Tuscany, Italy

Tuscany, Italy

Where to stay in Tuscany

So you’ve decided you want to explore one of the most popular wine regions in Italy, and even the world.  Even if you don’t drink wine, the homemade olive oils and pastas are not to be missed either.  You’ve been dreaming of the classic images of Tuscany…. the endless gold and green hills covered in vineyards and olive groves.  The only question is…. where should you stay?

We ran into this exact conundrum when planning our time in Italy. We knew we wanted to explore the iconic region of Toscana, but we had a lot of questions.  The Tuscany region was actually a lot bigger than we originally thought, and once you get off the highway, the roads are narrow and windy so it takes time to drive around. Slow country roads definitely have some advantages in the scenic drive category, but also present time challenges if you plan to explore multiple areas. There were some roads that we drove on that took us 30 minutes to cover 5 or 10 miles.


tuscan provincesTuscany is broken into 10 Provinces, each with very different characteristics.  It stretches from castles in the southern Provinces, to coastal towns, to mountain towns in the Garfagnana, to the city of Florence.  We’ve included a map that outlines the region for reference.  To best answer your question about where to stay, you will need to make two main decisions.  First you will need to decide if you want to stay in the city, or out in the country. Both have advantages and disadvantages, but this part really is a personal preference.  When we were searching, we found apartments in Florence (Firenze) overlooking the Duomo, and also villas and cottages nestled in vineyards far away from the hustle and bustle of the city. Both would have been amazing, it just really depends on what kind of vacation you want to have. The other decision you need to make is what you want to do and see during your visit and how much time you have to do so.  Do you want to see the leaning Tower of Pisa, do you want to see the ocean, do you want to do wine tastings, do you want to explore medieval castles? Once you decide on the things you’d like to do, and then pick city or country, you’re pretty much in the home stretch. One option, and our original plan, was to stay in Florence. Florence itself is a main attraction and a must see city in Italy. Plus from Florence, you have direct access to the highways (Autostrada) as well as trains. Most of the things you will want to see in Tuscany are close enough to Florence for a day trip. Everything from castles, to wineries, to Pisa, you can reach within about an hour.  Staying in the country will not be as convenient, as travelling between areas takes longer, and trains are often not available so a rental car may be needed. But the scenery, the relaxation, the small town locals, and amazing food make up for the convenience factor quite handily. You have probably noticed that we failed to add in our beautiful shot of Florence above, and that is because we don’t have any. Due to the fact that we had just spent time in Rome, we were city-ed out and wanted to relax in a country villa.  So we missed out on Florence for this trip and for decision 1- we went country.

Olive grove in Tuscany
Aerial view of Chianti Region

Decision 2 was deciding what we wanted to accomplish. Our list had 3 main objectives-

  1. We wanted to see some amazing wineries. Drinking a Chianti in Tuscany was an item on our bucketlist and we really wanted to enjoy some great Tuscan wine and food.
  2. We wanted to drive through the Val d’Orcia which is an area in Tuscany considered one of the most scenic drives and is also a UNESCO World Heritage site.
  3. We wanted to relax and have some down time and just enjoy our time here. We often rush between places and try to see so much because often we know we aren’t coming back soon.  In Tuscany, we just decided to open wine, stroll through vineyards, and watch sunsets.


Based on our wish list, and since we were driving up from Rome, we felt our best bet was to look for a place in the Siena Region. It includes the three main areas of Toscana wine (Chianti, Montalcino, and Montepulciano) as well as the Val d’Orcia which we wanted to drive through. We used Airbnb to look for private villas in the area.  There were many to choose from so we were able to scour through and pick the one that met our needs the best. Just make sure to specify the region in your search. If you just put Tuscany you could end up looking at properties that are no where near your desired location.  We opted for a beautiful stone Tuscan villa in the Chianti Region. It was 2 story, with an enclosed outdoor patio, a pool, and vineyards as far as you could see. It was exactly what we were looking for.

Our villa from above, Tuscany

Along with the amenities and the beautiful, peaceful countryside, it was in a perfect location. It was far enough away from things that you felt secluded, but only 10 minutes from a small little town called Castelnuovo if you want to grab groceries, or sneak a late night Gelato at the Cafe. But just remember… you aren’t in Kansas anymore (or even Rome) so don’t expect the locals to speak a lot of English. So practice up on your grazie’s and buongiorno’s and try to blend in a little.

Of our 3 objectives for Tuscany, number 1 was wine. Chianti is one of the most famous wines in the world and staying in the Chianti Region, you have as many choices as you have olive trees.  There are wineries everywhere around you serving the black rooster branded bottles, and you are within an hour of Montepulciano (Nobile wines) and Montalcino (Brunello wines) as well. We will be diving deep into our winery tours in much more detail in an upcoming post for those of you interested in great wineries to visit. For now… here’s a sneak peak.

Castello di Brolio

The great thing about driving around exploring wineries is it helped us accomplish our goal number 2…. the Val d”Orcia. When you see iconic photos of Tuscany’s golden landscapes with towering cypress trees, you are most likely looking at a picture of Val d”Orcia.

Val d’Orcia, Tuscany
Val d’Orcia, Toscana

Objective 3 was the most important and also the easiest. Sometimes you just need to take some time to yourself and enjoy your surroundings.  When you find yourself in a place this beautiful and slow down and look around, it can feel quite surreal.  We went to our favorite little local grocery store down the road and had the butcher carve us up some fresh meats and cheeses and picked up some fresh Tuscan pici pasta so we could prepare an authentic Tuscan dinner (as authentic as you can get with a non Italian cook anyway). Every night we grabbed some delicious, newly acquired wine, and walked out into the vineyards to watch the sunset.


We found a nice little stone wall to sit on overlooking the olive groves and turned it into our private little picnic area…. ok, it was really just wine and a blanket.

And speaking on sunsets… If you have never experienced the sun setting over Tuscany, you should consider yourself a lucky person.  You will spend the rest of your life disappointed as other sunsets will suffer in comparison.  The sky here is just so big and the clouds are immense which just added to the dramatic colors. We saw different colors every 10 minutes as the sun continued over the horizon. Pictures do it no justice.

Sunset in Tuscany


By the end of our time in Tuscany, we were extremely sad it was over. We really did fall in love with this part of the country. It satisfied everything we were hoping for and then some.  You know it’s an amazing place, when your next stop is the ocean and the Italian Riviera, and you don’t want to leave. At least we took 2 things with us that gave us some peace of mind…. one was some great wine, and the other was knowing we would be coming back to a different area of Tuscany in the not so distant future.  Until then… arrivederci Toscana!

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2 thoughts on “Tuscany, Italy

  1. What an exciting trip! Beautiful photos! I would love to see more photos of the villa that you stayed in.

    1. Thank you! Tuscany is amazing. We are going to upload some videos soon that will include a walk through of our villa.

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