Italy

Touring Tuscan Towns in the Siena Region

What do you picture when you think of Tuscany? Me, I think of the green rolling hills, towering cypress trees, curvy roadways, vineyards and hilltop towns. It’s rustic, laid-back, scenic and peaceful. A place where you can slow down and appreciate great food and wine. You can plan your trip around your passions and let that be your guide. Whether you’re a foodie and want to enjoy simple yet delicious cuisine and wine. Or maybe you love architecture and want to see where the Italian Renaissance started. Enjoy art history or cycling or maybe you’re are a sun worshipper and want to experience the Tuscan coastline. Whatever the reason, you’ll find it and a whole lot more. We, loved to tour the Tuscan towns, and here were some of our favourites.

The most scenic drives are in Tuscany, Italy. Visit Tuscan Towns of Siena, Pienza, Montepulicano, Cortona, Arezzo

Siena House

Every holiday starts with finding the perfect accommodations. I love finding those special properties that often become the highlight of our trip. The Siena House did just that. It’s a large villa beautifully restored to accentuate the authentic Tuscan features both inside and out. The modern interior is light, bright and airy. Every window is strategically placed to highlight the mesmerizing panoramic views. The hosts, Malvin and Amanda, are welcoming and make sure your stay is an experience to remember. There are four large guest suites named after the view. Ours was Siena. You have access to a large lounge, a mezzanine, a pool and an outdoor summer kitchen. You stay also includes a delicious homemade breakfast.

Stay at Siena House. A restored Italian villa in the Siena Region
Upon arrival, we were treated to a bottle of champagne and light snack situated to watch the Tuscan sun slowly starting to fade. It is a wonderful memory that still lingers today.
Stay at Siena House. A restored Italian villa in the Siena Region
Stay at Siena House. A restored Italian villa in the Siena Region
The large pool is surrounded by the uninterrupted Tuscan views.

Siena House is well-situated in making many of the sought-after towns a short drive away. Some of our best memories were driving those super-scenic small roads that linked together the views, villages and vineyards. Here were some of the towns we were fortunate enough to visit.

Montepulciano

Visit Montepulciano- a tiny medieval village in Tuscany

Closest to Siena House is Montepulciano, only a short 10 minutes away. It’s a lovely village that offers a few traditional shops, restaurants and wine tasting cellars. This area is known for its full-bodied red grapes, and there are many varieties to sample. The the small Piazza Grande shines bright with marble and travertine.

Montepulciano a small Italian village full of wonderful wine tasting cellars
Visit Pienza, a lovely hilltop town in Tuscany

About 20 minutes from Siena House, is Pienza. This UNESCO World Heritage hilltop town is famous for its Pecorino di Pienza, a hard sheep’s milk cheese. I immediately fell in love with this small, quiet, romantic town. Wander the delightful narrow stone streets, its inviting piazzas and breathtaking views, this is definitely a town you need to visit. 

Pienza, a hilltop Tuscan Town featuring the best views, unchanged Renaissance architecture and dining options.

Cortona

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.

Just over 30 minutes away from Siena House is Cortona. It looks and feels a bit different than the other towns we visited. It’s a stone-clad town with a magnificent medieval tower, as well as, a larger and busier piazza – perfect for people watching.  Under the Tuscan Sun, first the book and then the movie, put this town on the map. 

Views from Cortona, is just one of the reasons why you need to visit this Tuscan Town
The views from Cortona

Arezzo

Visit Arezzo, in Tuscany Italy. It is a larger city full of museums, art galleries, antique markets, fine shops, monuments, and historical buildings

A bit farther from Siena House, at about 45 minutes away, is a larger city full of museums, art galleries, antique markets and boutique shops. This city was the backdrop to the movie Life is Beautiful where in the historic city center you will instantly recognize some of the locations like the piazza, the Palazzo delle Logge and a couple of the churches or basilica. 

Visit Arezzo, in Tuscany Italy. It is a larger city full of museums, art galleries, antique markets, fine shops, monuments, and historical buildings
Visit Arezzo, in Tuscany Italy. It is a larger city full of museums, art galleries, antique markets, fine shops, monuments, and historical buildings

Siena

Siena, a large medieval city in Tuscany

The farthest away from Siena House, by almost an hour, is the city of Siena. This large medieval and gothic city can’t be missed. At its center, is the incredible Piazza Il Campo, the red palazzo pubblico and its tower. Next venture off and get lost in the winding alleyways, as there is a lot to discover. Of all the cities, this was the most touristy, but for good reason. 

Siena, a large medieval city in Tuscany
Siena, a large medieval city in Tuscany
Siena, a large medieval city in Tuscany

As a holidaymaker…

Tuscany is definitely one of those destinations that you are sad to leave and you long to return to. There are just so many small towns and villages dotted along the Tuscan hills. And, these were definitely some of our favourites. 

Visit some of the best Tuscan Towns in the Siena Region - Montepulicano, Siena, Pienza, Cortona, Arezzo
Visit some of the best Tuscan Towns in the Siena Region - Montepulicano, Siena, Pienza, Cortona, Arezzo

24 Comments

  • 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!

  • 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.

    • 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.

  • 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

      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!

  • 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.

  • 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.

  • 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!

  • 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!

  • 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.

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