One of the joys of Florence is that it is the gateway to Tuscany, and some of Italy’s most beautiful towns and vineyards sit within an hour or two. You could spend a week here and never leave the city happily, but if you have three days or more, a day out into the hills and the neighbouring cities gives your trip another dimension. Here are the day trips I recommend, which to do independently by train and which are easier on a tour, with the times and the practicalities.
Pisa
The easiest and most famous. Regional trains leave Florence for Pisa Centrale roughly every fifteen minutes and take about an hour to an hour and twenty depending on the service, for well under €10 each way. The Leaning Tower and the cathedral sit together on the green Piazza dei Miracoli, a short walk or bus from the station, and honestly half a day is enough to see them, buy your obligatory “holding up the tower” photograph, and move on. Which is exactly why so many people pair Pisa with Lucca.
Lucca
A short hop beyond Pisa, Lucca is a walled Renaissance town encircled by broad ramparts wide enough to cycle along, and it is one of the most relaxing places in Tuscany. The train from Florence takes around eighty minutes, usually with a change at Pisa, so many people do Pisa and Lucca together in one day. Rent a bike, ride the tree-lined walls, climb the Guinigi tower with its rooftop garden of oak trees, and eat well in the quiet piazzas. It is the gentle antidote to Florence’s crowds.
Siena
Siena is Florence’s great medieval rival, and its shell-shaped Piazza del Campo, the scene of the twice-yearly Palio horse race, is one of the most beautiful squares in Italy. The striped marble cathedral is extraordinary. Siena is reachable from Florence by train (though the station sits below the old town, needing a bus or escalators up) or by direct regional bus, each taking around an hour and a half. Give yourself a full day to do it justice.
San Gimignano and Chianti
For the Tuscany of the imagination, rolling vineyards, cypress avenues and hilltop towers, you want San Gimignano and the Chianti wine country, and this is the one region where I would take a tour rather than travel independently. San Gimignano, the “medieval Manhattan” of stone towers, has no train station, and the Chianti vineyards between Florence and Siena are scattered down country roads. An organised small-group day trip, the classic combination pairs Siena, San Gimignano and a Chianti winery with lunch, takes the logistics off your hands and usually includes the tastings, which is exactly what you want on a day built around wine.
Fiesole, the half-day escape
If you only have a spare afternoon, take city bus number 7 up to Fiesole, a small town on a hill just above Florence, about twenty-five minutes away. There are Roman ruins, a peaceful monastery, and a terrace with a beautiful view back down over the city, all for the price of a bus ticket. It is the easiest escape of all, and on a hot day the hillside breeze alone is worth the ride.
Bologna, for the food
If you love to eat, give a day to Bologna. The high-speed train gets you there in a remarkable thirty-five to forty minutes (regional services take about ninety and cost less), so you can be wandering the porticoed streets by mid-morning. This is the home of tortellini, tagliatelle al ragù and mortadella, best sampled among the food stalls of the Quadrilatero. Stand in the grand Piazza Maggiore, climb one of the leaning Two Towers, and walk a stretch of the UNESCO-listed Portico di San Luca. Many people consider Bologna Italy’s finest food city, and it is close enough to prove it over a single long lunch.
Arezzo and Cortona
East of Florence, Arezzo sits about an hour away by train and brims with art by its two famous sons, the painter Piero della Francesca and Giorgio Vasari; its sloping Piazza Grande is beautiful and far quieter than Siena. Nearby Cortona, the hilltop town made famous by Under the Tuscan Sun, looks out over the Val di Chiana from its steep stone streets. The two pair naturally on a guided tour if you would rather not manage the connections, and together they give you a gentler, less-touristed slice of Tuscany.
Val d’Orcia
For the postcard Tuscany of solitary cypress trees and rolling golden hills, the Val d’Orcia is a UNESCO-listed landscape south of Siena, studded with the wine towns of Montepulciano, Pienza and Montalcino. It is too far and too scattered to reach easily by public transport, so it makes a full, long day by organised tour, but the scenery and the Brunello di Montalcino and Vino Nobile tastings make it many travellers’ single favourite day out from Florence.
Booking your day trip
A few practicalities. Regional trains to Pisa, Lucca and Arezzo do not need booking ahead, you buy them at the station on the day, but validate a paper ticket in the little machines before you board or you risk a fine. High-speed trains to Bologna are cheapest booked online a week or two in advance, when fares start around €10; walk-up prices can be three times that. And for the tour-only destinations, Chianti, San Gimignano and the Val d’Orcia, reserve a small-group departure the night before at the latest in high season, because the good ones sell out.
How to choose your day trip
For flexibility and low cost, take the train to Pisa and Lucca together, or to Siena. For the vineyards and the smaller hill towns with no rail links, book a tour and let someone else drive so you can enjoy the wine. And if all you have is a few hours, ride the bus up to Fiesole. Whatever you do, treat these as a bonus rather than a substitute: Florence itself deserves your first two days undivided.
Frequently Asked Questions
What is the best day trip from Florence?
For most first-timers, the classic guided combination of Siena, San Gimignano and a Chianti wine tasting is the most rewarding, because it covers the quintessential Tuscan countryside in one day. For an easy independent trip, Pisa paired with Lucca by train is hard to beat.
Can you do day trips from Florence by train?
Yes, several. Pisa is about an hour away and runs every fifteen minutes; Lucca is around eighty minutes, usually via Pisa; Siena is roughly an hour and a half; Bologna is a fast thirty-five to forty minutes. Chianti and San Gimignano, which lack convenient rail links, are better by tour.
How do you get to Chianti from Florence?
Because the Chianti vineyards are scattered along country roads with no direct trains, the easiest way is an organised wine tour from Florence, which handles the driving and includes tastings. If you prefer independence, you would need to rent a car and collect it as you leave the city.
Is Pisa worth a day trip from Florence?
Pisa is worth half a day, enough to see the Leaning Tower and the cathedral on the Piazza dei Miracoli. Because it is so quick, most people pair it with Lucca, a walled town a short hop further on, to make a satisfying full day out of the two.
What is the easiest half-day trip from Florence?
Fiesole, a hill town about twenty-five minutes away on city bus number 7. For the price of a bus ticket you get Roman ruins, a quiet monastery and a lovely view back over Florence, making it the simplest escape when you have only an afternoon to spare.
Read also: The Perfect Florence Itinerary | How to Get to Florence | The Complete Guide to Florence
