Take the wheel on a 22 ft pontoon cruise on the Chicago River
Paddle Chicago's lakefront with skyline views and basic instruction
See Chicago fireworks from a floating tiki bar on Lake Michigan
Watch Chicago fireworks on a 90-minute tiki bar cruise
Host a private kitten yoga party with playtime at The Arboretum of South Barrington
Stretch, cuddle and take photos with rescue puppies in a private yoga session
Eat your way through Uptown’s immigrant neighborhoods in 2.5 hours
Taste Vietnam, the Middle East, and Sweden while exploring Argyle and Andersonville with a guide
Taste Lincoln Square’s European roots and Silk Road flavors on foot
Taste Chicago classics while exploring the city's landmark-filled streets
Explore Chicago through social adventures with fellow solo travelers
Bike and taste your way through Miami Beach’s Art Deco streets and local eats
Paddle Lake Michigan from Ohio Street Beach for two hours
Paddle Lake Michigan for Chicago skyline views
See holiday lights, market traditions, and Chicago's tree on a downtown stroll
Taste Chicago's holiday flavors and festive sights on foot
Cruise Chicago waters with up to 13 guests for a flexible three-to-four-hour outing
Explore Lake Michigan by boat, from Playpen outings to Chicago river cruises
Bring your group aboard for a captain-led Chicago outing
Cruise Chicago’s waterfront with a certified EMT captain
Cruise Chicago with a flexible captain for your 3–4 hour charter
Charter a 48 ft Sea Ray Flybridge for up to 13 guests on Lake Michigan
Chart a captain-led Lake Michigan or Chicago River outing tailored to your plans