Tuscany, Italy is one of my favorite spots on this Earth. I’ve been to Tuscany a few times but my last visit in May 2024 was the best. As an avid photographer, I wanted to take pictures of the cypress trees and quaint villages in Tuscany. I researched and put together a perfect 3-day itinerary to see the best photo spots in Tuscany!

Overview

If you would like see a video of my trip, you can watch it here from my Youtube channel!

Tuscany

There are many cities and towns to see in the Tuscany region of Italy. For this post, I will focus on the southern Val d’Orcia region in the province of Siena.

If you are interested in other parts of Italy, refer to my Italy destination page where I have links to other blog posts.

Val d’Orcia

The region of Val d’Orcia is located in the south of the province of Siena (an hour drive from Siena) and northeast of the volcanic mountain Monte Amiata. The name Val d’Orcia derives from the river Orcia, which runs through the valley and flows for about 70 kilometers through Tuscany.

Covering an area of 60,000 hectares and 5 municipalities, this region offers a unique combination of art, history, cuisine, and nature. Since 2004, this area has been on the UNESCO World Heritage List because of its special features. The Val d’Orcia is famous above all for its fascinating landscapes.

San Quirico d’Orcia

I based myself in this small town in the center of all the photo spots. Each day we headed out in a different direction with the furthest town or site only 45 minutes away.

The town of San Quirico is very cute and quaint. It’s not very touristic so we appreciated the calmness of the town each night when we returned from sightseeing all day. While all the food in Tuscany was delicious, I can recommend our favorite restaurant in San Quirico for its unique ambiance: Trattoria Toscana al Vecchio Forno.

I will separate this post into three different daily itineraries we did. Each itinerary included one or more towns and some sightseeing spots.

Day 1 Itinerary

Our first day, we headed west of San Quirico to see the below sites:

• Abbey of Sant’Antimo
• Montalcino
• Buonconvento
• Cypresses of San Quirico d’Orcia
• Podere Belvedere
• Madonna di Vitaleta Chapel
• Gladiator Avenue

Abbey of Sant’Antimo

Our first stop on Day 1 was just a 30-minute drive from where we were staying in San Quirico. The monastery of Abbazia Sant’Antimo is situated in a picturesque position between green hills, olive trees and vineyards. The 12th century abbey was founded by Emperor Charles the Great.

There was no fee to enter the church and there is a shop onsite where you can buy local products and souvenirs. You will find here nice surrounding hills and trails for walking.

Montalcino

Our 2nd stop on Day 1 was the scenic town of Montalcino where we sampled the famous Brunello red wine. We walked around the fortress and the cobblestone streets to enjoy the warm sunshine. You can cover all the streets of the town in less than an hour. There are a number of small enotecas in town where you can stop for a glass of wine.

The medieval town of Montalcino is situated on a hill of about 500 meters high. Its history goes back to the Etruscans, but the town today is protected by its five sided Fortezza which dates back to the 1300s.

The town is known for the Brunello wine produced from the vineyards that cover the slopes of the hill. Brunello is one of the most popular of the Italian red wines. We stopped at a wine bar to try the Brunello. I actually didn’t find it very special and worth the expensive cost compared to other wines from Tuscany.

Buonconvento

We had to fill up our car with gasoline and ventured off the path a bit to find a station. We ended up near a town called Buonconvento, so we stopped off for a bite to eat and a look-around. This was a very small village but worth seeing. There is a large parking lot just next to the village gate entrance. A quiet pedestrian street allows you to stroll through the town.

In Buonconvento, you will see the Porta Senese (Sienese Gate), a majestic tower gate built in 1379 with a Gothic arch over the entrance. The ancient church Chiesa, Dei Santi Pietro e Paolo (Church of Santa Peter and Paul), dates back as far as 1103. Henry VII, Emperor of the Holy Roman Empire, died here on August 24th, 1313.

Cipressi di San Quirico d’Orcia

Driving back home, we stopped to see a popular cypress tree photo spot. A wonderful place popular with photographers are the cypresses of San Quirico d’Orcia, also known as Cipressi di San Quirico d’Orcia.

I was in this spot in 2019 for a photography workshop (see Youtube video of that trip). On our visit this year, we had more time to walk around the area and see other vantage spots. There is no parking lot here so you have to find a place on the side of the road and be careful of the cars whizzing quickly by.

We walked up a path to see the second group of trees arranged in a circular formation. It was as if this small cypress forest was left in the middle of a field with a dirt road running through it.

We were lucky to not have too many people around for our photos. If you have a drone, it’s a perfect place to get the bird’s eye view of the circular cypress trees.

Visiting Tuscany in May meant having many wild flowers for the photo opportunities. Yellow and red flowers were abundant at this time. We also saw scattered poppies but never came across a big field of poppies.

Podere Belvedere

As we had more time to explore on our first full day, we decided to drive further down the road to see the famous Podere Belvedere. This building is an old farmhouse, surrounded by cypresses, in a beautiful hilly landscape with olive groves and vineyards.

On a sunny day, it doesn’t seem too spectacular. Most people visit this site at sunrise when there is a blanket of mist in the valley. This is how I initially saw the farmhouse on my photography workshop.

You can walk along a path to get different views of the Podere Belvedere. There is a big olive orchard you can walk through. We could see endless rolling hills covered with yellow flowers.

Cappella della Madonna di Vitalita

Just a bit further in the distance from the Podere Belvedere, you can see the famous Madonna di Vitaleta chapel. This is one of the popular spots for photos in Tuscany. We decided not to walk the long path up to the chapel, but there is an alternative way to get close to the chapel via a road.

This church was built in the 12th century in a spot where legend says the Virgin Mary appeared to a shepherdess. In 1533, a statue of the Virgin Mary by Andrea della Robbia was installed in the church.

The chapel was restored in 1884. We were lucky while we were in the area to see a lady riding her horse along the path that leads up to the chapel.

Gladiator House

The picturesque Gladiator House is well known due to the famous scenes from the movie Gladiator being filmed here. Maximus (played by Russell Crowe) is shown returning from years at war to his homeland on horseback. His journey brings him along a cypress tree lined avenue. It is then that Maximus realizes his little slice of paradise has been corrupted by the outside world and that he has arrived too late to save his family.

There are two spots to see the Gladiator area. We chose the closer view from the gate which is right off the road near the Podore Belvedere and the Madonna di Vitaleta Chapel.

Day 2 Itinerary

On our second day, we headed northeast of San Quirico with several interesting stops along the way:

• Red Flower Fields
• Pienza
• Montipulciano
• Zig Zag Cypress Hill
• Bagni Di Vignoni

Red Flower Fields

On the road from San Quirico to Pienza, we came upon some beautiful fields of red flowers (called crimson clovers). I insisted on stopping to take photos of these magnificent views.

Pienza

The first town we stopped in was Pienza, a UNESCO world heritage site since 1996. The town sits up on a hill that we saw on the first day near the Podore Belvedere (see my below photo).

Pienza had a lively feel to it. There were many people at 11 a.m. on this day despite it being a weekday. The town has a central square and a stone pedestrian streets running through it.

But the best part was the wide open stunning views looking onto the countryside. There was a nice restaurant perched on the side of the city walls with amazing views.

Much of the town’s features date from the Renaissance era. In the 15th century, Pienza (then known as Corsignano), struck gold when a citizen from the village was elected Pope Pius II. The Pienza Cathedral has a classically-inspired facade made from travertine marble. The triple-arched facade resembles ancient Roman temples.

Pienza is also known for its pecorino cheese. I didn’t buy any cheese here but I did order ravioli a couples times with pecorino cheese on it.

Montepulciano

Next on the itinerary and a 20-minute drive from Pienza was the town of Montepulciano, famous for its ‘Vino Nobile di Montepulciano’ red wine produced in the region. We actually had a bottle of this wine the night before and loved the taste.

With around 14,000 inhabitants, Montepulciano is the largest town in Val d’Orcia. This medieval town is perched on a steep 600-meter-high hill where you must walk to the top for the best views.

Upon arriving to Montepulciano, we had a delicious Italian lunch to get some energy for the uphill stroll. On the way down, I had to try the local gelato – salted caramel was delicious!

Piazza Grande, at the very top of the town surrounded by limestone walls, has a nice plaza and church. The town’s architectural beauty led Montepulciano to be dubbed the “Pearl of the 1500s.” You will also see a lovely garden with views onto the Tuscan hills.

Zig Zag Cypress Road – La Foce

After Montepulciano, we drove to the area to see another popular photo spot referred to as the Zig Zag Cypress Road. We were lucky to get there and snap some photos before the clouds covered the sun.

We also passed the ‘Dinosaur Hill’ that has trees on the top and resembles the back of a dinosaur.

Bagni Di Vignoni

Our final stop of Day 2 was the medieval town of Bagno Vignoni. This village is famous for its thermal baths and healing springs. The main square is filled with a unique thermal pool (49 meters long and 29 wide) instead of a typical piazza. You are not allowed to bathe in this pool but there is nearby natural hot water spring called Parco dei Mulini you can enter for free (we didn’t do this).

We simply walked around the pool in the center and stopped off at one of the bars for a refreshing drink.

Day 3 Itinerary

On our last day in Val D’Orcia, I had planned to head southeast of San Quirico to see some unique sites:

• Rocca de Tentennano
• Rocca Aldobrandesca
• Bagni di San Filippo
• Cypress Avenue Poggio Covili
• Monticchiello

Rocca de Tentennano

I had read about this tower to visit and had seen it from a distance on the previous days. We arrived mid-morning and the place was empty. You can buy a combined ticket for this tower as well as the neighbor castle Rocca Aldobrandesca.

After walking up a slight hill from the ticket office, we went inside the tower where there were steep steps to reach the lookout point. We had to carry our cocker spaniel dog up and down due to the steep and open steps. The 360 degree view from the platform was amazing.

As far back as 1100, the fortress was known to have been owned by the Ardenga lords, who later became the Counts of Tentennano. In 1170, the family also ruled over Bagno Vignoni, a large portion of San Quirico d’Orcia and other castles throughout the valley.

Rocca Aldobrandesca

After seeing the first monument, we walked a short distance across the town to visit the castle. The Rocca Aldobrandesca is named for the ruling family who controlled a vast territory and built the fortification. The first part of the castle was built in the 11th century and expanded in 1308.

You can walk all around the castle with great views on the Rocca de Tentennano and surrounding hillsides. We were fortunate not to have too many other visitors at the same time.

The fortress was abandoned in the 17th century and later restored to be a museum.

Bagni San Filippo

One of the places I had seen online and wanted to absolutely visit was the Bagni San Filippo. This area is considered the oldest natural and at the same time man-made spa in the world, provided directly with water from a hot spring. It is believed that the Etruscans and the Romans bathed in this spring.

We arrived to find so many cars parked along the small road. Being a warm day in May, it was very crowded with many people in the water pools. I had not planned to enter the water but just wanted to see the unique formations.

Cypress Avenue Poggio Covili

One of the most popular photo spots is the long picturesque avenue of the Poggio Covili farm. We stopped and parked on the side of the road. There were many tourists so it was a challenge to get photos without people in them.

You can’t enter the property but most people take photos at the end of the cypress drive.

Monticchiello

Although not planned, our last stop on Day 3 was the small village of Monticchiello. I had been here before, but we stopped at the end of the afternoon for a stroll through the alleys and to sample the local sparkling rose wine. Compared to the other towns in Val D’Orcia, this one is very small and peaceful town to walk around.

Summary of Tuscany Best Photo Spots

I hope you enjoyed my detailed 3-day itinerary and learning about the best photo spots in Tuscany! I’ve been to other places in Tuscany such as Pisa, Florence, and Siena, but I find the Val d’Orcia region the most beautiful. It’s a photographer’s dream to capture these scenes in the early morning light or at sunset. On this trip, I didn’t plan for those kinds of shots but if you want to see photo scenes like this, look at my photography workshop Youtube video.

If you are interested in other amazing places in Italy, check out my below posts:

• Things to Do in San Remo Italy
• Verona Italy in Two Days
• 2 Day Itinerary for Bologna Italy
• Few Hidden Gems of Italy
• Venice Carnival 2024
• Italy Destination Page

If you are looking for assistance to plan your next trip, I am here for YOU! I love to plan travel itineraries for myself and others. For more details on how I provide this service, please check out my Itinerary Planning page and drop me a quick email at jan@janadventures.com to get started!