Tuscany
Most people see Tuscany from Florence and never really leave the city. That is a reasonable first trip, but it means missing the part that made the region famous: the hill towns, the roads between them, and the fact that a forty-minute drive changes the landscape completely.
The practical constraint is transport. Siena, Pisa and Lucca are easy by train. Everything else, including Val d’Orcia, Montalcino, Montepulciano and most of Chianti, needs a car or a tour, because the bus timetables are built for residents and not for visitors.
These guides cover which towns are worth the detour, how to structure a road trip, when to come, and what a villa with a pool actually costs once you add the extras.
Tuscany guides
Tuscany Villa Rentals
What a villa really costs, when to book, and what the listing photos leave out.
Best Time to Visit Tuscany
Month by month: crowds, heat, harvest and what closes in winter.
Tuscany Road Trip
A route that works, with realistic driving times and where to sleep.
Siena
Piazza del Campo, the cathedral, and why it is a better wine base than Florence.
Pisa
More than the tower, and how long it is actually worth staying.
Lucca
The walled town most itineraries skip, and why that is a mistake.
Frequently asked questions
What is the best time to visit Tuscany?
May, June and September. April and October are quieter and still pleasant but you risk rain. July and August are hot, crowded and expensive, with the added problem that many family-run places close for their own holidays in mid-August.
Do you need a car in Tuscany?
For Florence, Siena, Pisa and Lucca, no: the train connects all four and parking in the centres is restricted anyway. For the hill towns, Val d’Orcia and the wine regions, yes. Public transport reaches them in theory and on a timetable that makes day trips impractical.
How many days do you need in Tuscany?
Five to seven for a first trip that includes Florence. Three days in Florence and three or four moving around the region is the split that works. Anything under five and you are choosing between the cities and the countryside rather than seeing both.
When should I book a villa in Tuscany?
By January for July and August. The properties with a pool, a view and space for a group are a limited stock and they are taken early. For May, June and September you have until around March before the good ones thin out.
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