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Italy - 3 days in Southern Tuscany

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Hi,

We will be staying 3 nights in Southern Tuscany to visit Montepulciano, Val D'Orcia, Cortona and a few nearby places. We first thought about staying in Montepulciano or a nearby vineyard hotel or B&B. But, now I am thinking maybe we should also consider staying in Cortona or somewhere else. We will have a car and won't mind driving somewhere else to eat. Also we will be staying in Umbria after this stay. Any other suggestions?

Thank you

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    First, regardless of whose advice you listen to, your plan is excellent. The scenery and charm of this region simply exceeds any meager attempt to describe it using human words.

    We visited the region 3 years ago and a return trip someday is #1 on my "list" In particular I highly recommend checking out the strada vino nobile website listed below, and please consider the very charming La Terrazza hotel in the middle of the old part of Montepulciano. Also, you should try to catch lunch at la Porta in Monticchiello. And many folks find 3 nights in la Foce (lafoce.com) to be a nice option, but when the sun goes down you are in the middle of nowhere. Any of the small cities in this region are fine bases and the lodging seems to be of fairly uniform value. but Montepulciano gets my vote for you as the drive from there to Umbria is quite easy.

    Here is an excerpt from my TR:

    " Finally reached our destination of Montepulciano after about 3.5 hours of tough driving. This little city is the prototypical little medieval European town where you are immediately lost upon entering town. Driving in the narrow streets did not seem to be a very pleasant option and many alleyways that seemed to go where we wanted to go became passable only on foot. So I found an acceptable parking spot and we set out on foot to find the Central square, which we did only after climbing several few steep inclines. Finally found the very charming little piazza, and we got tickets for a wine tour from the local wine consortium. The lady points to the middle of the piazza and says “There - you wait!” Ok, so after 3.5 hours of intense Italian Autostrada driving my adrenaline level is pretty high, so I’m not really into standing still at that point, and I have to wait in the middle of this piazza for almost ten minutes wondering if I’ve just been ripped off. Finally, a minivan shows up, we pile in, all very glad someone else besides yours truly was doing the driving, and me glad that this dude was proving to my family that other drivers could actually attempt some of the curves in the road faster than I did. The winery tour is very highly recommended, both for the delightful tour they give you as well as for the quality of the Vino Nobile wine. (http://www.stradavinonobile.it/new/ivini.en.php)
    Montepulciano is situated between the Valleys of the Chiana and the Orcia rivers. Most people feel the Val d’Orcia is the more picturesque of the two, but - wow – both are just incredibly beautiful. Had a lovely 3 hour tour of two local wineries. Scenery is simply indescribable. Wine was equally fantastic. Following that we checked into the little Albergo (hotel) la Terrazza (www.laterrazzadimontepulciano.it) run by the charming, if not slightly eccentric, Roberto. Roberto runs a fine hotel, part time enoteca, and claimed to be the ex-goalkeeper of the town football club as well as the current President of their local league. While there, I engaged in a nice conversation with a Canadian guest who is of Italian ancestry who knew the area well and she suggested a day trip itinerary for us for the next day. We visited the famous Temple of San Biaggio (16th century), the Abbey of Sant Antimo (11th) the Castiglione (fortress) d’Orcia (12th) – went swimming in a hot spring fed pond in the town of Bagno Vignoni, had lunch in the tiny hilltop hamlet of Monticciello, and ended at a small farm ( Cugusi http://www.caseificiocugusi.it/azienda.php) that made, on the premises, their very own sheep’s milk cheese called pecorino and a very high quality Olive Oil. – An outstanding itinerary and easy to do. – In particular the drive from Bagno Vignoli to Monticchiello is not on many maps, very rural, and just left me slack-jawed with the beauty of the landscapes."

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    I would pick either Montepulciano or Pienza to base. Cortona is just not as convenient for what you want to do. Montepulciano is bigger and has more choices (restaurants)and Pienza is flatter so easy to drive in and out for day trips.

    I would visit Cortona on the way to Umbria after your Val d'Orcia stay.

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