Tuscany was the main base of our September road trip. We are both big Italy fans, but had never explored the countryside of Tuscany before. Ever since it seemed likely that Italy’s borders would stay open for the summer, I started researching what I would love to visit in Tuscany, mainly setting my sights on the rolling landscapes with the symmetric cypress trees. We stayed the night in Florence and San Gimignano and explored the region from there. In this blogpost I will explain our itinerary from day to day, so you can use it when planning your Tuscany trip, because it is definitely a must visit region!

Our itinerary

Day 1: Arriving in Florence after lunch. Watching the sunset over the Duomo from our rooftop terrace.

Day 2: Full day in Florence. We made use of this full day to explore some museums and check out some viewpoints.

Day 3: Leaving Florence for San Gimignano after breakfast. Having lunch and dinner in San Gimignano and using the time in between to enjoy the swimming pool of our hotel.

Day 4: Daytrip to Siena, where we visit Siena’s cathedral. Afterwards we drive to Agriturismo Baccoleno to make drone videos at the famous cypress street.

Day 5: Having a swim and lunch at the beach of Bibbona. After this we drive through the cypress street of Bolgheri. We end this day with a dinner with a view in San Gimignano.

Day 6: We check out of our hotel before breakfast so we can arrive early at Bagni San Filippo. This is quite a drive and we love seeing the sunrise over the Tuscan countryside. Bagni San Filippo is located in Val d’Orcia which offers some of the most stunning views of the region.

Where we stayed

We stayed in Florence for two nights in hotel B&B La Terrazza sul Duomo. This hotel has an amazing rooftop terrace, offering amazing views over Florence and its Duomo. I wrote a blogpost about this experience, which you can check out here.

The next three nights we stayed in San Gimignano at Il Casale del Cotone. We chose this place because it offered a pool with ample lounge chairs, an extensive breakfast and its good location right next to San Gimignano. We paid € 100 per night, which was of okay value. The hotel has about 18 rooms, of which half were occupied and I can imagine the hotel having a better atmosphere when there is no pandemic going on. The place missed a bit of liveliness and service, even though the owner was kind enough. For example, pool towels were not offered standard, the cappuccino was not “real cappuccino”, you were not allowed to eat or drink at the swimming pool, wifi was bad and there was no opportunity for lunch or wine. The hotel looks absolutely gorgeous though, like a wedding location out of a movie, but it was missing a female touch. All in all, it was a fine hotel, but it didn’t exceed our expectations or offer amazing value. I do have to admit that many Italians seemed a bit sad; they had strict lockdowns and seemed to be struggling for income (understandingly so).

Driving in Tuscany

When you visit Tuscany you absolutely need a car or a driver. From Florence you can easily do some day trips to other cities by train, but otherwise you are going to need a car. You should want to have a car, because the best parts of Tuscany can only be reached by car. We absolutely loved driving in Tuscany, as we were admiring the views from every twist and turn (even though this made me really nauseous). Make sure you don’t just take the highway, because you don’t want to miss out on the amazing sights from the hilly roads. We didn’t think driving in Tuscany was too uncomfortable, but the roads do get less modern when you drive south of Florence.

Day 1 & 2: Florence

I wrote a separate blogpost about Florence, highlighting all the activities we did and even some other recommendations. Two nights in Florence is the absolute minimum, as there is so much history, art and gastronomy to explore in this lovely city.

Day 3: San Gimignano

We dedicated our third day to exploring San Gimignano and having a rest at our hotel pool. San Gimignano is a small, medieval town which is famous for its towers. From afar the towers look like skyscrapers, making San Gimignano the New York of the Medieval times. San Gimignano is really easy to visit by car as it features four parkings, just outside of town. When you just come to San Gimignano for dinner, you only need to pay the evening tariff which is € 1 for the full evening. During the day you pay about € 2 per hour. San Gimignano is pretty touristy and has a few little museums, which you can visit when you buy a city pass. To be honest, it wasn’t something that particularly interested me, so we skipped this activity and enjoyed a walk over the city walls instead. During the day the main square gets pretty crowded, but at night the city is really relaxed and quiet.

The medieval skyscrapers of San Gimignano, with the vineyards in front
View from the city walls

The restaurants in San Gimignano can be a bit on the conservative (not super original) side and with my dietary restraints it was a bit of a struggle to find a good place to eat sometimes. There are plenty of wine and aperitivo bars though, so if you are not pregnant you should be fine 😉 Over the course of the three days that we were staying in San Gimignano we found sufficient restaurants that we would recommend:

Enjoy.. drink food life: Don’t let the awful name distract you, this restaurant has amazing pizzas and you will be spoiled for choice! I had a delicious calzone and Hielke had a pizza with pumpkin. They definitely do not just offer the traditional options. When you are pregnant you admire different things on the menu and I really appreciated the option of having a virgin mojito, while Hielke was sipping on his local wine. The view over the region is absolutely stunning, so make sure to arrive timely to snag a seat at the border.

Olivieri Bistrot: This is one of the more upscale restaurants in San Gimignano. The styling is modern and the tables were set Corona-proof. Food and service were really good.

Bar Piazzetta: This is a bar that features a casual restaurant with some pasta dishes. We decided to sit down here, because we liked the reggaeton music they played, but the food turned out unexpectedly good. The wild boar pasta (local specialty) was just as delicious as in a traditional restaurant!

Day 4: Siena & Agriturismo Baccoleno

On day four we decided to visit Siena, which is about an one hour drive from San Gimignano. I was mainly exited to see Piazza del Campo, the main square where the horse races are held each year. Unfortunately, as is usually the case with squares, it was incredibly difficult to take a good picture of Piazza del Campo, due to the grandness of it and the number of tourists walking in your picture. So I didn’t take a good picture, but the square was still beautiful. My plan was to visit the Torre del Mangia, which is located on Piazza del Campo, but due to COVID-19 it was closed. Luckily, we found an even better tower to visit: the Facciatone tower which is located next to Siena’s cathedral. We bought the Panorama ticket for € 14, so we were able to visit the ruins of this tower. As the access to the tower is very restricted, I would recommend visiting early. We had to wait for over 30 minutes before we could enter and I can imagine this being much longer in the high season. From the Facciatone you get views over the Torre del Mangia, the black and white duomo and the whole area surrounding Siena. Absolutely magnificent 🙂 The duomo itself is also worth a visit, the detailing of an amazing level and the black and white marble adds a special touch. I usually find crypts a little bit creepy, but this one was really colorful and almost a bit Egyptian.

View of the Torre del Mangia in the back, it doesn’t get more unobstructed than this!
View from the Torre del Mangia from below!

After Siena we drove to Agriturismo Baccoleno, which has found Instagram fame because of the zigzagging driveway which is lined with cypress trees. We made it just in time for an insane sunset, I can totally understand why this place is so popular! You are not allowed to drive on the driveway, but we just left our car outside of the gate and entered the property by foot. When we visited there were about ten other couples who wanted to do photoshoots and make drone videos. However, this was not an issue at all as most people were patient and gave each other time to take pictures. Just don’t expect a hidden gem and you will be fine.

Drone video of Agriturismo Baccoleno

Day 5: Beach at Bibbona & Bolgheri

Hielke always loves to take a dip into the sea, so on day five we drove to Bibbona, which was one of the beaches closest to San Gimignano (still 1,5 hours of driving). I wouldn’t really recommend this beach as I found the beach clubs a bit run down, however it is a nice local beach with super blue water. After a good, long lunch we drove onwards to Bolgheri, a long lane lined with cypress trees. Too bad we were too chicken to take out the drone, because this road would have been epic to film. But at times it was quite busy with cars and we thought it would have been a little bit dangerous to fly.

Bibbona beach
Bolgheri cypress street

Even though this day was not filled with famous sights, we still loved this day as this itinerary took us through a more unexplored part of Tuscany. We often stopped our car, just to take some pictures, make a drone video or just to enjoy the view.

Drone video of a typical cypress street in Tuscany

Day 6: Bagni San Filippo

Somehow we managed to save the best for last as Bagni San Filippo was the highlight of our stay in Tuscany! Bagni San Filippo is a series of thermal pools, which lay hidden between rocks and a forest, just an absolutely gorgeous place! We loved Bagni San Filippo so much, that we gave it its own blogpost, which you can find here. The added value of Bagni San Filippo is that it is located in the middle of Val d’Orcia, which is a region protected by UNESCO offering dramatic views and historic villages. Being able to drive through this region made the long drive to Bagni San Filippo even more worth it.

You might be interested in

Leave a Reply

Your email address will not be published. Required fields are marked *