Day Trips from Florence: 6 Drives Through Tuscany
Tuscany is the region day trips were invented for. Siena is an hour away, the Chianti hills start twenty minutes past the ring road, and the towers of San Gimignano are visible from the motorway long before you reach them. The problem is never what to see; it is how much you try to fit into one day.
The six drives below are paced so that each is a real day rather than a checklist — one main town, one or two smaller stops, and time to eat properly. Driving times are counted honestly, and the ZTL traps are named. Open any day to see it stop by stop, then change whatever you like.
Day drives from Florence
Siena Day Trip from Florence
A shell-shaped square, a striped cathedral and a city that stopped in 1348
1 days · 184 km
A shell-shaped square, a striped cathedral and a city that stopped in 1348
Chianti wine road Day Trip from Florence
The SR222 through vineyards, with cellars and hill villages along it
1 days · 100 km
The SR222 through vineyards, with cellars and hill villages along it
San Gimignano & Volterra Day Trip from Florence
Fourteen surviving medieval towers, then an Etruscan town on a ridge
1 days · 122 km
Fourteen surviving medieval towers, then an Etruscan town on a ridge
Lucca & Pisa Day Trip from Florence
A city wall you cycle around, and the leaning tower half an hour further
1 days · 159 km
A city wall you cycle around, and the leaning tower half an hour further
Arezzo & Cortona Day Trip from Florence
Piero della Francesca's frescoes and a hill town over the Valdichiana
1 days · 154 km
Piero della Francesca's frescoes and a hill town over the Valdichiana
Bologna Day Trip from Florence
Porticoed streets and Italy's best eating, over the Apennine pass
1 days · 229 km
Porticoed streets and Italy's best eating, over the Apennine pass
Car or train?
Lucca, Pisa and Bologna are all fast, frequent trains from Santa Maria Novella, and for those three the train is simply better — no parking, no restricted zone. The car is worth it for Chianti, San Gimignano and the Arezzo–Cortona pair, where the point is the road between the towns and buses are slow or rare. One rule that matters more than any other in Italy: every historic centre here is a ZTL (limited traffic zone) with camera enforcement, and your satnav does not know where the cameras are. Park in a signposted car park outside the walls — Siena's Fortezza, San Gimignano's Parcheggio Montemaggio — and walk in. Fines arrive months later through the hire company, one per entry.
Driving out of Florence — the practical bits
- How do I avoid a ZTL fine in Tuscany?
- Assume every walled town centre is restricted, and park outside the walls. Look for the round white sign with a red border — that is the zone boundary. If your hotel is inside a ZTL it can register your plate for the nights you stay, but only if you give them the number in advance.
- Can I do Siena and San Gimignano in one day?
- You can, and plenty of tours do, but it makes for a rushed day — roughly two hours of driving plus two hurried towns. Doing one properly, with a Chianti stop on the way back, is a better day.
- Is Cinque Terre a day trip from Florence?
- Not comfortably by car — the villages are closed to traffic and the coastal road is slow, so you'd park at La Spezia and take the local train anyway. If Cinque Terre is a priority, go by train from Florence, or stay overnight.
- When is the wine country worth it?
- September and October for harvest, May for the countryside. Most small Chianti cellars want a booking a day or two ahead — walking in works at the larger estates only. And whoever drives tastes little; plan for that.
- Can I change the plan?
- Yes — swap any stop for one of three alternatives, or rebuild a whole day. The drive times and tolls recalculate as you edit.
Want a different day out of Florence?
Tell us where you're starting and how long you have, and we'll build the day around your own driving limit — then you can swap any stop.
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