visiting tuscany for 2 weeks


As we plan our trip to Tuscany, we have some question that perhaps someone can help us with and can provide some information that will be helpful to two people travelling to this area for the first time.
Accommodations: We are looking for a centrally (Tuscany) located apartment or B & B (a/c) that will allow us to take day trips and return back at the end of each day.
We like B & B's and they don't have to be in a village, they can be in the countryside as long as we can travel easily by car to and from the B & B. Apartment rental recommendations would also be greatly appreciated.
Restaurants, ancient ruins, galleries and museums, markets, festivals, are some of our interests.
Siena has drawn our attention, but we know there are other possibilities that would enrich our stay as well.

What would be a good itinerary for a two week stay? We are open to any suggestions as we have the time (two weeks or more); we have the stamina; we like to drive or take trains; we love good food experiences in local restaurants favored by those who live there.

We would appreciate any ideas, help or questions you may want to ask us. Thank you.


The Tuscan Expert ;-)
Staff member
I'd recommend split up your 2 weeks into stays in 2 different areas of Tuscany

Ciao Jkh,

It is really hard to recommend just one location for your vacation since much of Tuscany will meet most of your expectations regarding good food, museums, historical context and local festivals. Festivals abound in the summer season but are concentrated on the weekends. There are also festivals in the spring and fall but definitely less in comparison. Many of the smaller villages don't publicize theirs that far away, you just see these posters in the area saying that the following weekend there will be a "sagra" of something or other, most generally about food or a local product (such as porcini mushrooms, olive oil, the new wine).

So as for location, Siena would definitely fit the bill for central location.
But so would Chianti in general, which is the general geographical area between Florence and Siena. Since you'll have a car, anything in this area would be good.

Since you have 2 weeks, I'd also recommend splitting up the time into two 7 days and you can stay near Siena for one week, then the other week closer to the coast. That way day trips and exploration of the area can be more direct and close to the area you are at the time. For example, you could stay near Castellina in Chianti for the first week - check out some of these estates that offer apartment rentals:
- Romitorio di Serelle
- Il Cellese

Closer to Florence but still in Chianti -
- Chianti Suites just outside Greve in Chianti
- Fattoria Viticcio - this is a working wine estate, also right outside Greve in Chianti
- Fattoria Poggio Arioso - closer to Florence near Montespertoli

If you prefer a B&B, there are two in the area you should look at:
- Casolare di Libbiano - near San Gimignano
- and Palazzo Malaspina - in a small medieval village not far from Castellina but close to the Firenze-Siena road.

Then your other week, you could go to the coast - stay in Maremma at this agriturismo for example - La Valentina Nuova - or some of these other ones: Maremma Accommodation
or go to Elba Island (fantastic place and beaches!) and treat yourself to a stay at this enchanting boutique hotel, a very romantic stay: Hotel Ilio

Whatever you end up doing, you will wish you have more time because Tuscany is quite varied in landscapes and areas so there is something new around the corner to see. You won't go wrong with most of the food, excellent and fresh with great wines - each area has its own, definitely try the variety of each area so you can try something more than the big names that are known outside Italy.

Let me know if you have any other questions, I've been a bit behind in answering some threads on here but I'm trying to catch up! I'm around and will be happy to help :D