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Right area to experience the authentic Tuscany

Copenhagen, Denmark
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Right area to experience the authentic Tuscany

We are planning our first Holiday in Tuscany and are bewildered as to in which area we should book our accommodation. My husband and I are seasoned, international travellers and have visited Italy numerous times and also been on a day excursion to Siena - but we have never spent a full week in the Tuscan hills before. The more research we do and the more articles we read, the more confused we get as to where to stay - there seems to be sooo many beautiful little villages and rustic places to stay. Friends have told us, that Montepulciano should be the right place for us - but I've now found a few very lovely agriturismo places in the Chianti area (Castellina and Terriciola), so now we need your help please.


We are a midaged couple in our early 60th from Copenhagen, Denmark. We love to drive, so we'll be bringing our own car and hence have the possibiity of staying at rather remote little places as we can move freely about by means of the car.



We love beautiful landscapes and nature and enjoy driving through little winding countryroads visiting medieval hilltop villages and strolling the cobblestones lanes of same. We love vinyards and the mediteranean vegetation of cypresses and pines - and we would love to visit with local wine- and olive producers. We should also like to make strolls and hike through these landscapes. For sure we are going to drive the road between Montepulciano and Cortona, which we understand is where the lovely little film "Under the Tuscan Sun" was shot.


While we enjoy the ancient architecture and can appreciate the churches and Palaces etc., we are not particularly into visiting neither museums nor churches apart from a few brief "must see" experiences such as in Siena etc. We much rather have the focus on the nature, landscape and local life. That is, we enjoy experiencing the genuine life in Tuscany - sitting in the shade of an old tree on a local town Square drinking coffee or sipping a glass of local wine. Finding typical little local restaurants with authentic food prepared by "mamma" is a thing, we are looking especially forward to.


We are not city-people. So we don't want to spend much time in the big cities of Firenze and Pisa, but of course we'll like to pay them a brief visit to encounter the "must-see" sights such as the leaning Tower in Pisa etc. But as previously stated, we love little picturesque hilltop villages and the rural countryside. We do also love anything "mountain" like... that is, the more rolling hills the better. Olive groves and vinyards as long as the eye can reach, please. So we are looking for a lovely, rustic little village in the vicinity/foothills of same we can stay at a lovly agriturismo.


We are looking for a genuine authentic Tuscany experience and hence think that the socalled Agriturismo (farmhouses) located in the middle of an olive grove and/or a vinyard and built in the oldfashioned tuscanian rustic stone architechture is just what we would love to stay at. Not deluxe but with modern facilities and most of all, a lovely view of the hills/vinyards from the terrace. Eiher renting a small Apartment/cottage or a room sort of B&B like. And preferable with a host that do also offer some home cooked meals a la mamma and that can/will suggest nearby local places to eat and visit. We like the accommodation to be truly authentic in exterior as interior and preferable with our own terrace/balcony from which we can have a view of the vinyards/olive groves and sit enjoying a glass of wine in the afternoons. A lovely garden to stroll and relax in and a swimmingpool.


a) Stay the entire 8 nights in the same location?

b) Or should we split the stay in two locations?

c If we should choose only one location - is Montepulciano then the right one?

c) Or is Castellina // Terriciola in the Chianti area a better choice for us?

e) Do you have any better suggestions for us as to area to choose?

Any suggestions or comments highly appreciation. Looking forward to hearing from you.

All the best PURPLE

Montepulciano, Italy
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1. Re: Right area to experience the authentic Tuscany

Most of the filming for the movie Under A Tuscan Sun was done around Montepulciano / Val d'Orcia, only a few scenes were made in Cortona itself (and most of those were reconstructed in a studio). For stunning scenery, I would suggest you stay in an agriturismo in the heart of the Val d'Orcia itself as it is so beautiful and unspoilt (it's now a UNESCO World Heritage area). The list is endless as virtually every property in the valley today is an agriturismo. If you Google something like "Pienza Agriturismo" you'll find a long list and you can compare reviews on Trip Advisor. However, if you want a truly authentic Tuscan town experience you have to go further off the beaten track as tourism is creeping in everywhere. Even in Montepulciano now, the lower part of the main street (Corso) is becoming unpleasantly packed with tourist-related outlets and it's starting to look a bit tacky in places. And a couple of nasty looking stores have opened this season in Pienza too. We need visitors, sure, but I fear it's getting slightly out of control in places. Further afield, consider somewhere on the Tuscan / Lazio border as that too offers wonderful, wild countryside with less spoilt towns, perhaps around Radicofani, San Casciano dei Bagni or Cetona to the east? Best of all though for authenticity would be somewhere down in the Maremma or on the southern slopes of Monte Amiata - but I realise I'm only making your decision more difficult.

Copenhagen, Denmark
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2. Re: Right area to experience the authentic Tuscany

Thank you Lastraniera for your swift and very fine reply. So sad to learn that mass tourism has started having a bad impact on your lovely area too... That balance is so difficult as, understandable, you would like to have tourists come around to give business and employment - but it's indeed sad when souvenir stalls and tacky shops plasters the lovely streets and piazzas and superceeds the autencity and beauty of the places that are the very reason for visitors to come... But we are sure, that we shall enjoy the area anyhow.

Your suggestions sound very great and I'll now look up and do further reseach on the areas you stipulate. Yes, you have made it even more difficult for me/us to decide now :-), but we do appreciate local piece of advise so we are more than happy to learn of your suggestions. Being touristic - or not - we are convinced that we must stay and experience Val d'Orcia, sounds so beautiful! But it's still an good idea to combine with a few nights in another area to experience the more untouched parts, we think. So I'll look into the mentioned small Towns and/or Maremma.

From reading your message we gather that going to Castellina in Chianti is not going to meet our critea -nor the best alternative? Or rather, that the towns mentioned by you will be better options. I had stumbled over an agriturismo named "Podere Patrignone" by Castellina that looked rather authentic and with "mama" cooking homemade dinners a couple of weeks. Maybe you know it?


but maybe we can do better in one of the towns/areas suggested by you.

Anyhow, thanks again a million for your response. It's truly valued and we'll be studying all the suggestions closely the next days. Have a nice Sunday evening. Kind regards - PURPLE

north carolina
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3. Re: Right area to experience the authentic Tuscany

Right, what a well-written inquiry. If we can't help you, then we are just not much good.

You have many wonderful choices. I predict you can not go wrong, but I will offer a few things to look at.

Montepulciano would be extremely nice, but i have no experience of accommodations there. Castellina is very nice, we have stayed here: LaFerrozzola, http://www.laferrozzola.com, this is the home vinyards of the LaCastelina wine brand. The same people own the hotel in Castellina, at Squarcialupi Plaza. It is convenient to visit anything in Chianti, and from the house to Castellina, is either a stiff 12-15 minute walk uphill through the vinyard, or a 3 minute drive. Castellina is a delightful little town, only moderately touristy, nice restaurants, fabulous gelato shop (perhaps the best we have ever visited in Italy). The unit that we stayed in is what they call Iris T1, pool, two bedrooms, lovely, clean, comfortable, quiet. Lovely views from the private veranda in back of the apartment. We have never stayed at their hotel in town but I did tour a few of the rooms and use their bar service - it appeared to be quite nice.

La Castellina makes about 6 or 7 different Chianti blends. I found it interesting to taste and compare. Their premier blend is called Squarcialupi Reserva, and I think it is the best Chianti I have ever tasted.

Montichiello, just a bit South of Montepulciano is a very small town with easy driving access to many lovely places in the Val d"Orcia including Montechiello, Pienza, Montalcino. It is extremely quiet, but has three good restaurants, one of which is moderately famous. We stayed in the private little house (the apartment) run by these guys: http://www.lacasadiadelina.eu/ and loved it.

And I will highly recommend all of these which would serve you well:

Two in Chianti:

1. The Villa Lecchi. http://www.villalecchi.com/ Lecchi is a tiny, tiny village that will not appear on some maps but does appear on Via Michelin. From Florence take the RA 3 (fast highway) South, just past Poggibonsi take SR 2 South to Staggia, in Staggia take the Lecchi-Staggia road North about two miles to a poorly marked right turn to Lecchi which is perhaps 200 yards up the road. The Villa is on the right as you drive into Lecchi.

This place is well situated for visiting Siena, Castellina in Chianti, Radda in Chianti, San Gimignana and other areas of western or central Chianti. The Villa is very attractive with lovely rooms and ==>> the most stunning views we have seen anywhere in Italy. There is no elevator, and the climb to the top floor may be demanding (but worth it if you get one of the "tower rooms"). There is an on-site family operated restaurant that we thought was fabulous.

2. Borgo Argenina http://www.borgoargenina.it Just off of the road from Siena to Gaiole in Chianti, S408, again the last turn is poorly marked. It is roughly half way between Siena and Gaiole. It is within a short walk from the tiny village of Monti which shows on the Michelin map. This place has, unfortunately, been discovered - reservations well in advance. It is an idyll of scenery and tranquility. There are numerous restaurants within a reasonable drive. Good location for touring southern Chianti, Siena, Cortona, Arezzo, perhaps Montepulciano.

Three in Umbria:

1. I Capricci di Merion in Tuoro sul Trasimeno, http://www.capriccidimerion.it it is just on the Northern tip of Lago Trasimeno, very close to Tuscany border, at the eastern edge of Chianti and about ten miles South of Cortona. My wife says this is the most romantic place we have ever been in Italy (or anywhere else). Excellent location to visit Arezzo, Cortona, Siena, Perugia, Assisi, Deruto or many other areas of Northern/Central Umbria and Southeast Tuscany. Very attractive (moderately expensive) restaurant on site, but also easy to get to more casual, less expensive restaurants in Tuoro sul Trasimeno or Passignano Trasimeno. Take the main road into town, SS416 North, near the northern tip of Lago Trasimeno, off of either RA 6 or SS75bis, when you get to the little town center at the top of the hill, ask for Capricci di Merion, again the last turn is poorly marked.

2. appartmento San Martino, just north of Montone in Northern Umbria. This one is a real change of pace. No breakfast served, completely self-catering. About three miles North of Umbertide and twelve to fifteen miles south of Citta di Castello. Umbertide has a super-market (Italian style) and some decent restaurants and cafes. They have three apartments to rent, and the owners live there. Two apartments have two bedrooms and one has one bedroom. They are all quite comfortable and well-furnished. There is a fantastic view of the town of Montone sitting up on a hill about a mile away. While we were there we visited Citta di Castello, Arezzo, Umbertide, Perugia, Trevi and the Adriatic coast. Assisi is near, too.

Just one word of warning: the drive leading up to the house is daunting, steep, twisting up the side of a hill. I went up or down a dozen times without mishap, but each time you go up it gives one pause. The owners are British, quite friendly and willing to help. They have added a section to their web site that shows driving times to some interesting surrounding towns. I handled all the arrangements, and price haggling over the telephone with the owner and there were no problems of any kind.


3. San Potente/Villa Rosy http://www.sanpotente.it/listino_rosyGB.htm

We stayed in the one-bedroom apartment Magnolia, it was comfortable and quiet. Hidden back in the middle of an olive grove. There is a bench down the drive a bit with a lovely view of Assisi on a hill about a mile away. The little town Rivatorto is nothing at all, but there are many wonderful places to visit nearby. The San Potente folks have three agriturismos near Assisi, but we have only visited the Villa Rosy. Based on that visit, I would expect their other places to be good, also.

Edited: 07 April 2013, 21:04
Los Angeles...
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4. Re: Right area to experience the authentic Tuscany

I think you will be very happy in/about Val d'Orcia. How could you not be? It is truly breathtaking, as is seemingly evidenced by all the travelers flocking to the region!

I heard good things about this place: Politian apartments http://www.politian.com/ Good value in Montepulciano.

For a slightly more of a splurge, take a look at Montorio just outside of Montepulciano, self-catering apartments owned and managed by a very gracious lady.

5. Re: Right area to experience the authentic Tuscany

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6. Re: Right area to experience the authentic Tuscany

My choice for someone who has never been to the region before would be 4 nights in Val d'Orcia and 4 nights in Chianti, so I think your original plan is good. Castellina is a lovely little town and would be a good choice for that part of your trip. Roadgard has given you some great recommendations there.

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7. Re: Right area to experience the authentic Tuscany


This may help slowtrav.com/italy/tuscany/hs_planning.htm

Copenhagen, Denmark
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8. Re: Right area to experience the authentic Tuscany

WOW we are overwhelmed by the many fine suggestions made here. Thank you so very much everyone for having taken the time to write and comment - so much appreciated :-). We'll study each and everyone of the suggested Places - seems all to be very relevant and down our line. We are getting truly excited. Do believe we'll stick to the plan of splitting up in 2 x 4 nights to get the utmost out of the visit. And no doubt Val d'Orcia is going to be the one of them.

PS: Roadgard - thank you so very much for your very nice comment about our enquiry.

Once Again - thank you so very much everyone for your kind and helpful contribution. Kind regards PURPLE

Copenhagen, Denmark
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9. Re: Right area to experience the authentic Tuscany

Once again, thank you all for your various suggestions and info. We have now returned safely from our holiday and I should like to give you a brief feedback. Firstly, let me say - we had a lovely time in Tuscany and enjoyed our days there thoroughly. Secondly, we can advise, that splitting up the visit into two different areas of each 4 days turned out to be the very right decision as it appeared that the areas indeed were very different as to scenery and nature plus it saved us a lot of driving time not having too far distances to cover in connection with daytrips. Especially good as it appeared to us that driving the little backroads in Tuscany is a lot more time consuming than we had anticipated. In spite of a newly updated GPS and brand new detailed maps – we found ourselves lost over and over. As to accommodation we are likewise happy to let you know that both chosen places lived fully up to all of our expectations and provided us with the much sought after Tuscan authenticity and rustic ambiance albeit indeed very different in style and experience. We loved them both very much, and hence thought it would be nice to share them with you.

Our first stay: Agriturismo “PODERE PATRIGNONE”, by Castellina in Chianti:


This little hidden gem is remotedly located in the middle of the Chianti woods some 7 km Northwest of the medieval village of Castellina and is reached by a tiny gravel road only. It’s a socalled “agri-turismo” (working farm stay) producing olives and hosting a small number of visitors - and from which you enjoy the most lovely view of its groves and the neighboring vineyards. 5 apartments and some 7 rooms are available for guests on either a self-catering basis or B&B. The place is run by an Italian/British couple and is a genuine Tuscan in architecture with an old story. The owners have been – and are still ongoing doing – a great job restoring the place and are putting a great effort into keeping its authenticity alongside making it an eco-friendly farm. The apartments, rooms and shared facilities are lovely with open red roof tiles, wooden beams, terracotta floors etc. and furnished with old style furniture matching the style. Nothing fancy, but rustic and very lovely. You won’t find in room TV or phones etc. here – but a familiar, relaxed and very charming ambiance. And some of the bathrooms may not meet with the expectations of i.e. American visitors being tiny and/or lacking table space etc., but to us of totally no importance and all made up for by its charm. Most of the apartments do likewise have a little private outdoor space for al fresco meals or to just sit and enjoy a glass of Chianti. In the back of the house you find a large very lovely terrace, from which you have an extensive view of the surrounding olive groves and neighboring vineyards and the wooden hills in the far distance. This is where you meet up with your fellow travelers and enjoy your sundowner and share experiences and good chats. An even more breathtaking view is available from the lovely pool area located a bit away from the buildings allowing you to fully feel the tranquility and endless panorama surrounding you. Our absolute fave place! Although located in a rather remote area you are, however, not at any time far from the many sights and lovely touring – and during our stay we visited on day tours the more famous and cultural pearls of respectively Volterra and San Gimignano to the West and the pretty little medieval villages of Castellina, Greve and Barberino a bit North and East offering the laid-back Tuscan village life we had been looking for while likewise providing some lovely scenery while driving. The most important asset of Podere Patrignone is, however, their owners, who are so open, welcoming and not the least very dedicated in their doings that being the olive production or the hosting. We were greeted as family or friends rather than guests. They did everything to make our stay an most enjoyable one and spend lots of time before and during the visit sharing their knowledge of the area with us and making us suggestions for our tours, wine tasting and restaurant visits. Lovely places we would never have found or stopped at on our own – hence most valuable info to us. We can highly recommend this little gem to anyone looking for a rustic, charming, tranquil and very relaxed and authentic Tuscan experience.

Our second stay: Hotel “VILLA CICOLINA”, Montepulciano, Valle d’Orcia.


Villa Cicolina is a small, boutique hotel at the foot of Montepulciano located in a converted old noble house surrounded by the prettiest garden from which you find a “to-die-for” view of the valley below and mountain range far beyond. The “Villa” dating back to the 16th century is with its square three-story building typical for the Tuscan architecture and to-day housing 11 lovely rooms beautifully decorated with antique and/or old style furniture and fine textiles. Elegant and yet rustic. And everything done with the finest attention to detail. Very delicate, refined and lovely, indeed. In the “Villa” you do likewise find the reception located in a small room with old wall-paintings and Venezian glass chandeliers and a cozy lounge for reading and relaxation. In the basement, you find a puzzle of tunnels linking underground ancient wine-cellars boasting some of the finest Italian wine. The major treat of this lovely place is, however, its gardens – more resembling a fine park with various sections incl. a small rose garden with a pretty splashing fountain, a courtyard surrounded by manicured flowerbeds forming a delicate outdoor lounge area with elegant garden furniture, where you can enjoy a pre-dinner drink, a cup of coffee following your meal etc. - and not the least a tiny olive grove leading to a dreamlike pool-area boasting an infinity pool from which you have the most breathtaking view ! We could never get tired of sitting there gazing over the Tuscan scenery below and far out towards Cortona and the Apennines. In each little corner of this magnificent garden you would find sunbeds and garden furniture for secluded private relaxing or socializing with fellow travelers along the pool edge. Furnished with fine cushions and plaids. In a separate building – an old converted stable, I believe – you find the hotel’s very romantic restaurant with rough brick walls, rustic wooden beams, large glass windows and fine laid tables. Catering to the guests of the hotel only and hence very intimate, and personal. And a great place for easy getting to know the other guests. The food was delicious, home made from the ground and typical for the region using its many local ingredients. 4-course dinners and sumptuous breakfasts could be enjoyed here daily, while at lunch time you could have the kitchen prepare you a sandwich or a plate of Tuscan specialties to enjoy in the courtyard or outdoor dining area. Coming dusk the entire courtyard area transformed into an almost fairytale like venue with numerous of lit living candles placed everywhere… To top the fine buildings and surroundings, we found an outstanding staff extremely dedicated to their jobs. I cannot remember when we have last experienced such a high level of service! Already by placing our booking we felt a personal interest in our coming and stay, which only was further confirmed upon our arrival where our name immediately was recognized and we were warmly welcomed. Whenever we met a staff he/she would smilingly greet us and ask if they could be of any assistance to us. They prepared us a late afternoon snack although outside lunch-opening hours, helped us with suggestions for wine tasting in the area and made us hand drawn maps to follow - and when one evening we were discussing with fellow travelers whether Tiramisu should be made with Marsala or Amaretto, the waiter did immediately bring us a glass of the special sweet wine, they used in their special recipe for us to taste. Everyone we met were extremely helpful and made us feel more than welcome. Placed at the foot of Montepulciano, evidently you can visit this pretty little hilltop town by foot. Many other well known typical Tuscan hilltop town and villages are easily reached on day tours too – and we enjoyed especially visitng Pienza and Montalcino in the Orcia valley. The latter home of the famous Brunello Wine and hence the place where we stopped for wine tasting at more lovely estates. A drive into the somewhat more barren area of the truffel country to Asciano between Montepulciano and Sienna was also a lovely experience, although we lost our way numerous times on the little roads. Tempted to laze a day or two by the inviting pool, we ran out of time – otherwise, a visit to likewise nearby Cortona made internal in the movie “In the Tuscan Sun” was in our planning but will have to be explored next time. Needless to say, we shall be more than pleased to likewise recommend this little pearl of a relais to anyone appreciating beauty and understated elegance combined with a rustic Tuscan ambiance and top notch service.

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10. Re: Right area to experience the authentic Tuscany

Thanks for a wonderful Trip Report!