things to do in Chicago, IL

Explore Chicago’s shoreline with an experienced captain

Tailor a private Chicago boat outing with an experienced captain

Explore Chicago’s waters with an experienced local captain

Put an expert captain at the helm of your boat

A local captain for your Chicago day on the water

Put an expert captain at the helm of your boat

Set out on Lake Michigan with an experienced captain

Celebrate aboard a restored classic with three levels and open-air spaces

Cruise Chicago’s lakefront for skyline and Navy Pier views

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

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

Trace Chicago's skyscraper story with a donut tasting

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

Private skyline cruise with a local perspective

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

Celebrate on the Gypsy Spirit along Chicago’s waterfront

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

Discover the many lives of Wicker Park through its bricks and buildings

Sail Chicago’s lakefront on a private yacht with a captain, swimming and music on board