Touring Tuscan Towns in the Siena Region

What do you picture in your mind when you think of Tuscany? Is it images of green rolling hills, towering cypress trees, curvy roadways, fortified farms, vineyards and sun-soaked hilltop towns? The quintessential Italian experience is just that – it is rustic, laid-back, scenic and peaceful. It is where you escape to; to slow down and appreciate great food, wine and lifestyle. The best part of Tuscany is that you can plan your trip around your passions and let that be your guide. Whether you are a foodie and want to enjoy simple yet delicious cuisine and wine, or maybe you are a history or architecture buff and want to see where the Italian Renaissance all started, or love art history, or cycling; or are a sun worshipper and want to experience the Tuscan coastline. Whatever the reason, you will find it and more. We decided to somewhat abandon our itinerary and just slow down. Let me share.

For us, it always starts with finding the perfect home base. I love finding those special properties that often become the highlight of our trip. The Siena House did just that. It is a large villa property 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. Our wonderful hosts, Malvin and Amanda, were incredibly welcoming and make staying at their property not just an accommodation but an experience.  We were provided a tour of the property which encompasses 4 guest rooms (ours was called Siena), a large lounge, a mezzanine, a pool and an outdoor summer kitchen. Depending on the weather, your delicious breakfast prepared by Malvin, will be served outside or inside in the large dining space.

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.
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.


Closest to Siena House, only a short 10 minutes away, is a lovely small village that offers a few traditional shops, restaurants and wine tasting cellars (we liked La Gatta Vecchia). This area is known for its full-bodied red grapes, and there are many varieties to sample. The Piazza Grande shines bright with marble and travertine, it is small but worth seeing.

About 20 minutes from Siena House, this small hilltop town and a UNESCO World Heritage site is infamous 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. Click here to read my post on Pienza.

Touring Tuscan Towns - Pienza |
Touring Tuscan Towns - Pienza |
Touring Tuscan Towns - Pienza |


Just over 30 minutes away from Siena House, it looks and feels a bit different than the other towns we visited. It is a stone-clad town – with one magnificent medieval tower, a larger and busier piazza, perfect for people watching, chock full of winding alleyways to wander and many stylish shops (I eyed a leather jacket in the window, and still to this day, regret not buying it). Under the Tuscan Sun, first the book and then the movie, put this town on the map; and for good reason, you will definitely want to visit here.

The views from Cortona


A bit farther from Siena House, at about 45 minutes away, is a larger city full of museums, art galleries, antique markets, fine shops, monuments, and historical buildings. 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. Although we did prefered the smaller towns, we understand why many will add this city to their must-visit list.


The farthest away from Siena House, by almost an hour, is the city of Siena. This large medieval and gothic city cannot be missed. At its center, is the incredible Piazza Il Campo, the red palazzo pubblico and its tower, but then 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 how could you not come to this area and see it.

Photo credit:

Tuscany is definitely one of those destinations that you are sad to leave and you long to return to. Our short visit of 4 days was not nearly enough. Do we wish to return? Absolutely…hopefully one day soon.

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  • 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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