Florence is one of the must-see places for people visiting Tuscany for the first time, a region in central Italy famous for its art, gorgeous landscapes, hilltop towns and food. Standout sights include the perfectly preserved Medieval towns of Siena and San Gimignano, the iconic Pisa tower, and the gorgeous landscapes of the Chianti and Val d’Orcia.

8 Must see Places for first timers – Iconic Tuscany

1. Florence, Renaissance charm and famous art

At the heart of Tuscany you have its ‘capital’, Florence. This is one of Italy’s most celebrated cities, a place made beautiful by a series of artists during the Renaissance, like Brunelleschi and Michelangelo. A city where stunning architecture matches the beautiful setting, where scenic hills embrace the red-roofed city crossed by the Arno river. Its Cathedral is one of Italy’s highlights, with its outstanding dome, and so is the iconic Medieval bridge Ponte Vecchio, romantic to a fault.

Florence is the city of must-see galleries, like the Uffizi and the Accademia – home to Michelangelo’s David – but also of lesser known, fascinating museums like Bargello and San Marco. It’s a city of ancient churches filled with frescoes and celebrated sculptures. A place of botteghe, artisan workshops where leather, gold and pottery have been worked for centuries. Not to mention fabulous markets where you can fill your eyes with all the flavours of Italy.

=> Top 20 Experiences to live the real Florence!

=> 3 Days in Florence: a complete itinerary


2. Siena, Medieval wonder and Gothic beauty

Siena will intrigue you with its perfectly preserved Medieval architecture. The whole town looks like something out of a film, with the impressive Piazza del Campo at the heart of a maze of narrow streets. Siena is divided into 17 contrade or districts, that have a centuries-long history, each has its own museum and church. Ancient traditions are cherished here, including long-held rivalries that come alive every year during the Palio historic horse race.

Siena has one of the most beautiful Cathedrals in Italy, and some other churches and museums that will satisfy your hunger for wonder and history. Definitely one of the must see places to visit in Tuscany for first timers.

=> Top Things to do in Siena

=> 12 Amazing Hilltop Towns in Tuscany

iconic places to visit in tuscany for first timers

3. San Gimignano, the must-see Town of the Towers

On the way to Siena from Florence you find what has to be the ultimate hilltop town in Tuscany: San Gimignano. Why is this place so iconic and a must-see for a first timer in Tuscany? This is Medieval at its most authentic, enchanting best.

San Gimignano hasn’t changed much from the way it used to look in the 14th century. Because of its relative isolation throughout the centuries, it’s one of the few places to have maintained its original tower houses, that in the Middle Ages used to fill every warlike Italian town. You’ll also find a Cathedral whose walls are covered in impressive frescoes, a tower that you can climb and a couple of museums to keep you entertained for a whole day.

=> If you can’t get enough of the Medieval vibe, check out also the hilltop towns of Volterra and Cortona.

4. Pisa, where Miracles do happen

Pisa is one of Italy’s iconic destinations. It has its wondrous Leaning Tower to thank and the awesome setting of the Piazza dei Miracoli, or Square of Miracles. One of the most exciting sights in Tuscany, the Cathedral Complex comprises the stunning Baptistry and the bell tower that is famous for its weirdly picturesque tilt. Despite of the kitsch souvenirs and crowds of amazed tourists, this square will steal your heart. Especially if you come back at night, for a quiet stroll, once the tour groups have departed.

=> Discover all the secrets of the Square of Miracles on a guided tour!

Piazza dei Miracoli, Pisa – Image by VĂN HỒNG PHÚC BÙI from Pixabay

5. Chianti vineyards, land of wine and must-see views

The landscape of the Chianti, in central Tuscany, has thrilled the collective imagination for decades. It’s the land of endless olive groves, and vineyards that give birth to one the most cherished wines in Italy, the Chianti red. This is an area where cultivation and love for nature are taken extremely seriously. Not to mention food.

In the 70’s this area had already become known as ‘Chiantishire’, thanks to the number of expats that had discovered the pleasure of the good life in the Chianti region and bought up many of the old farmhouses. Happily, the Chianti still feels very much Tuscan. Retaining a very strong tie to old traditions and local community life is rich all year round.

=> Discover the Top 10 Towns in Chianti to visit

6. Val d’Orcia, UNESCO protected landscapes to visit for first timers in Tuscany

Imagine an elegant line of cypress trees leading up a round hill. This is Val d’Orcia, an area just south of Siena. The epitome of natural beauty. A place of infinite skies and pure grace, whose landscapes have graced infinite postcards and featured in films from Gladiator to The English patient. A landscape where nature and man have collaborated to create the perfectly idyllic countryside.

Pienza, known as the ‘ideal city’, is the main town of the area, its small historic centre picturesque to a fault. Montalcino and Montepulciano draw first timer visitors with their offering of famous, and pricey, wines.

Val d’Orcia

7. Lucca and its impressive city walls

In the latest years, Lucca has become one of Tuscany’s new hot spots. With its lively and friendly atmosphere, an abundance of good places to eat and drink, interesting shops and intriguing piazze, this town has to make the list of the top must see places to visit in Tuscany for first timers.

The impressive and perfectly preserved Renaissance walls embrace the city and its treasures: the Cathedral of San Martino, the Medieval towers that can be climbed for a unique experience, museums and beautiful squares. You can also do as the locals do: explore Lucca on an e-bike!

=> Best Towns in Tuscany to stay in

8. Tufa towns: one of the most impressive sight in southern Tuscany

Most first timers to Tuscany probably won’t travel south of Siena, and miss out one of the region’s most awesome sights. Pitigliano, Sorano and Sovana, the so-called ‘tufa-towns’. These are ancient places in a unique natural setting, already inhabited by the Etruscans. The tufa towns, that seem to grow out of the rock itself, have a almost magical quality to them.

=> See more attractions in the Maremma, southern Tuscany

southern tuscany
Pitigliano, one of the ‘tufa towns’

Tips for first time travellers to Tuscany

It’s true these are all great must-see destinations in Tuscany, but don’t try to do too much in one go. Better to take things slowly, and savour all the details and flavours of one area. Pick what interests you most – art, food, history, shopping, nature – and plan your trip accordingly. Here we have a few suggested itineraries that show you the best Tuscany has to offer

Another tip: if you can, avoid peak season – destinations like Florence, Siena, Pisa can get extremely crowded in Summer. Travelling to these places in late Autumn or Winter might be a better idea => check out more info about the best time to visit Tuscany.