One road that makes its way through three provinces: this is what the Senese Aretina is all about. At times elegant, at others malicious, this road goes from Grosseto to Siena, and for those who want to go further, you can continue on to Arezzo. Towns, castles and some great roads: a classic and much appreciated road for those who love to ride.
Departure/Arrival: from Montepescali to Arezzo
Duration: 1 day
Kind of road: mixed, hilly
Provinces: Grosseto, Siena, Arezzo
Set your GPS: Montepescali, Roccastrada, Monticiano, Volte Basse, Siena, Colonna del Grillo, Monte San Savino, Pieve al Toppo, Arezzo.
Like hawks set to attack, we prepare for the Senese Aretina from "the balcony of falconry" in South Maremma, the town of Montepescali, a lovely fort town which is even more famous during the Boar and Tortelli festival in August. From the Vecchia Aurelia, after two turns to the left, we head out onto the SS73 which goes straight for more than 10km. A major fork in the road breaks up the monotony. To the left is Sticciano: this curvy road climbs to the north western slope of Monte Leoni and reaches the town and church of Santa Mustiola. A lovely road lined with sea pines reminds us we are still in Maremma.
At km11, the ride suddenly becomes more exciting. Surrounded by typical Mediterranean flora, we head off towards Civitella Paganico. The road climbs and turns, and gets ever more interesting, and the countryside, too, becomes fascinating. At the 43rd parallel there's a sign that indicates an intersection. Go to the left for the Giugnano monastery and crypt; to the right for the Siena hinterland. Roccastrada is straight ahead, just a few accelerations away: and there you will find a medieval town which provides the perfect break.
The road goes down but the corners of the driver's mouth turns up in a smile. Curve and counter-curves follow each other in continuation. Sassofortino waves to us, but not even an invitation to the Chestnut festival at the end of October can interrupt the pleasure of driving. The province changes: SP157-SP73bis and the road descends. There's the monument to the victims of the massacre of Monte Cuoio by the Fascist Nazis, and we stop for a moment of reflection. At km 42 a large statue in the shape of a pecorino cheese makes us smile. Monticiano is the next town on the road where you can see the contemporary artwork of Roberto Ciulli, at km 45.
At the intersection with SP441 follow signs for the Abbey of San Galgano. It's a must. The road goes back to being straight, but only for a bit, and the curves and climbs return as we head towards Castello di Frosini. The intersection with the Maremma Traversa is indicated by the column of Montaretti, which was commissioned by Piero Leopoldo; the Senese Aretina road curves onwards to the medieval bridge of Pia, near the Eremo di Rosia.
The adrenaline fades a bit as we head towards Siena, cutting through Volte Basse and Costalpino. But there's no time for the city of the Palio, which we salute from Porta Pispini. After a bit of the Siena-Bettolle road, we pick it back up at the Colonna del Grillo, with a break for food at the trattoria in Bivacco.
The SS73 offers us a last burst which takes us all the way to Monte San Savino: watch your speed. 50km/h for motorcycles! You've got to know how to ride, but not to speed - that's what the GSSS teaches - and fun will be certain. Twenty km more and we're in Arezzo: cradle of history, culture and tradition.