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Itinerary for Tuscan countryside

New York City, New...
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Itinerary for Tuscan countryside

I will be traveling with my husband to visit our daughter in Florence next April. Our plan is to meet her in a nearby city of her choice (not yet selected) to spend a 4 day weekend, then return to Florence with her for 4 days. Next we'd like to spend a few days in the Tuscan countryside and I was hoping to get some feedback on our intended itinerary. Given that we will have already been abroad for 8 days, we really only have 3 days for the countryside. I'd like to know if this plan sounds reasonable, or if we are trying to squeeze too much into each day? Likewise, are we missing any must-see towns in the region? My thought was that first we would leave Florence and visit Sienna for the day. We would then travel to wherever we are staying (to be selected once I determine if the itinerary is workable) for the evening. The second day we might focus on the Chianti region, visiting Greve, Panzano and San Gimignano. The last day we'd go south and could visit Montepulciano, Montalcino and Pienza. Of course the days don't need to be in that order, but mostly I'd like to know if the towns are logical and if the plan isn't trying to cover too much. Finally, if this does sound reasonable, where is the most central place to stay for the 3 days? My first thought was Siena, but I'm guessing we will need a car to visit the other towns and I've heard parking is a problem in Siena. Still, we'll need to get back to either Florence or Rome, to fly out the next day, so I thought a train from Siena could be convenient. Any advice would be appreciated! Thanks!!

Montepulciano, Italy
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1. Re: Itinerary for Tuscan countryside

Sounds perfectly reasonable to me. Leave Florence taking the SS222 Chiantigiana via Greve and Panzano as this will give you an opportunity to spend a day seeing this more northerly part of the Chianti en route to where you are staying. I would opt for a base for your three nights within 30 mins drive of Siena either north, ie around Castellina, or east (Castelnuovo Berardenga) or even south east (around Asciano) reason being this would allow you to explore more of the southern Chianti (ie the part you haven't seen whilst driving down), day trip to Siena (where parking is very easy) and finally visit Montepulciano, Pienza and the Val d'Orcia. Virtually every other house in the Province of Siena offers accommodation nowadays so the choice of where to stay is huge and you are bound to find something that suits.

Sheboygan, WI
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2. Re: Itinerary for Tuscan countryside

We recently stayed 6 nights outside Certaldo and visited many of the places you are interested in. We did Colle Val d'Elsa, Volterra and San Gimignano in 1 day, and also Montepulciano, Pienza and Montalcino on another day. From Certaldo, the M-P-M day was long, and if I had to repeat it, would likely cut out Montalcino and have added La Foce, just for some variety.

Staying closer to Siena would be more central for you, but since you'll have a car, just stay out in the country rather than in town. Then you won't have to worry about overnight parking.

For the day you visit Siena, use this for parking: slowtrav.com/italy/driving/parking_siena.htm

New York City, New...
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3. Re: Itinerary for Tuscan countryside

Wow, thank you both so much! I think that confirms my plans. So my next question is, if staying in the countryside, is there anywhere where restaurants for dinner and maybe drinks afterwards are conveniently clustered? I guess the goal is to look for a place outside but not far from one of the towns?

Sydney, Australia
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4. Re: Itinerary for Tuscan countryside

Almost all the towns in this area are at the top of large and steep hills. There is nowhere that is in the countryside and also conveniently close to restaurants.

If you want to be able to have dinner with some drinks, you need to stay in one of the towns.

Montepulciano, Italy
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5. Re: Itinerary for Tuscan countryside

There are many seriously nice village hotels now with countryside views so you can enjoy the best of both worlds. If you pick a smallish village, it will feel very much like the country anyway. Alternatively, perhaps consider one of the restored "borghi" that are now vineyard estates with restaurant and rooms. They are usually at the pricier end of the scale but invariably very well appointed. Between Siena and Castellina, for instance, there's Fonterutoli (www.fonterutoli.com) but there are plenty more. Otherwise, consider Pienza which is on the flat and packed with options for both accommodation and eating in all price brackets. Piccolo Hotel, Corsignano, Il Chiostro, La Bandita Townhouse are just as a few that come to mind, the first three will certainly have rooms with fabulous Val d'Orcie views.

Sheboygan, WI
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6. Re: Itinerary for Tuscan countryside

We stayed in an apartment at a farmhouse outside Certaldo. Meals were available there, but we usually had a large lunch, then made sandwiches for supper in the apartment and ate on the terrace with views of Certaldo Alto and San Gimignano. Otherwise the drive into Certaldo was short, so going in for supper was not a problem. Our particular farmhouse had an honor bar available for guests to purchase bottles of wine and enjoy on the terrace, which many of the guests did every night.

I know many of the farmhouses we looked at staying had restaurants on site.

7. Re: Itinerary for Tuscan countryside

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