Most people who visit Tuscany never leave Florence. They do the Uffizi, they climb the Duomo, they eat carbonara in the wrong city (it is a Roman dish — but that is a different argument), and they go home certain they have seen Tuscany. They have seen a magnificent Renaissance city. They have not seen Tuscany.
The Tuscany of the postcards — the one with the cypress avenues, the medieval watchtowers, the vineyards turning gold in October, the piazzas where nothing has changed in five hundred years — is found when you rent a car and drive south. Here is how to do it properly.
Where Does the Hill-Town Route Actually Start?
The natural starting point is Florence, from which you drive south on the SR222 — the Chiantigiana road, the original route through the Chianti wine country. This is not a motorway. It is a narrow, winding road through vineyards and olive groves, past farmhouses advertising wine tastings and truffle hunts. Budget two to three hours to cover the 70 kilometres to Siena. Stop at Greve in Chianti, the unofficial capital of the Chianti Classico zone, for a morning coffee and to pick up a bottle (or three) from one of the enotecas around the central square.
The route is: Florence → Greve in Chianti → Panzano → Radda in Chianti → Siena → Montalcino → Pienza → Montepulciano → Val d’Orcia. You can compress this to three days at a sprint; five to seven days lets you actually inhabit it.
What Do You Need to Know Before Driving in Tuscany?
Italian driving is more manageable than its reputation suggests, but there are practical things to know.
ZTL zones (Zona Traffico Limitato) are the single biggest trap for foreign visitors. Every historic hill town — Siena, San Gimignano, Pienza, Montepulciano — has a restricted traffic zone in the historic centre, marked with signs and enforced automatically by cameras. If you drive into a ZTL, you will receive a fine in the mail weeks after you return home. The rule: never drive into the medieval centre. Park at the designated parking areas outside the walls and walk in. These are well-signed and usually free or very cheap.
Road quality: The SR222 and the scenic roads through the Crete Senesi are well-maintained. The smaller unpaved roads (called “strade bianche” — white roads) that connect vineyards and farmhouses are genuinely white gravel. A small rental car handles them fine; an SUV is unnecessary.
Petrol: Stations on smaller roads can be far apart. Fill up when you see one. Self-service (fai da te) pumps are common — you feed cash or card to the machine, select the pump, and dispense. The attendant-serviced pumps cost slightly more.
Speed cameras are common on the SS2 and other main roads south of Siena. Drive to the posted limits — they are enforced.
Why Is Siena Worth More Than a Day Trip?
Every guidebook tells you Siena can be done as a day trip from Florence. Every person who actually stays overnight tells you to stay overnight.
Siena’s historic centre — a UNESCO World Heritage site — is car-free, spectacularly preserved, and built on three interconnected hills, which means it is full of unexpected levels, stairs, and medieval alleyways that reveal themselves only when you wander without a destination. The Gothic Duomo is one of the most beautiful cathedral façades in Italy. The Piazza del Campo — the famous shell-shaped medieval piazza where the Palio horse race is run twice a year in July and August — deserves at least an hour of sitting and watching the light move across it.
But all of this is also true at 8 in the morning before the tour coaches arrive from Florence, and at 7 in the evening after they have left. If you stay in Siena — and there are excellent mid-range hotels and agriturismo options within the walls — you get those hours. The day-trippers do not.
The Contrade (the seventeen neighbourhoods whose rivalry drives the Palio) each have their own museum, church, and fountain, and wandering into the quieter contrade in the eastern part of the city is how you see Siena properly.
What Is the Val d’Orcia, and Is It Worth the Detour?
The Val d’Orcia is a UNESCO-listed valley south of Siena, and it is the Tuscan landscape that has been reproduced on a million calendars. Gentle hills, cypress trees lining dirt roads up to isolated farmhouses, ochre soil, and the kind of light at golden hour that photographers spend weeks chasing. The towns that anchor it — Pienza, Montalcino, and Montepulciano — are among the best-preserved hill towns in Italy.
Pienza was redesigned as a Renaissance ideal city by Pope Pius II in the 1460s: a perfect piazza, a cathedral, and a papal palace laid out according to humanist principles. It is tiny (you can walk the whole town in 30 minutes), but its Pecorino di Pienza — a sheep’s milk cheese that ranges from young and creamy to aged and sharp — is reason enough to stop.
Montalcino is a wine town. It produces Brunello di Montalcino, one of Italy’s most age-worthy and expensive red wines. The Fortezza (a 14th-century fortress with a wine bar inside the walls) is the obvious place to try it; the enotecas around the main square are less touristy and equally good.
Montepulciano is larger, hillier, and produces Vino Nobile di Montepulciano — another Sangiovese-based wine, slightly more accessible in youth than Brunello. The town climbs steeply uphill to the Piazza Grande, a large medieval piazza with a cathedral, a tower you can climb, and a view south into the Val d’Orcia that justifies the climb absolutely.
Where Should You Actually Stay?
For a hill-town circuit, staying in towns rather than Florence is strongly advisable. The options:
Siena (2–3 nights): The logical base for the northern section of the route. Hotels within the walls — even mid-range — are genuinely atmospheric. The Leonardo Boutique Hotel and Hotel Athena are reliable mid-range choices; the area around the Duomo has several smaller B&Bs and rooms in private palazzos. Booking.com (aid=2778866) has solid coverage of Siena accommodation including options within the ZTL walls for those who have confirmed parking.
Agriturismo in the Crete Senesi or Val d’Orcia (2–3 nights): A working farm that rents rooms — Tuscany has hundreds of them, ranging from basic country rooms to boutique operations with pools and organic restaurants. Staying at an agriturismo means waking up to vineyard views, eating dinner made from the farm’s own produce, and having a glass of local wine before the sun sets. Booking through Booking.com or directly with the property (many have their own websites) is equally reliable; emailing directly sometimes gets a slightly better rate.
Montepulciano or Pienza (1–2 nights): For the southern end of the route before heading back north or continuing to Rome or Umbria. Both are small, both have accommodation within the walls, and both are genuinely beautiful places to wake up in the morning.
Is San Gimignano Worth It?
San Gimignano — the hill town famous for its medieval towers (13 survive out of an original 72) — is on every Italy itinerary and in summer is genuinely overrun. The town itself is beautiful; the experience in July and August is of being moved through it in a slow river of tourists.
The honest answer: yes, if you go early (park and enter the Porta San Giovanni by 8:30am) or in shoulder season. If you arrive mid-afternoon in August, you are visiting a human traffic jam with a beautiful backdrop. The gelato from Gelateria Dondoli on the main square has won international awards and is worth whatever the queue throws at you.
How Does This Route Connect to the Rest of Italy?
The hill-town circuit is naturally sandwiched between Florence and Rome. From Montepulciano or Orvieto (just over the Umbrian border, worth a night), Rome is two to two and a half hours south on the A1. Florence is two hours north. If you fly into Rome and out of Florence (or vice versa), this route fits perfectly as the middle section of a two-week Italy trip — completing our guide to Tuscany and then continuing either to the coast or north to Bologna.
For the coastal alternative, see our full breakdown of the Amalfi Coast vs Cinque Terre.
Build a customised Tuscany route with the AI Trip Planner — it can factor in your start and end cities, travel dates, and how many days you want to spend at each stop.
Explore more: Tuscany · Florence · Siena · Rome
Also on the blog: Italy Rail Pass vs Point-to-Point Tickets: The Honest Answer · Best Italian Food by Region