Follow for Siena and leave road S.S.73, the "raccordo" Siena-Bettolle, take exit Castelnuovo Berardenga or continue and take the following exit Montaperti and Pianella. From both exits you will travel through beautiful scenery, the first exit will lead you through wilder countryside.
The two routes will join a short distance form Gaiole in Chianti; the first will take you, after Castelnuovo B.ga, to San Gusmé, a very small village famous for the fountain of Luca Cava, and from there you may ascend to Monte Luco (that is not on maps). You will have travelled on a beautiful road off the beaten track that traversing wild forests will lead you to the higher elevations of the Chianti hills from were you will descend passing through Castagnoli onto Gaiole.
You will experience and understand how a portion of the Chianti is beautiful but also wild and rugged. If you don't much care for the isolation of the forest, just before San Gusmè follow signs for Gaiole, this itinerary will take you through Villa a Sesta and under the Castello di Brolio, wine producer stepped in history were Bettino Ricasoli, il "Barone di ferro" (the Baron of Steel), in the '800 selected the vine varieties and set the formula for the production of the Chianti Classico.
From il Brolio continue on a more travelled route, never the less full of curves as most roads in the Chianti, that will take you through forests and vineyards to Gaiole in Chianti. If you exit at Montaperti, site mentioned in the Divina Commedia by Dante for the fierce battle in the year 1260 won by the Senese on the Florentines, once arrived at Pianella turn right for Gaiole in Chianti.
If you are not in a hurry along this route follow for San Sano, pass Lecchi and reach the Castello di Ama were you won't be disappointed by the excellent quality of their wines. Return following for Lecchi and take road S.P.408 to reach Gaiole, one of the three "terzieri della Lega del Chianti" the league of the Chianti, founded by the Florentine republic in the year 1384 to counter the Sienese. From here you can climb to Badia a Coltibuono, following for Montevarchi, or visit the parish church of Pieve di Santa Maria a Spaltenna, nice example of Romanic architecture of the XII century, then pass by the medieval hamlet of Vertine, continue on a short cut that, passing by San Donato in Perano, will lead you to Radda, capital of the historic league until it's disbandment in the year 1774.
From Radda you can visit the castle of Castello d'Albola or the castle of Castello di Volpaia, these with Badia a Coltibuono are amongst the most important estates of the Chianti a land so wild and unforgiving but capable thanks to the work of it's people of producing great wines. You will then return to Radda and take the road for Castellina, third historic member of the della Lega and from there take a small diversion for Castellare di Castellina, so famous for it's great wines. From here the Chianti scenery becomes more gentle and on your return you may reach Castellina Scalo and the under Monteriggioni take the highway direction Siena or follow the "Chiantigiana" road direction Siena, stop at Castello di Fonterutoli another famous winery and then once in Siena take the highway Siena - Bettolle that will take you back tired but satisfied to the Locanda dell'Amorosa.
Distances and drive time
L'Amorosa - Gaiole in Chianti
- L'Amorosa - Castelnuovo B.ga: km. 34,0 - minutes 32
- Castelnuovo B.ga - San Gusmé: km. 5,5 - minutes 7
- San Gusmé - Castagnoli (via Monte Luco): km. 15,6 - minutes 16
- Castagnoli - Gaiole in Chianti: km.6,1 - minutes 7
- Castelnuovo B.ga - Gaiole in Chianti: km. 21,6 - minutes 23
- L'Amorosa - Pianella: km. 46,5 - minutes 44
- Pianella - Ama: km. 14,7 - minutes 17
- Ama - Gaiole in Chianti: km. 11,4 - minutes 12
Gaiole in C. - Radda in C.
- Gaiole in C. - Badia a Coltibuono - Radda in C.: km. 15,3 - minutes 17
Detour Spaltenna - Vertine
- Gaiole in C. - Radda in C.: km. 10,0 - minutes 0
Radda in Chianti
- variante Radda in C. - Albola (and./rit.): km. 13,0 - minutes 14
- variante Radda in C. - Volpaia (and./rit.): km. 14,6 - minutes 18
'Radda in C. - Castellina in C.
- Radda in C. - Castellina in C.: km. 11,6 - minutes 13
- Detour Castellare di Castellina (and./rit.): km. 5,0 - minutes 6
Castellina in C. - Siena - L'Amorosa
- Detour Castello di Fonterutoli: km. 67,8 - minutes 72
- Detour Castellina Scalo: km. 77,6 - minutes 74
L'Amorosa - Gaiole in Chianti
- Itinerary A: km. 61,2 - drive time 1:02
- Detour Brolio: km. 55,6 - drive time 0:55
- Itinerary B: km. 71,6 - drive time 1:10
Gaiole in C. - Radda in C. - Castellina in C. - Siena - L'Amorosa
- Excluding detours: km. 89,4 - drive time 1:35
- Fastest route: km. 145,0 - drive time 1:50