Top 8 Dark History Tours in Italy

1.The Dark Side of Florence: Mysteries and Legends

★★★★★★★★★★5.0 · 2,785 reviews · 1 hour 45 minutes (approx.) · from $3Our pick

Walk from Santissima Annunziata to Ponte Vecchio with an English-speaking guide such as Antonio, Glenda, or Angela. Expect Medici intrigue, ghost stories, assassinations, torture, hidden symbols, and the memory of Florence’s 1993 mafia bombing. Dress warmly and wear good shoes.

“This was a tour that you need to do to experience another side of Florence. Antonio, our guide, was really funny and engaging - he delivered content in a way that was mysterious yet deadpan, he could honestly do standup comedy! We learned more about the history of Florence and there were some amazing things he pointed out that you otherwise would not have noticed while walking around the city. We spent 4 days in Florence and walked past the same places at least 3 times and never saw what Antonio pointed out to us, and the meaning behind them. Dress warmly if you are doing this in the cold…”

Check availability →Read our full review

2.Guided Bar Crawl with Drinks & Dark History

★★★★★★★★★★4.9 · 444 reviews · 3 hours · from $77

Start in Piazza della Madonna dei Monti for a three-hour English tour through Monti, Rome’s former red-light district. Guides such as Autumn, Ana, Michelle, and Michal mix local drinks, dark history, icebreakers, and several bars. Alcohol-free drinks are available, and the walk ends near Piazza Venezia.

“Marley is a historian of the city. Made my night so memorable!”

Check availability →Read our full review

3.Small Group Rome’s Dark Side – Ghosts & Legends Tour

★★★★★★★★★★4.9 · 343 reviews · 2 hours · from $23

Walk Rome’s darker streets with guides such as Ben, Arielle, Ivanna, and Ariel. In two hours, you’ll hear sharp stories about executions, poisoners, betrayals, and alleged ghosts while visiting Campo de’ Fiori, Ponte Sisto, Via Giulia, and Castel Sant’Angelo. Expect humor, cobblestones, and no theatrical jump scares.

“Best thing we’d done in Rome and wish we’d done it on the first night. We learnt so much. Excellent.”

Check availability →Read our full review

4.Tipsy Tour: Guided Bar Crawl In Florence with Dark History

★★★★★★★★★★5.0 · 271 reviews · 3 hours (approx.) · from $78

Join Carpe Diem Tours at 8 pm for a three-hour Florence night out with wine, two cocktails, a shot, and stories of Medici scandals, brothels, and wine windows. Guides such as Zofia, Juliette, Anna, Didar, and Tonia lead the walk in English. A private upgrade is available.

“It was an absolutely wonderful time. I was in a small tour group of about 6-7 people total so the experience was very personal. There was a lot of time at each location we visited which I found to be very important as it didn’t feel rushed whatsoever. I certainly learned a lot personally not only about some of the history and significance of each location that we had visited but also the drinks that we had at each location. I also am allergic to nuts and while normally for drinks this is not a concern (apart from Amaretto) I still was incredibly appreciative of the care that was taken…”

Check availability →Read our full review

5.Dark Secrets & Scandals Evening Walking Tour

★★★★★★★★★★4.5 · 120 reviews · 1.5 hours · from $16

Walk Florence after sunset with an English-speaking guide such as Stefano, Marcello, or Angela. Hear stories of Medici scandals, family feuds, and tragic romances while passing Palazzo Strozzi, Piazza della Signoria, Ponte Vecchio, Palazzo Pitti, and Ponte Santa Trinita.

“The tour was wonderfully A good easy walk. And Stefano was very patient, kind, and knowledgeable. Highly recommend if youre interested in a quick peek into Florentine history”

Check availability →Read our full review

6.Rome’s Dark Side Ghosts and Legends Tour

★★★★★★★★★★5.0 · 93 reviews · 2 hours (approx.) · from $24

Meet your English-speaking guide at Campo de’ Fiori at 8 p.m. for a two-hour walk through Rome’s darker history. Hear stories of magicians, popes, poisoners, and executioners, with a cafe break and a final stop at Castel Sant’Angelo. Groups are limited to 15 people.

“Our guide, Ben, was very knowledgeable, informative, entertaining, and made us feel safe walking around the city at night. The stories he told were fascinating and he held our attention the entire time. We learned a lot about the city's history as well as the creepy stories that go along with it! Would definitely recommend this tour!”

Check availability →Read our full review

7.Crypts and Legends: Exploring the Dark Side of Rome

★★★★★★★★★★4.5 · 69 reviews · 2 hours (approx.) · from $72

Start at 5 pm near Piazza Barberini and enter Rome’s eerie Capuchin Crypt before walking to Trevi Fountain, the Pantheon, Piazza Navona, Campo de’ Fiori, and Santa Maria dell’Orazione e Morte. Expect a small group, plenty of questions, and a mix of history, art, legends, and ghost stories.

“Estephania, our guide was very friendly and knowledgeable about all the stops on the tour. She was also full of local recommendations and insights to make our visit to Rome memorable. She did a great job interpreting the meaning of the Capuchin crypts.”

Check availability →Read our full review

8.Bologna: Sipping Through the City After Dark Tour

★★★★★★★★★★4.8 · 29 reviews · 1h 30m · from $57

Start beneath Bologna’s Two Towers and walk through Via Zamboni, Piazza Verdi, Piazza Aldrovandi, and Piazza Santo Stefano. With guides such as Lorenzo, Luciano, and Illaria, you’ll hear local stories, taste amaro and wines, and get advice on where to eat and go next.

“Luciano did a great job guiding us around the city and sharing knowledge and history.”

Check availability →Read our full review