A trip to the romantic Italian hilltop towns is not just about the amazing wine. Not that wine isn’t a fabulous reason for visiting beautiful Tuscany and neighbouring Umbria, but there is far more to see.

Below you will find our top 10 Italian hilltop towns that we would love to call home for a month, or possibly forever. We chose to visit by bicycle. For those not keen on cycling the hilltops of Italy our best suggestion is a rental car.

See our complete guide of most beautiful places to stay in Tuscany here.

10 Unbelievable Italian Hilltop Towns

1) Civita di Bagnoregio

Straight out of a fairy tale book, Civita sits on its volcanic tuft of rock where the Etruscans founded the town more than 2500 years ago. Known as the dying village as earthquakes and erosion caused the edges to give way, the population declined to just 6 residents. Recently a resurgence of tourism is bringing Civita back to life. It is also where Dave and I parted ways on our bikes and he got lost. True story to be found here.

Check prices to stay near magical Civitia di Bagnoregio

Italian hilltop towns

2) Cortona

When Frances Mayes wrote [easyazon_link identifier=”0767900383″ locale=”US” tag=”traveltalesof-20″]Under The Tuscan Sun[/easyazon_link] little did she realize that her description of the paradise of Cortona would make it so popular she would feel the need to escape. Retaining much of its 3000-year-old history behind Etruscan walls, Cortona is filled with jaw-dropping views, medieval architecture and many quaint shops and restaurants. Yes, we hiked up here to get this view for you.

Click for best prices to stay Under the Tuscan Sun in Cortona.

Cortona Italy Hilltop Town


3) Montepulciano

Known around the world for the wine produced in the area, Montepulciano towers over the rolling hills sitting atop a 2000 foot limestone ridge. The walls of the city date to the 14th century however recent findings show the town existed in the 4th century BC. The car-free streets allow blissful meandering among shops and wine tasting venues. One of my personal favourites of the Italian hilltop towns.

Check latest prices for our favorite spot in Montepulciano – Villa Cicolina

10 italian hilltop towns

4) San Casciano

This quiet Tuscan village sitting atop a hill  (how unusual in Italy I know) is just south of Florence. With local shops and a few good restaurants, this can be a quiet location from which to base your travels in Tuscany. A rental car would be required. One of Tuscany’s small but not to be missed towns.

Check latest prices in peaceful San Casciano

5) Montefollonico

Happening upon a wedding in this isolated medieval Italian hamlet, the happy guests in Montefollonico paid the onlookers no attention. I love attempting to learn some of the local language and so with my phrasebook managed to give best wishes to the newlyweds or possibly that it was about to rain. My heart was in the right place.

With walls of 13th century fired brick surrounding the little Italian hilltop town, the views left me astounded. Not to mention firmly planted. Who would want to ever leave?

Compare prices for accommodations in Montefollonico

montefollocino Italy hill town

6) Sorano

Often referred to as the City of Tufa for it’s perching placement on its volcanic tufa stone, Sorano retains much of the activity of centuries ago. Surrounded by vineyards, fields of wheat, grazing sheep and olive groves this town with carved caves in the porous rock transports you back in time.

We loved staying in this castle! Find the best prices for Hotel Della Fortezza in Sorano.

Who doesn’t want to stay in a castle?

Sorano Italy Hilltop Town

7) Bagno Vignoni

The thermal waters of Bagno Vignoni have been utilized since Roman times. Arriving at the end of a day in cycling I was prepared to jump in, bike and all. Pilgrims of ancient times who [easyazon_link identifier=”163121179X” locale=”US” tag=”traveltalesof-20″]traveled to Rome[/easyazon_link] discovered the spa-like setting. Since the 16th century, the town square has contained a rectangular tank capturing the original water source from the underground aquifer.

Italian thermal spa anyone? Click to see prices for hotels in Bagno Vignoni.



8) Montalcino

With 1400 residents but over 220 wineries in the area you might guess what Montalcino is famous for. Surrounded by gorgeous countryside with ancient villages and churches, the most famous landmark is the Abbey of S. Antimo built by Charlemagne.

Compare prices of rooms in Montalcino.

10 Italian Hilltop Towns

9) Orvieto

Sitting on a cliff, the city of Orvieto presents one of the most dramatic postcard like images of Italian hilltop towns. At the end of a cycling day, it gave me a picture of potential cardiac arrest. Orvieto was a major center of the Etruscan civilization and is a thriving city today. One of it’s most famous sites is the Cathedral of Orvieto. All right it’s not a town but so beautiful we had to mention it.


10) Monticchiello

Perhaps the most overlooked gem in all of Tuscany, the downhill ride into Monticchiello is a must-do for cyclists. The curving cypress-lined route fills magazines and brochures of the image of taking to Tuscany on a bicycle. With just over 200 inhabitants and a virtual unknown to tourists, the quiet charm of the village may be one of the best finds in Italy.

Where the Tuscan hills toll on forever. Book this Tuscan paradise in Monticchiello.



Now we pass to you a magic Italian wand. Time to start planning your trip.  Which town will you begin your Italian hilltop dream trip?


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