Tuscany – even the name makes us sigh. It is its landscapes that first seem to attract people to the region. Many eyes have widened with wanderlust at photos of cypress dotted hillsides, where rolling vineyards fade into burning sunsets. But beyond this earthly masterpiece there are many great things to do in Tuscany and some incredible places to go.
Tuscany brings together everything that we love about Italy. There’s the aforementioned landscape of course. But even this is worth mentioning again as mere changes in light can create dramatic views.
Then there’s the towns that hug its hilltops. Thick stone walls, fortresses and towers have evolved over centuries – they no longer defend towns, but are among the very reasons people visit them.
Then there’s the history – Roman, Phoenician, Renaissance and more shaping the region and its people, culture and food. Oh yes, the food – and for that matter the wine – Tuscany excels at both.
On a recent tour of the region, I visited some of its most popular destinations, I also experienced unusual but Italian-cool activities that shouldn’t be missed. Here’s five of the best…
History, art and culture make Florence one of the best places to go in Tuscany
It’s only right to start Tuscany’s highlights with Florence. Italy’s first capital city will satisfy anyone passionately seeking culture.
The Uffizi Gallery and the Bargello and Accademia house some of the world’s finest art treasures including Michelangelo’s David and Botticelli’s Birth of Venus.
But being the city of the cultured, wealthy (and at times, villainous) Medici family, Florence flaunts its treasures, with all manner of statues in squares like Piazza della Signoria.
A small group tour, a guide unveiled a history of merchants, bankers, philosophers and artists – Dante to Bruneschelli to Machiavelli – all left their mark on the city.
Then there are the buildings, of which the cathedral and baptistery are perhaps the best known. The red, white and green marble on the cathedral point to faith, hope and charity, and are also reflected in Italy’s flag.
It is, without doubt, the most impressive of Florence’s landmarks – perhaps Tuscany’s, from the outside, even if it doesn’t quite maintain the wow-factor inside.
Similar in its marble architecture, and full of some of the city’s most famous bones including Michelangelo and Galileo, the Santa Coerce, or church of the Holy Cross, is also worth a visit.
Then there’s the Ponte Vecchio – the oldest bridge in the city after the others were bombed on Hitler’s orders, to scupper the Allied troops’ advance in the Second World War. The bridge wears its age very well – it dates back to 1345 – and still has shops, now mostly selling gold, along its full length.
For the best views in the city, stay or have lunch, at the Grand Hotel Baglioni, or alternatively head up the hill to Piazza Michelangelo for a dramatic panorama.
A fine vintage – one of the coolest things to do in Tuscany
Chianti is known for its fine vintages, but less so its vintage cars. But this Fiat 500 tour of the Chianti hills, towns and vineyards was the best fun you can have in a tiny Italian car. See the video below to get a sense of what I’d rate as one of the most fun things to do in Tuscany.
A walk on the wall side – exploring Lucca
The town of Lucca was something of a revelation to me. I’d never heard of it before and when I was told we were going to walk its walls I had an entirely different idea of what that meant to Lucca’s reality.
The walls are more than 20 feet deep and have been transformed into an extraordinary park-like landscape.
Each side has a different species of tree lining it, bringing a change in scenery at every corner and there are broad paths for walkers and cyclists to enjoy views of the old town within and the modern one outside the walls.
The wall walk, or you can join the hoards hiring a bike from just €3 an hour to cycle it, also provides excellent elevated views of landmarks such as the town’s striped cathedral and Italian homes with window boxes overflowing with flowers.
But Lucca isn’t just about peace and relaxation. Head into the old town and there are boutiques and delicatessens to excite any fashionista or epicurean.
City of horses and history – trot around Siena
Another of Tuscany’s great cities, Siena wears its mediaeval history and religious heritage with pride. It also maintains one of the greatest traditions in the world. Each year 30,000 people gather in the round of Il Campo – its main piazza to race the Palio.
One of the biggest horse races in the world, the Palio, has been running since the 12th century and has created something of an equine city.
Evidence of this can be found in the iron hitching rings found along the city’s streets, as well as the Palio Stables.
Siena is also an important centre for Italy’s Catholic religion. It was home to Saint Caterina one of Italy’s two patron saints. There are two landmarks that should be visited to learn more about her – the Basilica Cateriniana di San Domenico, where perhaps gorily, her face and a finger are on display.
Then there’s the Sanctuary of Santa Caterina which houses two chapels and is also the site of her former home.
Meanwhile, Siena’s cathedral is one of the best places to go in the city. Unlike Florence’s cathedral, it’s not only beautiful on the outside, but the interior is a must for its dark green and white striped marble (which admittedly looks like black and white stripes, hence its nickname as the Bettlejuice Church).
Its painted library and floors depicting stories from the Bible, also beg to be seen.
Great gelato in a towering town – taste San Gimignano
Once upon a time, San Gimignano had 72 towers – built by wealthy families to show their economic power – peaking into the blue Tuscan sky and making the most of its uninterrupted views of green hills. Today the city has just 13 left after a change in architectural styles in the 13th century.
But the town, set at 334m above sea level, towers above its neighbours for many other reasons. Not only is there that view – worthy of the visit to San Gimignano alone, but it has numerous museums, including one all about wine.
San Gimignano has plenty of coffee shops selling delicious cakes making its main square Piazza della Cisterna, in particular, a great place to while away an afternoon.
But be sure you don’t miss out on one of San Gimignano’s major culinary attractions – it is home to world championship gelato shop, Gelateria Dondolini. The gelateria has its own herd of cows producing organic milk which it uses to create gelato with tongue-tingling flavours. Some of the most eclectic include white chocolate, pumpkin seed oil and cookies, white wine, and my favourite – pink grapefruit and sparkling wine, which had just enough tanginess to bring a level of fizz to the gelato.
San Gimignano has plenty of historic corners to explore so it’s worth spending a day there. And for those who miss the towers, you can get a sense of how the town was in medieval times at the 1300 Museum. It has a huge model of the original town.
See Tuscany for yourself
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