The Solo Traveller’s Guide to Tuscany

Tuscany offers dreamy landscapes and majestic cities that are easy to explore as a solo traveller
Tuscany offers dreamy landscapes and majestic cities that are easy to explore as a solo traveller | © Andrea Comi / Getty Images
Photo of Josephine Stockman
16 March 2022
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This dreamy region of central Italy is prime postcard material. Those iconic images of medieval hilltop villages ringed by misty cypress trees? You’ll find them here, along with some of the most magical cities in Europe, from Florence with its world-class art collection to honey-hued Siena, famed for its daredevil Palio horse race.

What’s the vibe?

You’ll find travelling solo in Italy is a breeze, with a great transport system, friendly locals and English widely spoken. Foodies will be in heaven: eating is a serious pastime here, with Tuscany championing the slow food movement with seasonal, local dishes and some of Italy’s finest wines.

Tuscany solo: a trip overview

The Giardino Bardini offers panoramic Florence views and is an idyllic spot for a little solo time | © iStock / Getty Images Plus

Allow at least a week to tick off Tuscany’s showstoppers, taking time to absorb its lyrical landscapes and serene villages, too. Considered Italy’s loveliest city by many, Florence is a perfect place to dive in. You could easily while away a day inside the splendid Uffizi Gallery, with Renaissance masterpieces from Botticelli to Titian hanging on the walls. Make sure you leave time for the magnificent Duomo and medieval Ponte Vecchio, lined with shops, and then take a break in one of Florence’s historic parks like Boboli Gardens or the Giardino Bardini.

Siena is another must-see city in Tuscany | © Chu-Wen Lin / Alamy Stock Photo

Less frenetic than Florence, but just as soul-stirring, Siena is a must-see with its sweeping Piazza del Campo, home of the high-octane Palio horse race. Next, it’s time to explore the picture-perfect Sienese hill towns. Here’s where a hire car comes in handy – follow snaking lanes through classic Tuscan countryside, playing join-the-dots with castellated villages and stopping off for pistachio gelato. San Gimignano is perhaps the prettiest, but swamped with visitors in summer – try less-crowded Volterra or Massa Marittima.

Make a stop at the picturesque Piazza dell’Anfiteatro while strolling around Lucca | © Thomas Mørkeberg / Getty Images

Need a break from sightseeing? Pause at Bagno Vignoni for a soak in its natural hot springs, or spend a lazy afternoon wine-tasting at one of Montepulciano’s famous vineyards. If you’ve still got energy, marvel at Pisa’s leaning tower, or spend an afternoon strolling around the cobbled streets of graceful Lucca. The best time to visit is April to June, or September to October – expect warm, sunny days without the summer crowds.

Where to stay in Tuscany as a solo traveller

From converted castles to rustic-chic farmhouses, Tuscany has characterful places to suit all pockets. You can really splash out here, with luxe retreats ranging from grand fresco-filled palazzos in central Florence to fine thermal resorts to sweeping country estates with sleek infinity pools, spas and Michelin-star dining – not to mention luxury villas. If your budget is more modest, agriturismi are an excellent option. These are working farms or vineyards, usually set in beautiful countryside, with accommodation ranging from simple to stylish. You’ll often get a pool and authentic home cooking, too.

What to do in Tuscany as a solo traveller

Track down a truffle

Tuscany is one of the best places to find truffles | © Guido Cozzi / Atlantide Phototravel / Getty Images

They’re gastronomic gold – and they sell for eye-watering prices worldwide. Tuscany is one of the best places to find truffles – head into the woods on a hunt with an expert tracker (accompanied by a trusty dog to sniff out the prize), then sample your finds over a bowl of local pasta.

Spend an afternoon wine-tasting

Tuscany boasts some of the best wines in Italy | © iStock / Getty Images Plus

Sniff, sip and swirl your way through some of Italy’s most famous wines. Tuscan wineries range from renovated 12th-century castles to slick, modern affairs. You’ll buff up on wine-making history before putting your tastebuds to the test.

Get to savour fine wines – and learn about the production process – when you travel with Culture Trip on its 10-day adventure, The Italian Job.

Join the party at a festival

The wine barrel race during the Bravio delle Botti in Montepulciano is one of many local Tuscan festivals | © REUTERS / Alamy Stock Photo

You’ve probably heard of Siena’s spectacular Palio, a bareback horse race that’s being going strong since medieval times. But Tuscany is awash with colourful less-visited festivals – try Pienza for its Pecorino-cheese contest, or Montepulciano for its Bravio delle Botti, involving a wine barrel race.

Eating and drinking in Tuscany as a solo traveller

The natural environment in Tuscany is the source of local culinary specialties

Unfussy but out-of-this-world tasty, Tuscan cooking is all about humble, seasonal dishes using top-quality ingredients. The rolling hills provide a natural larder, with wild game, foraged truffles and some of Italy’s sweetest tomatoes used to create hearty dishes such as fagioli con salsiccia (beans with sausage) or bistecca alla fiorentina, the celebrated thick-cut T-bone steak made for sharing. Sweet tooth? Try cantuccini, almond-flavoured biscuits dipped in a glass of Vin Santo, an amber-coloured dessert wine. Oenophiles will be spoiled, with some of Italy’s finest wines produced here – treat yourself to a rich Chianti Classico or bold Brunello di Montalcino.

Getting around Tuscany as a solo traveller

Travelling by car is the best way to explore the Tuscan countryside | © Marco Bottigelli / Getty Images

Train travel is efficient and inexpensive, linking all the major cities – you can easily hop between Florence, Pisa, Siena and Lucca without needing a car. But if you want to get a real feel for the Tuscan countryside, it’s well worth hiring a motor to explore some of the beautiful back routes. The roads are generally well-maintained, and you’ll be able to pause along the way to snap those Insta-worthy viewpoints. Avoid driving into Florence, though – the city centre is banned for non-resident drivers, and parking is very expensive.

Stay safe, stay happy in Tuscany

Be sure to watch out for whizzy scooters in the bigger cities – believe us, they can be quite dangerous when they’re travelling at speed.

Cultural need-to-knows

Italians are welcoming and easy-going, so you won’t find it hard to make friends and fit in. Do be aware, however, that when visiting churches, bare shoulders and knees should be covered – a light shawl or scarf should do the trick.

Fancy joining up with a group of like-minded travellers rather than going it alone? Sign up for Culture Trip’s 10-day small-group adventure The Italian Job: See the Highlights of Northern Italy in One Go – you’ll get to see highlights including Rome (by bicycle), Lake Como (sailing) and Milan (on a gastronomic tour).

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