJOY SAILING!
The Salty Dog Sailing Co.
Excellent
4.9
Based on 165 reviews
Larissa Fain
2 days ago
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!
Md Siam
4 days ago
Lucy Unger
3 weeks ago
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!
Mary
7 months ago
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.
WhoDat2001
8 months ago
great sunset cruise experience.
Danielle Robnett
8 months ago
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!
T G
8 months ago
Beautiful boat and dog, with an experienced captain.
Andrea Arango
8 months ago
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.
Douglas Rever
9 months ago
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!
Emily Drevdahl
9 months ago
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!!
Ali Brewer
9 months ago
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!
Jay Gerak
9 months ago
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!
sophia higuerey
9 months ago
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!
Stephen Stanley
9 months ago
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.
Nirja Trivedi
9 months ago
Safv
9 months ago
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!
Gretchen Scheidler
9 months ago
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!
Emilee Sorenson
9 months ago
Michelle Frenette
10 months ago
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!
Eryka Ciszek
10 months ago
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.
Sarah Gillespie
10 months ago
We had an absolutely amazing experience sailing to see the fireworks! We will definitely be back. Captain Kirk and Woody are awesome!
Branden McLeod
10 months ago
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!
Pavel Zeldin
10 months ago
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!
Zach Stephens
10 months ago
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.