We have hired a driver out of Florence, two separate days. I am looking for details for our itineraries each day.
First day tentative, Sienna (what to do here?), wineries on the route to see, Chianti (possible lunch here at winery), San Gigimano (specifically what to do here) then back to Florence
Second day, Val d'Orcia, tasting in Brunello, Pienza, Maltepulciano. Recommendations for each place? Or different itinerary?
Posted by
San Francisco Bay Area (USA)
15829 posts
Very busy day. First of all you'll need to go to Siena first as some sights may be open in the morning only and also Siena is the one that will have the most to do. There is the Piazza del Campo, Torre del Mangia, Palazzo Pubblico and the Civic Museum, the Duomo, the Baptistery, just to name the majors. All of the above could potentially take the whole day.
The Chianti road drive is a solid two hours even without stops, and wine tasting is open generally in the afternoons only. Castello di Brolio and Castello di Verrazzano are two popular wineries. I would find it difficult to fit both San Gimignano and the Chianti after Siena. Unless you severely cut the Siena visit, I don't think you'd have the time. San Gimignano can potentially be visited in less than one hour, but then you need the logistics to get there (it's between Siena and Florence, but not in the Chianti, which is in between.Montepulciano and Pienza are pretty towns. Montalcino is pretty also, and I think you can do some Brunello tasting even inside the Fortress of Montalcino, if they still have it.
Posted by
Gettysburg PA
6992 posts
Most wineries require reservations
You might ask your driver for help with that (assume driver has done similar trips)
Visit Siena as a day trip on its own day
Posted by
San Diego, California, USA
1026 posts
Siena is a city of 50K and has many sites and is worth a whole day. If you want to see it I would see it separately by bus or train since a driver is no advantage in city itself. The il Campo piazza, the Duomo is amazing and also has a roof climb, museum with a trip along the top of the unfinished cathedral facade and old church underneath are all worth seeing but you'll need timed tickets to get into the Duomo especially on a tight schedule. Siena is large and deserves more than a couple of hours of wandering around and sightseeing.
San Gimignano is good use of a driver and if you want another town I would add Volterra which is really difficult to get to without a car and is the everyday working version of the touristy SG.
As others have said wineries generally require reservations but many towns have tasting rooms from the surrounding area. SG in the morning, winery lunch and Volterra in the afternoon/evening sounds like a good day. Ironically SG favorite local grape is Vernaccia a tasty white wine in the middle of red wine country. We tasted various wines in a wine store/tasting room but this was a few years ago.
I haven't been but Fattoria Poggio Alloro is often mentioned as an amazing place to eat - it's about 10 minutes outside SG.
For sightseeing Montalcino, San Quirico d'Orcia, Pienza and Montepulciano are all clustered pretty close to each other. But be aware that will be at least 1.5 hours getting to that southern area and I would allow 2 hours both ways. The advantage of having a driver is that you don't have to worry about it but it's on the edge a what I consider a day trip.
Have a great trip, rural Tuscany is as beautiful as advertised,
=Tod