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Cortona vs. Montepulciano

Ely, Minnesota
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Cortona vs. Montepulciano

I have found great rentals to stay in each of these towns, so I'm down to the final decision. We plan to stay a week in early May (husband and two teen boys). We will have a rental car which I assume we'll park outside the walls of either town. We are from a small town ourselves (4,000) so don't need a ton of attractions, just a historical hill town with some interesting sights, restaurants, shops, that we can enjoy when we're not daytripping elsewhere. Is Montepulciano so focused on wine that there's not much else to check out (regarding shops, etc.)? Any difference between access to the town if we're parking outside the walls and our apartment rental is within? (We don't really want a 1/2 hour hike every time we need our car.) Other differences or suggestions?

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1. Re: Cortona vs. Montepulciano

It's a hard choice! Montepucliano is beautiful but Cortona has perhaps more to offer and it's just 30 km away from Arezzo which is a beautifull city (100.000 inhabitants) with a strong character.

I haven't been in Montepulciano for a while but I presume Cortona is slightly cheaper. Also from Cortona you can easily drive to Umbria and visit Perugia, Assisi, Gubbio, Todi, Città di Castello. Another suggesiton for a day trip would be visiting the islands in the nearby Lake Trasimeno.

The access to the city center of Cortona is pretty steep but you can leave the car in the parking outside the walls and get an escalator.

Sydney, Australia
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2. Re: Cortona vs. Montepulciano

You need to be aware that the centres of both Montipulciano and Cortona are *very* steep. My wife and I (both just over 60) stayed in Montepulciano for four days in September, and only once made it up to the top of the town.

Plymouth, New...
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3. Re: Cortona vs. Montepulciano


Both towns are lovely and on top of hills with steep climbs. Depending on your choic of accommodations you might have parking nearby and not be forced to leave your car outside the walls. (ask the owner when booking - and be specific) Both towns are larger than you might imagine - and Montepulciano has much, much, much more to offer than just wine shops!

Cortona is a quite a bit more commercial than Montepulciano (altho the recent filming of the "Twilight" movie in Montepulciano may have affected tourism a little) due to the ever popular "Under the Tuscan Sun" book/movie. Also the surroundings of Cortona are not as scenic as those around Montepulciano. But there are lovely streets to wander and many shops, views from the walls, ancient bldgs, ruins, monuments, little churches and piazzas - lots of cafes and restaurants.

Montepulciano is in our favorite part of Tuscany. The clountryside surrounding it is spectacular and it is very close to other wonderful hill towns like Pienza, Montalcino, Montichielo, etc. etc. Southern Tuscany is where you see those awesome panoramic photos of rolling hills and cypress trees - the Val D'Orcia and Crete Senese. (As I said, I am partial to this area)

My suggestion in either case would be to stay at a B&B or agriturismo in the nearby countryside of either town instead of staying right in the center! That way parking and day trips will be easy. Especially with two teens. There are many choices (that's the hard part) giving you easy access, lots of amenities - pools, hiking trails, bikes, etc. Many have reataurants onsite or close by - while others are down country roads in spectaculat settings. But for a less stressful stay with a car, it is much easier to be in an accommodation outside of town.

Whatever you decide - have a wonderful time! And don't miss driving thru Val D'Orcia or on the Crete Senese roads on on one of your day trips!

Buon viaggio!

Le Marche, Italy
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4. Re: Cortona vs. Montepulciano

I would prefer Montepulciano myself. Cortona is a bit isolated; not only is it way off the beaten path, you have to go all the way around Lake Trasimeno to get to anywhere to the south. I didn't find it anything special as far as appearance. Montelpulciano is prettier, and closer to other Tuscan towns you might want to visit.

As Nick says, both towns are very hilly. Cortona is perhaps steeper, but Montepulciano has a long and skinny shape, with ascents and descents to get from one end of town to the other.

Los Angeles...
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5. Re: Cortona vs. Montepulciano

As between these two, I would definitely pick Montepulciano. Cortona is surrounded by pretty unattractive commerce, which you would need to navigate through on your way out and back into town every day. Of course, you can do a day trip to Cortona, which would be about a 40 minute drive from Montepulciano.

The area around Montepulciano is pretty gorgeous with wonderful villages, e.g. Pienza, Montalcino, San Quirico, all within an easy drive; all housing good restaurants and shops.

The village of Montepulciano is very steep, true. Take a look at Montorio (google the name) right outside Montepulciano. These are self catering apartments owned and managed by a pretty phenomenal lady.

Upper Maremma...
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6. Re: Cortona vs. Montepulciano

My vote goes to Montepulciano too. Cortona makes for a nice daytrip but Montepulciano is in a nicer area.

Moncton, Canada
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7. Re: Cortona vs. Montepulciano

Stayed five days in Montepulciano this May/2009. We did a day trip to Cortona. I would highly recommend Montepulciano as it has a lot more to offer with accomodations,restaurants, shops and is very accessable to many other towns. We even ventured out as far as Sienna one day.Parking was available just outside our Locanda. We stayed at La Locanda di San Francesco located at the peak of Montepulciano.

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8. Re: Cortona vs. Montepulciano

i just spent 8 nites in cortona and we loved it

had no car and didnt need one

cortona has many easy to walk to restaurants

and museums etc

great place to spend time

if montalcino is like the other town you mention

your instinct is correct...montalcino while lovely

is 100 percent focused on brunello wine

and its so small compared to cortona

just email if you need more info

there is a great place to stay in cortona

if you want to overnite there for a few days

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9. Re: Cortona vs. Montepulciano


I noticed yourt blog with interest.

We are an Australian couple in our 40's making ourt first (semi-planned) europe trip.

Coming from Vienna into Venice and then 2 nights in florence we then have another 2 x nights free before needing to be in rome on the 14 Nov.

We are trying to figure out what to do re driving and where to stay?

Do you recommend driving from say Florence via San G and then Sienna and maybe on to around Pienza/Montepulciano or even Cortona?

Where would you recommend we stay for the two nights and where would you recommend dropping off the car to then train it into Rome?


Would you recommend we bus it to Sienna and stay over there for either 1 or 2 nights and maybe hire car from there.

It would seem a shame not to drive the country roads and stay somewhere out of the way.

Given our short time, do we need to give San G and/or Sienna a miss to do this?

All advice and where to hire/stay greatfully appreciated.


Le Marche, Italy
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10. Re: Cortona vs. Montepulciano

It sounds like a very rushed trip, not the kind I like to make myself. Where would you be renting the car? You really don't want a car in Florence, trust me on that. Since you will really have only one full day in Florence, I would suggest spending four nights somewhere in Tuscany, outside of Florence, instead of two nights in Florence and two nights somewhere else. Make it some place within commuting distance of Florence, where you can drive to a train station, park your car, and go into Florence for the day.

I would avoid San Gimignano at high season; it's practically sinking under the weight of the tourists. Cortona didn't overwhelm me, and it's really way off to the eastern edge of Tuscany. Somewhere north of Siena might be ideal, possibly near the train line that goes between Siena and Florence. I'm not sure on the specific town to advise, because I've never stayed in the area. However, I've heard that there are some nice places in the countryside surrounding Poggibonsi, and there is also a train station near Poggibonis that would take you to both Florence and Siena, and San Gimignano is also nearby. You could actually drive to Siena; there's ample parking outside the wall and there are moving stairs to take you up to the town. I would take the train to Florence, though.

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