In a nutshell
- Florence is an absolute must in Tuscany — it’s the capital and has more highlights than anywhere else in the region.
- The most beautiful Tuscan villages you really shouldn’t skip: Montalcino, Volterra, Pitigliano, and San Gimignano — winding alleyways, medieval squares, and seriously good views.
- Best seaside town: Castiglione della Pescaia — perfect if you want to combine sightseeing with a proper beach vacation.
- Don’t miss the Val d’Orcia: the UNESCO-listed valley with rolling hills, cypress-lined roads, and unforgettable sunsets — this is the best place to visit in Tuscany for that classic landscape experience.
Tuscany: Most Beautiful Places on a Map
On the map below you can see all the stunning places in Tuscany that we cover in this article:
Florence
- Perfect for: Sightseeing, Shopping, Dining
- Getting there: Train, Car, Bus
- How much time to plan? At least 2 days
Florence is the capital of Tuscany and the city with the most sights in Tuscany by a long shot.
From the Florence Cathedral to the Uffizi Gallery, through chic shopping streets, lively markets, and classic trattorias, or the secret passageways of the Palazzo Vecchio — Florence is simply not to be missed.
Don’t try to squeeze it into one day: to see everything that matters, you should plan for at least two nights here.
Florence is also a great base for a Tuscany road trip. Most of the most beautiful places in Tuscany are within about two to three hours by car. And if you’re relying on public transport, Florence is your best starting point.
Our hotel recommendation in Florence: Firenze Capitale, with a nearby parking garage, about a 10-minute walk from the cathedral.
Lies auch:
Siena
- Perfect for: Sightseeing, Shopping, Dining
- Getting there: Train, Car, Bus
- How much time to plan? One day
Siena is one of the most important cities in Tuscany. It’s much smaller than Florence, but every bit as worth your time.
Among the top highlights in Siena is the central square Piazza del Campo, where the famous horse race Palio di Siena has been held every summer for centuries. The unfinished Siena Cathedral, which towers over the city, is absolutely worth seeing too.
You really have to go inside — the interior is seriously impressive! Book in advance, though, because demand is high and spots fill up fast:
Book the Siena Cathedral Complex Pass
Our hotel recommendation in Siena: Palazzo del Papa, a historic country house with vacation apartments just outside Siena.
Lies auch:
Pisa
- Perfect for: Sightseeing, Shopping, Dining, Beach vacation
- Getting there: Train, Car, Bus
- How much time to plan? One day
Pisa is of course best known for the Leaning Tower — but there’s a lot more to it than that.
There are several other attractions in Pisa well worth your time: the Cathedral, the lively shopping street Borgo Stretto, the walkable city walls, and the beach at Marina di Pisa, just 11 kilometers away.
Most Tuscany visitors base themselves in Florence or Siena, which means Pisa always feels a bit more relaxed and less touristy.
Accommodation prices here are also much lower than in other Tuscan cities — so if you want to save some money without missing out, Pisa is a genuinely smart choice.
Our hotel recommendation in Pisa: The Rif, boutique hotel with its own garden and parking, a 5-minute walk from the Leaning Tower.
Val d'Orcia
- Perfect for: Sightseeing, Dining
- Getting there: Car
- How much time to plan? 1–2 days
When people ask us what you absolutely can’t miss in Tuscany, our answer is always the Val d’Orcia.
The valley is a UNESCO World Heritage Site and, with its rolling hills, vineyards, and cypress-lined roads, it’s the quintessential Tuscany postcard image — in real life.
You can leisurely drive the country roads, stop at viewpoints, or explore one of the dreamy villages like Pienza, Monticchiello, or Montalcino.
You could easily spend several days here — it’s simply breathtaking. And it’s at its most beautiful at sunset, when the hills are bathed in soft shades of yellow, orange, and pink.
Our hotel recommendation in the Val d’Orcia: Borgo Sant’Ambrogio, a large historic country estate with double rooms, vacation apartments, and a pool.
Read our article about the Val d'Orcia too:
Montepulciano
- Perfect for: Sightseeing, Dining
- Getting there: Car, Bus
- How much time to plan? Half a day
If you’re visiting the Val d’Orcia, a stop in Montepulciano is non-negotiable.
The town sits atop a hill in the valley and is best known for its red wine — the famous Vino Nobile di Montepulciano, which you can sample pretty much everywhere you turn.
But wine isn’t the only reason to visit: the medieval town is packed with sights and great vantage points overlooking the Orcia Valley.
The central square Piazza Grande is lined with cafés and historic buildings, including the medieval town hall with its bell tower, which you can climb for sweeping views.
Montepulciano is full of narrow alleyways and excellent trattorias — honestly, a visit here is absolutely worthwhile.
Our hotel recommendation in Montepulciano: Palazzo Carletti, a historic manor house with ceiling frescoes and classically furnished rooms.
Lucca
- Perfect for: Sightseeing, Shopping, Dining
- Getting there: Train, Car, Bus
- How much time to plan? One day
Lucca is a medieval town between Pisa and Florence and one of the prettiest towns in Tuscany. Its defining feature is the wide, completely intact city wall that encircles the entire historic center.
You can stroll along the tree-lined wall and completely unwind — or duck down into Lucca’s medieval alleyways below.
Other standouts include the Piazza Anfiteatro, built on the footprint of a Roman amphitheater, and the 45-meter-tall Torre Guinigi, whose observation platform is shaded by centuries-old oak trees growing right on top.
Lucca is very compact and works perfectly as a day trip — but there are also some lovely places to stay if you want to linger.
Our hotel recommendation in Lucca: Lucus, a modern bed & breakfast in a historic city villa with a garden.
San Gimignano
- Perfect for: Sightseeing, Dining
- Getting there: Car, Bus
- How much time to plan? Half a day
Between Florence and Siena lies the beautiful village of San Gimignano. It has everything you picture when you think of Tuscany: medieval alleyways, small trattorias, vineyards, and red-tiled rooftops.
What really sets San Gimignano apart from other Tuscan villages, though, are its 14 medieval towers. You can climb the 54-meter-tall Torre Grossa for views over the Tuscan hills that are simply unbeatable.
San Gimignano is small — half a day is plenty to explore it. The perfect day trip from Florence or Siena!
Our hotel recommendation in San Gimignano: Leon Bianco, centrally located with a great view of the surrounding countryside.
Pitigliano
- Perfect for: Sightseeing, Dining
- Getting there: Car
- How much time to plan? Half a day
At 3,000 years old, Pitigliano is one of the oldest villages in Italy, built on tufa rock cliffs 300 meters high.
The village’s reddish houses sit right on the edge of the cliff and look almost as if they grew out of the rock itself. For its extraordinary appearance alone, Pitigliano is a real highlight.
For a village of around 4,000 inhabitants, there’s quite a lot to see: a 17th-century aqueduct winding its way above the rooftops, an archaeological museum, many narrow alleyways, and even a Jewish Quarter — which is why Pitigliano was known as “Little Jerusalem” back in the 16th century.
Plan to spend a full day here. The drive from Florence takes about two and a half hours.
Our hotel recommendation in Pitigliano: Le Camere del Ceccotto, stylish rooms with wooden beam ceilings in the medieval center of Pitigliano.
Cortona
- Perfect for: Sightseeing, Shopping, Dining
- Getting there: Car
- How much time to plan? Half a day
Cortona sits in eastern Tuscany, about an hour’s drive from Siena and an hour and a half from Florence.
The small town is perched on a hillside, so sweeping countryside views keep appearing between the medieval buildings as you wander around.
Cortona is so quintessentially Tuscan that the old quarter has served as a backdrop for several Hollywood films — scenes from “Under the Tuscan Sun” and the Oscar winner “Life Is Beautiful” were both shot here.
There’s a cathedral, an archaeological museum, and plenty of lovely cafés and boutiques to keep you busy for a full day.
Our hotel recommendation in Cortona: Hotel Villa Marsili, an elegant hotel in a historic building within the city walls.
Volterra
- Perfect for: Sightseeing, Shopping, Dining
- Getting there: Car, Bus
- How much time to plan? One day
Volterra dates back to the 4th century BC and was once a major city of the Etruscans, Tuscany’s original inhabitants. The town sits at about 550 meters elevation, which makes it noticeably more bearable in the height of summer than the scorching plains below.
There’s plenty to see: the picturesque main square Piazza dei Priori, the 2,500-year-old city gate Porta dell’Arco, a massive Roman theater, and an archaeological museum.
Add to that the many medieval alleyways, several panoramic viewpoints, and the typical craft boutiques selling jewelry and objects made from bronze and alabaster.
Volterra isn’t huge, but there’s so much to explore that you can easily spend more than one day here.
Our hotel recommendation in Volterra: Hotel La Locanda, right in the heart of the old town with classically furnished rooms.
Lies auch:
Castiglione della Pescaia
- Perfect for: Sightseeing, Shopping, Dining, Beach vacation
- Getting there: Car
- How much time to plan? One day
Castiglione della Pescaia is a charming seaside resort on the southern Tuscan coast, directly across from the island of Elba.
If you want a beach vacation in Tuscany combined with a place that’s genuinely worth seeing, Castiglione della Pescaia is a great compromise.
The medieval alleyways of the old town wind their way up a hill, topped by a small castle. It’s privately owned and not open to visitors, but there’s a lovely viewing terrace with views out to sea.
And of course, there are plenty of excellent trattorias serving wonderfully fresh fish. We really loved Ristorante La Fortezza.
Our hotel recommendation in Castiglione della Pescaia: Aqua Boutique Hotel, with stylish décor and a private beach.
