Water Activities in Wilmette, IL

Cruise Chicago’s river in a vintage 1950s Milo Craft

Paddle the Chicago River after dark with city lights and stories from your guide

See Chicago from the water aboard a former Navy tactical boat

Cruise Lake Michigan with a full kitchen, two bathrooms, and skyline views

Cruise the Chicago River aboard a private floating tiki bar

Hire a US Coast Guard licensed captain for your Chicago boat day

Cruise the water with a captain for relaxed outings, playpen visits or evening fireworks

Make your Chicago celebration a private day or night on the water

Private Chicago river and lake charter with an included open bar

Relax together with a flybridge lounge, wide walkways, and onboard music

Sail Lake Michigan for Chicago skyline views and Navy Pier fireworks

Captain for hire on Lake Michigan, with payment options and holiday rates

Pilot a 2-person Craig Cat and cruise the Chicago River skyline

Build foundational kayaking skills on calm Chicago River waters

Float through Chicago’s skyline on a festive fall hayride

Set your own pace on a private Chicago yacht cruise

Sail Chicago’s lakefront on a private charter with time to swim and relax

Cruise with Captain Rudy at 31st Street Harbor

Cruise Chicago by private boat with an experienced captain

Hire a seasoned Lake Michigan captain with 40+ years of experience

Double-decker catamaran for private entertaining and water views

Sail Lake Michigan with Chicago skyline views

Sail Lake Michigan at sunset for Chicago skyline views from the water

Private cruising for relaxed gatherings and celebrations