Visit Tuscany in 5 days: what to do? What to see?

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Dreaming of discovering Tuscany, its hilltop villages, its rolling landscapes and its artistic treasures? Here is an ideal itinerary to visit Tuscany in 5 days, perfect for a first time. Whether you come as a couple, as a family or with friends, this guide will help you miss nothing.

Day 1: Florence, the heart of the Renaissance

Florence is a true open-air museum city, the cradle of the Italian Renaissance. For a first visit, it is best to focus on the historic centre, compact and easily accessible on foot.

Our must-sees in Florence:

Santa Maria del Fiore Cathedral (Duomo)

Start your day at Piazza del Duomo, one of the most emblematic places in Italy. Admire the cathedral's polychrome marble façade and, if you have the courage, climb the 463 steps to Brunelleschi's dome for a breathtaking panoramic view.
👉 Book your skip-the-line ticket in advance, often combined with the Baptistery, Giotto's Campanile and the Museo dell'Opera del Duomo.

The Uffizi Gallery (Galleria degli Uffizi)

A stone's throw from the Duomo, this museum is a must for art lovers. You can admire masterpieces by Botticelli (The Birth of Venus), Leonardo da Vinci, Michelangelo, Caravaggio, etc.
Allow at least 1.5 to 2 hours for the visit and book your tickets in advance to avoid the long queue.

The Ponte Vecchio, Florence's famous bridge

One of the symbols of Florence. This medieval bridge lined with jewellers' shops has a unique charm. Walk across it to reach the south bank of the Arno. Take the time to watch the golden reflections on the water and the bustle of the street.

Palazzo Vecchio and Piazza della Signoria

Return to the main square of Florence, Piazza della Signoria, dominated by the Palazzo Vecchio, the former town hall and seat of Florentine power. Outside, the Loggia dei Lanzi houses remarkable sculptures, including Cellini's Perseus.
If you still have energy, visit the inside of the palace to discover the decorated rooms, notably the Salone dei Cinquecento.

Piazzale Michelangelo viewpoint

Late in the afternoon, go up (on foot or by taxi) to this viewpoint to admire the most beautiful view of Florence, especially at sunset. The golden light illuminates the rooftops, the Duomo, the Ponte Vecchio… a magical moment.
Don't forget your camera!

A few good addresses for lunch:

Take a break in a local trattoria in the centre or in the Oltrarno district (for example around Via dei Neri) to try a typical dish such as pici al ragù, or a simple truffle panino at All'Antico Vinaio (very popular, sometimes with a wait).

• Trattoria La Casalinga – generous Florentine cuisine.
  
• Osteria Santo Spirito, for its truffle gnocchi.‍
• Il Santo Bevitore – for a more refined atmosphere.
  
  

Where to sleep in Florence?

Want to visit Tuscany in 5 days? For this first night, choose accommodation in the historic centre or in the Oltrarno, so you are within walking distance of all the sites. Options range from charming B&Bs to boutique hotels.
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Also read our articles: 

• Visit Florence in 1 day: Top 10 must-sees 
• Visit the Cinque Terre in 3 days: itineraries and activities
• Visit Puglia in 7 days: Top itineraries and villages to see 
• Top 10 most beautiful villages in the Dolomites
• Sleeping in the Bardenas desert: Top 5 best hotels 
• Visit Tenerife in a week: Top 10 things to do 
• 3-day city break in Barcelona: what to do? What to see?
• Visit the Algarve in 7 days 

Day 2: Visit Siena and San Gimignano

Set off early in the morning for Siena, a medieval town perched on the Tuscan hills, known for its authentic atmosphere and exceptional heritage. In the early afternoon, continue to San Gimignano, a small UNESCO-listed village, often nicknamed the "Manhattan of the Middle Ages" for its medieval towers still standing.

Our must-sees in Siena

Tickets to book (free cancellation):

• Horse riding in the Tuscan countryside
• Tour of Chianti and its most beautiful castles (by minibus)

Go to Piazza del Campo

Start your visit on this unique shell-shaped square, famous for the Palio, the horse race held there twice a year. The square is surrounded by cafés and dominated by the Palazzo Pubblico and the Torre del Mangia, which you can climb for a lovely view of the city.

See Siena Cathedral (Duomo)

A masterpiece of Italian Gothic with its black and white marble façade. Don't miss the mosaic floor and the Piccolomini Library, a little jewel decorated with frescoes by Pinturicchio.

Wander the lanes of the historic centre

Take the time to stroll the medieval lanes, get lost among the little squares, and try a local speciality such as ricciarelli, almond biscuits.

Our must-sees in San Gimignano

Visit the Cathedral and the Museum of Sacred Art of San Gimignano

San Gimignano Cathedral, also called the Collegiate Church, impresses with its 14th-century frescoes depicting biblical scenes. The adjoining museum houses precious religious works from the region.

Go truffle hunting

Head out into the countryside with a local guide and his dog for an authentic truffle-hunting experience. An unusual and tasty activity, often followed by a tasting of local specialities.

Wander the historic centre

Walk through this picturesque village with its fourteen medieval towers still preserved. Every lane reveals a view of the surrounding countryside, little craft shops and a charm that has remained intact.

Have a gelato to cool off

Stop at Gelateria Dondoli, several times voted the best ice cream in the world. The house flavours (lavender, saffron, red wine…) are worth the detour.

Climb the Torre Grossa

Climb this 54-metre tower, the tallest in the village, for a panoramic view over the Tuscan hills: an unforgettable moment at sunset.

Where to sleep? 

If you come to visit Tuscany in 5 days or are doing a road trip in the Val d'Orcia, sleep in San Gimignano itself or choose an agritourism stay in the surrounding area: a restored farm with a view of the vines and olive trees, where you can also taste local produce at dinner (wine, olive oil, cheeses…).

Day 3: Val d'Orcia – Pienza, Montepulciano and Montalcino

We continue our Visit Tuscany in 5 days road trip. The Val d'Orcia embodies the postcard image of Tuscany: golden hills, lines of cypress trees, winding roads and hilltop villages. This day immerses you in a UNESCO World Heritage setting, ideal for an immersion in nature, gastronomy and exceptional wine.

First stop: Pienza, the ideal Renaissance city

A little architectural jewel commissioned by Pope Pius II in the 15th century, Pienza charms with its flower-decked lanes, spectacular views over the valley and its pecorino (local sheep's cheese) shops.
👉 Not to be missed: Piazza Pio II, the cathedral, and the Via dell'Amore, a romantic walk with a panorama.

Second stop: Montepulciano, elegance and noble wine

This hilltop medieval village is famous for its Vino Nobile di Montepulciano, a powerful red that you can taste in one of the many historic cellars carved into the rock beneath the palaces.
👉 Climb up to Piazza Grande and visit the Cantina De' Ricci or the Contucci for a tasting.

Third stop: Montalcino, in the kingdom of Brunello

Surrounded by vines, Montalcino is a high place of Italian oenology. Brunello di Montalcino is one of the most prestigious wines in Italy.
👉 Visit the fortress (Rocca) for a 360° view, and stop at an enoteca for a tasting accompanied by local cured meats.

📸 Photo stop: the Vitaleta chapel

On the way, make a detour to the Cappella della Madonna di Vitaleta, a little chapel nestled between two rows of cypress trees, one of the most iconic photos of Tuscany. Accessible on foot from a dirt track, the place is magical especially late in the afternoon.

Day 4: The most beautiful villages of Chianti

The Chianti region, between Florence and Siena, is a concentration of authentic Tuscany: hills covered in vines, winding roads lined with cypress trees, medieval villages and historic wine estates. This day is perfect for catching your breath, slowing down and enjoying the gentle way of life in Tuscany.

What to do in Chianti? What to visit? 

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Here is a suggestion of activities if you come to visit Tuscany in 5 days.

• Chianti vineyard tour with tasting‍
• Tour of Chianti and its most beautiful castles (by minibus) ‍
• Half-day visit in Chianti ‍
• Typical day in Tuscany by Vespa 

Must-see villages of Chianti:

Here are a few places to stop by car during these 5 days in Tuscany: 

🟤 Greve in Chianti

Capital of Chianti Classico, Greve is known for its large triangular square lined with arcades. You will find cellars, restaurants and delicatessens.
👉 To see: the Wine Museum and the Macelleria Falorni, a renowned historic butcher's.

🟤 Montefioralle (optional but recommended)

A few minutes from Greve, this tiny fortified village is one of the most beautiful in Tuscany. Cobbled lanes, stone houses, views of the vines: a real jewel.

🟤 Castellina in Chianti

Charming medieval village, with a covered underground lane (Via delle Volte) that offers superb viewpoints.
👉 To visit: the fortress, now turned into an archaeological museum.

🟤 Radda in Chianti

Nestled between the hills, Radda is perfect for a lunch on a terrace. Its small historic centre, its ramparts, and its quiet lanes make it an ideal place to settle in.
👉 Try the pici with wild boar or truffle, depending on the season.

Main wine estates of Chianti

Throughout the region, many wine estates offer guided cellar tours with wine tasting. Chianti Classico, the local emblem, is recognisable by its black rooster logo.

Here are a few renowned estates:

• Castello di Verrazzano (near Greve)
  
  
• Castello di Brolio (near Gaiole in Chianti)
  
  
• Castello di Ama (near Radda, a very beautiful collection of contemporary art)
  
  

👉 Remember to book your visit in advance, especially between May and October.

Day 5: Pisa and Lucca

For your last day of these 5 days in Tuscany, head to the west of the region with two towns with remarkable heritage, but very different: Pisa, known worldwide for its leaning tower, and Lucca, an elegant and peaceful town surrounded by ramparts.

Our must-sees in Pisa: 

Although often summed up by its tower, Pisa deserves a little more time. Everything is concentrated around Piazza dei Miracoli, an exceptional architectural ensemble that is a UNESCO World Heritage Site.

See the Tower of Pisa

One of the most famous monuments in the world. Its leaning silhouette attracts millions of visitors every year.
👉 If you want to climb to the top, book your ticket online in advance (access limited to 45 people per time slot).

Visit the Cathedral & the Baptistery

The Cathedral of Our Lady of the Assumption, with its white marble façade, is a masterpiece of Pisan Romanesque art. Next to it, the Baptistery, the largest in Italy, stands out for its exceptional acoustics.
👉 Free entry to the cathedral if you have a ticket for the tower or another monument.

Our must-sees in Lucca 

Only 30 minutes' drive from Pisa, Lucca welcomes you in a calmer atmosphere to end your stay. Here are a few ideas of activities and visits to do on site.

Cycle on the ramparts

The ramparts of Lucca (4 km) are perfectly preserved and turned into a promenade. Hire a bike and go round the town along the shaded avenues – a typical and very pleasant activity. Hire your bike here.

Explore the historic centre

Walk through the cobbled streets, between palaces, Romanesque churches and little squares.
👉 Don't miss:

• Piazza dell'Anfiteatro, built on the ruins of an ancient Roman amphitheatre.
  
  
• The Torre Guinigi, topped with holm oaks, which offers a panoramic view over the whole town.

FAQ Visit Tuscany in 5 days 

Here are our answers to your most frequently asked questions:

What are the must-see sites to visit in Tuscany?

Among the must-sees of Tuscany are Florence, the cradle of the Renaissance with its cathedral, the Uffizi Gallery and the Ponte Vecchio. Siena charms with its Piazza del Campo and medieval atmosphere. San Gimignano, with its historic towers, is a UNESCO-listed jewel. The Val d'Orcia offers emblematic landscapes and villages such as Pienza or Montepulciano. Finally, Pisa and its famous leaning tower are a classic stop for any first stay.

What is the most beautiful part of Tuscany?

The Val d'Orcia is often considered the most beautiful part of Tuscany. A UNESCO World Heritage Site, this region offers postcard landscapes: gentle hills, slender cypress trees, winding roads and hilltop villages. It is also a region rich in local produce, prestigious wines and peaceful little towns. It perfectly embodies the dream image of Tuscany. For photo lovers, it is a real paradise.

How long does it take to visit Tuscany?

A stay of 5 to 7 days lets you discover the main sites of Tuscany without rushing. In 5 days, you can combine Florence, Siena, Chianti and a few emblematic villages. In a week, it is possible to also explore the Val d'Orcia, Pisa, Lucca, and even the Tuscan coast. For a more complete immersion, two weeks are ideal. Tuscany can also be discovered over several trips depending on the seasons.

Where to base yourself to visit Tuscany?

It all depends on your programme, but Florence is an ideal base if you are travelling without a car, as it is well served by train. If you hire a car, the ideal is to sleep in a central agritourism stay, between Siena and Florence, so you can easily fan out. The Chianti or Val d'Elsa regions let you reach the main attractions in less than an hour. For a calmer atmosphere, choose Pienza or Montepulciano.

What is the driest month in Tuscany?

The driest month in Tuscany is generally July, closely followed by August. However, these months are also the hottest and the most touristy. If you want to avoid rain while enjoying a pleasant climate, choose May or September: temperatures are mild, days are long and the landscapes magnificent. Spring and early autumn offer an excellent compromise between weather and crowds.

That's it, our article “Visit Tuscany in 5 days” ends here! We hope this itinerary makes you want to discover the essentials of this magnificent region of Italy! We wish you a great trip and plenty of good vibes!