Our Tuscan adventure began in the town for the most important part of any Italy trip: wine. We began in Montepulciano which is one of the most known Italian red wines all over the world. Known best, in fact, for its “Nobile di Montepulciano” wine, this quaint little hilltop town was the perfect spot to ease our way into the picturesque sights of Tuscany. We had driven down to Tuscany from Milan, straight along the motorway (about 4hours – we flew into Milan to see my boyfriend’s family first) and came off at Acquaviva, heading straight for Montepulciano.

It was such a funny feeling being in a place that you’ve always heard about but never really imagined existed. I suppose it’s a bit like visiting the Cheddar gorge after eating cheddar cheese your whole life (which I still need to do!), a funny experience! Anyway, the town itself was really cute, packed with winding streets, a beautiful square and an abundance of wine shops selling bottles made by all the local vineyards surrounding Montepulciano. As we were visiting at the end of March, it was relatively quiet, and cool, which I loved. We hadn’t eaten since breakfast so snuck into a little wine place (there are lots of them) and sat to enjoy a couple of glasses of different wines, along with some local cold cuts of cheese and hams. That is literally the exact thing I want to do as soon as I arrive in Italy – find a table under the sun, grab a glass of vino and a plate of taglieri…. bliss.

Our next stop on the agenda (we were only spending 4 and a half days in Tuscany, and were planning on cramming a LOT in the diary) was a leisurely drive through Val D’Orcia. If you or your partner love driving, this is the place for you. The Val D’Orcia is one of the famous areas of rolling hills in Tuscany, the cypress tree-lined roads and rustic vineyards go on further than the eye can see. Get a great playlist on and just get lost (we pretty much did get accidentally lost in the middle of a field, our car got stuck in the mud and neither of us had signal… luckily we managed to get out…though I could image worse situations than being stranded in a Tuscan vineyard!) Anyway, in short it’s jaw-dropping-ly stunning. I’m pretty sure the Val D’Orcia is where they filmed part of the Gladiator with Russell Crowe. It’s out of this world and if you find a yellow field at sunset, take some snaps during the golden hour, they’ll be unbelievably beautiful!

Next on the list was Pienza. This actually turned out to be my most special part of the trip, where my sweet guy, Luca, proposed to me…. hence it’ll be a place I never forget! It is another of the wonderful towns sets in the middle of the Val D’Orcia with the most spectacular views overlooking the entire valley. You can see a picture of the road leading up to Pienza that we took after finishing our afternoon drive through the Val D’Orcia, it’s the perfect spot to enjoy a coffee or afternoon ice-cream and take a stroll… or in my case, get engaged 😛

Our final stop for the night was Montalcino. We checked into our beautiful bed and breakfast, Porta Castellana and ended our first and very special day with dinner at Il Giglio, which I would highly recommend (Il Gigliois also a hotel!).



We enjoyed a leisurely stroll around Montalcino on our second day. We had breakfast in our cosy hotel room and despite having a wonderful garden that we could have sat in, it still wasn’t quite warm for that. Something I liked so much about our hotel in Montalcino was that it wasn’t right in the centre of the town, but just a 5 minute walk outside. It had the feeling that you were in the countryside, but was only a stone’s throw from the centre, so it’s perfect for that tranquil setting you might be after during your Tuscan adventure. We ventured into the town and enjoyed a morning stroll around the local market. I will say that Montepulciano is quite a bit bigger than Montalcino, but also more touristy, so you will have a smaller but less touristy experience in Montalcino.
Next stop on the list was Siena. What a beautiful place. I recently watched a documentary on Netflix called Palio which is about the Palio di Siena, an ancient horse race that takes part twice a year in the central piazza. The city is made up of contrade (like neighbourhoods) and each neighbourhood has a different symbol such as a dragon, a duck and so on. When the horses race in the Palio di Siena, each horse represents a contrada and the competition is fierce. It was just amazing to be standing on a square that such a historic race takes place even to this day… Whilst we were on the square we enjoyed a quick bite at Liberamente – have a spritz and a share a plate of burrata, it’s delicious! You can easily spend a whole day in Siena, especially if you love history and would like to learn more about the Palio di Siena. Before we left the city we also visited the Duomo di Siena, which is totally stunning. There are so many rooms to visit inside the cathedral, and you can also climb up the top of a view point near to the cathedral, but we didn’t have time to do all of that. Just be prepared, Siena is very hilly! It’s worth the climb, but definitely gives your legs a run for their money!
From Siena we headed up to San Gimignano. another beautiful hill top town, wonderful for an afternoon walk. We found an amazing spot for Aperitivo overlooking the Tuscan hills and also enjoyed a divine ice cream from Dondoli. They are known for their quirky and unusual flavours, Luca, my boyfriend, tried truffle and walnuts flavour.
Our final stop of the night was in a hotel near a town called Poggibonsi (we did not visit the town but I don’t believe it is big or of interest but I might be wrong). We had a room in a beautiful villa called Villa San Lucchese, a really pretty 4* place. It also has a great restaurant inside the hotel where we enjoyed a cosy dinner before calling it a night after a long day of driving and discovering!


Our third day was Easter Sunday in Italy and we spent a very lady day at a winery called Castello di Verazzano. For €50 per head we were given a tour of the castle and winery as well as a wine tasting session and 3 course lunch. It was a stunning winery and the tour was amazing, we found out their processes for the vines (which are totally organic) as well as how it takes 10 years to make their delicious balsamic vinegar. The castle is named after Giovanni di Verazzano who was an explorer in the 1400s and discovered much of the rest of the US after Christopher Columbus. It was a lovely 1 hour tour for history-buffs and wine lovers (our tour was in Italian but it can be done in English if you require) we started about 11:30 and finished around 3pm. I would highly recommend a day like this during your Tuscany trip, as it’s a chance for you to take a break from the road and switch off.
Following that we headed up to San Miniato, a very cute town, much quieter than San Gimignano but a lovely little place to stop for the night. We stayed in a hotel called Hotel Miravalle set on a stunning square in the middle of the town. The castle at the top of the town has the most incredible views, we climbed to the top the enjoy a spectacular sunset (I would advise grabbing a bottle of Tuscan wine, some snacks and enjoy a relaxing evening watching the sky change colours as the sun goes down). There are a number of pizzerias, restaurants and cafes in the town, so it’s very easy to find somewhere lovely to have dinner.


Our final day of our time in Tuscany was spent driving through one of the most famous areas of the region: Chianti. If you have a look at the map above, that was the route we took, but you really can just get lost stopping in different towns and wineries along the way. The particularly pretty towns in the area are Greve di Chianti and Radda, both of which are smaller towns than the likes of San Gimignano.
Since our tip was, of course, led by food and wine (as is any trip in Italy) we made sure to have a good place to stop for lunch. We had been told about the Antica Macelleria of Dario Cecchini, a butcher’s shop, turned restaurant. The tuscan region in general is known for it’s high quality meats (chianina – where cows graze freely on the val di chiana region), and particularly it’s Fiorentina steak. Dario, the butcher, was there in person welcoming guests and doing his job as a butcher. He’s a very well known personality in Italy in the food industry and often appears on italian cooking shows, so was quite the character. There was a queue initially but after being fed some wine and cheese while we were waiting, we were soon shown to our seats. The style of eating is in long tables sat next to each other as Dario wants his restaurant to feel like you are eating at his house. He came out halfway through the meal to say hello to everyone, and that since we were so brave to eat outside after the rain had cleared and the sun was out, the wine would be on him! Got to love the warmth and hospitality of Italians. And as a side note, Tuscany in general is very english friendly given the number of tourists visiting the region!
The next part of our trip would take us outside of Tuscany and into Liguria, as we were driving up to visit the Cinqueterre, however, it is very easy to spend a week or more in the region and just take your time having a relaxing break. Moving from hotel to hotel each night wasn’t ideal but as we had to cover a lot of ground, it was necessary for us! Some of the spots we didn’t visit which would have been the next pitstop on our itinerary would have been Pisa and Lucca. They say Pisa is only worth going for to see the tower and it is a very small town, while Lucca on the other hand is another beautiful Florentian town, probably similar to Siena. You can then of course visit more wineries and dive further into the various wines of the region, there are lots to get to know.
Last but not least would of course be to visit Florence itself (I have already visited so skipped it on this occasion) my tips for Florence would be:
– Dinner at Aqua al 2 – insane steaks (I’ve eaten there before and had the tasting menu, it was divine!!) Make sure you book as there are always queues.
– An afternoon walk through the Boboli Gardens (especially if you’re there late April/May when the wisteria is out)
– Climbing up to Piazza San Michelangelo for sunset
– Sundowner spritz on the rooftop bar of La Continentale Hotel
– Lunch/cake stop at Four Seasons Florence
– Visiting Florence Duomo
And that brings my road-trip guide to Tuscany to a close (finally)!!!!! I hope you have enjoyed this as well as found it helpful if you’re heading to Florence anytime soon – Buon viaggio!!!

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