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Fancy a Tuscany road trip? Love wine? Read this.

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Tuscany road trip
Road tripping between Montepulciano and Montalcino in Tuscany


A few years ago, I had the pleasure of drinking a bottle of 2008 Casanova di Neri Brunello di Montalcino. I instantly declared it one of the best red wines I had ever tasted and can still feel its perfectly smooth and silky finish. Fast forward to October 2017, when Nick and I travelled to Italy for the first time with his sister Ashley and her now husband Dale (who goes to Italy for their 35th country?! It was LONG overdue!) A Tuscany road trip to check out medieval hill towns and drink full-bodied reds was high on the priority list.


Wine is one of my favourite things. I started learning about wine from age 18 serving in fine dining establishments. Since then, I’ve made it my mission to sample many wines over a 19-year drinking career and visit a plethora of wineries in North America. Much of my social life revolves around wine, so the thought of a Tuscany self-drive wine tour complemented by seeing the highlights of the region seemed like the thing to do. It should be on any wine drinker’s Italy bucket list.


Our Tuscany road trip started after three days in Rome. We covered Montepulciano, Montalcino, Siena, and the Chianti region in our rental car before abandoning it for two feet and a heartbeat in Florence. Hubs did an awesome job driving, which was surprisingly easy (check out this article on driving in Europe if you’re worried). Six wineries, 13 gelatos, a forced shot of Grappa, countless sights, and 27 glasses of wine later (kidding, who’s counting?!), we chalked our road trip up to a 10 out of 10.


One important sidenote: it was truffle season. This may not mean much to you, until you sample the various delectable dishes with fresh truffles. October is a very nice month to visit Italy if you’re a foodie.


Tuscany road trip
Beautiful landscapes in the Chianti region of Tuscany


Side stop in Orvieto, Umbria en route to Tuscany


We started day one by leaving Rome and driving to Orvieto, in the region of Umbria. What a treat! Orvieto was DEAD compared to busy Rome, and the Piazza del Duomo (main square) had an unexpectedly quiet charm. We walked into the square and came face-to-face with the gorgeous, gothic Roman Catholic Duomo di Orvieto (Orvieto Cathedral), which was surrounded by quaint cafes with enticing patios and brightly coloured flowers.


Did I mention no one else was there? After marvelling at the cathedral, we sat down to a mouth-watering table full of Italian appetizers, paired with a flight of Italian wines at Enoteca al Duomo. The sky was blue, the sun was shining, the company was great, and we couldn’t have been much happier.


Tuscany road trip
Not many things are better than Italian food and wine – Enoteca al Duomo in Orvieto


Montepulciano + two wineries


Of all the places to visit in Italy, I doubt you’d find Montepulciano in many people’s top five. But what a charming medieval hill town! Amazing leather shops, gelato joints, and quaint cafes line steep, narrow streets with tall brick and stone buildings. Tourists were low volume. It was an excellent place to lose track of time.


We stayed at a quaint agriturismo (effectively a farm designed to also receive guests) called Agriturismo la Corte Del Cavalierino just outside of town. We had our own two-bedroom cabin with a kitchen, wood burning fireplace, and beautiful views of the Val D’Orcia and Montepulciano. This agriturismo also had a pool, hot tub, gym, and lovely hosts, so please consider an agriturismo for the unique experience.


Our time in town was filled with eating, shopping, wandering, and wine tasting. Highlights: get a spot on the terrace at Antico Caffe Poliziano for breakfast and a stunning view. If you want to be highly tempted to buy a gorgeous and unique pair of Italian leather shoes (or perhaps a leather coat), stop at Maladetti Toscani. Enjoying vino and charcuterie at an enoteca (wine bar) must be done. If you ask what’s on the charcuterie board, you may get an answer like, “It is my fantasy,” in an ever-so-Italian accent. YES PLEASE, SIR.


Tuscany road trip
Strolling through Montepulciano


The wineries: to taste the Vino Nobile di Montepulciano, be sure to stop in at De’ Ricci near the Montepulciano town square. The dark, cavernous and grandeur cellars dating back to Etruscan times make you feel like you’re in a scene from Game of Thrones, and you’ll be treated to a tasting at the end. Not our favourite wines, but still worth a stop for the experience.


Winos with more discerning taste buds should visit Avignonesi outside of town. It offers a lovely selection of red and white wines such as the Nobile di Montepulciano and a Sauvignon Blanc. The Tuscan vineyard scenery was stunning at sunset. So much so that as Ashley and Dale romantically strolled by the vineyards, I couldn’t resist yelling, “bend the knee!” to Dale (who proposed to Ashley days later in Lake Como).


Tuscany road trip
Under the Tuscan sunset… the vineyards of Avignonesi Winery outside Montepulciano


Montalcino + two wineries


Next our Tuscany road trip took us to Montalcino – a hill town I’d describe as a smaller, less exciting version of Montepulciano. It was a quaint place, but just didn’t have the same charm. So we focused on surrounding wineries.


Winery 1: On our drive to Montalcino, something wonderful happened. On a rural Tuscan road with nothing much around, hubs noticed a small sign with the Casanova di Neri logo on it. What?! The same winery that made pretty much THE BEST red wine I had ever had a few years back?? Jackpot! A gorgeous stone building led into a contemporary tasting room with no one there. We tried all the wines, including the famous Brunello di Montalcino (of which the 2010 Brunello di Montalcino Tenuta Nuova scored a perfect 100 by esteemed wine critic Robert Parker), then spent too much money on wine.


Winery 2: Our next stop was Poggio Antico for a tasting. Although the tasting fee was high (15 Euros for fives wines), there was a wide selection of choices, including the Rosso di Montalcino and Brunello di Montalcino, and we enjoyed the pours. The estate is lovely, featuring manicured cypress trees, olive groves and of course vineyards.


While in Montalcino, you may also want to check out Solaria, an all-female run winery that offers private tours and tastings (book ahead).


Tuscany road trip
Casanova di Neri Winery outside Montalcino – my fave of the trip


Chianti region + two wineries


On our way from Montepulciano to Florence, we spent the day exploring the Chianti region and visited two wineries near Greve in Chianti. We also found a restaurant that unexpectedly ended up being one of our best meals in Italy.


I love finding myself in somewhere I didn’t know existed. Just outside Greve in Chianti is the minuscule village of Montefioralle, one of the most ancient in the Chianti area, and a stunner. We started at the Montefioralle Winery for an outdoor tasting of its Chianti Classico wines. I found the Chianti wines lighter-bodied and not as refined as the Montepulciano and Montalcino wines. But we were the only people there, nestled under the olive trees enjoying wine and good conversation, so who am I to complain?


Tuscany road trip
View of the village of Montefioralle from the vineyards of Montiefioralle Winery


The closest restaurant for lunch was La Castellana, which was as cute as ever, with stone walls, fresh flowers and an intimate setting. It was probably the best meal we had in Italy (closely followed by pistachio lasagna in Rome), and was henceforth referred to as “the lunch.” The pasta was unreal and of course there were truffles involved. I’m salivating thinking about it.


Tuscany road trip
“The lunch” – truffle-y pasta goodness at La Castellana


From there we drove to Castello di Verrazano, another winery outside Greve in Chianti. More polished than the last, it was a “castle” with guided tours, a fancy restaurant, and many more people. We sat in the outdoor tasting area with vines of edible grapes hanging overhead. We tasted their various organic wines – Chianti Classicos of different quality levels and Bianco di Toscanas. This place is definitely worth a stop on your Tuscany wine tour.


Siena Day Trip


Siena is must-see city to hit up on your Tuscany road trip. You could easily spend more than a day there, but with our full itinerary we only spent one. Because of this, I’ll let your guidebook or one of my fellow travel bloggers be your full authority on Siena. But it was a great day so worth a mention in this post.


A sunny day in Siena had us again wandering, popping into shops, and gazing at the sights. All who visit must see Piazza del Campo – the main public space and one of Europe’s most famous medieval squares. We then ate Margherita pizza and downed espresso, before checking out the impressive Duomo di Siena. Gothic architecture is one of my favourites, so I was super impressed by the exterior and even more, the interior.


Tuscany road trip
Torre del Mangia in Siena’s Piazzo del Campo (historic square)




Every perfect Tuscany road trip begins or ends in Florence. I’m likely not the first person to tell you this city is amazing and would need another blog to rant about its abundant character. So here’s the high level, or you can check out this post on Florence for the top things to do. We didn’t visit any wineries here – most will head on a tour to Chianti or somewhere outside of the city.


Just get lost. Seriously, put on some damn comfy shoes and get lost in this city. Walking is the way to go – many of the main attractions are within walking distance from each other, and you’ll feel better about all those gelato, pasta, and wine calories. Don’t miss heavy hitters like the Duomo, Ponte Vecchio, and Piazzale Michelangelo, with its sweeping views of the city. Stop for AH-MAY-ZING gelato or delicious eats and cheap wine at enotecas that spill out onto the street. There’s excellent shopping too. If time permits, you may even opt for a day trip to Pisa.


It’s best to plan a few things in advance such as buying Uffizi Gallery and Galleria dell’Accademia tickets. If you’re there during a busy time of year or want a specific restaurant, make reservations in advance. Il Vivandiere was one of our favourites, with cheap and delicious Syrah right out of the barrel.


Tuscany road trip
View of the Ponte Vecchio in Florence from our Air Bnb window facing the Arno river


Final thoughts – Italy and a Tuscany road trip


I feel as though I’ll never see all I want to see in Italy. It’s one of those top-notch countries on everyone’s list with endless must-see destinations. But for my first time in this multifaceted country, Rome, a Tuscany road trip, and Florence was a great start. Although I loved soaking up Rome and Florence, the highlight of this trip was exploring the rural and less touristy spots on our road trip. And besides, everything is better with an Italian wine buzz.


Planning on road tripping more of Italy? Check out this post on How to road trip eclectic Sicily.


Road tripping and wine tasting my way through Tuscany is among my Top 10 Exhilarating Travel Experiences – check it out if you haven’t already!


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  1. Josy A

    This sounds EPIC! I mean, six wineries, 13 gelatos, a forced shot of Grappa, and 27 glasses of wine!? What a holiday!! 😉

    I know the cities are more famous, but I think I like the look of the small towns and teeny wineries best. It really looks like you fell into a little slice of Italian heaven!

    P.s. How much wine did you end up posting home!?

    February 13, 2019 Reply
    • YOLO Travel Experiences

      Haha Josy, yes it was pretty epic! And totally, Italy has cities with so much to see, but I love the quieter areas. I think we only brought 3 bottles of wine home but I now wish we would’ve sent more!

      February 22, 2019 Reply



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