things to do in Wilmette, IL

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

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

Trace Chicago’s Prohibition history across four neighborhood speakeasies

Taste your way through Chicago’s West Loop with a local guide

Cruise Chicago’s lakefront for skyline and Navy Pier views

Taste Chicago donuts while uncovering Fulton Market’s industrial past

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

Fly over Chicago landmarks with a private helicopter for up to 3

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

Celebrate on the Gypsy Spirit along Chicago’s waterfront

Step inside Chicago Loop landmarks and trace the evolution of its skyline

Bike Miami Beach and sample local food with a guide

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

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

Explore Chicago's Prohibition era through stories of class, nightlife, and rebellion

Eat Chicago’s five classic dishes with VIP access in River North and Streeterville

Cruise about two miles offshore for wide-open Chicago sunset views

Taste Santa Monica’s donut culture on an outdoor walking tour

Enjoy a weekday farm visit with tickets for just the activities you want to try

Take the controls in a 30-minute helicopter intro flight

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

Ride Chicago’s 1920s–30s gangster trail with actor guides

Private skyline cruise with a local perspective

Pedal through Chicago neighborhoods while tasting pizza, hot dogs, brownies, and optional beer pairings