A Guide to Central and Eastern Tuscany

Tuscany is an area famed for its three crowning jewels: Florence, Siena and Pisa. Every year, tourists flock to these cities to enjoy some of the most famous sites that Italy has to offer. I too have been one of those happy tourists; marvelling at Florence’s Duomo and taking classic, cheesy shots of the Leaning Tower of Pisa. I’ve even been spectacularly sick all over Siena’s streets (I’d like to say it was from excitement, but unfortunately not).


Despite these beautiful cities, however, it is the smaller, more sleepier parts of Tuscany that I have truly fallen in love with. Away from the large crowds, selfie sticks and intense summer heat, I’ve roamed medieval hillside towns, sipped some of the world’s finest red wine under olive groves and even married under a floral arch of roses and peonies in the Val d’Orcia. It’s an area of the world that holds a special place in my heart.


Below is a guide to some of my favourite spots of central and eastern Tuscany, which should be on every visitor’s itinerary. Prepare to fall in love.


A Unesco World Heritage site, pretty Pienza is one of the better known towns in the region and for a very good reason: its famous Piazza Pio II. Home to Palazzo Piccolomini, the former residence of the Pope (well worth a tour), this famous piazza has been awarded a place on the Unesco’s World Heritage list. This is a small town and can get immensely busy over summer weekends, so plan carefully to enjoy this beautiful spot at its best.

Top tip: Treat yourself to a takeaway pizza, whilst taking in the views of Tuscan hills from the wall that runs the length of the town.

pienza tuscany

Where to stay: La Bandita Townhouse

Relatively newcomers to the area, La Bandita Townhouse offers a luxurious stay in Pienza. With only 12 rooms, this restored convent is slightly pricier than other hotels in the area but offers an authentic experience of Tuscan living.

pienza Tuscany

Montepulciano (located in Val di Chiana)

Sitting atop a large volcanic rock, the town of Montepulciano provides the most exquisite views of the rolling Tuscan hills, and some of the most beautiful sunsets that I’ve had the privilege of enjoying. Its winding medieval streets offer less a leisurely pace and more an extreme calf and quad workout, but are well worth the pain (if only to reward yourself with a glass of wine when you reach the top!) Perhaps its most famous claim to fame is that Montepulciano’s Piazza Grande was used for scenes in the second film of the Twilight series – New Moon. Ohhh!

Top tip: Enjoy an evening tasting the region’s most delicious wine, Vino Nobile, in one of the town’s many restaurant terraces as the sun sets and swallows take to the skies.

Montepulciano Tuscany

montepulciano tuscany

Where to stay: Terre di Nano or Villa San Bartolomeo

Call me biased, having chosen to get married here, but if you’re looking for a peaceful, perfectly Tuscan setting in which to stay, head to Terre di Nano. With breathtaking views over the Val d’Orcia, this traditional agriturismo is run by the brilliant Illaria and cook Georgio, alongside three very soppy Italian blood hounds. Indulge in Georgio’s wine tasting tour during your stay.

terre di nano Tuscany

Another beautiful agriturismo, Villa San Bartolomeo is located 2km down the road from Terre di Nano and offers views out to Montepulciano. Visit when the roses and jasmine are in bloom: it’s a slice of paradise. The cakes on offer for breakfast are, alone, a good enough reason to book!

Villa San Bartolomeo tuscany

Top tip: For most of this region and eastern Tuscany you will need to hire a car. Without one, it would be difficult to explore the villages and smaller towns but fear not, driving is fairly straightforward, even on the smaller, windier roads.

Other notable places to visit in the area:

San Gimignano: Located in the Val d’Elsa, San Gimignano is very popular with visitors to Tuscany but remains authentic. With 15 medieval towers, it’s often referred to as the medieval Manhattan of Tuscany and is a town with a slightly dark history as most of its population were killed by the plague in 1348. If you’re looking for a town with real Tuscan charm and a palpable past, this is well worth an afternoon trip.


Monticchiello: Little Monticchiello, a sleepy hamlet on a hill opposite Montepulciano, will take you less than an hour to explore but provides picture-perfect views, both over the valleys and of the charming little alleyways of the hamlet.

Tuscany rolling hills

Montalcino: Famed for its wine making history, Montalcino is home to one of the world’s greatest wines (I can confirm this claim after many glasses): Brunelli di Montalcino. Pay a visit to sample the wine and improve your standing amongst wine connoisseurs.

Eastern Tuscany


Arezzo, located in Eastern Tuscany, is not an obvious choice for visitors exploring Tuscany to visit and, I must confess, is not a city I had planned to visit beforehand. However, with some time on our hands before we could check into our hotel nearby, we decided to visit Arezzo and I’m so glad we did.  Famed for its antique stores and annual antiques fairs, this sloping city is perfect for a lazy day exploring its streets and stores. If you’re a fan of Tuscan churches and cathedrals (like myself) Arezzo is a real treasure chest. We visited on the day that schools finished for the summer, and the buzz of the town as school pupils took to the streets in a giant water fight was fun, welcoming and relaxed.

arezzo Tuscany

Where to eat: Canto del Maggio

Canto del Maggio, which offers accommodation, an enviable infinity pool as well as the restaurant, was perhaps one of my culinary highlights of the trip. We were met by the owner Simona, who greeted us with the kindest of welcomes, firstly treating us to a tour, including that of the cook’s garden (bursting with herbs, vegetables and fruits) and the swimming pool with its stunning views, before settling down to dinner.


It’s easy to see that all the food at Canto del Maggio is served with love and real thought, with most of the dishes being made with the fresh garden products and delicately decorated with wild flowers. The highlight of the dinner was most definitely the chocolate cake! I certainly wouldn’t have found this restaurant without an insider recommendation and would urge you to add it to the list if you’re in the Arezzo area, as a true hidden gem.

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Where to stay: Tenuta Lupinari

After a manic wedding week and after waving goodbye to our friends and family, we headed to Eastern Tuscany for a few days of much needed relaxation. Situated in the rural countryside, hotel Tenuta Lupinari was the ideal location in which to unwind in peace and quiet, whilst enjoying delicious food and perfect views. This beautiful estate is actually a carefully restored village, surrounded by vineyards used to make the estate’s own Chianti wine (we tried this at dinner, it was delicious). Antonella, the daughter of the original owner who restored the estate, now runs Tenuta Luminary alongside her sister and mother, and was a warm and informative host.

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One unusual but lovely sight on the estate is the old farm houses that have purposely not been restored. Like little kids, we couldn’t resist exploring these buildings one afternoon, which despite being run-down had a magical feel to them, offering glimpses into the traditional agricultural working life of the area. Perhaps one day I can persuade Antonella to let me restore one of the houses as my home.

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This traditional agriturismo is located in the perfect location to explore not only Arezzo but also the Chianti region, Siena and Florence.

Top tip: This area of Tuscany is full of sleepy little villages that are perfect for a lazy lunch and afternoon walk. We were recommended the village of Dudova to visit whilst we were staying at Tenuta Lupinari and I think I left my heart in this beautiful, rustic village. Here, I enjoyed the most delicious cheeses (of various ages) and red wine, whilst watching summer showers pass through over the hills. Away from the bustling cities of Tuscany, I’m certain that the most authentic slice of Tuscany can be found in these villages.

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Other notable places to visit in the area:

Monasteries: this area is famed for its monasteries, particularly that of Monastery di Camaldoli, located North of Arezzo in the national park: Parco Nazionale delle Foreste Casentinesi.  This Benedictine monastery is buried deep in the forest of the park.


When visiting Tuscany, it can be easy to bypass the smaller towns and lesser known cities for the renaissance power of Florence, the vertigo inducing wonky tower of Pisa, and the medieval splendour or Siena. My tip? Make time to explore more of the region; take time to enjoy the slower pace of life in the area, sample red wine and cheese, watch the clouds float by over the Val d’Orcia and roam its beautiful buildings, a region where Brunelleschi and Michelangelo created some of their finest masterpieces.


You’ll soon fall in love.

5 comments so far.

5 responses to “A Guide to Central and Eastern Tuscany”

  1. Sarah W says:

    Such a great guide – thank you!!

  2. I was in Tuscany a few months ago and I fell in love. I loved Montepulciano. We stayed about a half hour from there at Bosco Della Spina and absolutely loved our time there. Where we stayed wasn’t in town but the view from the room’s is stunning, the restaurant has some of the best food we had while in Italy and the infinity pool on the edge of the hillside is stunning. I can’t wait to go back.

  3. valerie says:

    Hey there!
    I got sooo jealous by all of your amazing photos of Italy. Congratulations and blessings to the newlyweds!
    I was wondering if you know about a route to discover Tuscany by foot(backpacking kind of style) ?!
    I havent started research yet but maybe u have some advice?!
    Thank you in advance and keep your great work up (sorry for bad english as im german) 🙂

    • The Twins says:

      Hey Valerie! Hmm I don’t really I’m afraid. I know a lot of people cycle through Tuscany. I’m sure getting to and from the major cities would be fine and larger towns – by public transport. But I’m not sure so much about the smaller villages. X


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