9 Medieval History Tours in Italy to Book First

1.Private Tour of the Medieval Village of Ostuni by Tuk Tuk

★★★★★★★★★★4.5 · 278 reviews · 35 minutes (approx.) · from $43Our pick

Ride through Ostuni’s steep medieval lanes in a private tuk tuk with a local driver. You’ll pass churches, monuments, and viewpoints while getting a quick introduction to the White City. English is offered, but confirm your driver’s language and level of commentary before setting off.

“Sadly, this was such a disappointing tour. We’ve taken many wonderful viator tours but this was basically a guide that had very little to say, and we tore through the small, crowded streets for 30 minutes. Absolutely was not worth the dollars spent. We heard other guides while we explored on our own after and they gave much more information to their guests.”

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2.Discover the Medieval Charm of Siena on a Private Walking Tour

★★★★★★★★★★5.0 · 247 reviews · 2 to 3 hours (approx.) · from $187Top rated

Walk Siena’s historic center with a private English-speaking guide, from Basilica San Domenico to Piazza del Campo and the Duomo. Guides such as Barbara, Ludovica, Elena, and Julia tailor the pace and stories to your group, with optional Cathedral admission available onsite.

“What a wonderful tour! Our guide, Elena, is a Medieval scholar, and we so loved all of her knowledge of Siena. She was pleasant, funny, and interesting. Truly a highlight for our group of four.”

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3.Roman countryside Food & Wine Tasting in a medieval winery

★★★★★★★★★★4.5 · 220 reviews · from $115

Meet at Piazza del Popolo at 11 a.m. for an air-conditioned ride to Cantina Castello di Torre in Pietra. Sommelier guides such as Christian or Marco lead a cellar visit, then pair three wines with cheese, cold cuts, and Roman dishes. Allow about four hours, with time to shop for wine and olive oil.

“The food was delicious! But what I really enjoyed was the knowledge on how to taste the wine and pair it with food.”

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4.Renaissance & Medieval Florence Guided Walking Tour plus mobile App

★★★★★★★★★★4.0 · 140 reviews · 1 hour 30 minutes (approx.) · from $30

Walk central Florence with a local guide, from San Lorenzo and the Medici story to the Duomo, Piazza della Signoria, Ponte Vecchio, and Pitti Palace. The roughly 90-minute English tour includes the VOX CITY app for extra self-guided routes, but attraction tickets, headphones, and smartphone use are not included.

“Waste of precious vacation time and money. Was a total of 10 people. 6 French speaking and 4 English. The guide struggled with both languages and spent 70% with French folk and 30 with us English. The guide had trouble with both languages, but mostly with the english language. Trouble communicating about the subject matter. A refund should made!”

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5.From Turin: Half-Day Medieval Sacra di San Michele Tour

★★★★★★★★★★4.7 · 94 reviews · 4 - 5 hours · from $71

Travel by private coach from Turin to Sacra di San Michele, an imposing Romanesque abbey above Val di Susa. A live guide leads you through the Doorway of the Zodiac, Staircase of the Dead, and church. Choose a private or small-group tour, with Italian and several other languages available.

“We enjoyed this tour. I think it is a bit expensive for what it is. The site is great - however it wasn't quite delivered to us how it links to In the Name of the Rose. We also had a very hazy day so the view was not quite as astounding as it should have been but that's in no one's control.”

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6.Ferrara: Medieval Ferrara and the Jewish Ghetto Walking Tour

★★★★★★★★★★4.7 · 70 reviews

Join Elisabetta Concetta Gulino for a private two-hour walk through Ferrara’s Este landmarks, medieval business lanes, and Jewish ghetto. You’ll see the castle courtyard, cathedral square, Savonarola statue, Finzi-Continis garden route, and 15th-century synagogue with an English, Italian, Spanish, or German guide.

“Our guide, Elizabetha was very knowledgeable and gave us an interesting overview of the history of the town and how it is reflected in the various architectural styles. We especially enjoyed the Jewish ghetto part of the tour.”

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7.Tower and Power, Virtual tour in Medieval Bologna

★★★★★★★★★★4.5 · 54 reviews · 30 minutes (approx.) · from $21Best value

At La Macchina del Tempo in central Bologna, you’ll use an Oculus Quest headset to explore the city around 900 years ago, meet its inhabitants, and fly above the medieval towers. The visit lasts about 30 minutes, admits up to five people, and is offered in English.

“The VR tour of medeival Bologna was great; very well done. Enjoyable (even for a 58-year-old like me, and I'm sure kids would appreciate it even more) and informative. Choose the longer version (25 minutes).”

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8.Homemade Pasta in a Peaceful Medieval Village

★★★★★★★★★★5.0 · 44 reviews · 3 hours · from $105

Travel from Parma to Calestano for a three-hour pasta class with Virginia and her mother, Nadia. Make tagliatelle and ravioli by hand, then share antipasti, wine, your pasta, and tiramisu on a panoramic terrace with the family cats nearby.

“This was a wonderful cooking class where we learned to make ravioli and tagliatelle. Virginia and her mother welcomed us warmly into their home, which had a high standard and a beautiful terrace in stunning surroundings. Virginia taught us how to make pasta – she explained, demonstrated, and corrected our technique until we got it right. The result was truly delicious. We were also served a lovely starter and dessert. I really want to recommend this. 10/10.”

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9.E-bike between towers and medieval villages at the foot of Sirente Abruzzo

★★★★★★★★★★5.0 · 36 reviews · 4 hours (approx.) · from $47

Join Luca of SirentEbike for a private, roughly four-hour ride through the Aterno Valley. Electric bikes carry you between Beffi Castle, Roccapreturo, Acciano, Secinaro, and Goriano Valli, with village history, mountain views, helmets, water, and a local brunch included.

“This tour truly left me nearly speechless from the incredible views we saw on this e-bike tour. The guide was knowledgeable and easy-going. This was a very fun activity for my family to partake in.”

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