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Rome, Venice, Florence, these are the most common first destinations for people visiting Italy. And I like all three. They are vibrant, fun and full of history. But when you have more time, there are the hill towns of Tuscany. These are mainly located just south of Florence and north of Rome.

My wife and I just spent a week there in late May / early June. We picked Montalcino for our lodging. Montalcino is close to the center of all the Tuscan hill towns so it makes for reasonably short drives to any place you wish to see.

For lodging there are two distinct locations you can pick in Tuscany, in town and the countryside. I have enjoyed and can recommend both. This trip we picked a small in town hotel, Hotel del Capitani. It combined a few things my wife and I like; such as walking to a variety of restaurants if we need something close, plus, being on the edge of the town, it has a spectacular view (the photo above was taken from our window). And a pool, nice for after a warm day of hiking or sightseeing.

Montalcino is an average size hill town, noted mainly for being on a very steep hill and the only place in the world that produces the famous Brunello wine. (Tip for the budget conscious: if you like the taste of Brunello, but don’t like the paying the average $80 -$100 a bottle, Rosso di Montalcino is made from the same grapes and aged 3 years in oak barrels as opposed to the minimum 5 for Brunello, AND costs less than half.)

We celebrated Republic Day in Montalcino. It is their Fourth of July, Bastille Day holiday. Even in this small town the party was festive.

Exploring is the main purpose of staying in the hill country. If all you have time for is a day trip from Florence, then either Sienna or the classic, tower filled, (and overcrowded in the summer) San Gimignano are your best choices. They are just south of Florence, about one hour in a car.

I like both of these towns, but if you are staying in Tuscany for a while I think you can spend a full day in Sienna (and a couple of hours in San Gimignano). On the streets of Sienna you can be transported back to the 1500’s with its dark, medieval architecture. You can almost feel the rivalry of the 17 Contrada (sections of the city) with their colorful flags and banners hanging from their buildings. For more than 800 years they have competed twice a year in the Palio, a bareback horse race staged in the town square.

The drive to San Gimignano from Montalcino is about 2 hours on local roads. I prefer this in Tuscany to the freeway as you can stop in some of the local villages and explore and often have a wonderful Italian lunch or dinner at a small family restaurant that really is there only for locals.

On the drive back from San Gimignano, we made a last-minute decision to stop in a very small walled hill town, Monteriggioni. This stop is typical of what I recommend you do if you spend several days in the hill country. We had no idea what to expect and loved the small feel of it. To our surprise, there were several interesting shops, a couple of nice restaurants, and even a nice four-star hotel. And an ice cream shop we just had to try out. I wandered to the ‘back gate’ for the photo below.

On this trip we went to some of the more known hill towns close to Montalciono, all were fun to visit: Montepulciano, Pienza, and San Quirico d’Orci. There are vineyards and wineries and tasting rooms throughout the Tuscan hill country. So if that is your thing, you will not be disappointed.

We added something this trip which was a good fit for us. We decided to find a long hike we could make. It was warm so I wanted to combine some time wandering the vineyards with some time in forests and also adding a view. Using one of our hiking apps we found a four to five-hour loop hike rated ‘moderate difficulty’ starting and ending in the small spa village of Bagno Vignoni (the main hot springs shown in photo below). Bagno Vignoni is only 30 minutes from Montalcino and has several spas and restaurants, plus a very intricate set of hot springs, canals, waterfalls and ponds.

It started as a nice sunny day with a few clouds and we quickly started walking through the vineyards. I found this very fun as the trail was well marked and actually went through private property in many places. The vineyard owners put gated openings so that we really just walked on our own through many vineyards. Really made us connect more with the whole feeling of Tuscany.

After an hour or so of that we started up a slow winding trail to the top of the hill we were on. To our surprise the hilltop was occupied by the small hamlet of Vignoni. There were no commercial establishments here. So it felt like a bit of a ‘discovery’ for us. You can ask my wife about our ‘discovery’ of the young woman ‘sunbather’ as we left the hamlet.

On the way down the hill we had a great View of Rocca di Tentennano. No, we did not hike to the top of that, but after a nice pizza in Bagno Vignoni we did drive over to the old fortress. It is the highest peak for miles around so has a spectacular view from the top.

My wife does most of the driving in Europe as she loves a stick shift car. You can imagine her joy when she came up behind this Lamborghini. He did eventually ‘leave us in the dust’, as they say. 🙂

I hope you have been enticed to give a few days in the Tuscan hill country. A couple more photos below from our room in Montalcino to make sure you plan a trip soon.