The Ultimate 7-Day Tuscany Itinerary

It’s a tough decision, but Tuscany is arguably the most beautiful region in Italy. Home to incredible cities such as Florence, Siena and Pisa, which are home to Renaissance architecture, the world’s most famous art galleries, incredible churches, cathedrals and palaces, and dozens of fantastic restaurants, shops, and more, what’s not to love? Outside of the cities, Tuscany is straight out of a movie, with rolling vineyards and tree-lined roads, where you can stop at local trattorias and wineries. The region is renowned for its wine, and there are hundreds of historic and family-run vineyards in farmhouses and castles where you can learn about wine and do a tasting.

Tuscany is also home to smaller but equally important places like Lucca, San Gimignano and Montepulciano – although the latter is also known for its wine. Road-tripping is one of the best ways to see the region, as you’ll be able to stop at pretty towns and villages on your journey, however, if you’re planning on vineyard hopping, then using one or two places as your base, such as Florence and Pisa, is a great option so you won’t need to drive. Italy has an excellent train and bus network, and you may even save time. Tuscany certainly has something for every interest, whether you love wine, delicious food, art and history, or just want to see the sights, and with seven days you’ll be able to cover the best of the region.

7-day Tuscany Itinerary

Days 1 – 2: Florence

Starting your Tuscan itinerary in Florence is one of the best ways to begin.

The city is packed with history, is easy to navigate and has delicious food, but you’re going to want to spend at least two days here to get to know the city, as there is a lot to see!

Florence’s compact layout means you can walk between all of the major sights, plus it has a handy train and tram system for getting to other cities or to the airport.

Begin at the iconic Piazza del Duomo, which is the square at the heart of the city, home to Florence’s famous cathedral, Il Duomo.

You’ll need to book, but you can climb to the top for amazing views, or climb to the top of the tall tower next to it for slightly fewer queues.

Not far away is the Uffizi Gallery, which is unmissable.

Florence was the home of the world’s greatest Renaissance artists and architects, and this gallery houses famous paintings by the likes of Leonardo Da Vinci, Botticelli’s ‘The Birth of Venus’ and of course, Michelangelo’s David.

Remember to book these in advance too – David often gets booked up six months ahead in the summer!

Make time to sample local food at lunchtime at the Mercato Centrale, which has many Florentine specialities.

On your second day, you should explore the lovely Oltrarno district.

The Arno, hence the district’s name, is Florence’s main river, and this neighbourhood is on the other side to many of the major attractions.

To get there, cross the famous Ponte Vecchio, one of the few bridges in the world that has shops on it.

It is home to the amazing Pitti Palace, which has stunning interiors and the sprawling Boboli Gardens where you can spend hours wandering around.

The Oltrarno neighbourhood around here is home to some of the city’s best restaurants, bars, boutiques and gelaterias too.

Also on this side of the river is Piazzale Michelangelo, a spacious square up a hill, which has the most spectacular views of Florence.

On summer evenings, you’ll find hundreds of locals here with a drink, watching the sun go down over the city.

It makes a great spot to end your time in Florence before heading to the next destination.

Recommended tours:

• Florence: Timed Entrance Ticket to Michelangelo’s David.
• Florence: Uffizi Gallery, David & Accademia Small Group Tour.
• Florence: Dome Climb, Museum and Baptistry Small-Group Tour.

Day 3 – Pisa and Lucca

The third day of your Tuscan adventure should be spent exploring the charming cities of Pisa and Lucca.

Pisa is only around an hour by train from Florence or a short drive if you have a car.

It’s most famous for the Leaning Tower, which is a must-see while visiting, but first, begin your city tour at Piazza del Miracolo, where you can check out Pisa’s slightly less known buildings, like its cathedral, baptistery and the Camposanto Monumentale.

Of course, don’t forget to save time to snap a few tourist photos against the leaning tower!

Pisa has a huge choice of delicious dining options, so venture slightly outside of the tourist area and you’ll find lots of trattorias to fuel you up for the next stop.

Before you go, head to the riverside district of Borgo Stretto which is far quieter and home to lots of local shops and medieval architecture.

Just a 30-minute drive or train journey from Pisa is the city of Lucca, which, like Florence, has plenty of Renaissance architecture to admire.

The best way to see the city is from its walls, which you can walk or cycle around, stopping in scenic spots for views over the entire countryside.

In the city itself, make sure to visit Lucca Cathedral and the Guinigi Tower, which you can climb to the top of.

Otherwise, the easiest way to immerse yourself in Lucca is to get lost amongstst the maze of cobblestone streets that are filled with amazing boutiques, cafes and wine bars.

Pisa and Lucca are so close together that they’re ideal for pairing on a Tuscan itinerary and you can always extend your time in either if there’s more you want to discover.

Recommended tours:

• From Florence: Day Trip Pisa, Siena & San Gimignano w/Lunch.
• Reserved Entrance to Leaning Tower of Pisa & Cathedral.
• Tuscany: Day Trip to Pisa, Siena, San Gimignano, and Chianti.
• Lucca: 2-Hour City Center Walking Tour.

Day 4 – San Gimignano

On day four of your journey, head to San Gimignano, a medieval town with a beautiful skyline.

It’s only around an hour and a half drive from Lucca and particularly accessible by car, in case you’re using a different city as a base and want to make this into a day trip.

The main street in the town is Porta San Giovanni, which has the best shops and cafes.

In the centre of the town is also Piazza della Cisterna, the main square which also has some excellent dining spots and gelaterias.

After an ice-cream stop, climb the Torre Grossa, the town’s tallest tower which offers incredible views over the area and countryside beyond.

If you’re into art, then also don’t miss the Collegiate Church of Santa Maria Assunta, which is decorated with amazing frescoes by some of Tuscany’s most renowned artists.

San Gimignano, like most areas of Tuscany, is famous for its wine, so if you have some spare time then you could visit a local winery to do a tasting – they’re particularly well-known for white Vernaccia wine.

If you want to extend your itinerary slightly, you can add on the nearby town of Volterra about 40 minutes away, which has an amazing Roman theatre and ruins to explore.

Recommended tours:

• From Florence: San Gimignano, Siena, and Chianti Wine Tour.
• Tuscany: Day Trip to Pisa, Siena, San Gimignano, and Chianti.
• From Florence: Siena, San Gimignano & Monteriggioni Tour.

Day 5 – Chianti Region

Day five should be spent doing something Tuscany is particularly famous for – drinking wine!

Naturally, you may want to use of of the area’s many great tours for this, as you won’t be able to drink and drive.

There are lots that hop around multiple vineyards, or if you’re getting the train to different places you won’t have any issues.

The Chianti region between Florence and Siena is particularly well-known for its vineyards.

Greve is one of the most popular spots and the unofficial capital of Chianti.

Before diving into drinking, head to the Piazza Matteotti, which has lots of local shops and Antica Macelleria Falorni, a local deli and butcher’s where you can try local meats and cheeses.

Your first wine estate should be Castello di Verrazzano, which is a historic winery that offers guided tours of its vineyards, cellars and castle, concluding with a tasting of its esteemed Chianti Classico wines.

Make sure to soak it up at a nearby trattoria using a big bowl of pasta.

For a smaller, more authentic feel, visit the village of Radda, where you’ll find a historic winery called Castello di Volpaia or Badia a Coltibuono, an ancient abbey turned winery that offers tours, tastings, and even cooking classes, which is a short drive from the village.

You could continue forever; some tours stop at five or more wineries.

Before you leave, don’t forget to pick up a few bottles of your favourite drink to take home with you!

Recommended tours:

• Florence: Chianti Wineries Tour with Food and Wine Tasting.
• From Florence: Chianti Half-Day Afternoon Tour.

Day 6 – Siena

For the penultimate day of your holiday, dedicate a full day to exploring the hilltop city of Siena.

You can drive here easily, and otherwise, it has great connections by both train and bus – it’s only an hour from Florence.

The heart of the city is the Piazza del Campo, shaped like a huge half moon and ringed with shops and restaurants.

This square is where the city’s famous Palio horse race is held each year, which draws thousands of people.

Also in the main square is the Torre del Mangia, which you can climb for views over the Tuscan countryside.

Also check out Siena’s cathedral, which is adorned with works by artists like Michelangelo, Donatello and Bernini.

Siena can get touristy, particularly in summer, but it’s mainly focused on the narrow streets at the centre.

Explore the outskirts for lunch to find a restaurant serving local specialities like wild boar ragu.

In the afternoon, wander through the medieval streets to the Basilica of San Domenico, which is home to relics of St. Catherine of Siena.

Then, visit the Palazzo Pubblico, the town hall, where you can admire stunning frescoes and learn about Siena’s fascinating history.

Siena is very small, so take some time to wander from one side to the other and around its edges.

Although there are great views from the city itself, from further away and below the city, you can enjoy views looking up towards Siena and its pretty rooftops and cathedral.

Bear in mind that you can’t take a car into Siena’s old town, which is walled, narrow and pedestrianised but there are plenty of places to park up nearby, or you can walk to the old town if you’ve arrived by train.

Recommended tour: Siena: Siena Cathedral and Piccolomini Library Entry Ticket.

Day 7 – Montepulciano and Val d’Orcia

Although it’s your final day, the pace shouldn’t slow down as there’s still lots to see!

The stunning region of Val d’Orcia and the town of Montepulciano promise more history, wine and adventure.

Before you start drinking, take the time to drive around the countryside, which has classic rolling hills and vineyards.

You can also stop at local places like the UNESCO World Heritage town of Pienza, which is also known for its delicious pecorino cheese; the spa town of Bagno Vignoni and Castiglione d’Orcia.

Montepulciano is the most famous town in this region and a mecca for wine lovers, experts and enthusiasts.

Recommended tour: Montepulciano: Wine Tasting and Cellar Tour.

The town produces some of the best wine in the world, which you can sample after wandering around its central Piazza Grande and checking out the cathedral.

The renowned Cantina Contucci nearby is one of the oldest wine cellars in Montepulciano, where you can sample Vino Nobile di Montepulciano, a famous wine in this area.

Other famous wineries to add to your list include Boscarelli, De’ Ricci and La Braccesca, all of which offer tours, tastings and stretching views over the rolling vineyards for you to enjoy on your last evening in Tuscany.

Recommended tour: Val d’Orcia: Wine and Food Tasting at a Podere.

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