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Florence is one of my favorite cities in the world. I have visited Florence multiple times and even spent entire weeks in Tuscany, exploring everything from Val d’Orcia and Cinque Terre to the wine regions. As a Certified Sommelier, Tuscany is my favorite region in Italy and the wine country here is one of the best I have ever been to.
But here is the thing about Florence that most people do not realize until they arrive. The city is not just a destination. It is the perfect base to explore a large part of Central Italy. Medieval towns, world-class wine regions, stunning coastline, ancient Roman ruins and UNESCO World Heritage Sites are all within easy reach.
Whether you have one extra day or several, these are the best day trips from Florence. I have hand-picked these based on personal experience and I can tell you every single one is worth your time.
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The Best Day Trips from Florence
Tuscany spoils you. You step off a train or out of a car and suddenly you are standing in a medieval piazza that looks exactly as it did five hundred years ago.
The rolling hills, the cypress trees, the wine and the food never gets old no matter how many times you come back. These are the day trips from Florence that made me fall even harder for this part of Italy.
My Favorite Day Trips from Florence
Hand-picked from personal experience. Book these ahead, they sell out fast.
Siena
Siena is one of the easiest and most rewarding day trips from Florence. It is only 1.5 hours away and is best combined with San Gimignano and the Chianti wine region.
Most people do all three in a single day and you do not even need a car. Plenty of tour operators run this as a combined trip, including this popular Private Tour of Siena, San Gimignano and Chianti. All three combined make a perfect day trip and one of the most popular day trips from Florence.
One thing most people don’t realize is that Siena is actually a better base than Florence if you want to spend more time exploring Tuscany. It sits right in the heart of the region, is less crowded and has a completely different energy to Florence. I cannot believe more people do not visit Siena.
Siena is also one of my favorite cities in Italy. I have mentioned it in other posts but I genuinely think the Siena Cathedral is even more beautiful than the Duomo in Florence. The black and white striped marble, the gold mosaics, the painted ceiling. Siena is absolutely stunning and far less crowded than Florence.
The main highlights are the popular Piazza del Campo, one of the most beautiful medieval squares in Europe, the Torre del Mangia tower, and the Cathedral. Siena has a chill, lived-in vibe that is hard to find in more touristy Tuscan towns.
San Gimignano
San Gimignano is a small hilltop town between Florence and Siena. It is famously known as the Manhattan of the Middle Ages because of its dramatic skyline of medieval stone towers. It is a little touristy but absolutely worth a visit if you don’t plan to visit any other hill towns.
Unless you are planning a winery visit or a long lunch, you do not need a full day here. Three hours is plenty. Walk the narrow streets, browse the boutique shops, visit the Piazza della Cisterna and the Cathedral, and grab a gelato from Gelateria Dondoli, which has won the World Gelato Championship twice.
Since you don’t need a full day, you can easily combine San Gimignano with Siena and Chianti. On its own it is a half day at most, but paired with a wine tasting it becomes one of the best days you can have in Tuscany. If you don’t have time and need to choose between Siena or San Gimignano, I highly recommend Siena.
Chianti Wine Region
If you love wine, Chianti is one of the best day trips you can take from Florence. The rolling hills, the olive groves, the cypress trees and the vineyards look exactly like a painting. As a Certified Sommelier, Chianti Classico and the surrounding region holds a special place for me.
The Chianti region is home to some of the best wineries in Tuscany. If you want to have a taste of Chianti, visit Antinori near Bargino, Querceto di Castellina and Castello di Ama in Gaiole in Chianti.
Some of the wineries also operate as agriturismos (aka posh farmstays), which means you can stay overnight, have long lunches and really soak it all in. If you cannot spend a few days in Tuscany, then a Chianti day trip from Florence is the perfect way to get a taste of the countryside.
Val d’Orcia and Montepulciano
Val d’Orcia ranks in my top 5 regions in the entire world. It is a UNESCO World Heritage Site and is the region behind all those picture-perfect photos of Tuscany are from. With the rolling hills, the cypress trees lining the roads, the golden light in the late afternoon, it looks just like a painting. This is the heart of Tuscany and has the best views of the rolling hills.
The valley consists of several small towns that are all worth visiting. The best towns to visit in Val d’Orcia are Montalcino, Montepulciano, Pienza and San Quirico.
Montalcino sits at the heart of Val d’Orcia and is home to Brunello di Montalcino, the premium wine of Tuscany and one of the greatest wines in the world. Pienza is a perfect Renaissance town with incredible pecorino cheese. Montepulciano is a hilltop town with sweeping views of the valley and produces Vino Nobile, another of Tuscany’s finest wines.
If you could only visit one place in Tuscany, make it Val d’Orcia.
This valley also has some of the best agriturismos in Tuscany. I highly recommend staying a couple of nights if you can. But if a day trip is all you have, either rent a car or book a tour. And be prepared for a long yet fulfilling day.
Carmignano Wine Region
Carmignano is one of the most underrated wine regions in Tuscany. It is just 30 minutes from Florence, making it an easy day trip you can do from the city. If you cannot make it all the way to Chianti, visit Carmignano for a short day trip.
The wines of Carmignano are light, elegant and seriously delicious. Carmignano is one of Italy’s oldest DOCs (designated wine regions) and has been producing wine since the 14th century. Most travelers have never heard of it, which means you get the wineries and the countryside almost entirely to yourself.
Lucca
Most people visit Pisa and skip Lucca entirely and that’s a mistake. Lucca is one of the most beautiful towns near Florence and one of the most underrated in all of Tuscany.
The entire city is enclosed within remarkably intact Renaissance walls. You can walk or cycle along the top of the walls and look out over the terracotta rooftops for breathtaking views of the Tuscan hills. It is one of the most fun things you can do and unforgettable experiences in Italy.
Inside the city walls is completely car-free and wonderfully walkable. The main highlights are the Piazza dell’Anfiteatro, a stunning oval piazza built on the foundations of a Roman amphitheater, the Cathedral of San Martino and the Torre Guinigi, a medieval tower with oak trees growing from the top.
You can combine Pisa with Lucca as a full day trip from Florence, but I prefer to keep it relaxed rather than cramming everything into one day.
Pisa
Pisa is worth a visit but let me be honest with you. Other than the Leaning Tower of Pisa, the city is pretty underwhelming. The Piazza dei Miracoli where the tower sits is genuinely stunning and worth seeing in person. The Cathedral and the Baptistery right next to it are beautiful and most people walk right past them. But outside that square, the city does not have a whole lot going on and even a bit rundown.
My recommendation is to combine Pisa with Lucca in the same day. Spend a couple of hours at the Piazza dei Miracoli, see the tower and then head to Lucca for the rest of the day. That way you get the iconic photo and the much more rewarding experience of Lucca without feeling like you wasted a full day on one tower.
Cortona and Arezzo
Cortona is one of the most beautiful towns in Tuscany. It is perched high above the Val di Chiana with sweeping views over the valley and Lake Trasimeno. Most people recognize it as the town where Under the Tuscan Sun was filmed.
The house Frances Mayes bought, Bramasole, sits just outside the town and the film brought Cortona to the world’s attention. Walking through the steep stone streets and the main Piazza della Repubblica, it is easy to see why she fell in love with it.
The town has a wonderful unhurried energy. The main highlights are the Museo Diocesano with its impressive collection of Renaissance art, the Basilica di Santa Margherita at the top of the hill with panoramic views. Make sure to visit the small artisan shops and wine bars lining the main streets.
Cortona is the kind of place where you wander without a plan and somehow end up having one of the best afternoons of your trip.
Arezzo is about 30 minutes from Cortona and can be combined with Cortona in the same day. It is a proper Tuscan city with a stunning medieval center, a famous antiques market and one of the most beautiful squares in Italy, the Piazza Grande.
Arezzo is also the birthplace of Giorgio Vasari, the Renaissance artist and architect who wrote the Lives of the Artists. The Basilica of San Francesco contains Piero della Francesca’s famous fresco cycle The Legend of the True Cross, which is considered one of the greatest works of Renaissance art in Italy.
Many people don’t visit Arezzo as much as Siena or Florence but I highly encourage you to visit.
Cinque Terre
Cinque Terre is a collection of five colorful fishing villages perched on the cliffs of the Ligurian coast. They look exactly like a postcard. If you have been dreaming of visiting the iconic Italian coastline but cannot make it to the Amalfi Coast or Lake Como on this trip, Cinque Terre is the answer. It is absolutely worth the day trip from Florence.
That said, this is a longer day trip and requires proper planning. Cinque Terre can get chaotic if you do not know what you are doing. Take a train to La Spezia and then a second regional train to the villages. The trails between villages get crowded, the trains fill up fast and navigating different villages in one day without a plan can feel overwhelming.
I suggest either planning the day carefully in advance or booking a private tour so someone else handles the logistics.
The five villages are Monterosso, Vernazza, Corniglia, Manarola and Riomaggiore. You do not need to see all five in one day. Pick two or three and enjoy them properly rather than rushing through all of them.
Bologna
I cannot believe more people do not visit Bologna. If you are a food lover and travel for food (like me!), this is a must do day trip from Florence. It is one of my favorite cities in Italy.
Even though it is not in Tuscany, Bologna is just 35 to 40 minutes from Florence. You step off the train and you are in the food capital of Italy. The city that gave the world mortadella, tagliatelle al ragu, tortellini, lasagne and Parmigiano Reggiano. Every meal here is an event to savor.
The best way to experience Bologna is to take a food tour with a local. It is the best way to eat your way through the city with a local who knows where to go. Try the mortadella, the fresh pasta, the aged Parmigiano and a glass of Pignoletto, the local sparkling white wine.
Walk the famous porticoes, visit the Piazza Maggiore and climb the Due Torri, the two leaning medieval towers that define the city skyline. The historic center is beautiful and completely walkable.
Volterra
Volterra is one of Tuscany’s best kept secrets. Most people skip it entirely in favor of San Gimignano or Siena, which means you get this stunning hilltop town almost to yourself. If you want a taste of medieval Tuscany without the crowds, Volterra is your answer. It is one of the oldest towns in Tuscany.
The town sits on a ridge surrounded by eroded clay hills called balze. The views from the walls are spectacular. Volterra is famous for its alabaster workshops. Local artisans have been carving alabaster here since Etruscan times and you can still watch them work in the small shops lining the streets. Pick up a piece as a completely unique souvenir that you will not find anywhere else in Italy.
Take a stroll along the Piazza dei Priori, one of the oldest medieval squares in Tuscany. Don’t miss the Roman theatre and the Etruscan Museum, one of the most important in Italy. Volterra is reportedly one of the inspiration for Stephenie Meyer’s Twilight series!
Livorno and Bolgheri
Livorno surprised me. I was not expecting much from a port city but it has a genuinely cool vibe. With its waterfront promenade and easy, laid-back energy, it reminded me a little of Rio. It is close to the coast and feels completely different from the other Tuscan towns.
The Venetian quarter, known as Piccola Venezia, is the most charming part of the city. Small canals run between old buildings and the whole area has a relaxed, neighbourhood feel.
The seafood here is exceptional. Cacciucco, Livorno’s famous fish stew, is one of those dishes you need to try at least once. Walk the Terrazza Mascagni, a huge tiled seafront terrace right on the Mediterranean, for one of the best sunset spots on the Tuscan coast.
Bolgheri is a short drive along the coast from Livorno, and if you love wine you absolutely must go. Bolgheri is the birthplace of the Super Tuscans. This is where Sassicaia was born in the 1960s, the wine that revolutionized Italian winemaking and changed how the world saw Tuscan wine.
The famous cypress-lined avenue leading into the village, the Viale dei Cipressi, is one of the most iconic roads in all of Italy. Stop at an enoteca in the village, taste a Super Tuscan and understand why collectors around the world seek these wines out.
Assisi
Assisi is in Umbria but it is one of the most beautiful and moving day trips you can take from Florence.
The hilltop town is the birthplace of Saint Francis of Assisi and the Basilica di San Francesco is one of the most important pilgrimage sites in the world. It is a UNESCO World Heritage Site and the frescoes inside by Cimabue and Giotto are extraordinary. Even though I’m not religious, I could feel the spiritual energy of this city.
The pink and white stone streets of the medieval city center are completely car-free. Walk up to the Rocca Maggiore fortress at the top of the hill for sweeping views over the Umbrian valley.
Have lunch at one of the small trattorias in the center and try the local black truffle pasta, a specialty of Umbria. Visit on a weekday if possible to avoid the pilgrimage crowds on weekends.
Orvieto
Orvieto is Umbria’s other gem and one of the most dramatically situated towns in central Italy. It sits on top of a sheer volcanic cliff of tufa rock and the view of it rising above the surrounding valley as you approach by train is genuinely jaw-dropping. It is about two hours from Florence by direct train, making it one of the farthest day trips on this list but absolutely worth it.
The Orvieto Cathedral is arguably one of the most beautiful Gothic facades in Italy. The gold mosaics and intricate marble carvings on the front took over three hundred years to complete. Go inside to see the Chapel of San Brizio, which contains Luca Signorelli’s extraordinary Renaissance frescoes that directly inspired Michelangelo’s Sistine Chapel ceiling.
Orvieto is also famous for its white wine, Orvieto Classico. It is a crisp, mineral-driven white that pairs perfectly with the local seafood and truffle dishes.
Orvieto was built on top of centuries of tunnels, caves and Etruscan chambers carved into the volcanic rock. The underground city is something only locals and curious travelers know about. Book an underground tour and explore a completely hidden world beneath the streets. It is one of the most memorable things to do in central Italy.
A note on day trips to Venice and Rome
Both Venice and Rome are absolutely doable from Florence by fast train but neither does justice to a day trip. That’s why I have not included them as part of day trips from Florence.
Venice deserves at least two nights and Rome needs a minimum three days to even scratch the surface. Check out my full comparison of Florence or Venice to help you decide between the two and my 10 days in Italy itinerary covers how to combine all the best cities of Italy in one trip.
How to Get There: Day Trips from Florence at a Glance
If you are staying a week in Tuscany and want to explore different regions, I highly recommend renting a car. It gives you the flexibility to choose your trips and stop whenever you want. I personally love and use Auto Europe.
If you can’t rent a car, many of the towns and trips can be doable as day trips by train. Many towns have direct train lines from Florence. Trains in Europe are very reliable and booking in advance is super easy.
For the rest, guided small group or private tours are your best option.
| Destination | Travel Time | Best Way to Get There |
|---|---|---|
| Siena | 1.5 hours | Bus or guided tour |
| San Gimignano | 1.5 to 2 hours | Bus or guided tour |
| Chianti Wine Region | 45 min to 1 hour | Guided wine tour or rental car |
| Carmignano Wine Region | 30 to 45 minutes | Rental car or guided tour |
| Val d’Orcia and Montepulciano | 1.5 to 2 hours | Guided wine tour or rental car |
| Lucca | 1.5 hours | Direct train |
| Pisa | 1 hour | Direct train or private tour |
| Cortona and Arezzo | 1 to 1.5 hours | Direct train and rental car |
| Cinque Terre | 2 to 2.5 hours | Train or private tour |
| Bologna | 35 to 40 minutes | High-speed train + food tour in city |
| Volterra | 1.5 to 2 hours | Bus or rental car |
| Livorno and Bolgheri | 1 to 1.5 hours | Train to Livorno, rental car to Bolgheri |
| Assisi | 2 hours | Regional trains |
| Orvieto | 2 hours | Direct train |
Final Thoughts
Florence is one of the most popular summer destinations in Europe. It is also one of the best places in all of Italy for day trips.
Whether you have one extra day or several days, there is always somewhere worth going within easy reach. People who visit Florence but do not venture out of the city are missing out on some of the best things in Italy.
Some of my favorite day trips from Florence are Siena and San Gimignano, Val d’Orcia, Chianti, Lucca and Bologna. In fact, you can even get to Portofino from Florence.
If your schedule allows, consider basing yourself in Siena or the Tuscan countryside for a few nights and using that as your hub instead. You will see a completely different side of Italy.
For more on the wine regions mentioned in this post, read my guide to the best wineries in Tuscany. And if you are planning to stay in other regions of Tuscany, read my guide to the best agriturismos in Tuscany.
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