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One day countryside trip from Siena - July

Hey folks, was seeking some advice. The more research I do on my own the more I am convinced I need to move to Italy. There are too many beautiful places to visit.

Me and the Mrs will spend 3 nights in Siena as part of a 2 week trip. Day 1 we arrive at Noon, check in and explore Siena. Day 2 we rent a car at 9am on Monday and need to return it the next day at 9 am. Day 3 we stay in Siena

For the one day we have a car it looks like we should either go north of Siena and see 2 towns and then find a nice winery or have dinner somewhere. The other option which looks like it is more scenic for the drive is to follow the same thought process going south of Siena. Anything more than 2 main stops and I feel like we will be rushing too much.

North way: Thinking of driving to San Gimignano (1 hour) then to Monteriggio (40 mins). Realistically if we start at 9 am and allot proper time to visit/enjoy we are probably at 3 pm - 4 pm minimum. That leaves a few more hours to drive and see the countryside, find dinner and be back by 8 pm or so

South way: Definitely like this route: Montepulciano (1 hour drive) for a 2 hour visit and lunch, drive to Civita di Bagnoregio (1 hour 40 min drive) then we can get on SR2 which looks like a beautiful drive back (2 hours 30 min) which probably gets us back at 8 - 9 pm with a couple short stops in route. Civita has been on my short list for a while so it is tough to not consider this
Google map of the drive

The other southern route which gives us better visiting time is Montepulciano, Pienza, San Quirico d'Orcia and then SR2 back to Siena. I am really leaning this way. Shorter route

Obviously the drive is part of the experience. I gladly welcome any other suggestions or completely different itineraries.

Thank you!!

Posted by
8076 posts

It is not possible to have dinner in Italy and be back at home at 8PM. Doesn't happen. One option is to have the heavy meal of the day at one of the many big wineries that operates a restaurant with lunchtime tastings. Then have a light appetizer and wine dinner, perhaps closer to home (for driving reasons. Note strict enforcement in Europe ... ) Have you investigated parking for the night of the car rental? It's not a trivial matter at Siena, although I'm sure the distant lots have more spaces in the evening. Can you pick a big rental company that allows unattended drop-off? If you buy the insurance anyway (I mean the add-on ZERO deductible), you don't care about the inspection anyway.

Because Siena is such a big city, with so many attractions, I would suggest a route with smaller towns. I note that you go near Cortona, which I liked. Because the winery experience was so good (and the absolutely superb, 50(?) Euro lunch, with massive, repeated pours ... ) I would skip Montepulciano and make an appointment at Aviognesi Winery. Maybe visit Castiglione del Lago, especially if it's hot.

Did you fail to give the month of the year in your OP? That is a crucial factor in crowded, popular Tuscany. You also need to use the search box here to read many posts with important car rental information for Italy. Since you're only renting for 24 hours, you don't really care about paying for extra insurance and so on. You need a GPS, your own or theirs. You also should know from the US that Google Maps does not include even the most basic traffic and construction delays. You will not be traveling at the speed limit, which how GM does the computation. That 2:18 estimate is ridiculous. Parking and walking UPhill at each town takes a lot of time (and sweating, in the summer!)

Do not overlook that ANY "name" winery wants you to make an appointment, and probably pay in advance. Our luxury hotel was helpful in this respect, before we arrived. I gave them carte blanche to select and book three wineries.

Posted by
336 posts

All of the possibilties are fantastic spots to visit.
Having said that, my first choice would be the region of Pienza Montepulciano Val d'Orcia. Add to that Montalcino and Sant 'Antimo abbey.
The ride wouldn't be as long as your second choice, and this region is the postcard representing Tuscany.
You're also in wine country with the brunellos from Montalcino and the vino nobile from Momtepulciano.

Posted by
15 posts

Tim,
We are staying outside of Siena proper and have free parking available at the BNB. We did get the zero deductible plan also. Thank you for the heads up on Google maps also. We are going in July. I will look up Aviognesi and Castiglione del Lago. I appreciate the tips!