Whether you’re searching for a private sailing charter in Chicago, a relaxing Lake Michigan sailing experience, or one of the most memorable things to do in Chicago, The Salty Dog Sailing Co. offers an unforgettable adventure on the water. Since 2015, we’ve specialized in private Chicago sailing charters aboard Peony, our elegant 33-foot Dufour sailing yacht. Every charter is reserved exclusively for your group, allowing you to experience the beauty of Chicago’s skyline, the tranquility of Lake Michigan, and the excitement of authentic sailing without the crowds found on traditional sightseeing boats. From romantic sunset sails to family outings and special celebrations, every voyage is personalized to create lasting memories.
Our private sailing charters are perfect for romantic date nights, marriage proposals, anniversaries, birthdays, family gatherings, and unforgettable evenings watching the Navy Pier fireworks from the water. Whether you’re looking for a sunset sailing charter in Chicago, a unique Chicago boat charter, or simply want to experience the freedom of sailing on Lake Michigan, you’ll enjoy breathtaking skyline views, personalized service, and a relaxing escape from the city. If you’ve ever thought, “I want to go sailing in Chicago,” there’s no better way to experience the city than aboard your own private sailing yacht with The Salty Dog Sailing Co.