Our 10 favourite places in Tuscany

Italy may very well be THE country in Europe that attracts the greatest number of tourists from all over the world. There is something alluring about the images of cypresses on the hilltops, the ocher-coloured houses and the indigo-blue night sky full of bright stars…

And then there is the food. Of course! The Italian cuisine! In my opinion this cannot be matched anywhere in the world! And yes, the Italians do take their cooking seriously! Read more about this here! 

It has been many years since my own fascination with Italy started. It was the movie “Stealing Beauty” that started it all. Liv Tyler and Jeremy Irons on the list of stars. It had some stunning scenery, filmed on location in Tuscany. And I simply had to go down and see for myself!

This led to 10 summers in a row, with long drives in the small car from Denmark to all the places in Tuscany that just kept us completely fascinated. And the more we saw, there more appetite we got. It was a bit strange actually, but nevertheless thrilling! And I always used to have a laugh at those people who kept going back to the same places year after year! Well, Tuscany IS a large geographical area, so there is plenty of new things and places to see. Yet we saw ourselves seeking towards the old and familiar favourites as well. 

During our round-the-world journey I missed ONE thing above anything else: A history going further back than just “a few hundred years”. Everywhere we went they had an “ancient” or “original” population (aborigines, maoris, indians etc), but nowhere else in the world do they live in such a perfect harmony with history as they do in Italy. Simple as that! And you cannot help but to feel this when moving around, which is one of the reasons that I keep coming back.

Here is a list of our 10 favourite places/cities in Tuscany. They can be visited with or without children. Most of these are, by the way, partly or as a whole listed on the UNESCO World Heritage List.

Lucca: This happened to be one of the first cities that we stayed in. Love at first sight! The ancient city walls, surrounding the old city centre, have a park on top and you can walk all around the centre in magnificent surroundings. Children, youngsters, elderly… They all meet here and discuss the latest gossip. Joggers get their daily exercise… As you walk around the walls you can have small peeks into the old, walled gardens below and the large roof terraces, where the families gather around long, wooden tables as the sun sets and they eat their dinner in the evening shades. There are plenty of restaurants in the narrow streets and alleyways, so I can only recommend using Lucca as your base for a week or so, in order to try out the best restaurants. You can then drive to other cities and attractions during daytime. Do not miss out on the church San Michele in Foro and the "oval square” Piazza Anfiteatro. During the summer months there is usually a music festival on Piazza Napoleone. Here you can listen to some og the greatest names on the international rock and blues scene. A visit to Torre Guinigi should not be missed either. The tower has several old trees on top and can be seen over most of the city.


Volterra: An old Etruscan fortress. It appears to be somewhat “impregnable” but as soon as you are within the city walls you are met with a warm and calm atmosphere. Particularly the cathedral is a “must see”. It is beautiful. For much more information on the city of Volterra, please visit their site by clicking here!


San Gimignano: “The Manhattan of the Middle Ages”. They managed to preserve 14 towers in spite of war and natural disasters. They can be seen all over the inner city. 500 years ago it was a sign of status to have your own tower, and it provided you and your family with a certain sense of safety. It is a fascinating sight and the city is absolutely one of the most visited in all of Tuscany. Outside the mighty walls surrounding the inner city you find several parking lots, from where you walk the remaining few hundred metres to the gates. Do not miss Rocca di Montestaffoli, the ancient fortress ruin, from where you have magnificent views over the city and the surrounding area. Also, you cannot miss trying the best ice-cream in the world. This can be enjoyed at Piazza della Cisterna in the tiny shop Gelateria Dondoli. And yes, they do in fact have a diploma saying they are the best, and they even deliver to The White House and Downing Street 10.


Pienza: Home of the world famous Pecorino cheese. A cozy and friendly city centre. Palazzo Piccolomini and the Duomo are well worth a visit. 


Cortona: Another old “fortress city” which may seem a bit overwhelming when approaching from the country roads below. But Cortona is a very lively and friendly city when you get inside the city walls. Plenty of artists and craftsmen live here. The city got international recognition after the movie “Under the Tuscan Sun” was partly filmed here. The film is based on the book by the same name by Frances Mayes. The house that plays a central role in the book does in fact lie just a little outside Cortona. I have stayed in the city quite a bit and I always enjoy a walk through the city park, from where you have a splendid view over the valley and the surrounding parts of Tuscany. Cortona literally lies on top of an ancient Etruscan city, and there are PLENTY of things to see, among these an ancient “highway” going across the city, over the hilltop. 


Arezzo: Another strategic Etruscan city. Today it is famous for its fantastic antique-market. Piazza Grande with the beautiful Palazzo Communale fascinates me. There are some interesting cultural festivals held each year.


Siena: After Florence this is the city that attracts most tourists in Tuscany. Another “UNESCO gem” and particularly Piazza del Campo is worth visiting. At night, when darkness falls, it is so beautiful to see the lit-up facades of the buildings on the Piazza, while sitting in a sidewalk café eating Italian ice-cream, watching all the people passing by. It really looks like a theatrical setting, with the deep blue sky as the background carpet. Do not forget to climb the tower of Palazzo Publico from where you can see the beautiful terracotta roofs all over the city. 

Pisa: Of course you have to go to the leaning tower when in the area. And yes, there are MILLIONS of tourists here! The Japanese ones are seen in the typical positions, leaning against the tower or pretending to hold it from falling completely with their fingertips. The Americans are walking around in shorts and Hawaii-shirts and the local nuns are relaxing in the shade, while the endless row of stalls are hawking cheap and worthless souvenirs and overpriced canned sodas. Nevertheless, the place should be seen…. But only once!


Florence: The capital of Tuscany. Home of the best and finest things you can ever think of when it comes to anything “Renaissance”. Art, culture and history. The list of prominent attractions is nearly endless, but the cathedral and the bridge “Ponte Vecchio”, with its many small shops selling jewels, art and souvenirs, are among my favourite places. There ARE many tourist “traps” in Florence and there are masses of people everywhere. Hence I cannot recommend going with children during the peak season from June to August. The rest of the year you will be fine. 


Montalcino: Another cozy Etruscan city world famous for its “Brunello di Montalcino”. Not quite as overcrowded as the “sister” Montepulciano. Needless to say the city has its fair share of “Enotecas” - wineshops, and you should definitely visit a few of those if you are interested in Italian wine!


And then just a few places I recommend AVOIDING:

Montepulciano: In my eyes simply too hyped and resting on the laurels of past greatness. A famous wine region, yes, but they have certainly maximised their profits… Spend your time and money elsewhere. Go to nearby Pienza or Montalcino instead (see above).

The coastal areas: This is where ALL your prejudices come from! Tourist traps, traffic chaos and bad customer service EVERYWHERE. “Money-making machines”! Restaurants, bars and hotels are overcrowded. So are all the beaches! In my eyes this is where you see all the worst sides of Italy! There are a few exceptions, but they are rare!



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