There’s a way to see the Casentino that no car window and no walking tour can match: leaning into a curve in a vintage motorcycle sidecar, engine humming, the green folds of the valley opening up around you.
This 2.5-hour tour departs from Stia and threads together three of the most evocative medieval castles in Tuscany — Poppi, Romena, and Porciano — each one a chapter in the story of the Guidi counts who once ruled this valley, and each one touched, in one way or another, by the exile of Dante Alighieri.
Why See Casentino by Sidecar
The Casentino isn’t built for buses. Its roads climb and dip along the young Arno river, cut through chestnut woods, and skirt hillsides where fortresses have stood watch for a thousand years.
A motorcycle sidecar is the right scale for it: low, open, close to the road and the air, slow enough to catch the smell of the forest and the sudden view of a tower appearing over the ridge.
It’s an old-fashioned way to travel through a landscape that has changed remarkably little since the Middle Ages — and it turns the drive between castles into as much of the experience as the castles themselves.
Departure from Stia
The tour begins in Stia, a small mountain town at the head of the Casentino Valley, near the source of the Arno.
From here, the route follows the river valley south, with the wooded slopes of the Casentino Forests National Park rising on one side and glimpses of stone towers marking the way ahead.
Castello di Porciano
Just outside Stia stands Porciano, a fortified castle documented since the early eleventh century.
It belonged to the Guidi family until it passed to the Florentine Republic in the fifteenth century, and it is remembered above all for having sheltered Dante during his exile in the early 1300s — a stay commemorated today in the castle’s Salone di Dante.
Compact, austere, and largely untouched by mass tourism, Porciano offers an intimate first stop, with sweeping views over the upper valley from its garden.
Castello di Romena
A short ride south, three towers rise out of the trees above Pratovecchio: what remains of Romena Castle, considered the oldest fortress of the Casentino, first recorded in the year 1008.
Built to its greatest splendor under the Guidi counts, it is now a romantic ruin — drawbridge, prison tower, and patrol walkway still intact — and one of Dante’s own settings, referenced in Canto XXX of the Inferno.
The Romanesque parish church of San Pietro stands nearby, adding a quieter, older layer of history to the stop.
Castello di Poppi
The tour’s final stop is Poppi, the castle that dominates the entire valley and is, for many, the symbol of Casentino itself.
Built by the Guidi family between the late twelfth and early fourteenth centuries, its tower is said to have inspired the design of Palazzo Vecchio in Florence.
Dante lived here for a year during his exile, a stay recalled by the bust in the piazza below, and the castle’s frescoed halls — painted by Taddeo Gaddi, a pupil of Giotto — remain remarkably vivid.
From the tower, the whole Casentino unfolds below, the Arno tracing its path south toward Arezzo.
The Ride Back
From Poppi, the sidecar retraces the valley road to Stia, closing a 2.5-hour loop that moves through nearly a thousand years of Tuscan history — three castles, one river, and the open road between them.