04 Mar 2011

Tuscany is a varied region, with many different interesting areas, each with its specific character and features. Here is a very quick presentation of what travelers can see in the Siena and Grosseto provinces.

What to see in Southern Tuscany

what to see in southern tuscany

A few days ago, I started writing a long, long post about the many tourist areas in Tuscany and then I decided to split the content in more than one post because the original one was too much to read all at once. I posted a few maps with a lot of colourful “swatches”, but no explanation of what those colours represented. Today, I am going to present very quickly the different areas that people can visit in southern Tuscany.

Of course, there are common features, but there are also very distinctive characteristics that make each one of these areas unique and clearly distinguishable from the other ones.

Here is the map of Tuscany again, with the area where my village is marked in white, to show its location relative to the other destinations. It quite a good home base in southern Tuscany, I believe, because it is a short drive away from many different areas of southern Tuscany, so that visiting most of the most popular sites takes only a 30 to 60 minute drive. And you can always go back to a non-touristy, quieter village in the evening and make yourself at home in Tuscany!

where to go in southern tuscany

Like last time, I have marked down some of the most popular destinations, so that people can have some reference points.

And here is some information on each area!

Val di Chiana. It is the area where a beautiful city like Arezzo, and famous hilltop towns like Cortona, Montepulciano, Chianciano Terme and Chiusi are located. It borders with Umbria and is characterised by breath-taking views.


(Piazza Grande in Montepulciano – Photo by zu78)

Crete Senesi. One of the most spectacular and most representative areas of Tuscany. Famous for truffles and for beautiful towns such as Asciano, Buonconvento, San Giovanni d’Asso, Trequanda and Rapolano Terme. Other attractions include thermal baths, art sites (e.g. Jean-Paul Philippe’s Site Transitoire), and the beautiful Abbey of Monte Oliveto Maggiore.

crete senesi

Valdorcia, the green heart of the region and the place you want to go to to see picture-perfect Tuscany. Home to the hilltowns of Montalcino, Pienza, San Quirico d’Orcia, Bagni San Filippo, and Castiglion d’Orcia; to the Abbey of Sant’Antimo famous for the Gregorian chants; to one of the most popular Tuscan wines, Brunello di Montalcino; to beautiful castles and mills. This is the area of the rolling hills, of the open countryside, of the stone houses dotting the countryside. Contrary to what many believe, the Valdorcia is shared by the provinces of Siena and Grosseto.


(Pienza – photo by stiffunggegenstand)

The city of Siena and immediate surroundings. Siena deserves a mention on its own. It’s such a spectacular place. It is also the city of the very famous horse race called the Palio di Siena and of the most traditional Christmas sweets in Tuscany: ricciarelli and panforte!


Val di Merse. The wildest area of the province of Siena, with remote villages, forests, rivers and the beautiful Abbey of San Galgano, cradle of the Arthurian legends and home to the original sword in the stone. Val di Merse is a paradise for hikers, horseback riders and cyclists. And if you happen to be in the area in summer, you should not miss the Opera at the abbey.

San Galgano

(San Galgano – photo by ho visto nina volare)

Chianti. The most popular area of Tuscany, famous for its wine, for small picturesque villages such as Greve in Chianti, Gaiole, Radda and for castles such as Meleto, Brolio and more. The Chianti area covers parts of the provinces of Siena, Florence and Pisa, but the most popular part of it is the region called Chianti Classico, between Siena and Florence.


(Chianti – Photo by TonyDuckles)

Val d’Elsa has some densely populated areas and other areas that are essentially rural. It boasts famous towns such as Certaldo, Castelfiorentino, Gambassi Terme, which are actually in northern Tuscany, but I have included it here because it also encompasses areas such as the “montagnola senese” (literally “the sienese hill-land”) with villages such as Sovicille and towns like Colle Val d’Elsa, famous its crystal, and the popular villages of San Gimignano and Monteriggioni.


(Monteriggioni – Photo by Isabelle Puaut)

Casentino. It is a mountain area, mostly woodland. It’s quite wild, and very well preserved since the Middle Ages. For its quiet and beauty this area is almost mystical. It boasts famous hermitages such as Eremo di Camaldoli and Saint Francis’ La Verna. It is also a land of pievi, castles, and medieval villages such as Poppi. A large nature park preserves the forest.


(Parco delle Foreste Casentinesi – Photo by Sheilasan)

hills of the maremmaThe inland hills of the Maremma, also known as Alta Maremma (Upper Maremma). My home village, Civitella Marittima, and our vacation rental in Tuscany, Casina di Rosa, are here. The area is mostly rural and has traits of the Siena area and the Valdorcia and traits of the Maremma. It is very beautiful, a nature paradise with small hilltop hamlets, olive groves and the famous Petriolo hot springs.

Alta Maremma

(Photo by Gianluca Giannone)

Monte Amiata. The highest mountain in Tuscany: very different from any other place in the region, with chestnut tree woods, mountain villages and towns such as Arcidosso, Santa Fiora, Castel del Piano, Castiglion d’Orcia and the pretty abbey town of Abbadia San Salvadore.


(Arcidosso – Photo by Carlo Tardani)

Colline Metallifere. Also part of the Upper Maremma, this area has very distinctive features and it has been inhabited since the Antiquity because it was very rich in minerals. Massa Marittima is located in the area and it is a real gem.

massa marittima

(Photo by giovanni novara)

Maremma. Famous for the unspoilt coastline boasting both rocky and sandy coasts, pretty coastal towns like Castiglione della Pescaia and Talamone, luxury beach areas such as Argentario, a large nature park (Parco naturale della Maremma) and several Etruscan archaeological sites. It is also home to a popular wine: Morellino di Scansano. The Tuscan Archipelago, with the Isle of Giglio, the Isle of Elba and Giannutri, faces the coast of the Maremma.


(Photo by icara)

Area del Tufo. The heart of the ancient Etruscan empire, with towns such as Pitigliano, Manciano, Magliano, Sovana, Sorano and the famous spas in Saturnia. There are many archaeological sites and the breath-taking Vie Cave, ancient roads carved in the stone. Pitigliano also has a ancient Synagogue.


(Pitigliano – Photo by Andrea Contri)

Val di Cornia – Maremma Livornese. Val di Cornia includes beautiful towns such as Suvereto and Monterotondo Marittimo which are further north but also the famous Etruscan coast (Costa degli Etruschi). Ferries to the Isle of Elba leave from the town of Piombino. A very interesting place is the archaeological park in Populonia and the walk to the near cove called Golfo di Baratti.


(Golfo di Baratti seen from the Castle of Populonia – Photo by AlessandraElle)

Val di Cecina. This is the Valdorcia of Northern Tuscany. An area that is known to few travelers to Tuscany, and yet it boasts spectacular landscapes, characterized by gentle rolling hills and small hamlets such as Montecastelli and Castelnuovo Val di Cecina. It extends mostly in Nothern Tuscany but I have included it because it also boasts beautiful Volterra, which, contrary to what most people think, it is actually not in the province of Siena but in the province of Pisa.


(Volterra – Photo by Thomas Willemsen)

A final recommendation: take it slow! There is plenty to keep you busy for two weeks or more. You won’t be able to see everything anyway so choose according to your tastes, and remember to take enough time to actually experience Tuscany and its lifestyle and not just “see” it passing by its major landmarks.

Happy planning!


  1. Jim Zurer

    Gloria…excellent summary of the very distinct Tuscan locations….I always try to explain to clients about the diversity of Tuscany and this is a piece I can use to demonstrate the point.

  2. Thank you Jim! I always have to explain what people can do if they come to our little village and that Pisa, Cinque Terre and Siena is not a suitable itinerary for a week in Tuscany! :o)

  3. Che capolavoro! I’ve been coming to Italy for 25 years, and visited Tuscany many times, but I feel I must start again. Thanks for all effort.

  4. Hi Mike! Thank you for the kind comment! I am sure you have seen much of what there is to see in 25 years! 🙂 But there is always something more!! 🙂

  5. Gary

    Hi Gloria
    A very informative and well put together post. Thank you! I am planning my trip to Tuscany and Umbria and you have given me many useful insights. I agree with your advice: take it slow.

  6. Thank you Gary! For Umbria, check our Letizia’s Alla Madonna del Piatto http://www.incampagna.com/ or Rebecca’s Brigolante Guest Apartments http://www.brigolante.com THey are both near Assisi, so the place is very beautiful but the extra value is no doubt added by the inn-keepers! :o) Happy Planning!

  7. Chishikoff

    This is soo cool !! I really enjoyed reading this. Thanks so much for your photos! Good Design !

  8. Jeannette

    Researching Tuscany for my daughter’s wedding. We don’t want the tourist scene or the venues that do conveyor belt weddings.

    Was researching Val d’orcia when I came accross you maybe you would e-mail me and we could have a chat.

    Excellent post looking forward to speaking with you.

    Just want to get into the car and begin the adventure.


  9. Michelle Ortlipp

    I’m really enjoying this site and lots of great information. If we have 2 weeks to spend in Tuscany and Umbria should we base ourselves in Norhtern Tuscany and then Umbria to see the variety of countryside or could we spend one week in Southern Tuscany and one week near Assisi? It looks like we could base ourselves near Assisi using farmstay and still get to explore Siena and surrounds. Any suggestions?

  10. Hi Michelle! Thank you for your kind words! Northern Tuscany is very different from “classic postcard Tuscany”. If you want to see classic Tuscany, then Southern Tuscany is the place to be. Northern Tuscany is more industrialized and urban, with few exceptions.

    Tuscany and Umbria have similar features and yet are quite different. Enough that it is very interesting even for a local like me to go on holiday in Umbria.

    A week in Southern Tuscany and one in Umbria are a perfect combination which gives your a fabulous opportunity to see some of the most beautiful countryside in the country.

    Assisi is also a good base. I can highly recommend both La Madonna del Piatto and Brigolante Guest Apartments, depending on whether you are looking to stay in a B&B or in a self-catering apartment.

    When planning your holiday, remember that distances are short, but roads are very very slow. I would spend one week in each area. Besides, Italian culture is incredibly varied, and even in two neighbouring regions like Tuscany and Umbria you will find great differences in traditions, accents, landscapes, and food.

  11. Shivangi

    Hi Gloria,

    Your blog is very informative and clears up a lot of misconception and confusion when it comes to visiting Tuscany as we know it.

    My husband and I are planning a trip to Tuscany in easter this year. We are planning to fly from London to Pisa. As it turns out there are some cheap and direct flights to Pisa as opposed to Florence. We are renting a car from Pisa to drive to Chianti region and make base at San Donato in Poggio. Do you think it is a good idea to make our base there? Or should we make our base in some other region/village/area?

    I understand 4 days is simply not enough to explore it. But we are hoping to make the most of it. Could you also suggest what places should we explore bearing in mind that we have little time in our hands?

    Thank you


    • Hi! It’s a very pretty area! You can easily reach Siena and Florence, San Gimignano, all the villages in Chianti and even Volterra.
      The airport of Florence is small and not very nice. Much better to fly to Pisa. And as you say, lots of low cost airlines too!
      It is hard to recommend places to see. It all depends on what you like (city vs. countryside) and like to do (sports, food, art, etc.).
      Four days are not much if you include visiting the cities too. I would not miss Siena, a nice drive through the Chianti with a few stops along the way to enjoy the views and maybe a visit to a winery, a visit to Volterra or San Gimignano and if you have never been, a day in Florence might be nice. But go by bus if you can, since parking and driving in Florence is not much fun.

  12. kieren

    imm drunk but im thinking afer we ge t married, well after venie with 5 days im thinkig train from venice to florence then drive mareema and fligh out of pisa to paris, maybe 7 . i love your descriptions of the villages which our our style, we line at the beach so some thinh diff is g
    we love you

    • Hi Kieren, you made me laugh! Drunken comments are always welcome! To think that someone is browsing my blog while partying makes me especially proud! Congratulations on your upcoming wedding by the way!

  13. Hi Gloria, we will be in Italy for the very first time in 19 days!!! Most will be in Tuscany- would love to visit all of the places you have shown.. we will be driving.. any tips for us? My husband’s grandparents are from Corfino and Vibbiana so we will definitely go there.. please advise!!

  14. Hello, Gloria. Your blog is excellent!!!! Congratulations….
    I am going to visit Tuscany for the second time. When I went for the first time, I visited Florencia, Siena and San Gimignano. Now I am going to spend a week and would like to visit Southern Tuscany and Lucca. I am also going to spend 10 days in South Tyrol or Alto Trentino and two days for Cinque Terre…what’s your opinion?? Do you think it is Ok or do you have any other idea ???
    Your recomendations will be very appreciated….

  15. Hi Gloria! Excellent and very helpful post! We are planning on visiting Tuscany in a couple of weeks; we have seen your Umbria B&B recommendations and they are great, exactly what we are looking for, however in Tuscany 🙂
    We will be staying in one day around San Gimignano / Monteriggioni, one day in or around Siena, and one day around Asciano/Pienza/Montalcino. Could you please be so kind to recommend us such places?

    Thank you in advance for your help!

    Antonis & Christina

    • I wouldn’t know what to recommend, I am sorry!

  16. Hello Gloria,congratulations for your excellent blog.
    I am planning our next trip for September 2014, in Tuscany region for 5 or 7 days.
    We will rent a car from Florence.
    I prepared my visit points, but I see that the list is very long and I could not decide how to divide my stays. We don’t prefer to stay at the same place and visit the villages in the surrounding and come back. I do not know whether if seven days will be enough to visit all these points, how much time to spend on each point and where to stay?
    My list is as:

    Thanks in advance.

    • That’s a lot of places you want to see, some worth it, some less so. The way you choose to travel is not my own style, so I am afraid I am not the best one to give you advice! Most of those places are so close to each other that it really would seem to be more hassle than a benefit to change accommodation every single day when you are only moving 30 minutes away… Tuscany is big and small at the same time. Maybe you should leave a message on TripAdvisor where you are likely to find somebody who has chosen to change location often as you wish to do? Good luck!

  17. Linda Harris

    Hi Gloria,

    I loved your detailed descriptions of landscapes and areas in Tuscany with the beautiful photos!

    I’m traveling there in May, using public transportation to get around. I have a tentative itinerary but am getting stumped a bit in a couple of periods between stays in Florence and Rome and when leaving Rome (to make my way back to Milan for return flight.) What I am looking for in both of these periods is a place to unwind in the country or coast, in less touristic more “authentic” (admittedly an overused word) village(s) with good local food (I love seafood), red tiled roofs (pardon my clichéd way of thinking), historic pedestrian center where folks stroll in evening. I would love to wander, café sit, people watch, take a dip if warm enough, and or soak in thermal spring water.

    After the first stay in Florence I have 4 days. I am thinking of Sienna, and wondering if I could take buses to nearby towns—e.g., I read about: Bagno Vignoni, and if I can find a sort of low key pension stay overnight there and maybe walk around a bit in the countryside, as well as soak in thermal springs?

    My other unplanned time is May 31 to June 4. For that part of the trip I had been thinking Cinque Terre or Amalfi, but realizing those would be rushed I am wondering about some of the little towns along the coast where I could possibly catch the train ending in Milan on the 4th? Does any village or b&b pop into your mind that you could share with me? Maybe Orbetello, Cecina, (totally random ideas, which is why your input would be great.)

    An alternative is a lovely agritourismo I found (or seems lovely) outside of Volterra in the countryside. But I’ve been told that rural area may not be as beautiful as other areas and your blog seems to confirm that?

    If you only have time to answer one question (which I understand totally), please speak to the coastal village idea?. (on way Rome to Milan)

    Thanks and apologies for the long story….
    Linda Harris, Brooklyn, N.Y.

  18. Nicki Baker

    Dear Gloria,
    I love your website and your way of thinking. I know I cannot do Tuscany in one, two or even three trips but to start, i want to find a nice quaint base in Southern Tuscany and travel around from there on day trips, returning to a peaceful quiet little village at night for a good bottle of wine and some delicious it alien food. . What town would you suggest that you know of a place to stay that might be suitable. There will be two of us. I plan on coming 9/1/14. Is it very hot? I doubt places have air conditioning but I don’t want to swelter. Any suggestions for a reasonable but comfortable abode for a week or so that would be just right?

    Thank you so very much.

  19. Sue

    Hi Gloria, loved your info on your site. My friend and l are in Rome and planning on staying at a place in Monteroni d’Arabia near Siena. We are having difficulty in finding out how we will get from Siena to this place. We are travelling by bus from Rome to Siena. Could you offer some suggestions please? Regards Sue

    • Southern Tuscany is not very well connected by public transportation unfortunately. You can get a bus to Monteroni from Siena though. Check http://www.sienamobilita.it/

  20. Hi Gloria,

    I have been reading up on your posts for the whole morning and I can’t stop ready with all the beautiful photos! Truly glad I managed to find so much information for my trip in September!

    I was hoping I could ask you something about Lucignano. My girlfriend and I will be staying there for 2 nights as we will be spending the first 2 nights in Florence! The reason we wanted to stay in the Tuscan countryside was so that we could visit Val D’Orcia as it is what you mentioned a picturesque landscape.

    We were just worried about driving in Southern Tuscany. We have heard driving and navigating in Italy to be a little challenging so was wondering your opinion on this? Also, as we will possibly only have 2 full days there, is there a extremely must-see town within our short stay? Feel free to drop me an email instead for an easier chat! 🙂

    Thank you in advance! Looking forward to hearing from you soon too!

    Kind regards,
    Aaron & Gerri

  21. Karen

    Thank you for your insight . Most helpful

  22. great blog, will rent a camping car in October this year for the first time and come with the kids for a last swim in the med before winter
    will mark your page and use it on our journey


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