Tuscany’s Top Ten Towns and Cities
Mar 5, 2018

Tuscany’s Top Ten Towns and Cities

Tuscany is the Italy we see in films and on the silver screen – a scintillating region of pastel-hued fields and gently undulating hills crowned by crumbling medieval towns. Yet many visitors don’t realise how large this diverse region is. Tuscany covers an area nearly the same size as Sardinia and is packed with historic towns and unrivalled cities. Thankfully, we’ve put together a top ten list so you don’t miss the very best if you are planning a visit!

In at tenth place is Montecatini – a town of two halves. We love Montecatini Terme, set beneath a towering cliff face because of its amazing historic thermal baths, and nationally-important architecture. But we also recommend taking a vertigo-inducing monorail ride up to Montecatini Alto, where the streets are smaller and windier and feature petite trattorie and lovely local shops.

Montecatini Terme

Coming in at number nine is Pisa. It’s an enormously popular destination, thanks to its world-famous leaning tower and beautiful basilica. However, scratch beneath the surface and you’ll unearth an authentic Italian city rich with tranquil piazze, historic palazzo and excellent transport links for visiting other destinations.

Eighth place goes to Monteriggioni – one of Tuscany’s best-preserved medieval hilltop settlements. Surrounded by a complete fortress wall bristling with towers and ramparts, the inside feels more like a film set than a real, functioning Italian town. There’s a petite museum, rows of traditional houses and amazing views from the town walls, but the main draw may well be the fact that this gem is just 20 kilometres from Siena.

In at seventh place is the traditional beach resort of Forte dei Marmi. Frequented by locals, and exuding a classic Italian seaside vibe, this beautiful town is best visited just for a beach break. Rows of umbrellas and small-time gelato shops are order of the day, plus Pisa is just a forty minute drive away so it’s an easy day trip for city folk.

Montepulciano earns a well-deserved place on our list, coming in at number six. This hilltop town is a beautiful example of Tuscany’s medieval heritage. Higgledy-piggledy streets lace the hillside, while the rustic tower of the town hall rises above the terracotta rooftops. On the doorstep, visitors can discover the glorious gilded dome of the Church of San Biagio, plus there are wonderful local vineyards proffering the glorious red vintage named after the town.


Fifth place goes to the hidden-gem that is Pistoia. It has remarkable Tuscan architecture, with medieval examples dating back as far as the 12th century, and is especially vibrant on market days, when the hustle and bustle of the town can be enjoyed. It’s also known to be relatively free from the tourist trade that keeps nearby Florence and Pisa busy during peak months, ensuring you can enjoy this authentic town at your own pace.

In at 4th place is San Gimignano, affectionately known as the New York City of Tuscany. The name refers to the jaw-dropping collection of spindly sky-scraping medieval towers that surge up from the town’s time-worn cobbles. Nearly 800 years back, local families would compete to build the highest tower, and thus began a gravity-defying race for the sky. Only fourteen of these now remain, and they’re a true testament to the turbulent history of Tuscany. Climb one for a bird’s eye view of the town’s maze-like passages and the rural landscape surrounding the town, or instead sit with an Aperol Spritz and soak up the amazing medieval architecture of this must-visit town.

Taking bronze in our top ten list is lovely Lucca. We like to think of this romantic Tuscan city as a smaller, less-visited Florence, thanks to its variety of Instagram-worthy piazze, churches, and historic streets. Surrounded by a vast fortress wall that’s now in use as an elevated park, the town centre remains largely original, making it perfect for those seeking to discover the ‘real’ Tuscany. Don’t miss the Guinigi Tower – a 14-storey medieval tower with a garden right at the top, or the Piazza Anfiteatro, which is an unusual oval piazza surrounded by some of the town’s oldest and most picturesque buildings.

Siena is our very worthy second place choice. This historic Tuscan city spills over one of the region’s highest hilltops and commands mesmerising views of the undulating fields and forests of the Val d’Orcia. At its centre is the huge Piazza del Campo – home to the bi-annual Palio horse race and renowned as one of Europe’s finest squares. We highly recommend taking a climb to the top of the square’s Torre del Mangia as this 102-metre tower stands taller than the Statue of Liberty and offers unrivalled views of the city. Siena also boasts one of Italy’s finest cathedrals – an incredible medieval masterpiece that holds artworks by Donatello and Michelangelo. And if you need any more of a reason to visit, then just think about the hundreds of authentic Italian restaurants awaiting you… TripAdvisor lists 432 at time of writing, so maybe you’ll need to plan which to try first!

Siena Italy

Finally, we have reached the number one spot, and there is only one possible winner – Florence! Yes, this world-famous city of art and culture is undoubtedly Tuscany’s standout and a true bucket-list destination. Once home to Dante, Michelangelo, and Machiavelli, this vibrant Renaissance city is now a living museum of Italian culture. Discover Brunelleschi’s incredible Duomo– a two-acre cathedral boasting what was once the world’s largest dome, cross the romantic Arno River on the Ponte Vecchio bridge, home to centuries-old jewellers, or amble through world-class art galleries like the Academia where you can witness the majestic David. There’s also unrivalled leather shopping, sophisticated rooftop bars for aperitivo and beautiful parks including the famous Boboli Gardens to wander as the sun sets. Need we say more?

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