lots of suggestions of places to contact
Ciao Mark,
It took me some days to put this list together so I hope it is useful in your search. I don't personally know any of these accommodations, they are the results of looking on various sources for places that might be the best fit for your trip at each or near each of the daily destinations you've set for your trip. I suppose you might have to contact them all to have as many choices as possible and then check against your hiking maps to see whether they are doable.
Some tips: make sure to tell them you are
arriving on foot, and that you're staying one night because it is a hiking trip. The Tuscan countryside is full of farmhouses that have been converted into B&Bs and apartments so it is likely you have to widen your search to include these and not just hotels/b&bs
within a town. Ask whether they provide
dinner and
breakfast, or whether you are close enough to reach a restaurant or the closest village on foot. If you know they won't provide dinner, you can at least plan accordingly buying something along the way if you can or if you arrive early enough to know you can head back out to eat out nearby. Also give an
estimated time of arrival for check-in - you're on foot, so depending on the mileage you're planning for each day, the lodgings should know more or less when to expect you. If you happen to have a delay, because of some unforeseen detour or unintended stop along the way or just a longer stop along the way of a place you enjoy, it is better if they know you're arriving eventually

. Make sure to have
telephone numbers of all places you book with you - so if you have problems getting there or are really late, you can call them (you'll have a cellphone with you, right?). If, worse comes to worse, request help.
I hope I got the right towns for the ones where you abbreviated names.. there are many Castelnuovos and Castigliones in Tuscany so I tried to find the right ones on the map along the route you said you're following. You also don't give dates so I wasn't able to check availability where I found online booking. Just keep in mind that April 23-25 will likely be the hardest days to find availability because of Easter although it is better for you just to book ahead of time all days so that you won't have to worry about it - just do your walking heading to your destination knowing you already have a place to sleep at.
2nd Day: in
Castelnuovo - is it Castelnuovo Tancredi?
- La Ripolina - between Castelnuovo Tancredi and Buonconvento
- Castelnuovo Tancredi Estate - it seems they want a 4 night minimum stay, but who knows, contact them and ask in any case
- Casa Vacanza Bocci - Casa Martelli is an apartment for 2 - even if they don't have an English version of the site, you could contact them and ask whether they have availability for the night you're looking for.
- Podere Montorgialino
3rd Day: in
Castiglione - Castiglione d'Orcia?
We've actually visited the nearby
Bagno Vignoni and Castiglione d'Orcia last year. The first is a small hamlet set around the thermal hot springs so there that several hotels there that cater specifically to the hot springs goers. If you're passing through here, anyways, you might consider sleeping there.
Castiglione d'Orcia is really small - the Rocca or fortress was closed (you can see the pic in the
header of this hotel at the foot of the fortress, currently closed). We had a good lunch at this trattoria called Locanda del Cassero or something like that in the village. The castle in the village is also closed off. So aside from the view from far away, there wasn't much here.
- only one I found with direct booking: Agriturismo i Lecci, seems to be outside of the small town
- Hotel Orcia - on the way up to castiglione comeing from borgo vignoni
- Aiole - further out from Castiglione (south) but it has rooms by the night
- there is a hotel/restaurant in the town of Castiglione d'Orcia called Albergo Le Rocche but I was unable to find a website - here you might have to call - +39 - 0577- 887031
- further south - Bindozzino has an apartment for 2 that can be rented by night, you need to contact them and see availability and cost.. it would be on your way down to Pescina...
- now if you want to stay in a castle, in the hilltop across from Castiglione you'll find Ripa d'Orcia - the castle there is still in use, part of a wine estate with rooms, apartments and restaurant - so for something really special, try this place!
4th Day: in
Pescina
5th Day: in
Arcidosso
more options in Arcidosso since it is very close to Castel del Piano and there are more choices in and between the two
- Park Hotel Colle degli Angeli Spa & Resort - in Arcidosso, rates are pretty good per night
- Carpenti - this one says that apartments are not available by the night during high season, but contact them anyway, you never know.
- Podere Frati - website is not updated but theoretically is offers apartments (there is one for 2 people) by the night.
- between arcidosso and castel del piano - a campground with a residence - even if the residence is offered by the week, contact them to find out whether during this period they have openings for 1 night
- two hotels in Castel del Piano: Hotel Contessa and Hotel Stella
7th Day: in
Sovana
found two with online booking you can check
9th Day: in
Capodimonte (on Bolsena Lake right?)
Ok let's hope this list is useful --- do let me know if I missed the mark on a place or if you're looking for something else. Also, feel free to ask about any questions or doubts you might have - we like to hike in Tuscany so there might be something I might be taking for granted that you might already know, so I might have left it out!