THE ADVENTURE COLLECTIVE® · Independent discovery and booking for outdoor travel
Set sail from Chicago’s lakefront on a roomy 50-foot Sea Ray yacht with Knot My Boat Charters. Ideal for groups, this charter offers city skyline views, a dedicated crew, and flexible itineraries along Lake Michigan and the Chicago River.
Set sail from Chicago’s lakefront on a roomy 50-foot Sea Ray yacht with Knot My Boat Charters. Ideal for groups, this charter offers city skyline views, a dedicated crew, and flexible itineraries along Lake Michigan and the Chicago River.
Book with Knot My Boat Charters
Verified experiences and guided adventures in the surrounding area.
Operated by Knot My Boat Charters · Chicago, Illinois
Perched along Chicago’s iconic Lake Michigan shoreline at 3155 S DuSable Lake Shore Dr, Knot My Boat Charters provides an unparalleled way to experience the city from the water. Their flagship offering, a spacious 50-foot Sea Ray Sundancer yacht, stands out as a premium vessel for everything from intimate birthdays to corporate outings, accommodating up to 13 guests with ease and style.
This Sea Ray model features one of the widest beams in its class, creating an expansive open cockpit and cabin layout that invites conviviality and relaxation. Whether you’re setting off on a serene cruise toward Monroe Harbor or navigating the famously scenic Chicago River, this yacht balances comfort and adventure. The dedicated crew onboard manages everything from navigation to safety, giving guests time to soak in panoramic cityscapes or lively waterfront views.
The urban setting of Chicago’s lakeshore—replete with its towering skyline, historic bridges, and bustling harbors—makes this charter unique. Unlike traditional boating experiences farther from the city, Knot My Boat Charters seamlessly blends metropolitan grandeur with fresh lake breezes and outdoor ambiance. Guests can expect to glide past Navy Pier, admire the architectural marvels lining the riverbanks, or pause for photos at the lesser-known playpen area near Monroe Harbor.
Beyond the vessel itself, Knot My Boat Charters has carved a reputation for customizability and professionalism. Clients receive detailed pre-trip info including parking, itineraries, and local boating tips. With onboard perks like Bluetooth sound systems, restrooms, and a kitchenette, this charter is both practical and festive. For Chicagoans and visitors seeking a memorable waterborne escape framed by one of America’s greatest cities, the 50ft Sea Ray Sundancer is a top-tier option that makes every cruising hour count.
easy.
3–4 hours.
Minimal physical exertion required; suitable for most fitness levels
Yes, Knot My Boat Charters allows you to supply your own captain provided they meet certification requirements; just email the company with credentials.
Only service animals are permitted aboard, and they must wear a life jacket for safety.
Guests may bring food and clear beverages but red wine, glass containers, and heavily staining drinks are prohibited for safety.
The yacht comfortably fits up to 13 guests including children under 13, with regulations requiring life jackets for youth.
Charters meet at 31st Street Harbor on J Dock, located at 3155 S DuSable Lake Shore Dr, Chicago.
The vessel includes restrooms, a kitchenette, a Bluetooth sound system, cooler, cups, cutlery, and onboard cleaning services.
Chicago’s river system was famously reversed in the early 20th century to improve sanitation, shaping the modern waterways you’ll cruise.
The Chicago Park District and local organizations promote clean boating practices to protect Lake Michigan’s water quality and aquatic habitats.
Knot My Boat Charters operates guided outdoor trips and adventures with an emphasis on safety, stewardship, and memorable experiences.
Book with Knot My Boat Charters