things to do in Naperville, IL

Paddle the Chicago River and learn downtown architecture in 3 hours

Watch Navy Pier fireworks from a private yacht

Stretch, cuddle, and play with rescue kittens in a 1-hour indoor class

Host a private kitten yoga party with playtime at The Arboretum of South Barrington

Taste Vietnam, the Middle East, and Sweden while exploring Argyle and Andersonville with a guide

Paddle Chicago River routes in a single or double kayak

Paddle Goose Island and downtown as Chicago lights reflect on the river

Stretch, cuddle and take photos with rescue puppies in a private yoga session

See Chicago landmarks from the water on a private sightseeing outing

Photograph Chicago's skyline from a US Navy-built boat

See Chicago from the water aboard a former Navy tactical boat

Explore Chicago through social adventures with fellow solo travelers

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

Hire a Polish-speaking captain for your rented Lake Michigan boat

Cruise Chicago’s waterfront with a certified EMT captain

Cruise Chicago with a flexible captain for your 3–4 hour charter

Hire a Chicago captain for a Lake Michigan outing

Charter a 48 ft Sea Ray Flybridge for up to 13 guests on Lake Michigan