Tuscany to Rome Hill Towns Road Trip
A scenic drive from Florence through Chianti, Siena, Val d'Orcia, and Civita di Bagnoregio to Rome.
Connect classic Tuscan driving with a journey south to Rome in a one-way route that avoids backtracking. Spend a day each in Florence and Rome, with three consecutive nights in the Val d'Orcia to slowly explore hill towns, cypress-lined roads, and wineries, before entering Lazio via Orvieto and Civita di Bagnoregio. Perfect for travelers who want to enjoy pastoral landscapes without looping back to the start.
The wheat fields are vibrant green in spring and golden-yellow in early summer; autumn is ideal for winery visits.
Day by day
Day 1 · Highlights of Florence Old Town
Florence & Tuscany（Florence Cathedral (Duomo)、Galleria dell'Accademia、Uffizi Gallery、Ponte Vecchio、Piazzale Michelangelo）
Explore on foot all day without a car. The historic center is a ZTL (restricted traffic zone), and walks between sights take under 20 minutes.
The Uffizi and Accademia are closed on Mondays and require advance reservations.
Stay: Santa Maria Novella and Station Area
Day 2 · Chianti Wine Country to Siena
Florence & Tuscany（Chianti Wine Region、San Gimignano、Monteriggioni）
Pick up your car outside the city and drive along the Chianti highway SR222, then detour to San Gimignano (total driving time approx. 2.5 hours).
ZTL cameras in Florence and Siena issue automatic fines; do not drive into these restricted zones.
Stay: Siena Old Town
Day 3 · Siena & the Crete Senesi
Florence & Tuscany（Siena） → Val d'Orcia（Crete Senesi、Abbazia di Monte Oliveto Maggiore）
Explore Siena on foot in the morning, then drive through the clay hills of Crete Senesi to Pienza in the afternoon (approx. 1.5 hours).
Stay: Pienza
Day 4 · Brunello & Bagno Vignoni
Val d'Orcia（Montalcino、Abbazia di Sant'Antimo、Bagno Vignoni）
Drive west from Pienza to Montalcino (approx. 30 minutes), then loop back via Sant'Antimo Abbey and the thermal village of Bagno Vignoni (total driving time approx. 1.5 hours).
Winery tastings require advance booking; drivers must not drink.
Stay: Pienza
Day 5 · Cypress Roads & Eastern Hill Towns
Val d'Orcia（Cypresses of San Quirico d'Orcia、Podere Belvedere、Cappella della Madonna di Vitaleta、Pienza、Montepulciano、Tempio di San Biagio）
Wake up early to photograph the landscapes around San Quirico, then head east to Pienza and Montepulciano. Drives between towns are mostly under 20 minutes.
Some unpaved scenic roads can be difficult to navigate after rain; do not force your way through.
Stay: Pienza
Day 6 · Orvieto & Civita di Bagnoregio
Perugia & Assisi（Orvieto） → Viterbo（Civita di Bagnoregio）
Drive from Pienza to Orvieto in about 1.5 hours, continue to Civita di Bagnoregio in about 30 minutes, and arrive in Viterbo in the evening.
Civita di Bagnoregio is only accessible via a pedestrian footbridge and requires an entry ticket.
Stay: San Pellegrino & Papal Palace Area
Day 7 · Viterbo Old Town to Rome
Viterbo（Palazzo dei Papi、San Pellegrino Quarter） → Rome（Trastevere）
Explore the Old Town on foot in the morning, drive to Rome in the afternoon (approx. 1.5 hours), return your car, and enjoy an evening stroll in Trastevere.
Return your rental car outside Rome's ring road to avoid entering the historic center's ZTL.
Stay: Trastevere
Day 8 · Rome Ruins & Departure
Rome（Colosseum、Roman Forum / Palatine Hill、Pantheon）
Walk through the Roman Forum and the Pantheon in the morning, then take the airport express train to the airport in the evening (approx. 30 minutes).
This schedule is best suited for evening flights; for morning flights, please add an extra night.