The best day trips from Florence by car, train and guided tour. From medieval towns to wineries and areas of great natural beauty in Tuscany, these are the best side-trips from Florence Italy
There is only one reason why I would recommend visitors to leave the amazing city of Florence and that is the opportunity to go on a day trip to Tuscan towns nearby.
Tuscany is one of the most visited areas of the whole of Italy and it is easy to see why.
The land is dotted by historic, picture-perfect towns with beautiful views, wineries, olive groves and world-class food (think Chianti wine, cheese boards and steak!).
If this wasn’t enough, the distances are so reasonable you can start your morning in Florence, have lunch in the country, aperitivo on the sea and be back to your hotel by evening – not a bad day at all!
This is my selection of the best day trips and best day tours from Florence.
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Best day trips from Florence: less than 2 hours
Perfect for: food and wine lovers
The Chianti region is world-famous for its production of Chianti classico wine and it is a very easy area to visit from Florence.
Here, you are going to see beautiful countryside and will have your pick of wineries and restaurants to sample the local, amazing wood and see what this famous wine is all about.
The best way to visit this wine region is by car, if you have a designated driver in our party who will not partake in the wine tasting, or with a guided tour.
This is the perfect day trip for wine lovers.
Perfect for: shopping lovers outdoor enthusiasts, families with kids
Mugello, the area of Tuscany between Florence and the border between Tuscany and Emilia-Romagna.
The are has beautiful villages and the UNESCO listed Villa Demidoff however, many people visit this area for its famous shopping outlet, a paradise for shopping lovers thanks to the many, well priced finds.
The outlet is served by a regular shuttle service
Perfect for: culture lovers, foodies, families
Fiesole is so close to Florence city center calling this a ‘day trip’ may seem misleading.
However, it is such a gorgeous town that devoting to Fiesole any less than a full day is a real shame.
Fiesole sits on top of a hill overlooking the city and can be easily reached by car, taxi or public transportation and then discovered on foot.
The main landmarks not to miss here are the spectacular view over the Tuscan countryside, Fiesole cathedral and the beautiful Roman amphitheater, all within easy reach one from the other.
To make the most of your day, I recommend to break up exploration with lunch at the wonderful Maiano farm and indulge in their elegant offerings.
If you go, make sure you peek into the cloister: it is restored to its original splendour and truly gorgeous.
Perfect for: culture enthusiasts, music enthusiasts, families
Lucca is easily one of the most pleasant and charming cities in Tuscany and one of the best day trips from Florence for all ages.
Lucca is Roman in origin and during medieval times acquired impressive walls, still now framing the city.
The top of the walls is accessible by bike and local shops rent bicycles for pretty much all ages: it is a great way to stretch your legs and it gives a fantastic vantage point over the city.
After the exercise, you can have lunch in some of Lucca’s many restaurants and wander along its many medieval alleys.
Make sure you seek out piazza dell’anfiteatro, once a Roman amphitheater and now a bustling square with terraces and restaurant.
Perfect for: history lovers, foodies, shopping (few but high-quality handmade bags and pottery stores)
Monteriggioni is a tiny village perched on the top of a hill in the province of Siena, less than 50 km from Florence.
It is the quintessential Tuscan town, surrounded by imposing turreted walls and olive trees and (mostly) closed to traffic.
The town can be visited in a short time: the best things to do here are the walks along the bastions (if you are not afraid of height), having lunch in the medieval square and peek at the local shops.
If you can, try and visit the city in early July when the Monteriggioni medieval festival takes place (bring water and a sun hat as Monteriggioni is hot in summer!).
Perfect for: history and art lovers, families, fans of ‘Under the Tuscan sun’
Cortona is the backdrop for the famous Under the Tuscan Sun and it is easy to see why.
Perched on a wonderful Tuscan hill, Cortona is beautiful and despite being well known now, it feels very much like a real place, one where people live, work and rear children.
We visited Cortona in the summer, following the advice of my aunt, who has been spending here innumerable summers, and had such a lovely day that we decided to spend the night.
We choose the excellent hotel Dolce Maria, friendly, beautiful, clean and in the perfect central location.
If you go, take the time to get lost in its beautiful streets and do sample the local specialties: for a light bite, ask for ‘ciaccia’, the local interpretation of focaccia – have it with cured meats, vegetable tartines or local cheese for an explosion of taste.
San Gimignano, Unesco world heritage site
Perfect for: couples, history lovers, foodies
San Gimignano is a gorgeous medieval village perched on a hilltop in the heart of the Tuscan countryside.
Closed to traffic, the city is a medieval gem and you can spend a full day in San Gimignano discovering it small alleys, its many churches, its famous towers (its most distinctive trait) and enjoying the views over the surrounding countryside.
The only problem with San Gimignano is mass tourism: for a , try come by car so you can visit at your own pace and stay a little later.
Once the sun goes starts to set and crowds fade, sit at one of the local restaurants and have a glass of local ‘vernaccia’: it can well become the highlight of your Tuscany trip!
Perfect for: architecture lovers who don’t fear the crowds
I have heard in many time: ‘Pisa is overrated’, ‘I shouldn’t have bothered’, ‘you can take it or leave it’. I disagree.
I believe Pisa is one of the most beautiful, incredible, magical cities in the world and one that deserves its fame if not more.
However, there is a reason behind the bad experience of many and the reason is the crowds.
Piazza dei Miracoli, that gem if Italian architecture with the famous leaning tower of Pisa, often feels like a place out of Dante’s inferno: crowded, dirty and full of overpriced tourist joint.
Because of this, I believe the best way to visit Pisa is on your own.
If you are not yourself part of a group, you can wander the city away from the tower at your own pace and come back to Piazza dei Miracoli after the crowds have gone home – you will see why it has the name ‘miracle’ in it, and is a famous UNESCO world heritage site
Day trips from Florence 2 to 3 hours by car
Perfect for: slow travellers, families, art lovers
Very close to Cortona and an easy extra stop on this day trip is the wonderful city of Arezzo.
Often forgotten by mainstream Tuscany itineraries, Arezzo is a great stop if you want to experience a more local feel and a treat for art lovers.
Its medieval centre got destroyed during the second world war, but many important landmarks and masterpieces are still here and are worth a visit. Not to be missed are the Church of San Francesco with an important Piero della Francesca and the Church of San Domenico.
Perfect for: culture and history lovers, shopping enthusiasts
Siena is one of the most beautiful towns in Tuscany: the center and famous Piazza del Campo is jaw-dropping but the whole city is full of churches, pretty roads and palazzi that echo its medieval past.
Siena also has lovely shops and restaurants, which make it perfect also if you want a relaxing day getting your fic of Italian food and style!
Despite all these riches, Siena is easy to visit in one day: you can find my full guide to Siena here.
One of the unique things about Siena is that it was historically divided into ‘contrade’ or ‘districts.
Each contrada had their own symbols and flags: you can see them all over the city at all times but they truly come into their own at the palio, when the historical rivalry between them gets re-enacted.
In whatever season you happen to come here however, you will see that there are plenty of things to do in Siena that make a day trip from Florence here worth it.
Perfect for: food loves, seekers of the quintessential Tuscan countryside experience
A longer yet stunning day trip fro Florence is also that to Val D’Orcia, maybe the most iconic of all areas in Tuscany.
Val d’Orcia is where the rolling hills, cypress trees and olive groves that many associate with Tuscany actually are.
You can visit in your own time by car or you can get a guided tour that includes some of its most famous sites such as Pienza, Montalcino and Montepulciano
Tuscan Riviera and Etruscan coast
Perfect for: families with young children, beach lovers
Florence is surprisingly close to the sea.
The closest coastal area to Florence is the famous Tuscan Riviera but my favorite area is a little farther south, in the province of Livorno, in the localities of Quercianella, Follonica and Donoratico.
Unlike the posh riviera, famous for its nightlife, this area of Tuscany is pristine and family friendly, with sandy beaches and waters that go from shallow to rocky and perfect for snorkeling!
Cinque Terre is an area of outstanding natural beauty in Liguria (the region to the North West of Tuscany).
The 5 towns making up this area are nestled into small coves overlooking the sea and protected by beautiful cliffs.
They originated as fishing villages, a history that explains their charm.
The towns are connected by beautiful hiking trails (some open to tourist some closed) and it is from these trails that you get the picture perfect photos that grace the web and so many tourist magazines.
As you can tell from this description, Cinque Terre are not really day trip material however, if one day is all you have, you can visit them as a day trip from Florence .
The best way to go is by train or with a guided tour
If traveling with children, make sure you check our guide to Cinque Terre with kids: this area of Italy is not child friendly (for the terrain, not the people) and extra tips are useful.
I hope you enjoyed this overview of our favorite side trips from Florence. Safe travels!
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