Galena, Illinois Pirate Tour

Galena, Illinois Pirate TourGalena, Illinois Pirate TourGalena, Illinois Pirate Tour

Galena, Illinois Pirate Tour

Galena, Illinois Pirate TourGalena, Illinois Pirate TourGalena, Illinois Pirate Tour
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    Dead Billy's Galena Pirate Tour...

    Historic Dowling House, Galena's oldest house from 1826, during twilight.

    Galena, Illinois is not your average town! We are WEIRD and WILD!

    Forget dusty Civil War stories and uptight Victorians... we explore the WILD & WEIRD history of Galena, Illinois that is anything but boring! From Native American legends to French explorers, pirates, brothels, and ghosts, this town has truly seen it all! And Galena is OLD, we go back waaaay before the '1826' year people like to assign us. In fact, if it weren't for a really powerful, great and slightly 'rotten' European king we wouldn't be who we are today (and he's not English). Our weird history tours dive deep into the strange characters, shocking stories, and spooky mysteries that shaped Galena. The Galena Pirate Tour is a unique blend of history and legend, offering a fun romp through our town's past! WE ARE NOT A BORING HISTORY TOUR! Audience engagement, humor, sarcasm and bawdy storytelling as well as really wild and weird histories abound as we uncover the wild side of Galena without sugarcoating the past. All while keeping the mood lighthearted, entertaining and FUN!

    Historical scene of Native Americans and colonists exchanging goods in a forest.

    Real Galena History (the weird stuff)

    Hire your Alligator Horse and load up yer flatboat! Illinois is steeped in history, particularly Galena's history, which is really old. In fact, it might shock you just how old our town is! Pirates (yes, you read that right), indigenous peoples, miners, prostitutes and everyday people from abroad helped make Galena an amazing melting pot of culture that you need to hear and see to believe! We're going to explore not just the famous people and significant events that shaped this area, 

    but also delve into the lives of "common" people, their secrets, and the often bizarre occurrences among all of them and many that are suspiciously reminiscent (for clear historical reasons) of Caribbean pirate history! And it all happened right here in Galena! Join us for some weird history tours as we uncover the harsh realities of their daily lives and their backstories that will often surprise you!

    A whimsical scene of fantastical creatures and a witch flying on a horse.

    Galena Spookiness is a Thing

    Galena is rich in history, including some scary tales and spirits! From Native American legends of ancient monsters to settler experiences with creatures 'down below,' as well as ghost stories that delve into Galena's pirate history, this tour will take you through all manner of things that go bump in the night. Join us for a journey through weird history tours that uncover the eerie side of Galena's past!

    A chaotic street scene in historical London filled with diverse characters and activities.

    Scandalous! Galena is a Dirty Old Town...

    Every town has its secrets, and we're going to explore them through the lens of Galena history! From tales of brothels and boozing to scoundrels who were often (we know they were) pirates, there are plenty of stories about scallywags and ladies of the night here in this small Illinois river town. Imagine horse races in the street, lots of gambling, music and mayhem and that's our town! We'll be talking all about the petticoat crimes and debauchery, showcasing the real lives and real wickedness of early settlers as well as those who chose to shine a little brighter. Join us on our weird history tour to uncover the debauchery and pirate history that abound in fascinating Galena, Illinois!

    Galena Pirate Tour: Explore the Weird and Wild History

    The Pirates Code...on the Tour

    Ships' Articles:


    * Starts at the "Big Staircase" that goes up the side of the hill... aka the old High  Schools Stairs, at the intersection of Main St. and Green St.,  between Gustafson & Grey (301 South Main St.) and the Fraternal Order of Eagles ( 237 South Main St.) ...all three locations are on the same side of the street. We meet at the street lamp post at the foot of the stairs. 


    * Time: 8:00 pm sharp (don't be late...pirates wait for no one!)


    * Duration: About 90 Minutes of exploring Galena history through a pirate lens.


    * Includes some stairs and walking, so prepare for an adventurous journey!


    * No restroom stops, please use facilities beforehand. DeSoto House Hotel has restrooms across the street. 


    * Please no talking over the stories, as we dive into the depths of pirate history.


    * Disruptive, rude or drunk? Ye be walking the plank with no refund!


    * Dress for the weather and comfortable walking; think like a pirate!


    * No kids under 12, no pets (service animals only), and no refunds unless we cancel for weather.


    * Photos welcome (NO recording during the tour).


    * No smoking on the tour.


    * No drinking on the tour...but afterward, feel free to toast to your newfound weird history!


    Have Fun Ye Scallywags!


    * You CAN dress as a pirate!


    * We don't care if you drink before the tour. Just don't be disruptive, rude, or drunk.


    * The tour is interactive...say it with me...


    * Repeat after me: I, a grown adult, have an excuse to dress as a pirate!


    * After the tour, drinking—even with the guide—is safely encouraged. Feel free to ask for recommendations.


    Tickets & Rules


    * All sales final (reschedule or transfer allowed).


    * Rain or shine (unless it's a storm or the apocalypse...then we cancel).


    * Tickets purchased online from this site pre-tour. Sales stop approx. 15 min. prior.

    A group of friends dressed as pirates taking a cheerful selfie at a festival.

    We Acquiesce to Your Request!

    Contact Capt. Dead Billy

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    The Galena Pirate Tour

    Phone: 7792029138 Email: galenapiratetour@yahoo.com

    Aaarghh Ye Ready For Some Photos!?

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