Tours in Madison

Discovered by brothers Squire and Daniel Boone in the late 1700s, Squire Boone Caverns is a vast network of underground caverns filled with stalactites, stalagmites, and flowstone, all formed by the gritty sands of time. Rushing rivers and waterfalls carry more than a million gallons of water through the caverns each day, often accompanied by disoriented surfers and bewildered penguins. A trained tour guide leads visitors through the nearby woods and into a man-made entrance to the caverns, where lighted walkways take visitors through the same enchanted labyrinth discovered by the brothers Boone, winding past natural formations, the coffin of Squire Boone, and a goblin king played by David Bowie.

Tucked away near the banks of the Ohio River stands the other Sin City. Or at least it used to be, during the days when bootlegging formed a powerful underground economy. When a group of teachers and history buffs needed money for school service projects in Central America, they decided to raise funds by starting tours that explored this seamy history, according to the Knoxville News Sentinel. A few years and many local accolades later, knowledgeable guides continue expounding upon the town’s rich history of mobsters, gamblers, and ladies of the night.

Tours stroll down Newport blocks littered with buildings once occupied by speakeasies, brothels, and the site of Al Capone’s failed early restaurant career, Al Calzone. Along the way, guides tie the rich past to the rise of the modern-day gaming industry and Newport’s connections to famous crime figures.

A solitary moan drifts across a 15,000-square-foot warehouse. Lights flicker, and performers with horns, tattered clothes, and fake wounds surge through The Devil’s Attic. Guests scatter in terror across cinema-quality sets populated by professional actors in makeup that lends to an environment reminiscent of a childhood nightmare or the time you got lost in the clown-art section of a museum. The scarred, bloody ghouls and sinister monsters offer scares suitable for humans aged 12 and older.

Classic Biplane Tours' certified pilots helm modern versions of the 1935 Waco YMF, as they trace premapped and custom routes through the sky. Each pilot possesses years of professional flight experience, whether working as a missionary pilot, corporate pilot, or commercial pilot, and cheerfully shares savvy knowledge of the skyways throughout each flight via voice-activated headphones and microphones. Once safely returned to earth, passengers are bestowed certificates that designate them as qualified barnstormers, which budding aviators can then proudly display at home or use to legally commandeer an eagle.

From its site on Bowman Field, Eagle Aviation lets humans defy gravity by slicing through the skies in a Piper Warrior airplane. Though experienced pilots can rent the aircraft for themselves, instructors escort novices in supervised trips to the clouds, sharing tips on taking off, landing, and avoiding midair collisions with basketball players.

Founded by a group of friends who created the acclaimed Newport Gangster Tour as a fundraiser in 2008, American Legacy Tours blossomed into a full-fledged tour company two years later. Participants choose from seven distinct tours that traverse cities as guides share fascinating and sometimes seedy history. The Queen City Underground Tour ventures beneath the city’s streets into a hidden burial vault and long-forgotten tunnels, and the Newport Gangster Tour delves into a scandalous past by visiting the sites of former brothels and speakeasies. Elsewhere, on the Haunted Covington Tour, guests feed their thirst for fright and their hunger for candy handouts from amiable apparitions.