Siena is the gateway to your visit in Tuscany. You can arrive here by train or plane. If you fly, you will need to arrive in Florence and then rent a car or train. If you are able to rent a car, I would highly recommend it for this area because it will give you more freedom to explore. Alternatively, you can arrange for a driver; however, this will likely add up quickly. Siena was my preferred area to stay because it sits between the Chianti region, as well as the more southern central Tuscan hilltop towns like Montepulciano and Montalcino. If you have a preferred type of wine that you want to try, perhaps adjust your location based on your preferences. Although if you are generally open to different areas and want to explore – I would stay in Siena or surrounding towns. 

How to get there?

We arrived in Florence on the early morning flight from London. Vueling (a discount Spanish airline) flies from Luton with a regular early (8:40am) flight to Florence. Once we arrived, we picked up our rental car. Note, the Florence airport car rental has one shuttle from the airport every 10min (which you can catch just outside the arrivals terminal). All the car rental desks are located in one building where the shuttle will drop you off. Keep in mind that things in Italy go a bit slower and there may not actually be enough cars when you arrive for pick-up (this is a story we heard several times from different travelers). So be prepared to take it slower and go with the flow a bit.

We drove ~1.5hrs from Florence to our B&B just outside of Siena. There are toll roads between Florence and Siena, so be prepared with some spare coins. The drive between the two cities is beautiful. Once you exit the first toll road, you will begin to make your trek through the Chianti region with gorgeous rolling hills and estates atop each.

Where to Stay?

Hilltop B&B

We stayed at a B&B called Ca’Bianca, which is approximately 10 minutes outside of downtown Siena. I could not recommend staying at this location more! Simon and Juliana are the owners of this property, having moved down from Milan a few years before. Their hospitality, combined with the beauty of the property is second to none. The B&B sits atop a hill, complete with a pool, garden, tennis court, bocci ball court, game room, and about 10 hectors of land for Simon and Julian to grow olive trees (if you’re luck, you’ll leave with your own olive oil grown on the property!). The building itself is something of its own history being built in the 11^th century. There is even an old church right inside the property.

Each morning all the guests are welcomed with a cappuccino, American, espresso or whatever coffee of your choosing while sitting on the side porch overlooking the Tuscan hills. In addition, you have the option for freshly made eggs, tomatoes, mushrooms, and fresh bread. This was delicious, so I would recommend not missing this!

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What to do?

Truffle Hunting and/or Cooking Class with La Nonna Ciana at Le Pietre Vive

We woke up early to arrive at our truffle hunt by 8:30am. We were surprised to learn that the location of our truffle hunt and cooking class were only 10 minutes driving from the B&B, and Simon and Juliana were actually very good friends with the owners of Le Pietre Vive. So close that our B&B actually served the saffron honey to its guests on its cheese place (this is a must try!).

Once we arrived at Le Pietre Vive, we were greeted by 3 boisterous doggies.  Little did we know that these guys were going to be key to helping us find our black truffles on our hunt that morning. On our hunt, we had one truffle hunter, one translator (Heather), three dogs, and one family. Two of the three dogs were trained for truffle hunting since they were pups. Their names were Kemba and Bonnie. The other was dog of the owner of the property. Bonnie ended up being very successful and found lots of black truffles. We were on the edge of white truffle season and thought that we may have found those, but given that it had been a bit dryer, the hunter didn’t know if we would find any white truffles because the season doesn’t really begin in earnest until the beginning of October.

Fun fact: only registered truffle hunters are able to hunt truffles on protected truffle zones, for which Le Pietre Vive had registered the land surrounding its property as a Truffle Zone in order to control who can hunt on its land. Without that classification, anyone would be able to walk and find truffles along the property.

The black truffles sit just below the surface of the soil and typically attach themselves to tree roots. The dogs are able smell for the truffles and then ideally dig them up and bring them back to their owner for a treat. Pigs are used in other places and historically were used for truffle hunting, but unfortunately, they would eat the truffles when they found them. So that is why people have started to train dogs to find truffles instead of pigs.

In total, we found 20 black truffles and thought we may have found a white truffle, but it was just a tease as it was a tiny black truffle. The reason why a white truffle is so sought after is because it can be sold for almost 10x the price of a black truffle. This is primarily because of its rarity.

Le Pietre Vive ended up purchasing all of the black truffles from our truffle hunter for our cooking class for 100 Euros. The cooking class followed the hunt – inside the house where we prepared black truffle pasta, bruschetta, flour chicken with black truffle, and tiramisu.

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Nonna Ciana spoke in Italian the whole time and Heather again translated for her.  There are about 12 people in the class in total, and you are arranged around a large kitchen table in the family’s kitchen. A lot of the class is watching and learning how to make the dishes – but learning how to make pasta was the most interesting. It was actually a lot of work too to knead the dough and figure out how thin to get the pasta; that was my favorite part.

We started our cooking class around 10:30am and ended at 2:30pm. This class was so worth it! Remember, they take cash only. Make sure to bring some saffron honey home for yourself or friends/family.

Where to eat?

Osteria Babazuf (inside Siena) or Bengodi Enoteca (outside Siena)

Bengodi Enoteca in Castelnuovo is about 20 minute driving from our B&B. The restaurant is a traditional small Italian Enoteca known for its wine and Pasta. This place was definitely worth the drive, but if you want to read more, check our SlowEating.

Other Activities

Go Wine Tasting

La Fortuna (one of my favorite wineries of all time – a must go!) Boscarelli, and Carpazo were a few of my favourites

Visit Hilltop Towns

Montalcino – Drive to Carpazo vineyard in the morning. The vineyard is right on the pilgrimage from Canterbury to Rome (Via Francigena). So there will be lots of hikers stopping in for the 7 EUR lunch with wine on their way. You can’t beat the stunning views as you were driving in. This place is known for its Brunello’s, but also has a vineyard in the Chianti region. After, drive up to Montalcino for lunch. We went to La Fortezza, which is the fortress that sits on the outside of the walled city. I had amazing spinach and ricotta ravioli with a brunello wine tasting. In the afternoon, go visit La Fortuna, a small family run winery called just outside of Montalcino. It is AMAZING. The wife of one of the sons of the family who spoke English and was Romanian gave us our tour. They let us taste so many wines and the crush was happening, so we were able to try the grapes right off the vine!

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Montepulciano – Drive to Aquavivo for your first wine tasting just outside of town called Boscarelli. We loved this place! The wine was so good, and the tour was amazing. It was interesting and very informative. After, drive into Montepulciano for lunch at this place called La Bottega Nobile, which sits in caves right under its wine shop. This place is known for its meats. We tried the lamb – which was incredible – and the beef steak. Make sure to leave time to stroll through the town after. There are plenty of little shops worth poking your head into. Remember, the town is bigger than you think – so you could easily leave a few hours to explore. After lunch, drive down the hill to Salcheto Winery. If you’re lucky and visit during the crush, you’ll get to see the winery actually de-stemming the grapes and see some of the production process. We didn’t love the wine here, but the views of Montepulciano from this vineyard are amazing and make the visit worthwhile. We did try the wine from another vineyard called Romeo. Our friend had recommended that we try here and it was so good. Would love to go back and do a tasting here.