Trip plan for Tuscany


New member
My wife and I will be traveling to Tuscuny for a week starting from October 3rd. we will celebrate my wife's 40th birthday.
As we will be landing in Rome early in the morning, I would like to get your advise for the first day plan on route to Tuscany. we will be staying in Val D'elsa
Second, Could you recommend on a specific festival or event that will take place on the week starting from aoctober 3rd?
Thanks much!


The Tuscan Expert ;-)
Staff member
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.,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!


Well-known member
Just got back yesterday....first off, you will love it secondly, good luck driving from Rome, I did it and it was a brutally long trip. We stayed in Castellina and it took over 3 hours to get there. But once we got there it was amazing. As I told my fiancee, WHEN we go back I would fly into Rome and take the train to Florence and rent a car there.


Well-known member
From Rome to Val D'Elsa

Dear Nir,
I agree with Lourdes and want to suggest you drive along the coast and stop in Maremma. I personally love it and find it extremely beautiful.

I suggest you stop in Capalbio and visit the Tarot Garden nearby. In Maremma you'll probably find lots of local events, especially related to local food and products. As Lourdes wrote, keep a lookout for posters on polls as you drive :)

I hope these suggestions are helpful and don't hesitate to ask any further questions.


New member
Many Thanks!

Dear Lourdes and Valentina!
Thanks so much for the detailed and useful information you provided to me . It all matches exactly what I was looking for. I believe the way north to our destination would be much more interesting than taking the toll road. I appreciate it.
As I continue to plan our trip, I will not hesitate to contact you once again for additional information.
Thank much!:)