7 days itinerary of Tuscany

😎 Day 1

Start your journey by landing at Pisa’s airport. Once you’re there, head straight to the Leaning Tower of Pisa. It’s iconic, but honestly, you don’t need to spend much time here, as there isn’t much else in the city to see beyond the tower and the Piazza dei Miracoli.

After taking your obligatory photos and enjoying the square, head to Florence -about 1 hour 15 minutes by car or train.

Florence is such a walkable city that you don’t need to worry about public transport to explore it. Most of the main attractions are within walking distance of each other. Also, keep in mind that cars aren't allowed in the historic center unless you’re a resident, so it’s a good idea to leave your car outside the city.

Start by walking around the historic center and check out the Ponte Vecchio, the famous bridge with all the jewelry shops.

Then, for sunset, make your way to Piazzale Michelangelo. It’s got the best views of the city, especially at sunset.

😴 Overnight in Florence

😎 Day 2

Start your day with a visit to the Duomo. It’s impossible to miss and definitely worth checking out. You can climb to the top for amazing views of Florence, or just admire the stunning architecture from the ground.

Visit Michelangelo’s David, one of the most iconic sculptures in the world in Accademia Gallery.

After that, head over to the Uffizi Gallery. It's home to some of the most famous art in the world, including works by Botticelli, Leonardo da Vinci, and Michelangelo.

For lunch, grab a bite at San Lorenzo Market or any local eateries and try a classic Tuscan sandwich—maybe a lampredotto if you’re feeling adventurous.

In the afternoon, check out Piazza della Signoria, a lovely square filled with sculptures and historic buildings.

If you’re up for more exploration, head to Palazzo Pitti and walk through the Boboli Gardens.

😴 Overnight in Florence

😎 Day 3

Today, head out from Florence and make your way to San Gimignano -about 1 hour 15 minutes by car. This medieval town is famous for its tower-filled skyline, and it's like stepping back in time. Wander through the charming streets, grab a gelato (San Gimignano is known for having some of the best!), and check out the Collegiata di Santa Maria Assunta, a beautiful church with stunning frescoes.

After that, take a short drive to Monteriggioni -about 30 minutes from San Gimignano. This small walled town is incredibly picturesque, and it’s perfect for a peaceful walk along its medieval walls.

Both towns are small, so you’ll have plenty of time to explore at a leisurely pace.

😴 Overnight in Siena

😎 Day 4

Start your day by visiting the Piazza del Campo, one of the most famous squares in Italy. It’s where the Palio di Siena, the famous horse race -takes place. Take some time to sit and enjoy the vibe, people-watch, or grab a coffee at one of the cafes lining the square.

Next, check out the Siena Duomo. It’s pretty amazing inside, with cool marble floors and big, impressive artwork. If you’re up for it, you can even go up for some views of the city from the top.

Wander around the old town and explore the cute shops, cafes, and bakeries. Don’t leave without trying a panforte, which is a traditional dessert from Siena, made with fruit and nuts—it’s delicious!

For sunset, head to Basilica di San Domenico, which has great views of Siena and the countryside around it.

😴 Overnight in Siena

😎 Day 5

Today, get ready to explore the beautiful countryside around Siena. Start your day by driving to Asciano, a quiet town in the Crete Senesi area -about 30 minutes from Siena. The landscape here is stunning, with rolling hills and fields that look like something out of a painting. You’ll get that classic Tuscany vibe.

One fun fact about Asciano: they actually have their own version of the Palio, but instead of horses, it's donkeys! It’s a quirky, local tradition that’s definitely worth checking out if you happen to be there at the right time.

While you're in the area, take a short trip to Baccolone.

While you're in the area, take a short trip to Chiusure. It’s a tiny, charming village perfect for escaping the crowds. From Chiusure, make your way to Abbazia di Monte Oliveto Maggiore, a stunning monastery located just a few minutes away. The abbey is perched on a hill and is surrounded by gorgeous olive groves, offering breathtaking views.

After exploring the countryside, head to Montepulciano -about 1.5 hour from Chiusure. Check into your accommodation and spend the evening walking around Piazza Grande, grabbing dinner at a local trattoria, and maybe trying some famous Vino Nobile di Montepulciano.

😎 Day 6

Start your day by diving deeper into Montepulciano. Wander around its charming streets, and if you didn’t have time yesterday, definitely check out the Palazzo Comunale and the Piazza Grande. For some great views, head up to the Fortress of Montepulciano—you’ll get a panoramic look at the town and the beautiful countryside.

After exploring Montepulciano, take a short drive to Pienza -about 20 minutes away. This tiny town is like a living postcard, full of narrow streets and stunning Renaissance architecture. Pienza is also famous for its Pecorino cheese, so make sure to stop by one of the local shops and try some! You can even grab a wheel of cheese to take home if you want to bring a taste of Tuscany with you.

Next, head to Montalcino -around 40 minutes from Pienza. Known for its amazing Brunello wine, Montalcino is another hilltop town that offers stunning views of the Tuscan landscape. Wander around the historic center, and if you’re into wine, don’t miss a visit to one of the local wineries for a tasting.

😴 Overnight in Montalcino 

😎 Day 7

On your last day, you’ll need to head back to the airport. Depending on your flight time, you might have some free time for one last adventure. If so, consider stopping by a couple of villages on the way to the Pisa airport to squeeze in a final meal or take in the last views of Tuscany.

If you’re visiting in the summer, I’d totally recommend adding a few extra stops to your trip! They’re a bit out of the way, but they’re awesome if you have the time. 😎

1. Elba Island

Okay, so Elba Island is a little off the beaten path, but if you’re into gorgeous beaches and crystal-clear waters, it’s so worth it! You’ll need to take a ferry from Piombino, but once you’re there, you can chill on some beautiful beaches, explore the cute little towns, and just enjoy a slower pace.

2. Porto Santo Stefano

f you’re craving some coastal vibes, head to Porto Santo Stefano. It’s this adorable seaside town on the Argentario Peninsula. You can walk around the harbor, grab some amazing seafood, or even take a boat trip to nearby islands.

3. Cascate del Mulino

So, this one’s a bit of a detour, but if you love nature and some relaxation, Cascate del Mulino is a must. It’s a natural hot spring near Saturnia, and the best part is you can just hop into these warm, mineral-rich waters for free! It’s in the middle of the Tuscan countryside and looks amazing.