We’ve put together some Tuscany Itineraries around what interests you. From Art to Shopping, from Medieval history to Wine, we give you the lowdown on the top highlights you can’t afford to miss. Quick start itineraries that you can mix and match according to your taste.

=> 12 Fun and Unique Activities to do in Tuscany!

Tuscany itineraries – If you love the Medieval

If you have a passion for everything Medieval, Tuscany has lots to offer. In this itinerary we’ve selected impressive sights and attractions with pure Medieval appeal. Step into the time machine and head back to the 13th century.

Florence in 2 days – Florence is where many Tuscany holidays begin. The cradle of the Renaissance still shows signs of its Medieval past. Mighty palaces like Palazzo Vecchio and the Bargello, a splendid Baptistry and the Church of San Miniato al Monte are highlights. And of course the wonderful Ponte Vecchio.

San Gimignano & Volterra 1 day – Two of the most atmospheric Tuscan walled towns. There are Medieval towers, palaces, and a Torture Museum in San Gimignano, where you can experience the darker side of Medieval history.

With this San Gimignano, Siena, Monteriggioni Day Trip from Florence you’ll experience the best of Medieval Tuscany and you’ll have the chance to taste some of the region’s prized food and wine. Good value for money!

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San Gimignano – photo @Mariamichelle on pixabay

Cortona 1 day – This hill-top town gets full marks for atmosphere. It’s full of steep narrow alleyways and has spectacular views over the valley. You can visit the nearby Franciscan Hermitage Le Celle

Siena 2 days – Siena is the queen of Gothic architecture. Immerse yourself in the unique atmosphere of its squares and churches, and forget the present all together. Val d’Orcia 1 day – Explore the Romanesque country churches and Sant’Antimo Abbey, in one of the most scenic areas of Tuscany.

=> If you love Medieval times, you should check out also the 8 Amazing Castles that you can visit in Tuscany.

=> Discover all the best things to do during your Tuscan trip!

tuscany itineraries

If you love Art – See the top art in Tuscany

Florence in 3/4 days – Soak up Florence’s artistic atmosphere in the world famous Uffizi Gallery, and the Accademia with Michelangelo’s David. Enjoy some of the best frescoes in Tuscany in the Churches of Santa Croce, S. M. Novella Church and the Brancacci Chapel. And learn about Renaissance sculpture in the Bargello Museum.

=> Art passionate? Food lover? Where to go in Tuscany based on your personality type!

Pisa’s Leaning Tower and Piazza dei Miracoli (Half a day) – Head straight for the aptly named “Square of Miracles” where you can easily spend half a day.

Siena in 1 day – Art fans flock to Siena to see the splendid Gothic Cathedral, the frescoes in the Palazzo Pubblico and paintings from the Sienese school in the Pinacoteca Nazionale. Round off your art trail with a day trip to Arezzo and San Sepolcro and follow in the footsteps of early Renaissance master Piero della Francesca.

If you’re into contemporary art, Tuscany has a lot to offer => Check out the Top Art Galleries and Places to see Contemporary Art in Tuscany.

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Pisa – Piazza dei Miracoli

If you love picture-perfect countryside

A week in the Chianti and/or Val d’Orcia areas will satisfy your need for idyllic views and relaxing atmosphere. Base yourself in an agriturismo near Radda or Castellina in Chianti, or for Val d’Orcia choose Pienza or nearby Montepulciano. From here you can spend your day visiting small towns full of charm, country churches or simply walking and driving around in a countryside that looks like it has been painted on a canvas.

If you need some suggestions on where to base yourself in Tuscany, we’ve put together a great list of suggestions that you might find helpful.

⇒ Discover the most picturesque villages in Tuscany!

If you love Nature

Maybe you’ve already seen Florence and you need a regenerating holiday. If so, Tuscany has a lot to offer in terms of natural wonders. Plan your trip around the areas of Chianti and Val d’Orcia (3 days) where you can enjoy countryside and views that have jumped straight off a postcard.

Check out our scenic driving itineraries: Chianti Road Trip, a day exploring iconic Val d’Orcia and a 4 day itinerary through enchanting Maremma in southern Tuscany.

Have a look at the best Tuscany landscapes that won’t fail to impress even the most worldly traveler.

scenic drives in Tuscany
Val d’Orcia

Alternatively make for the mountainous area of Garfagnana or Casentino, or the unspoilt beaches and the coastal Uccellina Nature Reserve in the southern Maremma. Tuscany itineraries for nature fans should always take in one of these areas.

If you love Shopping

Tuscany holidays appeal for a lot of reasons, and shopping is definitely one of them. If you’re in the mood for a shopping spree, your best bet is Florence. Hunt down some bargains in the Florentine Markets, and browse the elegant shops around Via Tornabuoni and the Outlets just outside the city. You might enjoy this useful guide dedicated to Florentine artisan shops and products.

A day in Siena will be plenty to explore its many small boutiques and interesting food shops. Arezzo is full of antique stores and there’s the Outlet Valdichiana for more brand-name retail therapy.

If you love Wine – Tasteful Tuscany Itineraries

In Florence there’s a good range of wine bars or ‘enoteche’. They range from the traditional to the trendy, and a couple of days will give you time to sample many of the wines from Tuscany. But if you take your wine seriously, it’s best to explore the various wine lands themselves.

The Chianti is the home of the full-bodied Chianti Classico wines, and there are plenty of wine-tasting opportunities, some of the in castles and old monasteries.

Enjoy the delights of the Chianti region with the SAFARI Chianti Wine Tasting Experience : visit Chianti wineries, learn about the wine making process and taste some cheeses and gorgeous locally produced reds!

Further south in Montalcino you can relax over a glass of Brunello di Montalcino. The tiny hamlet of Bolgheri on the Etruscan coast is the scenic home of the much-lauded (if rather pricey) Supertuscans, some of the most prestigious wines in Tuscany.

=> Discover the Best 6 Town in Tuscany for foodies and the Top Tuscan food you must try while you’re travelling around the region!

=> Check out these Great Wine Tasting Tours in Tuscany

=> 8 Inspiring Places in Tuscany that will Spark your Imagination!

For more suggestions for your trip, check out our 20 favourite things to do in Tuscany. and some of the most picturesque villages to visit in the region. Buon viaggio!

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A view of the Chianti region