Tuscany Travel Guide: Tuscany itinerary & things to do

Un week-end en Toscane : entre villes et nature

Explore our Tuscany travel guide to plan your best Tuscany itinerary ever! Winalist gives you the essential steps to have the best weekend, week, or longer vacation in Tuscany.

Every year, thousands of travelers from around the globe are captivated by Tuscany’s allure; located just north of Rome in center-west Italy.

A hub for agriculture and fashion industries, it is also deeply rooted in a remarkable cultural/political history – making it essential to any voyage through Italy. Unsurprisingly, its provincial capital Florence draws many visitors with its incredible Renaissance art and architecture! To best discover the region’s terroir, indulge yourself one of many Florence wine tours.

Tuscany is brimming with some of the world’s most renowned art, such as Michelangelo’s David and works by Leonardo da Vinci and Botticelli.

Additionally, famous authors like Machiavelli or Catherine de Medici have all greatly contributed to Tuscany’s current importance in literature and art. Even Fra Angelico had a hand in preserving its historic significance!

Home to an array of spectacular natural wonders, Tuscany will take your breath away with its diverse geography. From the beaches on Elba Island to the Apennines mountain range and from olive groves to vineyards in Chianti Valley – every inch of this beautiful region is a sight for sore eyes.

The most picturesque way to make your way around it all would be by taking Chiantigiana (or SR 222) road which connects Florence and Siena through acres upon acres of famous DOCG producing Chianti Classico vineyards.


In order to visit and enjoy this region as it should be, we have put together a little travel guide for an unforgettable weekend in Tuscany! On the program: cultural visits, moments of relaxation, many culinary specialties and unusual wine tourism experiences to practice with the winegrowers of the region.

Tuscany travel guide Day 1: Florence

To start off our Tuscany travel guide, it is essential to visit Florence, one of the most beautiful cities in Italy. To do this, go to Caffe Rosano to take a coffee or tea with you and head to the Cattedrale de Santa Maria del Fiore.

This Gothic cathedral, built in 1296 and consecrated in 1436, can accommodate up to 20,000 people and offers breathtaking views of the city from the top of its 463 steps.

Tuscany travel guide - La Cattedrale de Santa Maria del Fiore qui domine Florence
The Cathedral of Santa Maria del Fiore which dominates Florence

Take a break to enjoy one of the traditional dishes from Florence: lampredotto. Known as the street food in this beautiful city, it’s made up of thinly sliced tripe cooked with court-bouillon. If you’re not a fan of bread (which is rare for French people), they can also serve it on its own plate! The best place to get your hands on some delicious lampredotto is at Da Nerbone at Mercato Centrale.

Continue your journey by visiting the Bargello Palace, once home to a prison. Inside its walls lies an untouched museum filled with works of art from some of history’s greatest minds; including Donatello’s bronze sculpture ‘David’ and Michelangelo’s very first piece – the Bacchus statue. Despite its beauty, it often goes unnoticed by travelers which gives you all the more opportunity to admire these amazing pieces in peace.

Arrêt indispensable lors de votre week-end en Toscane : à la découverte des vignerons
Essential stop on our Tuscany travel guide: discovering the winegrowers

To end your day in Florence on our Tuscany travel guide , we invite you to go to the south of the city, to Prato, to the Tenuta di Capezzana Estate. The winegrowers will introduce you to the estate and give you a guided tour of the rose garden, the old cellar and the oil mill. In order to discover the wine specialties of the region, a tasting of two wines will be offered to you.

On other option is to head to the fabulous Villa Travignoli, one of the 150 most antique enterprises in Italy.

Tuscany travel guide day 2: Pisa

For the second day of your weekend in Tuscany, leave early in the morning for Pisa, a city with exceptional charm.

Tuscany Travel Guide - Wine experiences in Tuscany
Discover the secrets of a good Italian wine production

Very well known for its famous tower, Pisa has other assets such as its wine-growing lands. On your journey between Florence and Pisa, stop at Villa Cosmiana to discover the secrets of good Italian wine production. The winegrowers of the Domaine will guide you to the cellars, the vineyards but will also take you on a tour of their organic farm and their kitchen! You can have lunch at the estate.

First essential stop on Winalist’s Tuscany travel guide’s second city: go to the Tower of Pisa. Leaning at an angle of 3.59 degrees to the south, this tower was built at the beginning of the year 1173 and its construction spanned two centuries. Indeed, in 1178, the tower began to lean following the addition of a third floor and construction was then interrupted for 90 years.

You can then go to the Battistero di San Giovanni, or the Baptistery of Saint John, which is the largest baptistery in Italy with its 55 meters high. This historical monument unites two different architectures: Romanesque and Gothic.

In a style very different from what is given to see in Italy, meet in front of the Church of Sant’Antonio Abate to do an introspection of its facades. On one of them, you will come across the “Tuttomondo” mural painted in 1989 by American artist Keith Haring.

This work represents global harmony and the thirty characters present each offer a different aspect of peace in the world. You will see a woman holding a child in her arms to represent motherhood or two men lifting a dolphin and thus representing the relationship of man with nature.

Tuscany travel guide - San Rossore Massaciuccoli natural park

After this cultural getaway, we invite you to recharge your batteries in the Migliarino – San Rossore – Massaciuccoli natural park. Inaugurated in 1979, this park consists of a lake and covers approximately 24,000 hectares along the coast. We find there fish, turtles but also 250 species of birds. The natural park includes the Massaciuccoli marsh as well as the remains of the ancient Pisan forest.

End of the Tuscany travel guide

Before bidding farewell to the splendid Italian countryside, last in our Tuscany travel guide is the village of Chianti and the rolling hills between Florence and Siena.

The views are majestic in this part of Tuscany, earning its reputation as Tuscany’s “true heart”. It is also renowned for a red wine of the same name that has become globally popular. What better way to celebrate your Tuscan weekend than with an indulgent Chianti tasting?

tuscany travel guide, tuscany itinerary - Tuscany Travel Guide: Tuscany itinerary & things to do - 2024 - 7

End your weekend in Tuscany in style by visiting the winery Barone Ricasoli, the largest winery in the Chianti Classico area.

When traveling through the Tuscan villages, be sure to visit an Italian winemaker for a glass of Chianti – you won’t regret it!

If you’re looking for an extended stay in Tuscany, make sure to explore the diverse and stunning cities that this region has to offer. From their culture and beauty, to their wine-growing skills – there’s something here for everyone! Our partners on Winalist provide some of the best winetourism experiences around, so don’t miss out!

Did you have the false impression that navigating the Chianti wine route would be a straight line or circular journey? Contrary to what you may think, it will take some zigzagging through winding roads of Tuscany. Not to worry though – your efforts won’t go unrewarded! Stunning views of nature and quaint medieval towns await as you sip on exquisite samples of Chianti wines. So don’t forget to bring your camera with you!

Visit Chiantigiana and be inspired by the many historic towns along your journey. For a truly unique experience, take some time to visit several of the local vineyards too – most are open for visitors but make sure to check first! This is an opportunity you won’t want to miss out on.

Thanks for reading our Tuscany travel guide – we are sure it’ll help you plan the best Tuscany wine trip!

Just in case you’re visiting other cities or wineries in Italy during your vacation to Italy, Winalist has you covered.

Tuscany Travel Guide FAQs

What are the most beautiful villages in Tuscany?

– San Gimignano
– Fosdinovo
– Monteriggioni
– Montalcino
– Pitigliano
– Cortona
– Montepulciano
– Volterra

What to taste in Tuscany?

Other quality products are renowned, all over the world.
In the Valla dell’Orcia, in Pienza, the best Pecorino PDO Toscano is produced (the ancient sheep’s cheese that is found in all regions and especially in Sardinia). Many establishments in the surrounding countryside offer tastings.
The Pienzasolp company, for example, produces, in addition to the classic Tuscan pecorino, ricotta, caciotte and jams to spread on cheese.
For those with a sweet tooth, there is the “Chocolate Valley“: a valley that includes Pisa, Pistoia and Prato, renowned for the production of chocolate and a new way of looking at its consumption. For the visit, it is the De Bondt laboratory: a small artisanal company located in the historic center of Pisa which produces a very varied range of flavored chocolates. And then there is the olive oil of course! The PGI Extra Virgin Olive Oil consortium has 11,000 companies. Castagneto Carducci, located about 60 km from Livorno, is considered one of the towns of oil: a feast for the tasting takes place every January.

When is the best time to visit Tuscany?

The best month to visit Tuscany, Italy, is April: the beginning of spring offers a gorgeous weather and kicks off the beginning of the tourist season. Many hotels that close during the winter, reopen in spring for the Easter season. You’ll be immersed in Italian festivities for the Holy Week, Liberation Day on April 25 and the Flower festivals in May,