If there is a place in Italy where time seems to stop, that is, hands down, Tuscany. Who hasn’t thought about retiring here for a few weeks or even months under the shelter of the green hills dotting the landscape? We have, obviously, and more than once.
However, even though the whole region is idyllic, there are 5 places you simply cannot miss while in Tuscany:
1. San Gimignano
Surrounded by green fields and an unmistakable skyline, San Gimignano, the so-called medieval Manhattan is one of the more touristy villages we can find in the Italian region.
But don’t let this be a reason that keeps you from going to this amazing place, where impressive buildings cohabitate with a gastronomy that is just a delight. There are so many restaurants and ice-cream shops as streets beyond its city-walls. And by the way, each better that the last one.
With 13 of the 72 towers there used to be still standing, wandering around its streets at dusk, when there are practically no tourists, is one of the nicest experiences you’ll ever have if you decide to spend the night in the European Manhattan.
San Gimigniano is 60 kilometres away from Florence and it does not have a train station so the best way to arrive there is by renting a car or taking a train to Poggibonsi, the closest train station, and then hop on a bus from there to San Gimignano, which takes around 25 minutes.

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2. Siena
Siena is one of the most popular cities in Tuscany. Not surprisingly, on 2 July and 16 August, Siena holds the Palio, a horse race dating back to medieval times that pitches different districts in the city against each other and congregates thousands of tourists in one of the most beautiful cities in Italy.
Even if you are not lucky enough to visit it during the Palio di Provenzano (2 July) or Palio dell’Assunta (16 August), don’t let anything stop you from spending a few days here.
Siena is a charming city –very rich in history and architecture– that any tourist looking for the authenticity of a Tuscan city will appreciate.
It should also be noted that the city’s old town has been declared a World Heritage Site by UNESCO and its gastronomy is a treat for the eyes and stomachs of the most demanding gourmets.
Visiting Siena will not take longer than a day for it is pretty easy to go around on foot and all the tourist hotspots are quite close from one another.
You can reach Siena by train from every other Italian city.
3. Montepulciano
Rising over a hill, 600 metres above the sea level, Montepulciano awaits as if it was never affected by time.
Known internationally for its exquisite red wines, with Vino Nobile di Montepulciano leading the list, Montepulciano will not only gift you with this delicious nectar but also with some other incredible treats. There are very few places we can say we have had such incredible food as in Montepulciano.
But this gorgeous city does not only live off its gastronomy. If you want to learn a bit about the city, you have to devote a couple of hours to pound the streets and discover incredible places such as Pizza Grande, the Cathedral, the Palazzo Bucelli, Sant’Agnese and Sant’Agostino church, all of which are symbols of one of the finest-looking cities in Tuscany.
Just as we mentioned earlier for San Gimignano, the best way to arrive to Montepulciano is by rental car. If you do not have access to one, from Siena you can catch a bus that will take you to the city in approximately 2 hours.
4. Volterra
In Volterra you’ll find the perfect place to go for a stroll and wander around inside the magnificent region of Tuscany.
Famous today for being the place where the hugely popular «Twilight Saga» was shot, flanked by Etruscan walls, with an astounding archaeological museum, a fortress and a Roman theatre, it is, without a doubt, the perfect place to stop for a day or even two and relax while traversing the green fields dotting the landscape.
There is no way you’ll ever forget the natural beauty surrounding the city, which can be appreciated from any of its many viewpoints.
The closest airport to Volterra is in Pisa, which is 63 kilometres away. There is no direct connection by train, so the most comfortable option, just as we recommended for San Gimignano, is renting a car and just move around freely without having to stick to a schedule.
5. Lucca
Between Pisa and Florence we find Lucca, a city surrounded by an extraordinary wall, which is still standing and protects a city that will surprise you every step of the way.
If you didn’t initially think of Lucca as the typical Tuscan city, it will just take you a couple of minutes exploring its medieval streets and old Romanesque churches, blended with fancy artisanal shops, to realise how wrong you are.
In Lucca there are tons of places that are worth visiting, such as the XVI century city walls, the Guinigi Palace and Tower, the Basilica of San Frediano, the Lucca Cathedral or the Clock Tower. But its more famous enclave, for being unique in the world, is the Piazza dell’Anfiteatro, built over the remains of the old amphitheatre, whose oval shape makes it a rather unusual construction.
Declared meeting point for tourists and locals, you’ll have the chance to delight yourself in any of its cafés, restaurants, shops and city markets.
You can arrive to Lucca by train –the train station is beyond the wall, Florence and Pisa being the main connecting points–, or by bus, also connecting with the main cities in Tuscany.
However, just as we mentioned earlier, if you happen to be travelling to Italy, our recommendation is that you plan a road trip around Tuscany (in a rental car), which is what we did. That way you’ll get to discover some of the hidden gems in this area, without having to worry about schedules or means of transport, and with the bonus of being able to move around freely.
We take this opportunity to remind you that the legal tender in Italy is the Euro, so if you are from any other country in the Eurozone, we recommend that you use your GlobalCard multicurrency prepaid card. Otherwise, you can exchange your currency with Global Exchange.