Italian Hill Towns – Beautiful Places to Stay in Tuscany

Irresistible. Mesmerizing. Addictive. Italy weaves a magical spell on travelers. The food, the wine, the friendly people, the culture, the history, but none so entrancing as the Italian hill towns of Tuscany. One visit is never enough. No matter how long the stay once home, travelers long for glorious days of exploring vineyards and ancient hilltop towns.

Frequently asked for travel advice, the small towns of Italy often make the top of our suggestion list. Safe, slow-paced and jaw dropping beautiful, it is hard to go wrong with a stay in almost any of the Italian hill towns.

But where to go in Tuscany? With so many astounding hill towns in Italy, the prospect of planning can be overwhelming.

Below we list five of what we believe to be the best Italian hill towns. We hear the arguments beginning as dozens of other towns should make the list.

Below each of the locations chosen you will find our recommendations for the best places to stay in Tuscany. Our choice is one we have stayed in ourselves and is typically mid range price. Hill towns of Italy tried and tested.

A budget and luxury hotel has also been added for you to compare.

We will tell you what we loved about the Tuscany destination and also what we think you should be aware of before booking. We have not been sponsored by any of the hotels.

Where to stay in the Italian hill towns of Tuscany

Cortona

Little did Frances Mayes know what her romantic telling of her paradise ‘Under The Tuscan Sun’ would bring. Cortona, perching on hills that seem to bow down before its own beauty, made an incredible setting for the best selling book and subsequent film. The home Mayes occupied in one of the most beautiful Italian hill towns became so popular she felt the need to escape and left Cortona.

Retaining much of its 3000 year old history behind Etruscan stonewalls, Cortona delights with stunning views, medieval architecture, quaint shops and restaurants offering traditional and local cuisine. The charming city offers some of the best views in Tuscany.

Cortona under the Tuscan sun

Where to stay in Cortona

We stayed at Hotel San Michele

What we liked about Hotel San Michele

Besides being the most central of all accommodations in this walled Tuscan city, Hotel San Michele is within the 15th century Baldelli Place. Beautifully restored, the Ministry of Cultural Heritage lists the hotel as a national monument.

Furnished with antiques, the hotel is modernized with amenities and facilities. Each of the 40 rooms is uniquely designed. We took the short walk to the main square where stands of delicious chocolates and local artisan wares are sold.

Ask the staff to point out the wall painting of Madonna with child dating to the 1400’s. It feels a bit like traveling back in time with all the conveniences of modern day.

What we want you to know about Hotel San Michele

The hotel is on a hill. Welcome to Italian hill towns. When leaving or arriving you will be immediately heading uphill or down. This was not an issue for us but we do want you to be aware of the incline if you have significant mobility challenges.

Sitting area in Hotel San Michele

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Sorano

This ancient medieval Italy hill town is often referred to as the City of Tufa. Given its perching placement on volcanic tufa stone it comes by its nickname honestly.

Sorano retains much of the activity of centuries ago. Hovering above the Lente River, the hilltop town is surrounded by vineyards, fields of wheat, olive groves and grazing sheep.

Thought to be inhabited as far back at 3rd century BC, the Etruscans found the porous volcanic rock easily carved. Caves cut out centuries ago for tombs and hideaways are today used as garages and storage sheds. Talk about re-using and re-purposing!

View of Sorano from hotel window of Hotel Fortezza

Where to stay in Sorano

We stayed at Hotel Della Fortezza

What we liked about Hotel Della Fortezza

This one of a kind hotel is within the Fortezza Orsini di Sorano fortress. Walking across the drawbridge over a moat to one’s accommodation is not something we have ever encountered. The rooms each have a different design, some more spacious than others, but all with extraordinary views of Sorano.

Located in the center of this Italian hilltop town, exploring the ancient stone and stucco buildings of Sorano is easily done. Or if you have had enough of walking hill towns in Italy have a refreshment in the courtyard of your own castle.

What we want you to know about Hotel Della Fortezza

This is not a deluxe hotel. The hotel is decorated in good taste and fits well with the age of the building. As you will guess that since it is an ancient fortress, the hotel sits at the very top of what we consider one of the best Italian hill towns we visited. Exploring the town on foot requires significant stair climbing.

Who doesn’t want to stay in a castle in Tuscany?          

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San Casciano

The quiet Tuscan village sitting atop a hill (how unusual in Italy we know) can be found mere minutes south of Florence. Away from rush of one of Italy’s busiest cities, taking haven in San Casciano is one of the best of Tuscany.

As part of the agricultural area of Chianti, the local restaurants serve extraordinary wines, extra virgin olive oil and organic food of the region. The village is small but has good restaurants and pubs. Little shops sell groceries and pastries. During our visit, which happened to be on a Saturday, a marketplace was set up on main street.

One of the more secluded Italian hill towns San Casciano

We stayed at Sette Querce

What we liked about Sette Querce

Sitting at the edge of this Italian hill town, each guest has an entire suite. Arriving after a day of cycling, how luxurious to have a small kitchen and living area with a sofa. So much space to spread out our gear.

Each of the suites has a small terrace and the building is surrounded by oak trees. Breakfast is served to each of the brightly colored rooms. Frankly I found it challenging to pack up and get back on my bike. Home away from home in this Tuscany destination.

What we want you to know about Sette Querce

With the hotel being surrounded by beautiful trees, the views at Sette Querce tend to be of the forest and the village. The dramatic vistas of Tuscan rolling hills are more easily seen from viewpoints within San Casciano.

Kitchen area in room at Hotel Sette Querce

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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. Not far from the larger city of Sienna, the walls of this Tuscan city date to the 14th century. Evidence has recently shown Montepulciano was in existence as early as the 4th-3rd centuries BC.

Stretching for 1.5 kms (0.9 mi), the main street of this hill town of Italy will ensure you have a thorough work out. With car-free streets,  blissful meandering among shops and wine tasting venues Montepulciano receives high points from visitors.

The city is well known for its ancient churches and Renaissance history. Perhaps most stunning of all are the astounding panoramic views of the valleys that surround one of the best situated Italian hill towns.

Montepulciano

We stayed at Villa Cicolina

What we liked about Villa Cicolina

Once a noble family called Villa Cicolina their retreat. With frescoed ceilings and antique furniture one feels as though you may be apt to meet royalty on the way to the infinity pool.

Located outside the city, the flowers and fields surround the entire property. Garden areas and walkways lead to a small church should you be so inclined. The olive trees near the pool provide welcome shade from the Tuscan sun.

What we want you to know about Villa Cicolina

Sitting outside of Montepulicano will mean you need to drive into the city or cycle. If you are looking to walk easily to amenities during your stay then this may not be the right spot for you.

Villa Cicolina infinity pool looking over the Tuscan hills

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Bagno Vignoni

Located in the heart of Tuscany, Bagno Vignoni is best known for its thermal waters. The springs of this Italian hill town have been soothing travelers since Roman times. At the end of a day of cycling the Italian hills, peering at the famous waters held in a 16th century rectangular tank, the temptation to jump in, bike and all, crosses my mind.

Pilgrims of ancient times slogging to Rome stopped in Bagno Vignoni to soak in the waters springing from a volcanic aquifer. The hot springs definitely have staying power and still draw tourists to the town surrounded by the valley of the Orcia River.

We stayed at Hotel Osteria Dell’Orcia

What we liked about Hotel Osteria Dell’Orcia

The setting of Hotel Osteria Dell’Orcia may be on of the most beautiful in Tuscany. Nestled just below one of the quaintest Italian hill towns, rich with history, the rolling hills go on forever.

As the sun set silhouetting the cyprus trees, we meandered through the pristine gardens. I still recall turning to Hubby and suggesting we should come back for a month. Following one of the most delicious dinners we had in Tuscany I suggested we move in permanently.

What we want you to know about Hotel Osteria Dell’Orcia

The hotel is a five minute walk across a foot bridge to Bagno Vignoni. Call him a unique watch dog or town crier, the hotel also has a resident donkey.

Originally purchased with the thought of giving rides to children of guests, donkey was not keen on the idea of trotting wee ones around. Thinking better of it, the owner changed donkey’s role to marketing.

Hotel Osteria Dell’Orcia is well known for the hee-haw calling tourists to inquire why there is a donkey. Once on site the beauty of the setting is hard to resist.

Hotel Osteria Dell’Orca

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