The best day trips from Florence - from Siena and San Gimignano to Cinque Terre and the Chianti wine roads. Here's exactly where to go, how long each takes, and what I'd skip.
If you're still planning your time in the city itself, start with my Florence travel guide and my Florence in one day itinerary first.
Florence is one of the best-positioned cities in Italy for day tripping - Tuscany radiates out from it in every direction and almost everything worth seeing is within two hours. I've used Florence as a base more times than I can count and every time I find a new reason to leave the city for a day and come back wanting to live here permanently. Here are the day trips I keep going back to, and a few honest notes on which ones to skip.
Best Day Trips from Florence
1. Siena - Tuscany's Most Beautiful City
About 1.5 hours from Florence by bus or car, Siena has the Piazza del Campo, a soaring Gothic duomo, and medieval streets that feel genuinely lived-in rather than touristy. I'd go on a weekday and give it a full day - it's the best day trip from Florence, full stop. Read my Siena travel guide before you go.
2. San Gimignano - The Medieval Manhattan
A walled hilltop town famous for its towers and gelato (Gelateria Dondoli here has won the World Gelato Championship multiple times - the saffron and pine nut flavor is extraordinary). It gets crowded by midday, so I'd arrive early and combine it with Siena or Volterra for a full Tuscan day. Read my San Gimignano guide for what to actually do beyond the main piazza.
3. The Chianti Wine Road
The Chiantigiana - the scenic road winding through vineyards between Florence and Siena - is one of the most beautiful drives in Italy, and the wineries along it welcome visitors for tastings most days of the week. I'd rent a car, pick two or three estates, have a long wine lunch somewhere in the middle, and drive back slowly.
4. Lucca - The Walled City
Lucca is completely encircled by its Renaissance walls - which you can walk or cycle on top of - and has a beautifully preserved medieval center with almost none of Siena's crowds. I love it for a half day: climb the tree-topped Torre Guinigi, walk the walls, eat well, and be back in Florence by evening. Read my Lucca guide for the full picture.
5. Pisa + Lucca Combined
The Leaning Tower is worth seeing in person - it really is genuinely weird and impressive - but Pisa alone doesn't fill a full day. I'd combine it with Lucca (40 minutes away by train) to make the most of the journey. Read my Pisa guide for what to see beyond the tower.
6. Val d'Orcia - The Rolling Hills Drive
The iconic Tuscan landscape of cypress-lined roads and rolling golden hills is about 90 minutes south of Florence by car. I'd base the day around Pienza for pecorino and lunch, drive to Montalcino for a Brunello tasting, and stop at the Cappella di Vitaleta for the photos everyone's trying to get. Read my Val d'Orcia travel guide before you go.
7. Arezzo - Tuscany's Hidden Town
About 1 hour from Florence by train, Arezzo is one of the most beautiful and most overlooked towns in all of Tuscany - a medieval hilltop city with a Piero della Francesca fresco cycle that ranks among the greatest works of Renaissance art in Italy. The antique market on the first Sunday of every month fills the piazza and is one of the best markets I've been to anywhere. Read my Arezzo guide for everything to see.
8. Bologna - Italy's Food Capital
Only 35 minutes from Florence by high-speed train, Bologna is the greatest food city in Italy - tagliatelle al ragù (the real bolognese), mortadella, tortellini in brodo, and the best covered market I've seen in Europe (Mercato di Mezzo). Most tourists skip it entirely because they're in Tuscany and that is a genuine mistake. Go for lunch and come back with leftovers.
9. Cinque Terre - Yes, But Go Early
The five clifftop villages of the Ligurian coast are about 2.5 hours from Florence by train and absolutely worth it - but the trails and the villages are genuinely packed in summer by midday. I'd take the first train out, hike from Monterosso to Vernazza in the morning before the crowds arrive, have lunch in Manarola, and head back by late afternoon. Read my Cinque Terre guide for the best route.
10. Volterra - the Etruscan Hilltop Town
Less visited than San Gimignano but in my opinion more interesting - a dramatic hilltop town with Etruscan walls, an alabaster carving tradition that goes back centuries, and some of the best views in Tuscany. About 1.5 hours from Florence by car (awkward by public transport). Worth it for anyone who wants to avoid the crowds.
11. Bolgheri - Tuscany's Wine Coast Secret
A tiny medieval village on the Tuscan coast about 1.5 hours from Florence, surrounded by the vineyards that produce Sassicaia and Ornellaia - two of Italy's most prestigious wines. The famous cypress-lined avenue (Viale dei Cipressi) leading into the village is one of the most photographed roads in Tuscany and blowing up on Instagram right now. Combine with a winery visit and a seafood lunch on the coast.
12. Towns Near Florence - Pick Your Own
If you want to explore the Florentine countryside without a specific destination, I have a full guide to the best towns near Florence that covers lesser-known gems worth a half day each.
How to Get Around
By train: The easiest option for Siena (bus is better), Lucca, Pisa, Arezzo, Bologna, and Cinque Terre. Florence's main station is Santa Maria Novella - central, well-connected, and easy to navigate. Buy tickets on Trenitalia or at the station.
By car: Essential for the Chianti wine road, Val d'Orcia, Volterra, and Bolgheri. I'd rent from the city center but return it before peak traffic hours - Florence's ZTL (restricted traffic zone) is aggressively enforced. For Siena and San Gimignano, a car gives you much more flexibility than the bus.
By bus: SITA buses run regularly to Siena and San Gimignano from Florence's main bus station next to Santa Maria Novella. Cheap, reliable, and scenic.
How Many Day Trips Should You Do?
I'd do one or two maximum per week in Florence - the city itself deserves at least three full days and it's easy to exhaust yourself rushing in and out of it. Pick your top priorities, give each one a proper day, and let the rest of your time be Florence.
Best Time for Day Trips from Florence
April through June is the best window - Tuscany is lush, wildflowers are out in Val d'Orcia, winery terraces are open, and the crowds haven't peaked. My favorite time of year to be in this part of Italy.
September and October: Grape harvest season in Chianti, truffle season starting in the hills, and beautiful light. Equally good.
July and August: Cinque Terre gets very crowded. Val d'Orcia is stunning but hot. Chianti wineries are busy. It's all still worth it - just go earlier in the day.
Travel Tips
- Book Cinque Terre hiking passes in advance. The trails require a paid pass in peak season and sell out.
- Go early to everything. Most of these towns are overwhelmed by 11am in summer. I'm on the first train or in the car by 8am and it makes the whole experience better.
- For Chianti, book winery tastings ahead. Most estates require reservations, especially for the better tours.
- Siena by bus is easy and cheap. The SITA bus from Florence takes about 1.5 hours and drops you close to the center - no need to rent a car.
- Don't try to do Siena AND San Gimignano in one day. It sounds doable on a map. It always ends up feeling rushed. Pick one and do it properly.
- Bologna is always worth it. It gets criminally overlooked by Tuscany visitors. Just go - you won't regret it.
FAQ
What is the best day trip from Florence? Siena, without question - it's close, beautiful, historically rich, and far less visited than Florence despite being just as extraordinary. Read my Siena guide to plan your visit.
Can I visit Cinque Terre from Florence in a day? Yes - it's about 2.5 hours by train each way. Take the first train out, hike in the morning, eat lunch by the water, and head back mid-afternoon. Read my Cinque Terre guide for the best route.
What is the easiest day trip from Florence? Lucca or Arezzo by train - both under an hour, both manageable without a car, and both genuinely beautiful. Lucca in particular is deeply underrated.
Is Pisa worth a day trip from Florence? Worth a visit but not a full day on its own - I'd combine it with Lucca to make the most of the trip. Read my Pisa guide for what to see beyond the tower.
What's the most underrated day trip from Florence? Arezzo for culture, Bolgheri for wine and scenery, and Bologna for food. Any of the three will make you feel like you've discovered something most tourists completely miss.
