Touring Tuscan Towns in the Siena Region

Tuscany is a vision. The green rolling hills, towering cypress trees, curvy roadways and those beautiful hilltop Tuscan towns. The best way to explore Tuscany is by car. Driving through the Tuscan countryside from town to town is a highlight in of itself. With so many beautiful towns and villages how does one choose which ones to visit? Especially if you like to visit ones that are a bit under the radar and off the beaten path. Here are the ones that I found to be most authentic and the best places to visit in the Siena region of southern Tuscany. 

Why travel to Tuscany

Tuscany is a part of Italy where life gets a little slower and much simpler. Let your passions be your guide when planning your trip. Whether you’re a foodie and appreciate great food and wine. Maybe you love art history and architecture and want to see where the Italian Renaissance started. Enjoy cycling or maybe you’re are a sun worshipper and want to experience the Tuscan coastline. Whatever the reason, you’ll find it all in Tuscany, plus a whole lot more. Touring the countryside from one hilltop town to the next is one of the top things to do in Tuscany. 

Some of the most beautiful places in Tuscany. Hilltop towns like Montalcino, Pienza, Montepulciano, Cortona, Arezzo and Siena

About the Province of Siena

The province of Siena is one of the most popular areas of Tuscany. Why because it has so many of the best places in Tuscany to visit. This region borders the province of Florence in the north, the province of Arezzo to the north east, the Umbria region to the south east, the region of Lazio to the south, the province of Grosseto to the south west and the province of Pisa to the west. 

RELATED READING | You can find our Guide to Florence here 

Best Places to Visit in Tuscany


Some of the most beautiful places in Tuscany. Hilltop towns like Montalcino, Pienza, Montepulciano, Cortona, Arezzo and Siena

Montalcino is a picturesque hilltop village with a medieval town centre full of well-preserved buildings dating back to the 13th century. This Tuscan village is famous for its delicious Brunello di Montalcino red wine produced using the grapes from the surrounding vineyards. 

Top Things to do in Montalcino include:
  • Medieval walls 
  • the Fortress
  • Neo-classical cathedral
  • Church of San Francesco 
Pienza is a hilltop Tuscan town located in the region of Val d’Orcia of the province of Siena. This romantic town offers visitors panoramic views of the beautiful Tuscan countryside in Italy.

Pienza is a well-preserved Renaissance town that has been virtually untouched since the 15th century. As such, it’s designated as a UNESCO World Heritage site. One of the draws to this historic town is the view of the Val d’Orcia countryside and the Pecorino di Pienza cheese. You can’t visit this hilltop town without trying some. 

Top things to do in Pienza include:
  • Cathedral or Duomo 
  • Palazzo Comunale, the town hall
  • Palazzo Piccolomini, used for government
  • Palazzo Vescovile, home to two museums, the Diocesan Museum and the Museo della Cattedrale
RELATED READING | You can find our Guide to Pienza here 


Some of the most beautiful places in Tuscany. Hilltop towns like Montalcino, Pienza, Montepulciano, Cortona, Arezzo and Siena

Montepulciano is one of Tuscany’s prettiest towns and is known for its wine. Wine enthusiasts will love sampling the latest vintage in the cozy wine tasting cellars. The walls surrounding this medieval town date back to the 14th century. Montepulciano is a car-free village and all of the top attractions can easily be explored on foot.  

The top things to do in Montepulciano include:
  • Palazzo Comuale, the city hall 
  • Palazzo Tarugi, made entirely of travertine
  • Santa Maria Assunta Cathedral from the 16th century 
  • Santa Maria delle Grazie Church
  • Santa Lucia, a Baroque church


Cortona, a stone-clad town in Tuscany, Italy with a magnificent medieval tower. It's larger and busier piazza and endless winding alleyways to wander means you need to add this to your list.

Cortona looks and feels a bit different than the other Tuscan towns. This hilltop is an elegant stone-clad town from the 13th century with a larger and busier piazza and endless amount of winding streets. Under the Tuscan Sun, first the book and then the movie, put this town on the map. And for good reason, it’s definitely worth a visit. 

Top things to do in Cortona include:  
  • Palazzo Casali, today houses the Etruscan Academy Museum 
  • Cathedral
  • Churches San Francesco and San Domenico 
  • Santa Maria del Calcinaio
  • Etruscan tombs
RELATED READING | You can find our Guide to Cortona here 


Some of the most beautiful places in Tuscany. Hilltop towns like Montalcino, Pienza, Montepulciano, Cortona, Arezzo and Siena

Arezzo is an ancient Etruscan city founded in the 9th century. Wander the historic city centre and gaze upon the medieval details – the balconies, lanterns, courtyards and all its lovely alleys. Arezzo is so charming it served as the backdrop to the movie Life is Beautiful. 

Things to do in Arezzo include:
  • Cathedral of San Donato
  • bi-annual medieval tournament called the Giostra del Saraceno
  • Medicea Fortress 
  • Santa Maria della Pieve
  • Palace of the Lay Fraternity
  • Palazzo Cofani Brizzolari and tower


Siena, a large medieval city in Tuscany

Siena is a large medieval and gothic city that can’t be missed. This popular Tuscan city is a tourist’s favourite, and for good reason. At its center is the incredible Piazza del Campo. The 13th century shell-shaped design is considered to be one of Europe’s greatest medieval squares.

Top things to do in Siena include:

  • Palazzo Pubblico
  • Torre del Mangia, the tallest tower in Italy
  • Siena Cathedral 
  • Santa Caterina, Baroque church
  • Palio di Siena festival is a world famous horse race played out in the piazza
RELATED READNG | You can find our Guide to Siena here 

Recommended Place to Stay

The Siena House is a large villa beautifully restored to accentuate the authentic Tuscan features with a modern twist.. Every window is strategically placed to highlight the mesmerizing panoramic views to the hilltop villages off in the distance. Siena House offers 4 large suites for guests with private quarters to living space, mezzanine, an outdoor kitchen and pool. The hosts, Malvin and Amanda, are welcoming and make sure your stay is an experience to remember, and that includes a delicious breakfast.

Siena House is well-situated in making many of the sought-after towns featured here an easy drive away. Here are destination points from Siena House for your reference: 

  • Montepulciano – 16 minutes
  • Pienza – 25 minutes
  • Cortona – 30 minutes
  • Montalcino – 40 minutes
  • Arezzo – 40 minutes
  • Siena – 45 minutes

Click here for Siena House– to see room rates, availability and to make a reservation.

As a holidaymaker…

As far as destinations go, Tuscany is the perfect one. It’s not easy to know where to go when an entire region is so beautiful. That’s what makes the region of Siena so attractive. It’s such a central location to many of the picturesque villages surrounded by romantic vineyards. I hope this list has inspired and helped your travel planning. 

Some of the most beautiful places in Tuscany include the hilltop towns of Montalcino, Pienza, Montepulciano, Cortona, Arezzo and Siena.
Some of the most beautiful places in Tuscany include the hilltop towns of Montalcino, Pienza, Montepulciano, Cortona, Arezzo and Siena.

Disclosure:  As an Affiliate Associate of if you click on the link contained in this post, at no additional cost to you, I will earn a small commission if you decide to book. Thank you.


  • Natascha

    We spent 2 weeks in Tuscany this spring and loved it! We especially liked Pienza, I town often overlooked by tourists, we feel. And you are right – the cheese there is to die for. However, we missed Arezzo on this trip.

  • Ami Bhat

    You just made Tuscany climb up by notches on my list. Those small towns are just so amazing. Lovely landscapes and so much of history. Am enamored by Pienza and Siena does makes me curious. Lovely post.

    • The.Holidaymaker

      This area of Tuscany is a feast for the senses, wonderfully romantic and so much history. I’m sure you’ll love it! Hopefully you’ll get a chance one day soon.

  • Pamela Mukherjee

    Tuscany has been on my list for a long. I loved the place as this place has so much to cherish. I have seen so many movies which have been shot here. Really want to visit this place.

  • Jennifer Prince

    Oh my goodness! Tuscany is so amazing – I need to head there. I love how it’s so laid back as you described it. The scenery is gorgeous, and I’d love to spend time exploring all of the historical sites you’ve highlighted. What a wonderful trip to take!

  • Trisha Velarmino

    When I hear of Tuscany, what comes to mind is verdant, quaint, alluring, and medieval. Looking at these photos, these are lovely paradises I can only dream about. Pienza looks idyllic!

  • Jan

    I love the Tuscay region. We drove through these rolling hills many years ago and visited Siena and Arezzo. Perfect drive to get scenic views, greenery and some history too. I would love to tour here once more and explore places that I missed. Enjoyed your blog post. 🙂

  • Agnes

    Tuscan Towns in the Siena Region is one of the most charming places in Europe for me. I love this part of Italy, its landscapes and wines. I love walking medieval streets. I agree that Montepulciano is one of the prettiest. And I love it’s wine as well. I also like Siena Cathedral and Cathedral of San Donato in Arezzo. It’s a perfect guide to the Siena region!

  • Debra Schroeder

    This post has inspired a strong need to travel to Tuscany now. I’ve yet to visit and your photos are compelling. Pienza would be my first stop because cheese is one of my weaknesses.

  • Linda (LD Holland)

    We definitely did not spend enough time in the Tuscany region around Siena. We did not have a car so did day trips that we could easily do by bus or train. But I can see we need to rent a car on our next visit and see some of these amazing small towns around Siena. I must admit I sighed when I read this post. My longing to return to Italy is so great!

    • The.Holidaymaker

      Always happy to inspire or relive those past memories. We are so glad we decided to rent a car for that very reason, driving the countryside in Tuscany was a definite highlight in of itself. Hope you are able to return to Italy one day soon.

  • Danik

    I loved exploring this region, the rolling hills of the countryside, the vineyards and of course the main city, Siena, so beautiful perched on top of the hill. I spent quite a bit of time here in the non-tourist season with good weather and enjoyed every moment of it.

    • The.Holidaymaker

      Glad to hear that you have experienced this region as well, and enjoyed Siena. Thanks for sharing your experiences as well.

  • Brianna

    What beautiful landscapes! I can totally see myself relaxing here, wine in-hand…. It sounds like you had a marvelous time, and the pictures are wonderful!

    • The.Holidaymaker

      That is exactly the point Brianna, to slow down, relax and enjoy life…which is all about food and wine in Tuscany. Hopefully you get to visit it one day! Thanks so much for stopping by and reading the post!

  • yukti

    Tuscany towns are very interesting and beautiful as they have a perfect blend of beautiful nature and Italian countryside living. The architecture of Pienza and Cortona looks splendid.

    • The.Holidaymaker

      You are exactly right…and they are never too far away from a big city, in this case Florence! I really did fall in love with both Cortona and Pienza. Thanks for commenting!

  • Yara

    Siena was one of my first travel adventures in 2010, it sprung my love for traveling and discovering the world. Thank you SO much for taking me down memory lane, the photos are stunning.

    • The.Holidaymaker

      I am glad it sparked some memories for you. Siena was a great city to visit, so much different than the others. Loved the gothic feel of the city and history. Thanks for commenting.

  • April

    Never been to Europe yet and if ever our chances will bring us there I want to make it to Paris, Italy, Venice and France. I love the pictures it is enticing to look at and it’s one of our bucket lists! Thanks for the info!

    • The.Holidaymaker

      Thank you for commenting April, and hope you get to travel to Europe. No matter the country, it offers a diverse range of options and all with an incredible about of history.

    • The.Holidaymaker

      Doesn’t hurt does it? We are planning a trip in the near future to visit Umbria. That has been on my list. Hope you get there one day soon!

  • Nitin Singhal

    Italy is my Top 5 bucket list destination and I had not even considered Tuscany before. So many beautiful but different towns at a short distance from each other. Open fields with mountains in the backdrop, old town with incredible architecture, and so much history. I would definitely add Tuscany on my Ital travel destinations

    • The.Holidaymaker

      Yes, Tuscany is all that and more. If you had the time, I recommend that you include it as part of your trip and offset it with being in a big city, like Rome. It is incredibly scenic and relaxing, and offers great food and wine as well. I hope you get there one day soon!

    • The.Holidaymaker

      You are quite welcome. If that is your favourite wine, then you need to one day visit. The wine cellars are plentiful and a great way to taste the different varieties. Thanks for stopping by and commenting.

  • Nicola

    These photos are just dreamy, I love that combination of rolling hillsides and rustic towns with so much history and such beautiful architecture. This is a region of Italy we’ve not managed to visit just yet but looking at these images we really do need to get there!

    • The.Holidaymaker

      Tuscany is such a large region in Italy, that it really does require some time or multiple trips to explore. I hope you get to see it one day. Thank you for your kind words.

  • Joanne

    You have me longing to visit Tuscany. I’m tucking this post in my back pocket for when we finally start planning. The Siena House looks perfect for our family. I love that its in the Tuscan landscape but still just a short drive away from beautiful cities that we would definitely want to explore.

    • The.Holidaymaker

      I am so happy that this may have inspired some future travel plans. Siena House is such a wonderful place to stay, check out their website for the entire set of photos. Feel free to reach out if you would like any further advice. Happy travels!

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