Things to Do in Chicago
Chicago offers world-class museums, award-winning restaurants, vibrant neighborhoods, and one of the most spectacular skylines in the world. If you’re searching for unique things to do in Chicago, few experiences compare to seeing the city from the water aboard a private sailing yacht on beautiful Lake Michigan.
Since 2015, The Salty Dog Sailing Co. has been creating unforgettable private sailing experiences in Chicago, offering guests breathtaking skyline views, peaceful sailing, and personalized charters designed exclusively for their group.
Whether you’re visiting Chicago for the first time or looking for a fresh way to experience your hometown, a private sailing charter provides a relaxing escape from the crowds while showcasing iconic landmarks including the Chicago skyline, Museum Campus, Burnham Harbor, Navy Pier, and the shoreline of Lake Michigan. Every sailing charter is customized to your interests, whether you’re planning a romantic sunset sail, celebrating a birthday or anniversary, watching the Navy Pier fireworks, or simply spending a beautiful afternoon on the water with family and friends.
Unlike large sightseeing boats, every Salty Dog Sailing charter is completely private. You’ll enjoy the comfort of your own sailing yacht, the freedom to help sail or simply relax, and the personal attention of an experienced captain who knows Chicago’s waterfront better than anyone. Our 33-foot Dufour performance sailing yacht, Peony, accommodates private groups of up to six guests, making it ideal for couples, families, and small groups looking for a memorable experience on Lake Michigan.
If you’re looking for the best things to do in Chicago, consider one of our most popular sailing experiences:
- Private Sailing Charters – Experience Chicago from the water aboard your own private sailing yacht.
- Sunset Sailing in Chicago – Watch the sun set behind the city’s spectacular skyline.
- Romantic Sailing Charters – Perfect for date nights, anniversaries, and marriage proposals.
- Chicago Fireworks Sailing Charters – Enjoy Navy Pier fireworks from the best seat on Lake Michigan.
- Morning & Afternoon Sailing – Relaxing daytime cruises with panoramic skyline views.
Whether you’re celebrating a special occasion or simply want to discover one of Chicago’s hidden gems, The Salty Dog Sailing Co. invites you aboard Peony for an unforgettable private sailing experience on beautiful Lake Michigan. Book your charter today and discover why sailing is one of the most memorable things to do in Chicago.
Let’s go sailing in Chicago!