This seemed such an obvious walk - between two great Italian Renaissance cities about 50 miles apart - that we were surprised to see so little about it on the net.
This may be because Italy has no tradition of footpaths, or walking as a hobby (so no signposts), or because the maps are not very accurate, or because the scenery, though beautiful, does not vary much between the towns.
However, we found it worked well once we had learned to use the map properly. The walking itself isn't difficult, and dogs were less of a problem than in, say, France (i.e. almost always behind bars).
1. Days needed
We took five days of walking, plus a day of sight-seeing and travel at each end, making nine days in all. We could have shortened it by travelling during the night, or (especially) by cutting out the extra day in Florence, which didn't endear itself to us as much as Siena.
2. Getting there and away
From London: fly to Pisa. There is no airport at either end of the walk.
We heard of a train direct from Pisa to Siena at 1 pm, via Empoli and avoiding Florence which would have been good; but we were later and went by bus. At the airport there is a bus station and a ticket booth for both Florence and Siena; we bought a through ticket and caught a bus to Florence Central Station. The driver indicated the connection - a bus station about 75 metres away, with frequent buses to Siena.
Going home, we caught the Florence/Pisa airport bus around 1 pm going the other way. Buses are cheap and frequent, and the traffic on leaving was OK, but on our arrival in Florence (about 6 pm) it was appalling.
There is a Kompass map #2458 that covers the walk exactly. It's at 1:50,000 and is absolutely essential. It's a lovely-looking thing, and claims to be waterproof... which it is except at the edges, where the water gets between the layers. It's also very light on contours, making it hard to 'read' the countryside. It shows a myriad of small roads, often marked red, meaning 'trail'. These we used, but came to see that the trails were sometimes tarred, sometimes tracks, sometimes paths, sometimes very rutted. Also there were more than were marked, and the map was not always accurate.
However, the direction of a trail was accurate, so a compass was essential, and extremely reassuring even if, like us, you're not an expert at using it; because you are mostly going north, or slightly west of north, or slightly east of north. We used the map to find suitable stopping points, and liked our route with one exception (day 4, see below).
4. The route
In Siena we stayed in the
Albergo La Perla - one minute from the Piazza del Campo.
Day 1: Siena to Vagliagli
Getting out of Siena was easy; leave by the Porta Ovile follow the green-marked road, and down through the car park to the roundabout. We crossed to the yellow road marked 408, failed to find the red road off it, but joined it just above Bottega Nuova, at the bus stop ('H' on the map). At the Church of Cipriano, the trail goes off the tar, going slightly east of north (a lovely bit).
We made our way towards Ponte Bozzone, and found a nice cafe by the car park.
We then walked north up the right-hand of the two possibilities which, being a bigger road, was quite boring. (We had hoped the wiggles further up were interesting, but they weren't).
Because we were staying at Borgo Carpineto (which also did a lovely evening meal) we turned right off the main road before Vagliagli on to a lovely track.
(Italian B&Bs may be unoccupied when you arrive, so texting them beforehand could be good... otherwise, wait.)
Day 2: Vagliagli to Radda.
The same track continued on, via S. Pollo in Rosso, to a bigger road just beyond S. Giusto in
Salcio. 'Go left', our hosts had said, and sure enough a little while after starting the trail
there was a multiple-choice moment, and the left track down a hollow way was the one. Once on the bigger road we failed to find the red-trail route directly into town, so came in the long way round. We stayed at the
Baldini Romanita, on that road just before you get into town. It looks unprepossessing from the front, but the balcony below (for breakfast) is stunning. (We had a bad experience at the Elio Pistolesi in town, and wouldn't recommend it.)
Day 3: Radda to Greve.
We walked out east-ish on the main road, to a jumble of possibilities, and eventually found the white road (coloured red and green) to Bugialla. We then took the red track (lovely) north to Baddiachia where there is a cafe.
After lunch we walked north along the main road until we came to a signed(!) track to Mon San Michele (further up than marked on the map). We then saw more signs to Casole (direction, west-ish). They were conflicting, but we picked the ones with red and white paint(!). Once at Casole the path is a tarmac road going north-west to the main road and into Greve. (The area around Greve does have footpath signs, and it was nice to see them.)
We stayed at the Grano e Lavanda B&B.
Day 4: Greve to Strada.
We left on the road going easterly, took the little red road short-cut and on to Il Chiesino. We then carried on north-easterly, to pick up the long north-westerly track through Bosco di Querceto. Unless you really love woods I recommend that you keep more to the West, in the lower ground - we couldn't see a thing! We then walked on the bigger road into Strada.
We stayed at the Chiantihome B&B.
Day 5: Strada to Firenze.
We walked north up the main road, taking a right at the restaurant on the red road to C. Pozzo. We then joined the green road and walked north to Grassina for lunch. We followed the yellow road under the Autostrada (now getting very busy) to the big marked roundabout. There we took the left turn (yellow road), but very soon the right turn on a white road (sometimes plus green, sometimes red) that goes all the way into Florence.
We stayed at the Hotel Ferrucci, which is south of the river and almost on this road.