Welcome to our Florence and Tuscany 3 day itinerary. This one’s all about taking in the very heart of Italy. It whisks you from the cobbled streets of UNESCO-tagged Florence, through the rolling winelands of Chianti that spread south of the city, and finally into the Val d’Orcia, the area that most people say sums up the charms of rural Tuscany the best.
Each day focuses on something unique about this corner of the Italian boot. The first is about checking off the priceless Renaissance artworks and uber-famous medieval architectural wonders of the Tuscan capital itself. Day two is all about the wine. Day three takes you through unforgettable hill villages and even into some of the broiling hot springs that Tuscany has ad infinitum.
You can do this itinerary in either direction, but we think starting with Florence makes more sense because it’s easier to get to. Another thing: You’ll need a car here. There’s really no getting around that, since the highlights of Tuscany largely come in the form of hill villages and wineries and lookout points that are simply unreachable on public transport.
Day 1 – Florence itself
We don’t think there’s any better way to begin the ultimate Florence and Tuscany 3 day itinerary than with the city of Florence itself. Welcome to the capital of the whole region, and one of the most artistically rich, culture-brimming towns in the whole of Europe. You can arrive here on direct flights these days (Florence now has its own international airport). Alternatively, catch the high-speed train up from Rome or one of the regular hourly trains from Pisa.
In the morning, make for the Piazza del Duomo. We love the bustling Cafe De La Paix for a morning espresso. It’s tucked onto the north side of the square, right beside the carved marble wonder of the Porta della Mandorla (one of the exquisite medieval doorways to Florence Cathedral). A coffee and a gelato will set you back a handful of euros. And you’re just steps from the Cathedral of Santa Maria del Fiore…
Head around to the majestic frontal façade of the building and wonder at the alternating marble tones. It’s actually a modern restoration of an older façade. Glance behind and you’ll spot the iconic dome, which is still the largest brick-built dome on the whole planet. Inside the church, the highlight is probably The Last Judgement piece on the ceiling by Vasari and Zuccari. However, the better views are the panoramas of the whole city that unfold from the top of Giotto’s Bell Tower, which you can scale if you think you have the energy for 400+ steps!
After the central piazza, make south to the side of the Arno River. There, you’ll discover that iconic view of the Ponte Vecchio bridge, which hosts jewelry stores that have been there for centuries. Don’t cross it just yet – one of Italy’s most iconic galleries awaits: the Uffizi Gallery. No trip to Florence could be complete without seeing the wonders that await within, Botticelli’s The Birth of Venus among them.
Now cross the river and begin to scale the hillside to the Giardino Bardini. As evening closes in, these are lovely green spaces to stroll, with blooms of bougainvillea overhead and walkways shrouded in wisteria. They’ll emerge close to the Piazzale Michelangelo, where you’ll find perhaps the finest golden-hour panorama of the Florence downtown, church dome, mountains, and all. For dinner, retreat back to the area of Santo Spirito at the start of the Ponte Vecchio, where you’ll find hearty Trattoria VASARI offering authentic Tuscan cooking and wine.
Day 2 – Chianti and Montepulciano
Day 2, time to leave Florence itself. Drive straight south, ignoring the main A1 motorway that links with Rome in favor of the winding, wiggling SR222 country road. We think it gets progressively prettier the farther you go from the city. Past Grassina, the landscapes crumple into hills and the roads are flanked by dusty olive groves.
Your first pitstop should be the town of Greve in Chianti. This historic town is known as the gateway to arguably Italy’s most iconic wine region: Chianti itself. Notice the abundance of cellar doors and vineyards that beckon as you cruise in. Some of the best around are the Montecalvi Winery to the north of Greve and the grand Castello di Verrazzano, also to the north. Remember, though – none of the red stuff for designated driver just yet. There’s lots more driving to be done today!
After stepping on the lovely central piazza of Greve, head up to the high-perched castle town of Montefioralle. It offers wonderful views of the surrounding vineyards, from where you can start to get an idea of just how important the grape crop is to this corner of northern Tuscany. There’s also a medieval castle there, some excellent wine shops, and a plaque marking the birthplace of explorer Amerigo Vespucci (the man who inspired the name “America” for the New World, no less!).
From there, push even further south into the region of Chianti, to the town of Castellina in Chianti. Another gorgeous hill village that’s strewn along a thin ridge, it’s got wonderful views and hosts the Archaeological Museum of the Chianti Area. After sifting through the ancient findswithin, you can drop into Osteria Rosticceria Il Re Gallo that’s right next door to devour a lunch of Fiorentina steaks and hearty ragu.
For the afternoon and evening, drive out of Chianti to the famous hill town of Montepulciano. We have a real soft spot for this one, and not just because the local Vino Nobile is some of the best stuff produced on the whole boot. It’s a gorgeous place to get lost amid the honey-hued palaces and the zigzagging cobbled lanes. The piazza at the top is steeped in Etruscan history and has some fine aperitivo bars for sunset. Have a truffle tagliatelle for dinner – those fungi are a specialty of the region!
Day 3 – The Val d’Orcia: Hill towns and hot springs
For the third and final day of our Florence and Tuscany 3 day itinerary, we push even deeper into the heart of what’s arguably Italy’s most famous region. Again, it’s all about the adventure of the drive here, so hop in the car as early as possible and hit the road. What awaits is one of the most breathtaking corners of The Boot: the Val d’Orcia.
Stretching for about 30 miles or so from the castle town of Radicofani to the hills south of Siena, it’s a patchwork of sublime landscapes that really sums up what Tuscany is all about. You’ll see sweeping fields of corn dancing in the breeze, gullies and gorges carved out over millennia of volcanic activity, hemlock and oak woods, and roadways flanked by pretty Mediterranean cypress trees. Have the camera at the ready – you’ll need it!
First stop? Radicofani itself. A coffee and pastry on the piazza there can fuel you up for the climb to the castle that stands above. It’s an amazing citadel that was once under the control of Italy’s Robin Hood, a notorious pirate and highwayman called Ghino di Tacco. Learn all about his swashbuckling story and then hop back in the car to drive over to Bagni San Filippo.
Bagni San Filippo is known for its steaming hot springs (a real trademark of highly volcanic Tuscany). They’re free to enter and straddle a long riverway that drifts through pockets of thick woodland. The highlight is the so-called White Whale, a huge travertine terrace with naturally warm waterfalls that cascade into bathing pools below.
The drive north from there to Monticchiello and Pienza is one of the most spectacular in all of Italy. Take your time over it – there are lookout points aplenty and vineyards that ooze rustic charms. The towns themselves are also fantastic places to explore if you have the time. Pienza for its part is known as one of the first ever planned cities in the world. Built in the 1400s by a pope as an escape from Rome, it’s supposedly raised for good ventilation and efficient use of public spaces.
As evening approaches, aim to hit the city of Siena. This is where we’ll end our Florence and Tuscany 3 day itinerary. It’s a cracking spot for it, offering a vision of one of the most amazing piazzas in the country – the Piazza del Campo – and a whole web of ancient neighborhoods with wine bars, trattoria, churches – you name it.
After our Florence and Tuscany 3 day itinerary – where to go?
There’s LOADS more on offer in Tuscany once you’re done with our three-day trip. We can wholeheartedly recommend pushing on to the north to the hill town of San Gimignano. It’s considered by many to be the single most attractive village in Italy, and there are some seriously romantic agri hotels and trattoria to get through. Alternatively, you can drive east towards the mountains. There, famous places like Assisi and the vast lake of Trasimeno await with totemic cathedrals and ancient history sites.