Autumn in Tuscany is all about asphalt and open windows. The crisp air carries the sharp scent of fermenting must and burning olive wood, while the endless curves of Chianti transform into a gallery of yellows and reds. Driving here in late October means embracing a landscape that has finally shed the tourist buses and oppressive heat, leaving only the hum of the engine and quiet medieval squares. It’s the perfect time to hit the road.
On the road, I’ve found that there’s no better way to experience this land than by following your instincts among cypress trees and isolated chapels. Each curve offers a different view, and every stop at a countryside inn invites you to slow down. Ready to set off? Here’s your day-by-day itinerary, packed with practical tips and secret addresses known only to locals.
Ready to hit the road? Here’s your day-by-day itinerary, filled with practical advice and secret spots that only locals know. If you want to soak in the atmosphere of the Renaissance cradle before you start driving, kick off your journey by meandering through the monumental avenues and historic trattorias described in our guide to Florence in autumn.
Day 1: Florence – Art and Gastronomy#
- Morning: Start your journey in Florence. Park your car in one of the underground lots near Piazzale Michelangelo (like Garage Michelangelo) to avoid city traffic.
- Must-see: Visit the Duomo, Ponte Vecchio, and the Uffizi Gallery. Book your tickets in advance to skip the long lines.
- Lunch: Stop by Trattoria Mario, close to the Central Market, for a mouthwatering Florentine steak.
- Afternoon: Stroll through the Boboli Gardens and enjoy the autumn colors.
- Night: Stay at an agriturismo just outside the city for an authentic atmosphere and an easy start the next day.
Day 2: Florence – Chianti – Siena#
- Morning: Leave early to explore the Chianti Road (SR222). This stretch is a dream for driving enthusiasts, with gentle curves and picturesque villages like Greve in Chianti and Castellina in Chianti.
- Tip: Stop for a wine tasting at one of the local wineries. I recommend Castello di Brolio, which offers spectacular views of the vineyards.
- Afternoon: Arrive in Siena and park at Parcheggio Santa Caterina, just a short walk from Piazza del Campo.
- Must-see: The majestic Siena Cathedral and, if you have time, climb the Torre del Mangia for a stunning aerial view.
- Dinner: Try the ribollita soup or pici cacio e pepe at Antica Osteria da Divo.
- Night: Stay in a B&B steps from Piazza del Campo to enjoy the charm of this medieval city.
Day 3: Siena – San Gimignano#
- Morning: From Siena, drive north to San Gimignano, the famous tower town. The best parking is at Parcheggio P1 Giubileo, but arrive early as it fills up quickly.
- Must-see: Wander through the medieval streets, discover Piazza della Cisterna, and climb the Torre Grossa for an incredible view.
- Lunch: Don’t miss a gelato from Gelateria Dondoli, considered among the best in the world.
- Afternoon: Explore the artisan shops, and if you enjoy white wine, try the Vernaccia di San Gimignano.
- Night: Stay at one of the nearby wineries for a unique experience.
Day 4: Volterra – Pisa#
- Morning: Drive to Volterra, another formidable stone outpost. Its ancient walls and Roman Theater will take you back in time.
- Lunch: Enjoy a plate of wild boar stew at La Vecchia Lira.
- Afternoon: Continue to Pisa. Park outside the center, perhaps in Piazza Vittorio Emanuele II, and walk to Piazza dei Miracoli.
- Must-see: The Leaning Tower of Pisa, the Cathedral, and the Baptistery. I recommend booking tickets online to climb the tower.
- Night: Stay in a hotel near the historic center or at an agriturismo nearby.
Day 5: Lucca – Montecatini Terme#
- Morning: After a short drive, reach Lucca, the city of walls. You can even rent a bike to ride along them!
- Must-see: Piazza dell’Anfiteatro, the Guinigi Tower (with a garden on top!), and the historic center’s charming streets.
- Lunch: Stop by Trattoria da Leo, famous for its tordelli lucchese.
- Afternoon: Head to Montecatini Terme for a relaxing afternoon at the historic spas, like Tettuccio.
- Night: Choose a spa hotel for a night of pure relaxation.
Day 6: Val d’Orcia – Pienza – Montepulciano#
- Morning: Depart for the Val d’Orcia, a UNESCO World Heritage site. The roads here seem painted, with cypress trees lining every curve.
- Must-see: Visit Pienza, famous for its pecorino cheese, and Montepulciano, renowned for its wines like Vino Nobile.
- Lunch: Savor pici all’aglione and a glass of Brunello at La Grotta in Montepulciano.
- Tip: Avoid parking too close to the historic center; it can cost a fortune!
- Night: Stay in a stone farmhouse with views of the hills.
Day 7: Arezzo – Return Home#
- Morning: Conclude your journey in Arezzo, a city often overlooked but rich in artistic details ignored by the crowds.
- Must-see: Piazza Grande, the Church of San Francesco with Piero della Francesca’s frescoes, and the Cathedral.
- Lunch: Dine at Trattoria Il Saraceno, a historic spot with authentic Tuscan cuisine.
- Practical Tip: If you have a flight from Florence or Pisa, allow at least 1 hour and 30 minutes for the return.
- My pet peeve: Watch out for roundabouts here—if everyone used their turn signals, we’d spend much less time on the road!
Practical Tips for Your Road Trip#
- When to go: Autumn is perfect for nature’s colors and avoiding summer crowds.
- Car rental: Opt for a compact car for the narrow country roads. Always check that the vehicle is in good condition before you set off.
- Toll booths: Always carry coins or a card for tolls, as some booths don’t accept cash.
- Parking: Keep an eye on parking signs. Many historic centers have limited traffic zones (ZTL), and fines are no joke.
Tuscany is a land that speaks to the heart of anyone who loves road travel. The beauty of this itinerary is that it’s not just about reaching a destination, but enjoying the journey itself. Jump in your car, turn up the music, and get ready to discover the true essence of this unique region.
Safe travels, and… see you on the road!