Last Updated on October 23, 2017

For those who haven’t been there, what they say about Tuscany really is true. Hilly countryside roads leading through chains of medieval villages really are lined with vineyards and olive trees. The locals really do move in slow motion, and between all of the wine drinking and pasta sampling, tourists to Tuscany easily adjust to this pace in no time.

While you could spend the majority of your trip in a rustic rural villa, swimming, sipping and sleeping the days away, either if you are on your own or if you are using an organised tour of Tuscany,  it is also important to get out and take in the culture and life of Tuscan people as well.Siena gate viewThe two most famous stops on the circuit are Florence, to see Michelangelo’s statues, the famous cathedral and the Ponte Vecchio bridge, and Pisa with its Leaning Tower, but the top five towns that won our hearts were actually neither of the above.

San Gimignano

The fourteen tall towers of San Gimignano greet visitors from far off in the distance. The town, perched atop a hill 50km south of Florence, is completely contained within the original city walls and the limestone houses along narrow lanes are filled with shopping selling wine, jewellery, and art inspired by the surrounding countryside.
san gimignano piazza della cisternaThe small town of 7,000 keeps these streets car-free, allowing visitors to stroll at a snail’s pace, sampling Italian sweets, cheese, bread and wine-tastings, the gelaterias with the creamiest gelato and pizza places keeping taste buds bursting with deliciously unique combinations. Work it all off with a climb up the hundreds of steps to the top of Torre Grossa on Popolo Square for 360-degree views of the most picturesque Tuscan countryside of anywhere in the region.view over san gimignano & towers from torre grossa

Piazza della Cisterna is the main square in the town and the well in the middle is a great spot for people watching. It is also where the world famous gelato maker Sergio has his Gelateria di Piazza, praised on television and in magazines around the world. If you happen to be there on a Thursday, you can visit the Tuscan farmer’s market here. The area of the old Rocca castle, the highest point of the town, offers splendid views over San Gimignano and the surrounding countryside.

Tuscany Tip: pick up a selection of cheese, olives, Italian bread and cheap, quality Italian wine and take in the sunset picnicking up on the Rocca – the perfect end to a day in San Gimignano.siena fruit store


Another medieval town on a hill in the heart of Tuscany, Siena is a much larger city whose historic town center, a UNESCO World Heritage Site, is smack dab on the beaten path. Siena is famous for the annual Palio di Siena horse race held for centuries right on the central shell-shaped Piazza del Ciampo. This horse race is easily the biggest spectacle on the events calendar throughout the region each year.siena Piazza di Campo

The 300 steep steps of the Torre del Mangia right on the Piazza del Ciampo can be climbed, its tower also affording terrific views over the town and Tuscan countryside. Siena’s 12th century cathedral, with its striking black-and-white facade, is filled with paintings and sculptures by Sienese artists who were amongst the best and most influential in medieval times, before Florence became the focal point with Michelangelo and Da Vinci.

Because Siena is both a fair-sized city and a university town, we found a good blend of medieval history and a modern creative streak, which resulted in quirky shops, street art, and pubs and bars filled with local characters.siena cathedral columns & lion


What if we said Volterra, just 30km west of San Gimignano, is another hilltop Tuscan town – would you be surprised? Yes, that’s just the way they made ’em back then, but each town, including Volterra, has its own unique characteristics.

Firstly, Volterra may be familiar to Twihards (fans of Stephanie Myer’s Twilight saga) as it is an important location in the popular books.volterra viewVolterra’s city walls are completely in tact, and once you enter through one of six majestic gates, the winding roads are free of cars and the cinnamon-colored houses along the quiet alleys have been inciting inspiration from the town’s early days.

Italian artisans continue to create works of art here, as did the Romans centuries ago, which can be seen in the remains of a classic Roman amphitheater. Theover 800 year-old city hall also served as the inspiration for the Palazzo Vecchio in Florence.

Tuscany Tip: Make sure to head up to the panoramic viewpoint at the Piazza Martiri di Liberta on the south side of town where you can sit down on the wall and enjoy the views over Tuscany and Volterra’s red roofs.volterra roofs


Though just a quarter of the size of Florence, Lucca is by far the biggest city on our list, with it’s population of 90,000. Located in a valley, not on a hill, Lucca’s historic center is still completely surrounded by fully-preserved defensive stone walls, but unlike other walled cities, the Lucchesi, or people of Lucca, built walls of stone 20m thick inside of a substantial moat.
Locals and visitors alike cycle, jog and stroll along the top of these massive walls, so make sure to rent a bike or take a 4km walk along the top of Lucca. The town dates back to the Roman Age, mostly visible in the oval-shaped Piazza dell’Anfiteatro where the amphitheater was located. Today, the oval ‘square’ is surrounded by typical Italian houses painted yellow with green shutters. Take in a cappuccino here, or indulge in pizza at one of several pizza pasta joints on the popular Piazza.lucca piazza dell'anfiteatro gateLucca is famous for its many churches, especially the Duomo di San Martino, Lucca’s cathedral, San Giorgio church whose bell towers is one of the most remarkable ones in northern Italy, and San Michele in Foro with its striking facade.

The city’s compact size makes it easily walkable, needing just a day or two exploring its labyrinthine alleys to get a good feel for the place. Lucca has everything, from excellent street markets and dining gems to great music venues and charming hotels.

Stumble upon fabulous little pastry shops and pizzerias or have an espresso at any of the coffee bars throughout town. There are art exhibits and fashion boutiques, which, even for window shoppers are fascinating in cupWe’ve recommended climbing the towers in the towns above for the views, but head up on top of one of Lucca’s medieval towers for the rush of the experience. Other towers have been recently renovated, stairs reinforced. Not in Lucca. Here, the wooden stairs to the top, over 200 in all, look like the original 13th century wood.

Climb the Torre Guinigi, has ancient oak trees on top, or the Torre delle Ore, for views not only of the countryside, but also the Torre Guinigi.

Tuscany Tip: It costs €3.50 to climb one tower, or you can get a ticket for both for only €5.lucca tower & trees


Barga is far from the Central Tuscan towns above, nestled in the green mountains much further north of Lucca. There are no typically Tuscan rolling hills here, and very few tourists, either.Barga houses & cathedralPassing more cats than people, we made our way up to the magnificent medieval cathedral on top of the mountain, and what a difference to Siena’s cathedral which is filled from open to close with tour groups. Seriously steep and too narrow for cars, the  little streets wind undisturbed up the hill, sometimes suddenly replaced by a steep set of stairs instead.

The views from the top of the hill are terrific, of course, and we felt that, due to all the climbing, we deserved a pizza reward. We stopped in a mom-n-pop corner place and ended up having some of the most scrumptious pizza and antipasti of our entire time in Tuscany.montaione pizzasTuscany Tip: Barga is our top choice for a day trip from Lucca, only 35 kilometers north of the city.

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Tags : Tuscany


  1. I thought Volterra was nice. There is an original gate leading into the city that dates back to 400 BC.

    Add Montepulciano to the list (of the famed Montepulciano wines). It is also a walled medieval city.

    1. We didn’t make it to Montepulciano this time – it had been recommended to us but we just went out of time. Next time though for sure!

    1. We have a long list of towns that we didn’t make it to, as well – there’s always a reason to go back… Tuscany is just so beautiful, I think we could go there once a year to get our ‘Tuscany fix’ 😉 – stroll through these gorgeous towns, eat gelato, drink wine, …

  2. Wow, my dears, another very nice post on Tuscany!And I am so happy to have visited all these towns you mentioned.not usual for a local ;-)…
    Don Faust is right Montepulciano is another pretty one, but if we have to add all the Tuscan walled medieval cities it is not enough one blog! hahaha 🙂 (monteriggioni,certaldo,san miniato,monteriggioni,ecc…………

    1. Thanks Lauro! Next time we come to Tuscany we will go to Montepulciano for sure and all the other places you mentioned… and of course we’ll stop by at Belmonte Vacanze 🙂

    1. Thanks Debbie – Tuscany is well worth a visit!! There really are countless cute little towns and villages, we could’ve spent months there exploring all these towns. We can’t wait to go back to see more.

  3. Yes, all beautiful, but for me the best is always Florence! To sleep, eat and drink, the streets of the center and its hills … For me must be put at the first place 🙂

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