Guides spin true tales of Windy City history and architecture, or society's gritty underbelly takes center stage in gangster and ghost tours

Sailboat tours of Harbor Islands, sunset sails, nighttime city light tour & Tall Ship viewings include free soft drinks & snacks

Two-hour rentals aboard paddleboards or kayaks, or three-hour stints piloting roomy pontoon boats for up to eight people

3-hour fishing charter traverses Cuyahoga River on pontoon boat helmed by experienced captain, in search of bass, bluegill, or northern pike

Seasoned boat captains teach four students to steer, raise sails & navigate Santana 22 keelboat safely

Nine-hour cruise grants guests plenty of time to explore Kelleys Island & Put-in-Bay

Naturalists lead bike tours & hikes on flat paths through nature-rich wildlife refuge to Ibis Pond, where alligators & herons congregate

Passengers relax or help raise sails & steer on BYOB cruises in the evening or beneath the moonlight

Fishing and ski boats take up to six guests over freshwater waves of Clear Lake or Lake Conroe after brief training

Expert instructors teach basic skills, such as tacking, while students operate sailboat in Chesapeake Bay