Since we spent an overall 16 days in Italy - starting with 4 days in Rome - we wanted the latter part of our trip to focus more on smaller towns and picturesque countryside. Tuscany and the Dolomites ended up being our favorite parts! When we were in Florence, we were not feeling too great and did not do as much as we may have hoped but still had a great time.
This was my second time in Florence and I honestly think 2 days is enough, though three days may be ideal. My first trip to Italy was in 2015 and I visited the 3 big cities: Rome, Florence, Venice. After that trip, I had ranked Florence as my personal favorite. After this trip, I ranked Rome way higher than Florence. We were there at the end of May, and we found that Florence was already very hot and crowded (versus when I had visited in March 2015). It overall felt a bit dirtier to me this time and the crowds made it less enjoyable since it is a considerably smaller city than Rome - but we were also sick the whole time, so take my review with that in mind!
Tuscany on the other hand was a dream and I would highly encourage anyone visiting Italy to dedicate some time to exploring the region, even if just a day trip from Florence. We adored the town we were based in, but the region is so large and has such a variety of unique history and culture! We cannot wait to go back. Check out our Tuscany 3-Day Itinerary--with optional Florence 2-Day add on--below!
Day 1:
We picked up our rental car in Rome and started our 2.5 hour drive to our Tuscany home base: Pienza. There were multiple options for stops on our drive, but we chose Civita di Bagnoregio (1.5 hours from Rome). This hilltop town was beautiful and ended up being where we got engaged! Before renting a car in Italy, be sure to study up on the signage, and make sure you especially know the sign for ZTLs, or limited traffic zones (red circle with a white background). Most Italian towns have these zones where only locals are allowed past and you can incur a steep fine if you find yourself driving through such a zone. Some hotels in city centers will allow passes for the ZTL but need forewarning to send your license plate information to the local authorities.
We parked at one of the parking lots in the town of Bagnoregio (Parcheggio Battaglini), though there are some closer to the main entry. We were concerned about possible crowds but visiting on a Monday at the end of May, there were very few people. We ended up having about a 30 minute walk to the info point/ticket booth. Entry to this picturesque village is 5 euro a person (definitely worth it). You walk across and up a long pedestrian viaduct to get to the hilltop that the town is perched on. The views across were stunning and the architecture and small streets were fun to explore. This city has over 2,500 years of history! There was a main square with some shops and restaurants off of it with people enjoying their time, but overall it felt like we had the place mostly to ourselves. There were plenty of feline friends who call the village home (more of them than people!) and they were fun to see. My husband proposed in a small, beautiful courtyard with no one around and it was magical--the rest of our time in the village was a blur of happiness!
After pulling ourselves together enough to continue our drive, we went straight to our accommodations: Agriturismo Il Casalino. This was about a 1.5 hour scenic drive. If you are in Tuscany, you must stay in an agriturismo! They are like bed and breakfasts that bring guests usually to a working farm in the stunning countryside. There were several around Pienza, and many offered homemade breakfast and dinner options. Ours provided breakfast baskets with pastries and drinks as well as a small kitchen in our rooms. Our accommodations also had a separate bedroom, a living area attached to the kitchen, and a nice sized bathroom along with AC. I believe there were about three rental units at our site but we never ran into anyone else; the owner checked us in before he headed back out to the olive fields, and he was so kind and helpful and gave us a lot of recommendations for the area. The olive oil was also delicious and we took home several bottles! The view from the grounds felt like it was out of a dream with cyrpus trees lining lush green hills and lounge chairs to soak in the view. We loved every minute of our stay. We were also impressed with the price: at the time in May 2021, we paid just under $500 for 3 nights!
For dinner on our first night, we went to a restaurant recommended to us by the owner of our agriturismo: Trattoira da Fiorella. It was delicious! Pienza is an UNESCO World Heritage Site, a beautiful example of a small medieval Tuscan commune. Like many Tuscan towns, Pienza is situated on a hill overlooking the countryside, with plenty of parks and restaurants to soak up the view. After dinner we enjoyed wandering through the town at night, feeling like we were in a fairytale. While you cannot drive into the historic center itself (it is a ZTL), there were plenty of parking lots just a flight of stairs down from town.
Day 2:
After a leisurely morning, we decided to hike through the countryside from our agriturismo to the city of Pienza and explore the shops a bit. The area we walked through behind our lodging was a filming location for the movie Gladiator! In town, there were several wonderful local artists and we were lucky to pick up a unique souvenir. We also really enjoyed the paninis at Baccano Il Panino Toscano.
Once we made it back to our agriturismo, we hopped in the car to head to nearby Montepulciano. This town is also a ZTL, but there were once again plenty of parking areas (such as Parcheggio P8 - Il Bersaglio, which we used) on the outskirts. The lot we used had steep steps into the town, so be prepared for a bit of a workout. We enjoyed some wine at Enoliteca Consorzio Vino Nobile, which was located in the town's medieval fortress and had a great patio area with wonderful views. My husband and I have a thing for the occult/ghosts/spooky, so when we saw signs for the Torture Museum (Museo della Tortura di Montepulciano), we knew we had to check it out--it ended up being one of our favorite museum experiences! This museum was advertised all over the place, so we thought it might be gimmicky, but that was not the case at all. The space was small (can easily walk through in 30 minutes), but it housed an impressive collection of instruments. We were the only guests there and the lady at the front desk made the experience all the more enjoyable as she was had such specialized and local knowledge that really added to our visit!
For dinner, we drove to another nearby agriturismo for dinner: Podere Spedalone. This was a highlight of our trip! For the cost of a nice date night out in the US, we had multiple farm-to-table courses, a scenic setting to enjoy at the outdoor dining table, and the greatest company. We did not stay at this agriturismo because it was already full when we started looking (it is very popular). Our friends had come here multiple times and knew the owner, so they put us in touch and he was able to accommodate us for a dinner. The owner Alessandro has since left this agriturismo to open a smaller one closer to his home, but I am sure Podere Spedalone is still amazing, as well as Alessandro's new Agriturismo Torrenieri. We were greeted with local wine, a whole cured pork leg for prosciutto shavings, and fresh bread with olive oil. While we enjoyed the appetizers, we got to walk around the beautiful property and talk to travelers staying there as well as others just stopping by for dinner. The dinner was 4 courses and included homemade pasta and a meat dish; we also were able to buy a bottle of wine to enjoy with our meal.
Day 3:
Our plan for our third day was to rent a Vespa and explore the countryside, and I would still recommend this as an option. We planned to rent from Vintage Tours, but they had you test the scooter on a gravel parking lot--which was challenging for us since we had never ridden one before--and ultimately we decided to go with electric bikes. Shortly after leaving, though, I started to feel sick (my allergies were bad in the region, and I picked up a cold) so we ultimately returned the bikes and opted for an exploration day in our car.
For lunch, we picked up sandwiches in Pienza and did a circle route around the region stopping at: Cipressi di San Quirico d'Orcia (the famous cyprus tree shot), Monticchiello (we did not find much to do/explore here), and then ultimately back to our favorite Montepulciano. We opted to skip the top site Cappella della Madonna di Vitaleta because it involved a short hike which I was not feeling up for at the time. We enjoyed wandering around Montepulciano some more and grabbing a delicious dinner. There are several Michelin-starred restaurants here and reservations are recommended. We ended up finding a walk-in table at a restaurant down near Torre di Pulcinella which was delicious! We found a nearby viewpoint to watch the sunset, enjoying our last moments of beautiful Tuscany.
Optional Florence Add-On
Day 4:
After checking out, the drive from Pienza to Florence was about an hour and a half. We lucked out with finding a gorgeous Airbnb about a block away from the Duomo, which we highly recommend! It was a great price for the area as well, coming in around $380 for two nights. Since Florence is also a notorious ZTL zone, we reached out to our Airbnb host before arrival to see if they had recommendations for parking our car (which we still needed for later in our trip), and they recommended Parcheggio Villa Costanza. This was so easy! We left our car there for two nights and were able to take the tram right to Santa Maria Novella station. Plus the bakery and amenities at the station were very nice. It was only 7 euros a day! One-way tickets on the tram were less than 2 euros and the ride was about 20 minutes.
Since I was still recuperating from my cold, we mostly enjoyed relaxing in our very comfortable Airbnb, though we did take a walk to my favorite viewpoint in the city: Piazzale Michelangelo.
Day 5:
We started the day with amazing sandwiches at Panini Toscani, right by the Duomo. There are several famous sandwich shops in the city, but we enjoyed this one since each time we went there was virtually no line and the views while eating were pretty great. They let you try everything so you can build your perfect sandwich! After fueling up, we walked through the famous Leather Market and had fun haggling a bit and buying souvenirs.
We had a 2:15 reservation for a guided tour of the Uffizi Museum, and since we found ourselves with some time before our tour, we headed over to the Museo Galileo next door. This was a great science history museum, but my husband was most excited about the preserved middle finger said to belong to Galileo himself (I told you we had a thing for the occult!). The Uffizi was spectacular, the Botticelli room being my favorite. We also loved the Caravaggio room and the Da Vinci pieces. Having a tour guide really helped me to appreciate what I saw so much more!
After touring, we stopped by one of the best gelato shops in Florence--Vivoli--for refreshments. We spent the rest of the day wandering the beautiful city and were able to snag a table at Trattoria San Lorenzo Firenze for dinner, which we thoroughly enjoyed. During our time in the city, we also made several stops at Mauro Frutta Primizie, a wonderful little fruit stand near our Airbnb.
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