Explore Chicago’s waterfront on Lake Michigan with Captain Tanner’s expertly guided boat charters. Swim at iconic anchor points, cruise the river, and enjoy vibrant skyline views that transform any outing into a memorable adventure.
Explore Chicago’s waterfront on Lake Michigan with Captain Tanner’s expertly guided boat charters. Swim at iconic anchor points, cruise the river, and enjoy vibrant skyline views that transform any outing into a memorable adventure.
Book with Knot My Boat Charters
Verified experiences and guided adventures in the surrounding area.
Operated by Knot My Boat Charters · Chicago, Illinois
For adventurers seeking a unique and exhilarating way to explore Chicago’s iconic waterfront, a boat charter with Captain Tanner Ciaramita offers an unmatched experience on Lake Michigan. Located at 31st Street Harbor on J Dock, this trip combines the thrill of water sports, the tranquility of scenic cruises, and lively social atmospheres, all against the breathtaking urban backdrop of Chicago’s skyline. Captain Tanner, a seasoned boater with years of hands-on experience including yacht deliveries and performance boats, knows the lake’s secrets and best spots for swimming, relaxation, and photo opportunities.
Lake Michigan, one of the five Great Lakes, is renowned for its clear freshwater and sweeping city views. This charter is exceptional because it blends natural beauty with an urban edge, providing access to anchor points like the Playpen north of Navy Pier and Monroe Harbor near the Shedd Aquarium. These spots offer pristine water ideal for swimming and sunbathing just steps from downtown vibrancy. For those seeking a quieter adventure, a river cruise with the captain allows guests to dock at popular waterfront eateries such as Portfino's and enjoy meals directly off the boat.
Captain Tanner’s charters are tailored to both party-goers and those who prefer a laid-back outing. His knowledge of Chicago’s boating scene creates an inviting atmosphere where guests can play music, swim, or simply soak up the sun while cruising past iconic landmarks. The boat seats up to 13, perfect for intimate groups or couples wanting a memorable day or evening on the water. Evening cruises illuminate the skyline beautifully, making night trips a star attraction.
What sets Captain Tanner apart is his commitment to personalized service, including a captain and deckhand onboard to assist, serve drinks, and ensure guest safety. While food and beverages are purchased separately, he offers helpful catering recommendations and assist with logistics to enhance the experience. Guests are encouraged to bring essentials like towels, sunscreen, and a playlist for the ultimate vibe.
Safety is paramount — children under 6-7 are generally not recommended due to safety concerns from lake wakes and limited space, and guests should know basic swimming skills. Glass containers are prohibited, and some restrictions apply to ensure a fun, secure trip.
Whether you’re a Chicago local or visiting the city, Captain Tanner’s boat charter brings a fresh perspective to exploring one of America’s most dynamic waterfronts. This is more than a boat ride; it’s a chance to connect with nature, culture, and community on the water.
With four years of captaining these adventures, Tanner’s enthusiasm and professionalism shine through in every trip, making this a standout choice for Lake Michigan water activities.
easy.
3–4 hours.
Moderate physical condition recommended mainly for getting on/off the boat and swimming if desired.
Children under 6-7 years old are generally not recommended due to safety concerns from lake wakes and limited space, but older children are welcome with life jackets.
Food and drinks are not included; however, Captain Tanner can recommend local catering options and assist with bringing food onboard.
Yes, guests can bring their own floaties or use the boat’s lily pad for lounging on the water.
If conditions prevent a safe trip, the captain will work with guests to reschedule the charter.
Basic swimming is highly recommended for safety, especially if you plan to swim at anchor spots, though it’s not mandatory.
All charters depart from 31st Street Harbor on J Dock in Chicago with prompt boarding times advised.
Lake Michigan has long been central to Chicago’s development, with boating forming a critical part of the city’s recreational culture since the early 20th century.
Responsible boating practices are encouraged to protect water quality and local wildlife habitats around the harbor and anchorage areas.
$100/hr plus gratuity!
Book with Knot My Boat Charters