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Things to see & do in Tuscany

Most feel feel like they’ve got the measure of Tuscany before they’ve seen it. Florence, Chianti, medieval citadels and poppy fields, right? Well…yes. But there’s also everything in between, from the mountainous Apennines to hiking paths between vines that haven’t made it out of Italy yet. Read our Tuscany travel guide to find out more.

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Things to see & do in Tuscany

There are plenty of wrong ways to see Tuscany. We’re just going to say it: coach trips are the devil’s work. And whoever’s (literally) bumped into a Segway tour in Florence in high summer will understand how local lad Dante might’ve been inspired to write Inferno.

The trick is finding the right way to see Tuscany. And for that, you need a small group or tailor made tour with a guide who will show you the backstreet cooking schools, sit you down to dinner with the families that slowly till the foothills, or show you the lesser-known vineyards of the Tuscan hills.

It’s especially true of cycling, walking and wine tasting holidays, when an Italian-speaking guide will not only show you the best way but also make sure that your luggage is transferred between stops. So no need to worry about lugging a clinking rucksack of Chianti across the countryside. Read on to discover our highlights of Tuscany.

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Walk the old ways

Walking holidays in Tuscany are about as idyllic as they sound. The only way to get truly off-road is on two feet, wandering through centuries-old olive groves and vineyards, picking across hidden charcoal trails and following still-used shepherd tracks on a guided or self guided tour.

Approaching the famous cities and hamlets from afar, you get to take in the whole picture of how the Tuscan landscape shapes the lives of everyone who lives here. Rumbling up to a San Gimignano coach park or walking there through farmland, where you can see the 14 towers gradually rise like a mirage? We know which we’d rather choose. And as for the cities, the locals all know they’re best explored on foot anyway.

And while the postcard picture of striped vineyards, swaying sunflower fields and medieval castle towns is nothing to be sniffed at, it’s also worth looking to northern Tuscany. This is Garfagnana, where the hills clamber up into the mountains and meadows of Orecchiella Park.

This area is better known for its pilgrimage paths and autumn chestnut festivals. It’s wilder; less farmed. In spring, you might glimpse wolf and mountain hare tracks in the melting snow; in summer, it’s not uncommon to spy a golden eagle keeping its beady eye on you. In autumn, burnished leaves and chestnut festivals bring in local tourists.

Aim high, and you’ll be rewarded with some spectacular (and people-free) views. Monte Sumbra (1,765m) peers over the Apennines and Ligurian coastline; the eerie sunken village under Lago di Vagli lies below, too. Or head for the Crinali ridge (1,600m), which doubles as a dramatic borderline between Tuscany and Emilia-Romagna.

The Chianti wine route

Fancy a nice Chianti to go with your fava beans? Then you’re in the right place. Tuscany is the birthplace of Chianti Classico, where vineyards come topped with castle towns like Castello di Brolio.

You’d be forgiven for thinking Chianti was the only Tuscan wine, but there plenty of others to add to your tasting wish list. Lovely Montepulciano is the namesake of the DOCG Vino Nobile di Montepulciano dating back to at least the 8th century. It’s doesn’t taste like the Montepulciano you’ll find back home…or maybe it’s just that it tastes better with a side of Tuscan hill views.

Winemakers in Castelo di Brolio bottle up Barone Ricasoli wine, which the Wine Spectator named one of the best five wines in the world. Meanwhile, in Siena you can learn to tell your aromas from your bouquets at the Tuscan Wine School. For full immersion into the Italian way of life, sign up to a wine tasting holiday that walks you from vineyard to osteria to winery.

Of course, you’ll need some good food to soak up that wine – and Italians are always happy to provide. Many trips stop off in farmhouses for seasonal dinners of wild boar pappardelle or a bowl of hand-rolled pici. Or your tour guide can recommend a family-run restaurant that still cooks up bean soup just as mamma made it. Fancy having a go at making it yourself? Cooking holidays to Tuscany show you the ropes of pasta and risotto making, and arrange meet-and-greets with mozzarella farmers.

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When two wheels are better than four

Cycling holidays serve up all those classic Tuscan views. The rides tend to be leisurely to moderate: wide, empty roads lined with cypress trees meander up to medieval cities while country backroads take you through working hamlets. You rarely have to worry about Italian drivers on the backroads of Tuscany, where eight cyclists stopping off for lunch at a hamlet is a busy day.

Most holidays will dip into the Via Francigena – an ancient pilgrimage route between Rome and Canterbury in the UK. But one of the most scenic roads in Italy weaves through the Chianti hills from Florence to Siena. San Quirico d’Orcia, Montalcino, Buonconvento – the tiny towns are pretty bucolic, too. And the short but steep Rospatoio Pass works up to an amazingly scenic freewheel into the valleys below.

You won’t need more than a week to cycle around Tuscany. Depending on whether you choose a small group or tailor made holiday, you’ll share your week with likeminded cyclists or get an individually tailored trip – great for those who’d like to choose how many days they ride and how many days they rest. Most cycling holidays hop from town to town each day, so luggage transfers come as standard.

Florence, Siena & co.

We have perhaps been a little unfair to the cities of Tuscany. Florence, Siena, Pisa and Lucca – they’re all masterworks of the Renaissance. Gorgeous and completely over the top, they’re piled high with oversized duomos, palazzo museums, aristocratic gardens and more Made in Taiwan statues of Michelangelo’s David than you can shake a stick at. You’ve just got to be prepared for the crowds.

An organised holiday will help with that, connecting you with the best history walks (who knew that Florence was the first city with paved streets?) and the best bars for aperitivi after a hard day’s exploring. If you’ve got the time to spare, trains are often the best way to roll into a city. Not only are you delivered smoothly into the centre – you’re greeted by a train station as sculpted as a cathedral.

It’s worth keeping an eye on festivals, too. Some tours don’t run on festival weeks to avoid the crowds; others throw you into the melee in true Italian style. Because although the Piazza del Campo in Siena is crammed for the Palio horse races in July and August, the atmosphere is absolutely electric. Just grab a glass of Brunello, wedge yourself onto the stands and choose a horse to cheer on.