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
Private skyline cruise with a local perspective
Pontoon time for fishing, lounging, and pets
Cruise Chicago’s river in a vintage 1950s Milo Craft
Taste Chicago donuts while uncovering Fulton Market’s industrial past
Ride Chicago’s 1920s–30s gangster trail with actor guides
Eat Chicago’s five classic dishes with VIP access in River North and Streeterville
Tour and tasting for two with a tasting room reservation and wine
See Chicago landmarks from the water on a private sightseeing outing
Bike Miami Beach and sample local food with a guide
Cruise about two miles offshore for wide-open Chicago sunset views
Take in Chicago's parks, waterfront, and landmark sights in one ride
Take the controls in a 30-minute helicopter intro flight
Discover Logan Square’s past through handcrafted greystones, historic churches, and ornate storefronts
Fish, lounge, or bring your pet aboard a Lake Elizabeth pontoon
Paddle the Chicago River after dark with city lights and stories from your guide
Taste Santa Monica’s donut culture on an outdoor walking tour
Make your celebration hands-on with cookies and personalized party touches
Ride a foodie bus to restaurants seen in The Bear, with tastings along the way
Discover the journey from fresh grapes to wine during Chicago's harvest season
Photograph Chicago's skyline from a US Navy-built boat
Pedal through Chicago neighborhoods while tasting pizza, hot dogs, brownies, and optional beer pairings
Speed across Lake Michigan with your own music and skyline views