driving up and local events
Ciao Nir,
I assume you're driving up from Rome since you're asking what to do on that first day on your way north into Tuscany. Assuming you will be visiting
Siena,
Florence, the
Valdorcia area to the south of Siena, the
Chianti between Florence and Siena and the Val d'Elsa during your week here in Tuscany, I recommend on your way up to take the coastal route up through Lazio and into Tuscany. That way you will see the coast and, if you're really lucky with the weather and get nice bright sunny days, you should stop at a coastal town and walk along the sea, either on the beach or a promenade.
Here is a map from Rome Fiumicino along the coast to Grosseto, passing through
Maremma.
http://maps.google.com/maps?f=d&sou...=42.285437,11.681213&spn=1.517817,3.56781&z=9
Along the way, I recommend once you are near the Monte Argentario to take a detour onto the promontory and visit either
Porto Ercole or
Santo Stefano. Both are port towns with fortresses overlooking the sea. Then return to the road you were on and continue up, if you have time you could briefly visit
Grosseto - the cathedral and the Medici fortress are the main sightseeing points in the small historical center.
If you want to see a little bit of beach, from Grosseto go to
Castiglione della Pescaia with its beautiful fortress overlooking the sea.
From this area, since I am not sure where you're staying at, you can take several roads in toward Siena and Colle Val d'Elsa. If you take the road that passes through
Massa Marittima, stop briefly to visit the town and then continue on to Monticiano - the
San Galgano Abbey is a beautiful old church without a roof that I'm sure you've
seen in photographs before. Very beautiful spot. The nearby chapel has a sword in a stone, legend has it the original belonging to San Galgano. This itinerary could take you all day so that you arrive at your destination in the late evening - the stops are totally up to you, it is fun to drive off the main toll roads because you can stop along the way in the villages that catch your fancy as you drive through or near.
As for events, keep checking this
events calendar in Tuscany over the next 2 weeks as we keep finding out about events and adding them.
There are several events on the day you arrive but I doubt you'll have time to drive up and be there - you could, for example, decide to skip the long drive along the coast and just drive directly to Poggibonsi for their "Pigio", their local festival connected to the grape harvest and to the new wine production (Poggibonsi is on the border of the Chianti region).
Keep in mind many local events - particularly food festivals called
sagre here - are not publicized online at all. You just have to keep a lookout for posters on polls as you drive and in towns that announce the festivals going on in the area. October is a good month for festivals involving chestnuts, new wine (called
novello) and porcini mushrooms so there is bound to be something nearby. You should also know most of these events take place from Thursdays/Fridays through the weekend. It is rare for any to last longer than that but many events take place over several weekends during the month.
Hope this information is helpful!