25 Things to Do in Tuscany: Wine, Villages & La Dolce Vita

There’s no shortage of unforgettable things to do in Tuscany — from exploring ancient hill towns and vineyard-covered valleys to soaking in hot springs and learning to make pasta the Italian way. Golden hills roll into infinity, terracotta rooftops glow in the evening sun, and life moves at the perfect unhurried pace.

I’ve been back to Tuscany several times, and each visit leaves me plotting the next. The light, the food, the people — it’s all impossibly good. So if you’re planning your first trip or coming back for another taste of la dolce vita, here are some of the best things to do in Tuscany, Italy — the hill towns, hidden corners, and food-filled moments that make this region unforgettable.

Florence: The Heart of the Renaissance

Florence is one of those cities that wins you over in minutes. The Duomo dominates everything — climb to the top for that classic sweep of red rooftops and Tuscan hills, and you’ll see why everyone falls in love with this place. I like to end the day at Piazzale Michelangelo, when the city turns gold and the bells start ringing — pure Florence magic.

In between, pop into the Uffizi (yes, Botticelli’s Birth of Venus really is that good) and grab lunch upstairs at Mercato Centrale, surrounded by locals tucking into bowls of fresh pasta.

➡️ Read next: Things to Do in Florence and Winery Tours from Florence

Siena: A Medieval Masterpiece

Siena feels like stepping back in time — a maze of old streets that all seem to spill into Piazza del Campo. It’s one of those squares where you just sit, sip coffee, and let the city go about its day. Inside the Siena Cathedral, the black-and-white marble stripes and intricate floors will stop you in your tracks.

For a view worth the climb, head up the Torre del Mangia and watch the light fade over the rooftops. Siena glows at sunset — it’s one of my favourite sights in Tuscany.

➡️ Planning a stop here? Read my full Best Things to Do in Siena guide.

San Gimignano: Towers and the Best Gelato in the World

San Gimignano looks like a film set — a jumble of medieval towers rising above vineyards and olive groves. The view from Torre Grossa is unreal, but the real star here is down in the main square. Gelateria Dondoli has been named the best gelato in the world more than once, and honestly, it deserves it. I tried their saffron flavour (made with local Vernaccia wine) and immediately considered going back for seconds.

Wander the lanes, pop into tiny artisan shops, and let yourself get lost — it’s that kind of town.

Pienza: Cheese, Charm & Val d’Orcia Views

If there’s a place that feels made for slow wandering, it’s Pienza. The streets smell faintly of pecorino, and you’ll see whole wheels stacked in every shop window. Grab a slice of it with honey or truffle and eat it while looking out over the Val d’Orcia — the views go on forever.
I usually stop here for lunch on a terrace and end up staying longer than planned. The pace of life feels softer somehow, and it’s impossible not to relax into it.

Walk along Via dell’Amore, where the whole valley seems to open up before you, and stop for lunch on a terrace serving fresh pasta with pecorino and a glass of local wine. It’s small, calm, and impossibly pretty — a perfect snapshot of Tuscan life.

Montepulciano: Wine & Stone Streets

Montepulciano is one of those towns that makes you slow down without trying. The streets climb gently past wine shops and cafés, and every turn opens onto another view of the hills. I like ducking into the old cellars for a quick tasting of Vino Nobile — they’re cool, quiet, and smell faintly of oak and earth.

When the light starts to fade, grab an aperitivo in the square and watch the town settle into the evening. It’s simple, beautiful, and very Tuscan.

➡️ Love good wine? Don’t miss my post on Winery Tours from Florence — the easiest (and most delicious) way to explore Chianti.

Montalcino: Brunello & Timeless Views

Montalcino is smaller than you expect, and that’s part of its charm. Everything seems to circle back to Brunello, the town’s famous red wine, but even if you don’t drink, the views alone are worth the trip.

I spent an afternoon sitting on the old fortress walls with a glass in hand, just watching the shadows stretch across the valley. It’s the kind of moment that sums up Tuscany perfectly — quiet, golden, and hard to leave.

Tuscany’s Hidden Gems

Volterra: Quiet Streets and Endless Views

I have a real soft spot for Volterra. It’s one of those places that still feels like Tuscany before the crowds — a little wild, a little mysterious. The town is high above the countryside, with views that seem to go on forever. I remember wandering through its quiet streets lined with workshops selling alabaster, the stone this area is famous for.

Stop by Piazza dei Priori, grab a seat at a café, and just take it all in. As the light changes, the stone buildings turn gold and the whole town glows — it’s honestly breathtaking.

Abbey of San Galgano: Tuscany’s Open-Sky Church

There’s something quietly beautiful about the Abbey of San Galgano. It sits out in a field, open to the sky, its roof long gone but its walls still standing strong. When you walk inside, sunlight filters through the arches, and you can hear birds darting overhead. It feels calm, slightly eerie, and completely unforgettable.

Just nearby there’s a tiny chapel said to hold the real sword in the stone. Whether you believe the story or not, it adds a bit of mystery to a place that already feels special.

Tarot Garden, Capalbio: Tuscany with a Twist

Down in southern Tuscany, near the coast, lies something completely unexpected — the Tarot Garden. It’s a surreal wonderland of giant, brightly coloured sculptures by artist Niki de Saint Phalle, hidden among olive trees.

It’s playful, bold, and a little bit bonkers and reminds me of Gaudí’s creations in Barcelona — a perfect detour if you’ve been doing a lot of classic hill towns and need a change of pace.

Pietrasanta: Where Art Meets Espresso

If you love art but prefer it without the crowds, Pietrasanta is worth a stop. The town has long been a favourite of sculptors and painters — even Michelangelo sourced his marble from the nearby quarries. Today, you’ll find workshops tucked behind old stone facades, where artists still chip away at blocks of Carrara marble.

Spend a lazy afternoon wandering between galleries, cafés, and the little piazza where locals gather for aperitivo. There’s an easy rhythm to life here — a mix of creativity, espresso, and conversation that feels both local and timeless.

The Maremma Coast: Tuscany by the Sea

When the hills start to feel a little too hot, the Maremma Coast is the perfect escape. This stretch of southern Tuscany feels wonderfully untamed — long beaches, pine forests, and low-key fishing towns where life moves to the rhythm of the tides.

I like Castiglione della Pescaia for its mix of laid-back charm and old-town views. The evenings are best spent with grilled seafood, a glass of crisp white wine, and the smell of salt in the air. Further south, the beaches near Monte Argentario are wilder, with crystal-clear water and quiet coves that feel far away from the usual tourist trail.

If you’re in the mood for something different, take a detour into Parco della Maremma, where you can hike, spot deer, or ride horses along the sand dunes. It’s Tuscany — but with a salty breeze and the sound of waves instead of church bells.

Best Time to Visit Tuscany

Tuscany changes with the seasons, and each one has its own charm.

• Spring (Apr–Jun): Wildflowers and perfect weather.
• Summer (Jul–Aug): Festivals, beach days, and long evenings.
• Autumn (Sep–Oct): Harvest season — truffles, olives, and golden vines.
• Winter (Nov–Feb): Quiet, cosy, and full of hearty food.

Getting There & Getting Around

By Air: Fly into Florence or Pisa.
By Train: High-speed routes connect Florence with Rome, Milan, and Bologna; local trains reach towns like Siena and Lucca.
By Car: Still the best way to explore — just keep an eye out for ZTL zones in town centres.

Once you’re here, mix driving, short train rides, or small-group tours depending on how you like to travel.

Where to Stay in Tuscany

Tuscany has stays for every kind of traveller — hilltop farmhouses, vineyard villas, and boutique hotels hidden in medieval towns.

Here are a few top-rated places that capture the region’s charm:

➡️ Planning your trip? You might like my guides to the best Where to Stay in Florence, Boutique Hotels in Florence, and Cool Hotels in Florence — all packed with real recommendations and stylish picks.

Map of the Best Places to Visit in Tuscany

Here’s a handy map with all the places mentioned in this guide — from the hill towns and vineyards to the hot springs and coast. You can zoom in, save it to your phone, or use it to plan your Tuscany road trip.

How to Use the Map

• Tap or click each pin for my quick notes and location tips.
• Use the layers to toggle between Towns & Cities, Food & Wine, Hot Springs, and Hidden Gems.
• You can open it in Google Maps for directions or to save it to your favourites.

FAQs About Visiting Tuscany

How many days do you need in Tuscany?
Ideally, give yourself at least five to seven days. That’s enough time to mix a few cities like Florence and Siena with slower countryside days in Chianti or Val d’Orcia.

Do you need a car to explore Tuscany?
For the countryside, yes — a car gives you the freedom to explore villages and wineries at your own pace. Trains work well between cities, but driving is part of the fun.

When is the best time to visit Tuscany?
May, June, September, and October are the sweet spots — warm weather, golden light, and fewer crowds.

What is Tuscany best known for?
Tuscany is famous for wine, olive oil, truffles, and Renaissance art — plus those rolling hills dotted with cypress trees that you see on every postcard.

Can you do day trips from Florence?
Absolutely. Popular day trips include Siena, San Gimignano, Chianti, and Pisa — all within easy reach by car or organised tour.

Is Tuscany expensive?
It can be, but it doesn’t have to be. Stay in agriturismos, eat where the locals eat, and travel outside the peak summer months for better prices.

Some places are flashy; Tuscany just serves you another plate of pici and waits for you to catch up. Between the hill towns, vineyards, and that easy rhythm of eating and wandering, it wins you over without trying. It’s less about ticking sights off and more about living a little slower — preferably with a glass of Chianti.