Water Activities in Wilmette, IL

Paddle the Chicago River past the Wild Mile and downtown skyline

Cruise Chicago by private 47 ft yacht with space for up to 12 guests

Paddle the Chicago River and learn downtown architecture in 3 hours

Private 1962 vintage motorboat cruise on the Chicago River for up to 6 guests

Cruise the Chicago River for skyline views and Riverwalk sights

Private yachting for celebrations, family gatherings, and corporate outings

Cruise Chicago’s lake and river on a historic fireboat with docent-led stories

Cruise Chicago’s waterfront with a professional crew and private gathering spaces

Charter a 47’ Carver yacht with kitchen, bathrooms, and Bluetooth audio

Private 6–8 hour fishing charter for up to 6 on Lake Michigan

Private 40' Sea Ray yacht rental in Chicago for up to 13

See Chicago landmarks from the water on a private sightseeing outing

Paddle Chicago River routes in a single or double kayak

Paddle Goose Island and downtown as Chicago lights reflect on the river

Private Sea Ray yacht charter on Lake Michigan with 3–8 hour options

Celebrate on a tiki-themed yacht with an open bar and Chicago skyline views

Enjoy a Chicago charter with a USCG-licensed captain and 15+ years of experience

Hire a Chicago captain and cruise to the Playpen, Monroe Harbor, or the river

Celebrate on the Gypsy Spirit along Chicago’s waterfront

Set sail aboard a 50' Sea Ray with a kitchen, bathrooms, and Sonos audio

Cruise a 47-foot Carver with space to relax, dine, and play your music

Private Chicago cruising with a kitchen, bathroom and Bluetooth sound

Charter a private 38' yacht on Lake Michigan for up to 13 guests

Photograph Chicago's skyline from a US Navy-built boat