things to do in Naperville, IL

Chart a captain-led Lake Michigan or Chicago River outing tailored to your plans

Host a private Chicago event with open-air decks and a professional crew

Set sail on Chicago waters with a captain at the helm

U.S. Coast Guard-certified captain for your Lake Michigan charter

Bring your group aboard a rented vessel with a 100GT Masters Captain

Explore Chicago’s shoreline with an experienced captain

Tailor a private Chicago boat outing with an experienced captain

Put an expert captain at the helm of your boat

Set out on Lake Michigan with an experienced captain

Discover Chicago architecture and fireboat history on a guided river cruise.

2-hour happy hour cruise with skyline views and a full bar

Live Electric Brew jams aboard a historic Chicago fireboat

Live stand-up, touring comedians, and skyline views aboard a historic fireboat

Sail Lake Michigan with Chicago skyline views

Share a peaceful Lake Michigan sail with Chicago skyline views

A quiet private weeknight sail with Chicago skyline views

Sail Lake Michigan on a private weeknight cruise with sunset and skyline views

Anchor at Chicago’s Playpen for swimming, skyline views, and a laid-back day on the water

Private Lake Michigan fishing with an expert crew

Cruise Chicago’s lakefront for skyline and Navy Pier views

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

Speed across Lake Michigan with your own music and skyline views

Cruise offshore from Navy Pier for fireworks and skyline views

Look beyond the brickwork to uncover a neighborhood's surprising stories