Live stand-up, touring comedians, and skyline views aboard a historic fireboat
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
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
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
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 Uptown's 1920s heyday through the stories behind its buildings
Private 3-hour sail to view Navy Pier fireworks with a USCG-certified captain included
Sail Chicago’s lakefront on a private yacht with a captain, swimming and music on board
Private Lake Michigan sailing with swimming, snacks, and a certified captain
Sail Chicago’s lakefront at sunset aboard a private 37-foot yacht
A private sail for proposals, photos, and a champagne toast
Charter a 47’ Carver yacht with kitchen, bathrooms, and Bluetooth audio
Set the mood on board with your own food, drinks and music