Wandering Through Tuscany: A Journey from Pisa to Siena with San Gimignano and Monteriggioni
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Tuscany: Running Through Time, Walking Through Light
Tuscany, with its rolling hills, medieval towns, and timeless charm, has long danced through my daydreams. In late spring, I finally stepped into that dream—a nine-day journey anchored in Siena, woven through stone alleys, golden fields, and misty mornings. What unfolded was more than a trip; it was a gentle unravelling of time, pace, and presence.
A Night in Pisa: Beyond the Lean
I arrived in Pisa as most do: expecting a quick glimpse of the famous tower before moving on. But the city gave more. Just before closing time, I climbed the Leaning Tower under a sky already shifting to twilight. From the top, rooftops and countryside unfurled in golden light. Later, along the Arno, pastel buildings shimmered in the river’s reflection, and dinner came in the form of fresh pici and red wine on a quiet street near Borgo Stretto.
The next morning began with a run—me, alone under vast skies, through the San Rossore park’s symmetrical trees and soft mist. The city waved me goodbye with light on water and the calm of a place that surprised me in the best way.
Settling into Siena
The train to Siena took just over two hours, running every 30 minutes—reliable enough that I barely noticed time passing. From the station, it was a 20-minute walk to my apartment at Eleroom, just beyond the historic walls. Check-in was smooth, the late afternoon light soft against the terracotta skyline.
Siena's rhythm is slower, deliberate. Each morning I returned to Piazza del Campo, watching light bend across its shell-shaped fan. I explored the Duomo’s striped marble and climbed Torre del Mangia for views that silenced thought. My days settled into a gentle cadence: mornings lost to medieval lanes, afternoons on trails that braided through olive groves and vineyards, evenings editing photos with a glass of wine in hand.
A Photographer’s Week: Day by Day
Sunday – The White Roads of Val d’Arbia
From Siena, I followed the Via Francigena south, along the white gravel roads to the fortified Grancia di Cuna and on to Lucignano d’Arbia. The Crete Senesi opened wide before me—soft hills, sun-cracked clay, timeworn stone. Each step felt ancient.
Monday – Blue Hour Siena
I stayed local, chasing light through narrow alleys. Siena’s gothic textures come alive in the blue hour—marble softening, lanterns flickering, silence folding over stone.
Tuesday – Train to Asciano
A short ride to Asciano opened access to looped trails among the ochre ridges of the Crete. I booked train tickets in advance—Tuscan time is beautiful but not always punctual.
Wednesday – Exploring Porta San Marco
The area around Porta San Marco became a recurring backdrop. I scouted locations nearby, hunting corners of soft shadow and quiet rhythm.
Thursday – More San Marco and Beyond
Revisited the gate in different light. This part of Siena felt lived-in and layered, less curated for tourists—more like a secret kept by locals.
Friday – Towers and Twilight
I ran Siena’s four towers at dawn, finishing at Torre del Mangia just as light hit the upper ledges. Later, I revisited my favourite shots for a final set of twilight edits.
Saturday – Walk to Asciano via Via Lauretana
The trail from Siena to Asciano is 20+ km of pure Tuscan soul—cypress silhouettes, hilltop farms, fields etched in time. I caught the 16:07 train back, exhausted and exhilarated.
Sunday – San Gimignano to Monteriggioni
Caught the 6:36 train and a quick bus to San Gimignano. The towers still cast long morning shadows as I set off on foot toward Monteriggioni. This stretch of the Via Francigena was challenging and magical—old stone paths, wildflowers, and that quiet sense of walking through centuries. Lunch inside the walls of Monteriggioni: wild boar pasta and chilled Vernaccia. Heaven.
A Last Day of Light and Letting Go
On my final day, I slowed down. With my luggage stored, I wandered back into the Duomo, revisited the museum, and let Siena say goodbye in its own way. A final espresso. A final photo.
What I Learned: Tuscany’s Pace is the Point
This trip wasn’t about seeing everything. It was about seeing deeply. The details—train timetables, check-in windows, bus routes—formed a frame, but inside that frame was light, texture, story.
I set out chasing photos. What I found was a rhythm of walking, waiting, running, noticing. Tuscany doesn’t just ask you to look. It asks you to linger.
