Best 199 things to do in Naperville, IL

Ride a Yamaha Waverunner with Chicago skyline views

Private 6–8 hour fishing charter for up to 6 on Lake Michigan

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

Sail Lake Michigan for views of Chicago’s shoreline and skyline

Live blues, Lake Michigan sailing, and Chicago skyline views

See Chicago’s skyline from Lake Michigan on an evening sail

Cruise out for Navy Pier fireworks with skyline views and bar service

90-minute group sail for Navy Pier fireworks and Chicago skyline views

Guided Fox River paddle followed by live blues music

Explore interactive exhibits and artifacts from Joliet’s past with access to galleries for all ages

Coordinate tactical games across a wooded private battlefield

Flow through gentle poses and play with rescue puppies during a 1-hour indoor session.

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

Ride a foodie bus to restaurants seen in The Bear, with tastings along the way

Visit four Chicago pizzerias and compare four pizza styles by bus

Taste donuts and learn Harvard Square history on a 2-hour walk

Taste your way through downtown Boston on a private donut walk

Watch fireworks and Chicago sights from a floating tiki bar

Watch Chicago fireworks from a floating tiki bar with a full onboard bar

Parasail up to 500 feet above Lake Michigan for skyline views

Cruise Chicago waters with up to 13 guests for a flexible three-to-four-hour outing