In this 5 day itinerary travelling around Tuscany, we whisk you from the awe-inspiring Piazza dei Miracoli, to some of the world’s Medieval treasures and, of course, through some of the best scenery that Tuscany has to offer in the Chianti and Val d’Orcia.

First things first. Florence isn’t included in this itinerary because it’s a world in itself, and you’ll need to spend at least two full days in Florence to appreciate it.

Tuscany Driving Itinerary – See the best of Tuscany in 5 days

ITINERARY DAY 1 – See the iconic Piazza dei Miracoli in Pisa

This itinerary starts in one of the most famous squares in Italy, the legendary Square of Miracles in Pisa. You’ll be amazed by the architectural wonders and the slightly crazy atmosphere of this piazza.

You’ll need a couple of hours to really appreciate it, and to see the cathedral and the cemetery. If you’re planning to climb the Leaning Tower, book in advance, though we don’t recommend it. Leave the rest of the day to see Pisa‘s historical centre, a lively and friendly city with beautiful walks along the Arno.

Discover some interesting facts about the Piazza dei Miracoli.

where is tuscany
Pisa – Piazza dei Miracoli

ITINERARY DAY 2 – The hilltop towns of Medieval Tuscany

Explore the Medieval wonders of San Gimignano and Certaldo. Spend the morning in the delightful hilltop town of Certaldo Alto. You can walk up from the more modern part of Certaldo, or there’s a cable car if you’re in a hurry. Inside the town’s citadel-like walls is a miniature Medieval world, tranquil and unspoiled, that gives you the first taste of Tuscan picturesque ‘Medievalness’. This is a land of castles and towers, of gentle hills where towns were built for defence. Today only the best scenery is on offer.


Next it’s on to San Gimignano (distance from Certaldo 13 km.) where you can spend the night. The evening is the perfect time to enjoy this town aptly known as the “Mahnattan of the Middle Ages”, famous for its towers. When the tour buses have left, and the light caresses the tall towers and the beautiful stones, the atmosphere is just magical. Visit the Cathedral, and make sure you climb the Torre Grossa for the best view ever.

If you’re a fan of the Medieval, check out our article about three Medieval gems in Tuscany.

(DISTANCES: Pisa – Certaldo 75kms – Certaldo to San Gimignano 13kms)

ITINERARY DAY 3 – Travelling around the Chianti vineyards

The Chianti region, that stretches between Florence and Siena, is one of Tuscany’s all time favourites. And there are many reasons why. The endless views of vineyards and olive groves, the sunsets, the traditional products, the food and excellent wines, and the gorgeous scenery.

A drive around these hills will show you just what all the fuss is about. Travel to Greve in Chianti, stop at Chianti’s key towns, Radda and Castellina. Choose one of the agriturismi in the area, or spend the night in lively Radda that has great restaurants and enoteche that will make the perfect evening. You can combine some wine tasting if you plan in advance with the winery.

Or you could join a Wine Tasting Tour of the Chianti to visit some cellars and learn about the production of Chianti wine.

See our detailed Chianti driving itinerary for the perfect day in the Chianti.

(DISTANCES: San Gimignano to Greve in Chianti 45 kms – Greve to Radda in Chianti 18kms)

tuscany itinerary 5 days

ITINERARY DAY 4 – Immerse yourself in the Gothic wonders of Siena

Siena deserves a full day and a night, minimum. Start early in Piazza del Campo and have a cappuccino at one of the outside tables. Looking at the square it’s not hard to imagine a time when knights and Lords would cross here. Il Campo, as the Sienesi called it, is one of the most beautiful squares in Italy, A real travellers’ treat.

Visit the splendid Cathedral and if you’re in the mood for another museum you could opt for the unusual setting of Santa Maria della Scala Museum to learn a bit about Siena’s history, or the Pinacoteca for a great collection of medieval paintings. But just walking around will give you a taste of this incredible town that has maintained its charm and its traditions for centuries.

(DISTANCE: Radda in Chianti to Siena 40 km)

tuscany itinerary 5 days

ITINERARY DAY 5 – Explore picture-perfect Val d’Orcia

Travelling south of Siena you enter the idyllic world of the Val D’Orcia. Less populated than the Chianti, endless wheat fields and idyllic views reign. This is the land where cypress tress are beautifully arranged on peaceful hills, a world of poetry and other worldly beauty.

Take your time driving, this idyllic postcard-esque scenery needs to be appreciated slowly. Stop at San Quirico d’Orcia and then carry on to delightful small town of Pienza, a UNESCO Heritage site and the quintessential romantic destination. Lastly pop in to the Palazzo Piccolomini and enjoy the gorgeous views.

Check out our driving itinerary in the Val d’Orcia, which includes the best attractions and the most scenic routes.

(DISTANCE: Siena to San Quirico d’Orcia 47kms. – San Quirico to Pienza  10kms)

Don’t have a car? If you have a week and you want to include Florence the best thing to do is base yourself in the city and take day trips to Siena, Pisa and San Gimignano (you can reach all these destinations by public transport). Bear in mind that to properly explore the Chianti area and the Val d’Orcia a car is essential.

Discover the top things to do during your Tuscan trip!