This journey began with a decision shared between four people. Together with two friends who are also passionate about photography, we chose Tuscany for our first trip abroad planned entirely by ourselves. Less than a week later, the flights were booked, a rental car and a house were reserved, and Google Maps was already filling with places we hoped to photograph. Until then, travelling abroad had always involved the security of an organised itinerary. This time, every decision was ours: where to stay, how long to drive, which sunrise was worth a 4:30 alarm, where to wait for sunset and what to change when the weather refused to follow the plan. That freedom was exciting, but it also meant accepting responsibility for everything that could go wrong. We did not travel to Tuscany simply to collect famous viewpoints. We wanted to understand the landscape through the camera — to see how the roads pass between the fields, how the cypress trees divide the open hills, how villages rise above the countryside and how the same place changes between early morning and evening. Val d’Orcia is not untouched wilderness. It is a working agricultural landscape shaped over centuries by farming, settlements and roads. During the Renaissance, the countryside south of Siena was deliberately developed around ideas of productive land and visual order. Farmhouses, cultivated hills, fortified villages and cypress-lined routes became parts of a landscape that still feels carefully composed. For photographers, that history is visible in almost every direction. The journey between two marked locations is rarely empty. A bend in the road, a solitary house or a line of trees can become the reason to stop. Very quickly, we understood that our route through Tuscany would not be measured only by the places saved on the map.
Four Photographers and a Map Full of Pins
We prepared the luggage, checked the photography equipment more than once and left home carrying the mixture of excitement and uncertainty that comes with doing something for the first time. Our morning flight landed in Pisa around noon. We collected the rental car, arranged the bags around four people and their camera gear, and began the drive towards the house.
In less than three hours, we were settled in. The sensible thing would have been to rest, but the first views of Tuscany had already started to pull us away from the plan. We went out to buy groceries and stopped several times along the way, not because the places were marked on the map, but because the landscape beside the road was enough.
That evening ended in a restaurant at a small hotel near the house. We ate spaghetti, discussed the next morning and returned early to our rooms. The first alarm was set for 4:30. From then on, most of our days would begin in darkness and end after sunset.
During the journey, we gradually learned the rhythm of the smaller towns we visited. In some places, English was not enough, but the people we met remained patient and always found another way to communicate. Their calmness was very different from the hurried pace we were used to. Our impression was that nobody seemed particularly interested in rushing simply for the sake of arriving sooner.
We also discovered that our photography schedule did not always fit easily around local restaurant hours. Many kitchens served lunch, closed for the afternoon and reopened in the evening — often just as we were leaving for sunset. This occasionally required improvisation, but we never remained hungry for long.
The greatest practical lesson arrived almost immediately: in Tuscany, the road itself belongs to the photographic experience. Fields opened on both sides, distant farms appeared above the hills and cypress trees turned ordinary entrances into clear visual lines. We had planned a route between locations, but the landscape kept creating reasons to stop between them.
The First Alarm at 4:30
Getting out of bed at 4:30 on the first morning was difficult. We made coffee almost in silence, loaded the equipment into the car and drove through the darkness towards Cappella della Madonna di Vitaleta.
The small chapel stands among the hills between San Quirico d’Orcia and Pienza, separated from the main road by fields and a dirt track. It is one of the most photographed places in the region, and we arrived hoping for the mist that often transforms the familiar scene into something softer and less predictable.
There was no mist. The sky was clear and the landscape was already beginning to reveal its spring colours. For a few moments, disappointment tried to take the place of concentration, but the light continued to change. We spent almost two hours photographing the chapel, the surrounding hills and the flowers in the foreground. The conditions were not the ones we had imagined, but the place still offered enough possibilities when we stopped waiting for a different morning.
From Vitaleta, we continued towards the well-known cypress grove near San Quirico d’Orcia. We explored the possible angles, photographed from the ground and made the first drone flights of the trip. Seen from above, the circular form of the trees became even clearer against the cultivated fields.
The next stop was Pienza. Early in the morning, before the streets filled with visitors, the town felt quiet and open. Pienza began as the medieval village of Corsignano and was transformed in the fifteenth century under Pope Pius II into one of the clearest examples of Renaissance town planning. That order is visible in its centre, but what stayed with us most was the calmness of walking there before the day had properly begun.
After photographs, food and coffee, we continued towards Monticchiello and followed the winding roads around the village. Much of the afternoon passed in Montepulciano before we returned towards Pienza and stopped at Pieve di Corsignano to wait for the evening light.
The Romanesque church and its cylindrical bell tower gave us a very different subject from the open fields. Thanks to Miro’s sharp eye, we noticed the sun moving towards one of the tower openings. We adjusted our positions and caught the moment when the light passed through the stone structure and formed a clear starburst.
For sunset, we went to the dirt road near Terrapille, known from the final visions of home in Gladiator. The sky remained clear and the sunset never developed into anything dramatic. Still, we photographed the road and the soft hills around it. The first day taught us that a famous place does not guarantee perfect conditions — and that useful photographs often begin after the expected image has failed to appear.
A National Holiday Among the Clay Hills
The second day coincided with 25 April, Italy’s Liberation Day. We headed towards Asciano, unsure what the holiday would bring and whether the town would be quiet or crowded.
The journey took us deeper into the Crete Senesi, a landscape very different from the softer green hills of Val d’Orcia. Here, exposed clay shapes the slopes into ridges, folds and pale eroded sections. The soil comes from ancient marine deposits, and the changing light reveals forms that can appear smooth from a distance but become far more complex when viewed closely.
As usual, we stopped several times along the road. Some places were only quick observations, while others were saved for a possible return. By then, our map was no longer just a collection of destinations. It had become a record of light directions, possible foregrounds, parking places and views that might work better at another hour.
In Asciano, we found a procession accompanied by a brass band. Musicians in uniform gathered in front of the municipal building, flags moved through the street and local people followed behind. After the silence of the previous mornings, the sound and movement brought a completely different rhythm into the journey.
From Asciano, we continued to Chiusure, where the annual Artichoke Festival was taking place. The small village was overflowing with people, food stands, music and conversations. The festival celebrates a local variety of artichoke and the rural traditions connected with it, but for us the strongest impression was simply how thoroughly the event had transformed the village.
We enjoyed the atmosphere, yet the crowds made it difficult to understand the place itself. Almost immediately, we agreed that we needed to return on an ordinary morning, when the streets and square would belong to the village again.
Nearby stands Abbazia di Monte Oliveto Maggiore, founded in the early fourteenth century by Bernardo Tolomei and his companions. The Benedictine complex lies among woods and the eroded clay landscape near Chiusure. Its church, cloisters and frescoes carry a history very different from the temporary noise of the festival.
The contrast between the two places gave the day its character. Within a short distance, we moved from music and crowded streets to a monastery shaped by centuries of routine and silence. Tuscany was already proving that the places between our photographic viewpoints mattered just as much as the viewpoints themselves.
Roadside Dawn, Poggio Covili, and Pienza at Dusk
We welcomed the third sunrise at one of the many places we had noticed while driving. It was not a formal viewpoint and it did not have a famous name attached to it. There was simply a farmhouse, a group of cypress trees and the layered shape of the hills behind them.
This was exactly the kind of scene that had made us stop so often. Tuscany’s most recognisable elements were present, but they did not feel arranged for visitors. The house belonged to the working landscape, the road continued towards ordinary fields and the morning light briefly brought the separate elements together.
We photographed from the roadside and made a few drone flights before continuing towards Poggio Covili. The long avenue of cypress trees leading to the farmhouse is one of the most familiar compositions in Val d’Orcia. Its strength comes from its simplicity: two repeating rows of dark trees, a pale road between them and a building placed at the end of the visual line.
The place also reminded us that many celebrated Tuscan views are not public attractions created for photographers. They are working farms, private properties and access roads. The photograph has to be made without entering fields, blocking traffic or treating someone else’s land as part of a studio set.
From there, we continued to Castiglione d’Orcia. We walked through the town, stopped for coffee and made several aerial photographs. We had hoped to visit the fortress, but it had not yet opened. Instead of waiting, we accepted the change and moved on.
That small adjustment was typical of the whole journey. We had a detailed plan, but the plan was not allowed to become more important than the day itself. Closed doors, unsuitable light and unexpected crowds were not failures. They were simply information for the next decision.
After lunch and a short rest, we returned to Pienza. During the first visit, we had experienced it in the stillness of morning. This time, we remained until evening and watched the light fade across the valley from the edge of the historic centre.
The day ended in a small restaurant. For once, there was no rush towards another marked location. The cameras were beside us, the early alarm was already waiting, but for a little while the journey slowed to the pace of the town.
Vitaleta Again, Then Into the Cities
On the fourth morning, we returned to Cappella della Madonna di Vitaleta. It was another attempt to photograph the chapel with mist, and once again the air remained clear.
Returning to the same location under similar conditions can feel like repeating a failed idea. Yet no morning is completely identical. The direction and strength of the light had changed, the foreground offered different possibilities and we now understood the place better than during our first visit.
Photography trips often create pressure to keep moving — to search for a new subject because returning appears less productive. Vitaleta reminded us that repetition can be useful. The second visit was not about recreating an image we had seen elsewhere. It was about noticing what we had overlooked the first time.
After sunrise, we left the countryside and drove to Siena. The transition was immediate. Open fields and isolated buildings were replaced by narrow streets, stone façades and a much denser rhythm of people and architecture.
We visited the cathedral, Piazza del Campo and the Palazzo Pubblico. The shell-shaped square is divided into nine sections, recalling the Government of the Nine that ruled Siena during part of its medieval prosperity. Standing there made the relationship between the city and the countryside more visible. The same Sienese culture that shaped its civic buildings also influenced the ordered agricultural landscape we had been photographing farther south.
From Siena, we continued to San Gimignano. Its surviving medieval towers create one of Tuscany’s most recognisable skylines, but our strongest impression came from the number of visitors. The streets were crowded and long queues had formed outside the most famous gelaterias. Naturally, we joined one of them.
San Gimignano was impressive, but we did not feel the same connection we had found in the smaller villages. Sometimes a place can be historically rich and visually striking, yet difficult to experience when the movement of tourism becomes louder than the place itself.
We ended the day in Montalcino. The historic town is dominated by its fortress and surrounded by the landscape of Val d’Orcia. After the intensity of Siena and the crowds of San Gimignano, its streets gave us a quieter final walk before the drive back to the house.
Chiusure After the Festival
For the fifth sunrise, we returned to Poggio Covili. We arrived while the road was still quiet and found positions from which the cypress avenue could be photographed without obstructing access.
Not long afterwards, a large group of photographers appeared. The available space beside the road was limited, and the calm composition in front of us contrasted sharply with the movement behind the cameras. Tripods were adjusted, people shifted by small steps and everyone waited for the light to reach the same line of trees.
Popular viewpoints create a strange kind of concentration. Several photographers may stand almost shoulder to shoulder, all facing the same subject, yet each tries to find a slightly different relationship between the road, trees, shadows and farmhouse. Arriving early had given us enough time to work before the place became crowded.
After the morning light, we returned to Chiusure. Without the Artichoke Festival, the village seemed almost unrecognisable. The same streets that had been filled with music, food stands and visitors were now quiet. The square belonged to a few local people, the cafés and the slow beginning of an ordinary day.
We walked without needing to avoid crowds, stopped for coffee and breakfast and finally saw the village we had imagined during our first visit. The stone well, brick façades, narrow passages and small arrangements of flowers became visible as individual details rather than parts of a busy event.
Later, we returned to Abbazia di Monte Oliveto Maggiore and photographed the surrounding landscape with the drones. By this point, our movements through Tuscany had started to become less dependent on the original route. We were returning because we had learned something from the first visit — about the light, the access or the atmosphere.
For sunset, we chose one of the most popular photography locations in the region. Since many of the familiar images had been made there, we expected other photographers. What we did not expect was the new fence and the designated viewing area. Signs clearly prohibited drone flights.
Some visitors ignored the restriction and launched their drones anyway. We kept ours packed. A photograph does not become more important simply because we travelled far to make it. When access changes or a restriction is clearly marked, respecting the place has to remain part of the photographic decision.
We finished the evening with the cameras from the permitted area. The position was not the one we might have chosen freely, but the hills, the red flowers and the long cypress road still gave us one of the defining views of the trip.
The Last Sunrise and a Return to Gladiator
We spent the final sunrise at the cypress grove near San Quirico d’Orcia. Returning there at the end of the journey felt very different from our first visit.
We already knew where the paths led, how the circular trees related to the surrounding fields and how quickly the sunlight would begin to change the scene. Familiarity did not make the place less interesting. It removed part of the uncertainty and allowed us to work more deliberately.
After the photographs, we explored the countryside around Castelmuzio and walked through the small fortified village. By then, coffee and breakfast in a café on a quiet square had become as characteristic of the trip as the alarms and tripods. These pauses allowed us to look through the morning images, discuss what had worked and decide how much of the remaining plan was still realistic.
We continued to the weekly market in San Giovanni d’Asso and then drove towards Murlo. The small village was another place where stone walls and narrow streets seemed to belong naturally to the surrounding hills.
In Murlo, we visited the archaeological museum — the first Italian museum we had entered during the trip. Its collection includes finds from Poggio Civitate, an important nearby Etruscan site where the remains of an elite residence from the seventh and sixth centuries BCE were discovered. After several days focused on light and landscape, the museum offered a different way of understanding how long people had been shaping and inhabiting this region.
For our final sunset, we returned to the dirt road near Terrapille, associated with the famous scene from Gladiator. We had already photographed it on the first day, under a clear sky that gave us little of the dramatic colour we had hoped for.
The return was not simply an attempt to correct the earlier photographs. It gave the journey a natural ending. We were standing again at one of the first places we had visited, but we were no longer approaching Tuscany as four people following a map full of unfamiliar names.
The mist we had imagined never appeared. Several sunrises and sunsets remained quieter than expected. Some doors were closed, some locations were crowded and some plans had to be abandoned. None of that made the journey unsuccessful.
We had organised our first independent photography trip abroad together with two friends who shared our ideas. We had learned how much preparation helps, how quickly a plan can change and why the best decision is sometimes to return rather than continue.
We came home with photographs, but also with something that could not be reduced to a single frame: the confidence that the four of us could build a journey around our own interests, make the necessary decisions and find our way through the unexpected parts together.
