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View of Siena from the Tower of Mangia

How NOT To Drive Through Tuscany

Vineyards, vistas, and pasta.

If I say the words "Tuscan Roadtrip" your mind likely floods with images of rolling sun-bathed hills, welcoming vineyards, weathered stone buildings, generous portions of fresh pasta, and long dreamy rows of Cyprus trees. Tuscany is all that and more.

It's with good reason that this destination draws global adoration and tourism year after year. In fact, 100 million tourists visited in 2017 according to Tuscan tourism, and that number keeps growing! My husband and I were two such tourists that dry, hot summer in Italy.

Tuscany is unapologetically romantic, breathtakingly beautiful, and dotted with incredible towns offering world-class food, architecture, history, and jaw-dropping scenery. There is a reason it's a classic. Even though it's an extremely popular area, there are still places with room to breathe.

Our 2017 Italian road trip was amazing. A whirlwind drive from Rome to Venice, stopping in a small sampling of Tuscany's most stunning towns and cities along the way. We ate our way from Rome to Venice, one bowl of Bolognese at a time.

Read on to see where we went and how I screwed up this trip, royally.

Breakfast in a Roman cafe.

Leaving Roma

After a carb-heavy breakfast in Rome, we picked up our rental car and started navigating our way out of the busy, sweltering city. We headed north towards Tuscany, with the thought of fields, trees, and Tuscan towns on our minds. I couldn't wait to set my eye on Tuscany for the first time!

Once the semi anxiety-inducing drive out of Rome was complete, we relaxed on the gorgeous open highways of Italy, snacking on (you guessed it) all manner of carby snacks while watching Italy roll by. It. Was. Amazing.

Our little Fiat Panda was perfect for our two-person mission through Italy. Air conditioning, check. The radio worked and, much to our surprise, the Italians were really loving Ed Sheeran that summer. I think we heard Galway Girl every hour on the hour! We cruised along, singing our hearts out on our way to postcard perfection.

Our first road trip stop? Montepulciano.

Our little Fiat Panda in Rome Italy.
Fiat Panda leaving Buonconvento, Italy.

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Montepulciano, the medieval and Renaissance hilltop town, made the perfect introductory Tuscan experience. First of all, there are no words to describe the beauty of this place, but here we go anyway!

Montepulciano is one of the many hill towns of Tuscany, perched at the end of a winding and movie-worthy Italian road. The photos and videos we captured just don't seem to do justice to the beauty we saw in person.

We climbed the steep, cobbled streets which were flanked with the town's flags, jutting out from buildings and fluttering in the breeze. The long climb to the top of the hill is worth it for the gorgeous views of the surrounding countryside and the stunning central piazza.

Naturally, we stopped for a well-deserved pizza and glass of wine at the top of the town, basking in the mid-day heat and people watching in one of the most stunning places I've been to.

Montepulciano and the region surrounding it are known for their wines, as is the entire Tuscan region, and this gorgeous city has wine cellars and tastings for you to explore.

If you're going to Tuscany, get this town on your list NOW.

The streets of Montepulciano Italy.
Views from the streets of Montepulciano.
The main piazza of Montepulciano italy.
Alleyways of Montepulciano Italy
Delicious pizza in the main piazza of Montepulciano.
The Hesitant Adventurer sittign in the main piazza in Montepulciano.
Delicious pizza in the main piazza of Montepulciano.

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Exhausted after a day of driving and site seeing, we decided to head to our Agriturismo in Buonconvento early, so we could settle in, swim in the pool, and, most importantly, find 2 massive bowls of pasta.

To begin with, we knew nothing about the tiny village of Buonconvento other than that it was a place to lay our heads. The small, but the charming town turned out to be one of the nicest evenings on our trip.

Things got off to a rocky start after struggling to find something to eat. Panic set in and we started to worry about finding something AT ALL. Many shops and restaurants were closed because of the day of the week (Sunday If I remember correctly), but after some driving around with growling stomachs, we made our way down to the old part of town and found carb heaven.

You can find the small restaurant Ristorante Roma nestled in cobbled streets of the old town. After filling our bellies with pasta, scallopini, potatoes, and cake, we lazily strolled the streets in the evening light, watching groups of young locals drink and eat at the neighbouring trattoria. We slowly made our way back to our Fiat and headed to the agriturismo to sleep.

If you're looking for a small, lesser-known town to visit, Buonconvento might be just the spot. In any case, it made the perfect stop between Montepulciano and Siena. Drive through the Val d'Orcia from Montepulciano to Buonconvento for the perfect day in Tuscany.

Driving through the Val D'Orcia, Tuscany.
Albergo Roma, Buonconvento, Tuscany.
Cake from Albergo Roma, Tuscany.
Albergo Roma, Buonconvento, Tuscany.
Cake from Albergo Roma, Tuscany.
View of Tuscany from our Agritourismo.


We arrived in Siena early in the morning, after leaving our Agriturismo at near dawn. Thanks to jetlag these early morning departures were a breeze.

We walked the shady streets and alleyways from the outskirts of town into the centre. The walk into Siena was uphill, but not a steep incline like Montepulciano, which was a real treat for our burning calves. Shops and cafes were just opening and beckoning us in for an espresso.

After a few turns, mostly following the other tourists in front of us, we found ourselves stepping out of the shade into the sun-soaked Piazza del Campo, framed by cafes, restaurants, and the Pubblico Palace, and the Tower of Mangia (Torre del Mangia).

The nearby Duomo is also stunning and a must see.

Thankfully, I was able to talk Max into climbing the Tower with me, as the Tuscan heat crept into the Piazza. We climbed the tower and I cannot recommend it enough! It was a hot July day, but the views are well worth the effort.

After a couple of hours exploring Siena, we hopped back in the Fiat and made out way to our final Tuscany destination, Florence!

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View of Siena from the Tower of Mangia
View of Siena from the Tower of Mangia
View of Siena from the Tower of Mangia
Climbing the Tower of Mangia in Siena.


After a busy 2 days visiting Montepulciano, Buonconvento, and Siena, we ended our Tuscan journey in Florence.

Comparatively speaking, Florence felt like a HUGE metropolis in stark contrast to the sleepy hill towns we had been visiting up until this point. We slowly strolled around the crowds of tourists, trying to find space where we could. While the crowds were oppressive during our July visit, famous sites such as the Ponte Vecchio did not disappoint.

The Duomo was jaw dropping and we spent most of our first evening eating gelato and just staring at it. It is to this date one of the most impressive sights I have been lucky enough to see.

After one evening in Florence, we left Tuscany heading for Bologna, Modena, Verona, and Venice.

So, how did I screw this trip up royally? You may already be able to tell. Scroll down to read.

The Duomo in Florence, Italy
The Duomo in Florence, Tuscany.
Eating gelato on a bench near the Duomo in Florence.
The Duomo in Florence, Tuscany.
Streets of Florence, Italy.
Florence, Tuscany, Italy

How I Screwed Up Our Trip

So, how did I screw up our Tuscany road trip in a major way? Here it is.

This trip was TOO SHORT. I don't mean, "Oh I just don't want to leave", or "There is never enough time in the day to see it all" kind of short. I mean gruellingly quick.

The entire road trip was like a lightning bolt. A bang, and a flash, and then gone. We only spent 2 days total from Rome to Florence. Two. DAYS!

Roadtrip Re-do?

We packed way too much into too short a trip and it made it tiresome. We were hot, exhausted and always on the move. It was too much, too quickly, and I wish we could go back and do it over (which we very well might in the near future).

This trip pre-dates our nomadic lifestyle. We had a finite number of vacation days to use, so our trip was short. In true vacationer mode, I overpacked the roadtrip, trying to fit in every single thing.

We have learned since then to slow down, smell the vino, and take a breath.

Now, we are fully nomadic, which means we are able to spend a whole month in a single city, as opposed to 2 cities per day like on this trip. While I'm kicking myself for how aggressively I planned this Tuscany trip, I hope we will have the opportunity to go back and do it properly.

Now that I have my planning hat on, tell me where you've been in Tuscany! Have a small town, village, or city I need to see on my next trip? Send me an email and let me know!


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