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
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
Private 3-hour sail to view Navy Pier fireworks with a USCG-certified captain included
See Chicago landmarks by helicopter with a 5-passenger twin-engine aircraft
Explore forest preserves on a guided horseback trail ride
Ride countryside trails at sunset, then relax by a hilltop bonfire
Take on a challenging guided trail ride along the Fox River
Ride challenging hills and creek crossings, then gather around a sunset bonfire
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
Coordinate tactical games across a wooded private battlefield
Ride a foodie bus to restaurants seen in The Bear, with tastings along the way
Taste Mexican cuisine and discover Pilsen’s mural-covered streets
Cruise Chicago’s river in a vintage 1950s Milo Craft
Paddle the Chicago River after dark with city lights and stories from your guide
Paddle Lake Michigan’s shoreline for city views and guided instruction
Pilot a 2-person Craig Cat and cruise the Chicago River skyline