TUSCANY: Wine, Countryside, Hill Towns

Andrew and I woke up early on a Saturday morning, packed our bags, and said “ciao” to Sorrento. While we loved exploring the southern part of Italy, we were looking forward to our next Italian excursion.

We had planned to rent a car, drive about 4 hours north into the Tuscan region of Italy, and stay in one of the small hill towns for a couple of nights. In order to rent the car, we had to make our way back to Naples. After the 20+ stops on the metro train on the way to Sorrento from Naples a few days prior, we opted for the Express train on our way back, which only had 3 stops. I was a bit under the weather due to the amount of limencello we had at dinner the night before (complimentary from our server!), so I appreciated the route with less stops.

Once arriving in Naples and exiting the train station, we noticed the vast difference between this part of Italy and Sorrento. They are only an hour apart by car or train, but the cities are completely different. Naples is crowded, with lots of graffiti, and there are signs to watch out for pickpockets everywhere. We made our way to the Hertz rental car station and got our car, which turned out to be a Fiat 500XL. We have seen a lot of Fiats around Italy, so we weren’t surprised. It turned out that getting out of Naples was extremely difficult. We couldn’t read any of the signs since they were all in Italian, however, fortunately we were able to make it out of the crowded city all in one piece. We had a great time on the 4 hour drive up to Tuscany, taking in some incredible views and singing along to some great jams.

We had decided the night before we were going to spend two nights in the hill town of Montepulciano, which is in the heart of Tuscany. However, about an hour outside of Montepulciano, sits Civita di Bagnoregio, which is the ultimate Italian hill town. It’s a 2,500-year-old, traffic-free village that is only accessible via a long pedestrian bridge. Andrew had found out about this through some research he did, so we figured it was a site worth the stop, and it definitely did not disappoint.

Civita di Bagnoregio

Inside Civita di Bagnoregio

The view from inside Civita di Bagnoreio

After some pretty heavy rain the last hour of our drive, we arrived to our hotel in Montepulciano around 6ish.

Beautiful rainbow after the rain in Montepulciano

Since this is a small hill town, most of the hotels/B&B’s are family-owned. Upon arriving to our hotel/B&B, there was a small sign that said to press the buzzer and the owner would answer. We called and she said she would come to meet us in about 10-15 minutes. Finally, about 30 minutes later, she arrived, but not with good news. It turns out she had given our room to another guest earlier that day and there was some sort of mix-up on her part. We weren’t quite sure what to do because in this city you can’t really drive around looking for another place to stay. The streets are small and most places don’t look like hotels/B&B’s from the outside. However, she told us that she had reserved a room for us at her friend’s place, yet it was going to be a higher rate. After much back and forth with her, she called her friend and they agreed to let us stay at this new place for the agreed upon rate we had been given for the first place. We checked into the other place, which turned out to have an amazing owner named Roberto, who was an older Italian man from Siena. Roberto made us feel very welcome, albeit the mix-up earlier that day. We ended up going out for an authentic Tuscan, Italian dinner and then calling it an early night as we were tired from the long drive.

We woke up early the next morning and took a walk around the town of Montepulciano. It’s pretty incredible that this entire city sits upon a hill with some incredible views. We enjoyed exploring a bit and even found a great breakfast spot where we got a bite to eat and some cappuccino, which I attempted again, still not a fan.

While we had planned to spend 2 nights in Montepulciano, due to the hotel fiasco, we decided to just spend 1 night. We figured we would spend the next day driving through Tuscany and stay in Siena, stopping at a few wineries along the way. We were in awe at the continued beauty of the countryside. The views were just incredible, greenery everywhere, along with miles and miles of vineyards.

Unfortunately it turns out that most wineries are closed on Sundays, and if they aren’t, they are most likely full if you don’t have a reservation. We stopped by about 4 different family-owned wineries along our drive and they were all either closed or busy for the day with prior appointments. We finally decided to head to the city of Montalcino, not to be confused with the previous Montepulciano. Montalcino is famous for the Brunello di Montalcino wine, which is 100% Sangiovese grapes and aged in the barrel for at least 5 years in the Montalcino region. We ended up doing a tasting and had lunch at this cute wine bar that was within a castle in Montalcino.

View from Montalcino

Exploring the city streets

We then hit the road and continued up to Barone Ricasoli, which is a winery in the Chianti region of Tuscany. It is home to a castle, Castello di Brolio, and is the largest winery in the Chianti Clasico region. In fact, we learned that Baron Bettino Ricasoli invented the Chianti formula over 140 years ago.

Beautiful view driving up to the winery

Excited to try some Chianti wine!

Not excited about this extremely steep hill we had to walk up to get there…

Castello di Brolio

We got a great shot of the castle, but it turns out the actual wine tasting room was back down the hill, so after another 20 minute walk, we enjoyed a great Chianti tasting, before buying a bottle to enjoy later!

Barone Ricasoli

After what seemed like a million twists and turns on the road, we arrived in Siena at Hotel Athena. We were pleasantly surprised at the modern upgrades within the hotel, along with a rooftop bar with incredible views. We walked around the city a bit and then had dinner before heading back to the hotel for the night. When we had checked in, the lady at the front desk gave us 2 free drink tickets for the bar since it was our honeymoon, so we hung out in the inside bar (too cold outside) and played some card games for the rest of the night.

Such a gentleman – he offered to carry both of our bags into the hotel

The main plaza in Siena – Piazza Del Campo

Flags that represented the different districts that race in the Palio di Siena – A very popular horse race, in Siena

After enjoying the complimentary breakfast in our hotel, we packed up our things and headed out. We definitely think we could have spent another couple of nights exploring Siena, but unfortunately we had already planned to be in Florence the next day, so we’ll have to stay longer next time! We’re excited for our extended stay in Florence, where we’ll be staying for an entire week to check out all of the sites and Italian city life in the capital of Italy’s Tuscan region.