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Day trip to chianti or Siena/San Gimignano from Cortona

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Day trip to chianti or Siena/San Gimignano from Cortona

Hi,

I'd like some opinions as I am hesitating between these 2 itineraries (we stay close to Cortona and are driving a rental car)

First choice was driving straight to San Gimignano, visit, probably have lunch, then head to Siena on our way back, visit for 2-3- hours (probably around Piazza del Campo), then back to our hotel.

2nd choice was going straight to Greve in Chianti (by Siena then SR222), visit, have lunch with a friend there, then drive down to Castellina in Chianti and make our way east to Montavarchi, stopping in Radda in Chianti, Gaiole in Chianti and Badia Coltibuono. Then hop on A1 in Montavarchi and head back to Cortona.

So many people told us not to miss San Gimignano and Siena that I'm still hesitating about choosing Chianti region.

But I must add we intend to go back to Tuscany in the next 2-3- years and probably stay around or in Siena, so skipping San Gimignano might not be that much of a problem.

Thanks for any feedback.

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Cortona
Cortona
Province of Arezzo, Italy
San Gimignano
San Gimignano
Province of Siena, Italy
Siena
Siena
Province of Siena, Italy
Piazza del Campo
Piazza del Campo
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Siena, Italy
Greve in Chianti
Greve in Chianti
Province of Florence, Italy
Castellina In Chianti
Castellina In Chianti
Province of Siena, Italy
Radda in Chianti
Radda in Chianti
Province of Siena, Italy
Gaiole in Chianti
Gaiole in Chianti
Province of Siena, Italy
10 replies to this topic
Garstang
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1. Re: Day trip to chianti or Siena/San Gimignano from Cortona

I would definately visit Siena (I lived there for a while) - it's larger than San giminiano and has a lot more to see/history wise as well. You could spend a few hours easily just walking around the old town which hasn't ever been modernised.

Not saying SG isn't lovely - but if you only had time for one then Siena it would be.

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Siena
Siena
Province of Siena, Italy
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2. Re: Day trip to chianti or Siena/San Gimignano from Cortona

Lunch with a friend sounds good. If you're coming back again then there's time for Siena and San Gimignano then. Siena deserves more of a flying visit. we did that once and didn't much care for it and so glad we went back and spent a lot more time discovering what it does have to offer

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Siena
Siena
Province of Siena, Italy
San Gimignano
San Gimignano
Province of Siena, Italy
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3. Re: Day trip to chianti or Siena/San Gimignano from Cortona

Paul S: lunch with a friend is part of the Chianti itinerary LOL

Eagle River, Alaska
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4. Re: Day trip to chianti or Siena/San Gimignano from Cortona

Save Siena for when you have time, several days, staying within the walls. It is such a jewel it deserves more than a passing glance. You won't be sorry. :-)

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Siena
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5. Re: Day trip to chianti or Siena/San Gimignano from Cortona

So far thanks for the answers

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6. Re: Day trip to chianti or Siena/San Gimignano from Cortona

"going straight to Greve in Chianti (by Siena then SR222), visit, have lunch with a friend there, then drive down to Castellina in Chianti and make our way east to Montavarchi, stopping in Radda in Chianti, Gaiole in Chianti and Badia Coltibuono. Then hop on A1 in Montavarchi and head back to Cortona."

This sort of works. However, if it were me I would head straight to Greve (via the A1 exiting at Montevarchi) but realise that may have you arriving there too early for lunch. Still, you could go up Montefioralle or even Badia Al Passignano first as both are fairly nearby and very picturesque. Then have lunch and continue with the drive south down the SR 222. Finally, it's possibly just me but I don't like that run from Radda to Montevarchi, it's a slow, windy road and not the most picturesque (also, Gaiole is one of the least attractive of the Chianti towns). Instead, after Castellina I would head down to the FI / SI expressway at Monteriggioni perhaps stopping at Monteriggioni for 15 mins (it doesn't require much more) before continuing on towards Siena taking the Siena - Bettolle - Perugia road at Siena Sud and then back to Cortona. From Monteriggioni onwards it's a fairly fast road, scenic too all the way to the Cortona exit on the Bettolle - Perugia.

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Greve in Chianti
Greve in Chianti
Province of Florence, Italy
Siena
Siena
Province of Siena, Italy
Castellina In Chianti
Castellina In Chianti
Province of Siena, Italy
Radda in Chianti
Radda in Chianti
Province of Siena, Italy
Gaiole in Chianti
Gaiole in Chianti
Province of Siena, Italy
Cortona
Cortona
Province of Arezzo, Italy
Montevarchi
Montevarchi
Province of Arezzo, Italy
Monteriggioni
Monteriggioni
Province of Siena, Italy
Bettolle
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Sinalunga, Italy
Perugia
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7. Re: Day trip to chianti or Siena/San Gimignano from Cortona

Thanks lastraniera.

I am trying to figure out what would be the best road between the Montevarchi exit and Greve (SR69 then SP 16?).

I read somewhere here on TA that the road from Greve to Montefioralle was not even taken by buses. If it is hilly and very curvy I know my wife will refuse to go there for sure.

What's the best road to either Montefioralle and/or Badia al Passignano?

Thank you very much for your help

I understand you prefer my 2nd option and think I should skip San Gimignano this time.

Edited: 11 May 2018, 22:39
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Montevarchi
Montevarchi
Province of Arezzo, Italy
San Gimignano
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8. Re: Day trip to chianti or Siena/San Gimignano from Cortona

Once again lastraniera.

On our way down to Siena by SR222 according to your advice, is Radda in Chianti worth the game for a short detour?

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Siena
Siena
Province of Siena, Italy
Radda in Chianti
Radda in Chianti
Province of Siena, Italy
Montepulciano, Italy
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9. Re: Day trip to chianti or Siena/San Gimignano from Cortona

The scary, narrow, windy with sometimes deep drops over one side and no protective barrier sounds to me more like the Greve / Lamole road, the Greve / Montefioralle and then on to Badia is gentle enough as you climb slowly up through the olive groves and vineyards. Can't comment on why the bus may not go up there but it's not a difficult drive in a car.

Re getting to Greve from the A1, admittedly it's not easy on the cross-country stretch for whichever exit you take (Valdarno (nr Montevarchi) or Incisa (the next one north)) you then have to wind your way around the country lanes. My husband is looking over my should saying it's easier from Incisa but I suspect that's because I once got us horribly lost in Montevarchi town centre whilst trying to find the road out to Greve. (It's easier to find the road to Gaiole / Radda.) We all have bogey towns when it comes to driving, mine are Montevarchi and Poggibonsi. If you have a GPS or a good map reader with you, you should be fine and remember getting lost in the countryside is Tuscany is always an enormous pleasure.

Finally, I reckon Radda is definitely worth a detour, it's a very pretty town set atop a small hill with a beautiful passeggiata around the town walls affording superb views of the vine covered countryside. Good restaurants, some nice shops, I'm personally very fond of it.

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Hotel Valdarno
Hotel Valdarno
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Montevarchi, Italy
Montevarchi
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10. Re: Day trip to chianti or Siena/San Gimignano from Cortona

Thanks a million.

I found the way to Greve from the Incisa exit, it should be OK. My wife is not really a card reader but I'll manage with my iPhone's GPS and a good Michelin card (paper version).

I also think we should have time for a detour by Radda before heading South to Siena then Cortona.

Once again you were very helpful.

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Siena
Siena
Province of Siena, Italy
Cortona
Cortona
Province of Arezzo, Italy
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