Drive the hidden side of Tuscany in nine days: Florence, Etruscan Cortona, cliff-top Pitigliano, ancient Volterra and walled Lucca on a loop most visitors never discover.
Most Tuscany road trips follow the same loop: Florence, Siena, the Val d'Orcia, back through Chianti. It is a wonderful route. But there is another Tuscany, just as beautiful and far less crowded: the eastern Val di Chiana plains, the Etruscan cities of the Maremma, the cliff-carved towns of the tufa plateau. This nine-day Tuscany road trip itinerary covers that other side.
This is not a route you can do by train or bus. The best moments happen on empty provincial roads between small towns: the approach to Pitigliano around a bend when the town suddenly appears above the cliffs, the drive into Volterra as the walls come into view across the ridge, the descent from Cortona through olive groves at golden hour. A car is the only way to experience these places properly.
Florence is the obvious start: the best airport, the largest car hire selection, and two full days of things to see. The Uffizi Gallery is the centrepiece of any first morning. Arrive as it opens, tickets pre-booked, and the Botticelli rooms are manageable; arrive late without a booking and the queue stretches back past Piazza della Signoria.
Spend the afternoon in the Oltrarno neighbourhood on the south bank. The Pitti Palace, the Boboli Gardens and the craft workshops along Via Maggio have a different character from the tourist-facing north bank. In the evening, climb to Piazzale Michelangelo before sunset for the view every Florentine takes for granted.
Cortona sits 600 metres above the Val di Chiana plain, its Etruscan walls enclosing a perfectly preserved medieval and Renaissance town. The drive from Florence takes just under 90 minutes, mostly on the A1 motorway and then back roads that climb steeply through olive groves to the town gate.
The Museo Diocesano holds a Fra Angelico Annunciation that most visitors would not expect to find in a small Tuscan town. The views from the terrace above the Basilica di Santa Margherita extend to Lake Trasimeno and, on a clear day, to the hill of Assisi across in Umbria. Use the second day for a day trip to Arezzo, 30 minutes away: the Piero della Francesca fresco cycle at San Francesco is one of the great things to see in Italy.
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The drive south from Cortona is an hour and a half through the Maremma hills. Pitigliano announces itself around a bend in the road: an entire town built on and into the face of a tufa cliff, its houses rising from the rock as though carved rather than built. Nothing quite prepares you for it.
The town is small enough to walk in an hour, but the atmosphere rewards more time. The medieval Jewish quarter, established when Jewish families fled persecution in the 16th century, is one of the most complete in Italy. The restored synagogue is open to visit. In the afternoon, walk the Via Cava di San Rocco, one of the ancient Etruscan sunken pathways cut up to 20 metres deep through tufa rock. It begins just outside the town and takes 30 minutes one way.
The longest drive of the route runs northwest from Pitigliano to Volterra: nearly two hours of empty roads across the Maremma plateau before the land rises toward Volterra's ridge. Arrive in the afternoon and the light is already golden on the alabaster stone.
Volterra is three thousand years old. Its Etruscan walls predate Rome; the Roman theatre below the town dates to the 1st century BC. The medieval Palazzo dei Priori looks much as it would have in the 13th century. Spend the first afternoon in the Guarnacci Etruscan Museum, one of the best in Italy, and the morning of the second day walking the perimeter of the Etruscan wall circuit and the Balze cliffs where the ancient city has been eroding into the valley for centuries.
The alabaster craft tradition here is genuine. Workshops throughout the town produce pieces from a stone quarried in the Volterra hills since Etruscan times. The quality varies; the best pieces are expensive and worth it.
Volterra to Lucca is an hour north, through the hills and olive groves of the Pisan hinterland. Lucca's Renaissance walls are the defining feature of the city: a complete circuit of 4 kilometres, wide enough at the top for promenades, gardens and café terraces. Rent a bike from one of the hire shops at the city gates and cycle the full circuit before lunch.
Inside the walls, Piazza dell'Anfiteatro, built on the oval footprint of a Roman amphitheatre, is one of Italy's most unusual public spaces. Lucca's restaurants are seriously good and rarely mentioned in the same breath as Florentine or Sienese food. They should be.
An hour's drive east along the A11 motorway returns you to Florence. Enough time for a final coffee and pastry on Piazza della Repubblica before the airport or station.
April to June and September to October are ideal: mild temperatures, green countryside and manageable crowds. July and August are hot throughout Tuscany, and the Maremma can be particularly humid in summer. The light in October is extraordinary across the Val di Chiana from Cortona.
Tuscany's ZTL zones (Zona a Traffico Limitato) are camera-enforced in Florence, Cortona and Lucca. Park in designated car parks outside the historic centres. A fine for accidental ZTL entry arrives with the hire car company 2 to 3 months after your trip, long after you have forgotten the incident.
Book Florence museum tickets well in advance. For Cortona and Volterra, advance booking is not required but arriving early avoids the afternoon coach-tour rushes. In Pitigliano, the synagogue has limited opening hours; check in advance.
A small car navigates Tuscan hill towns considerably more easily than an SUV or estate. The access roads to Cortona and Pitigliano are narrow in places, with tight bends. Carry some cash throughout: smaller restaurants, farm shops and agriturismos often do not take cards.
A nine-day self-drive loop from Salzburg that takes in the fairy-tale lakeside village of Hallstatt, the switchbacks of the Grossglockner High Alpine Road, and Innsbruck's cable cars rising straight from the medieval Altstadt.
The full route — stops, maps, and driving times — is on Routebook by Kington.
A 9-day loop from Florence through Tuscany's lesser-trodden east and south, connecting Etruscan Cortona, cliff-top Pitigliano, ancient Volterra and the walled city of Lucca.
