Tuscany is beautiful year-round, but fall is when the region truly shines. The rolling hills turn golden, vineyards glow with harvest colors, and medieval towns become quiet escapes away from the summer crowds. For travelers seeking authentic experiences, September to November is the perfect time to take a road trip.
This guide explores the best under-the-radar road trips to see fall foliage in Tuscany—routes that go beyond the usual Florence–Siena circuit. Expect winding drives through vineyards, hidden hill towns, local trattorias, and countryside views drenched in autumn color.
If you’ve ever dreamed of Tuscany without the tourist rush, this is your chance.
Why Choose a Fall Road Trip in Tuscany?
- Fewer crowds: Summer brings millions of visitors, but fall slows down. You’ll have quiet streets and open tables at restaurants.
- Perfect weather: Cooler temperatures (15–22°C) make driving and exploring comfortable.
- Harvest season: Wineries open their cellars, and festivals celebrate truffles, chestnuts, and new olive oil.
- Affordable stays: Hotels, agriturismos, and Airbnbs slash their rates outside of peak season.
Pro Tip: Renting a car is essential for exploring Tuscany’s countryside. You can easily compare prices and book a vehicle here.
Hidden Road Trip Routes for Fall Colors
1. Val d’Orcia: The Classic, but Quieter in Fall
The Val d’Orcia is postcard Tuscany—rolling hills, cypress-lined roads, and fortified villages. In autumn, vineyards blaze red and gold, and towns like Pienza and Montalcino host food festivals.
- Must-stop: The cheese shops in Pienza for pecorino tasting.
- Autumn highlight: Brunello harvest in Montalcino.
- Scenic drive: The SR2 road between San Quirico d’Orcia and Bagno Vignoni, lined with golden foliage.
2. Casentino Valley: Forests & Castles in Full Color
Tucked between Florence and Arezzo, the Casentino is a hidden gem of oak and chestnut forests. The Foreste Casentinesi National Park turns into a painter’s palette in October.
- Must-stop: Poppi Castle, a medieval fortress with sweeping valley views.
- Autumn highlight: Chestnut festivals in October, where locals roast fresh chestnuts.
- Scenic drive: SS310 from Stia to La Verna, winding through forested slopes.
3. Garfagnana: Untamed Tuscany Near Lucca
North of Lucca lies Garfagnana, an area often skipped by tourists. With rugged mountains, river valleys, and untouched forests, it’s ideal for fall exploration.
- Must-stop: Castelnuovo di Garfagnana, a cozy town with autumn markets.
- Autumn highlight: The foliage on the Serchio River valley framed by the Apuan Alps.
- Scenic drive: SS12 from Bagni di Lucca to Barga, one of Tuscany’s prettiest hill towns.
4. Chianti Hills: Vineyards and Wine Harvests
Chianti may be famous, but in autumn it feels different—quieter, more intimate, with grape harvests in full swing. Drive the Chiantigiana road (SR222), stopping at wineries for tastings.
- Must-stop: Greve in Chianti’s wine museum.
- Autumn highlight: Vendemmia (grape harvest) experiences—some wineries let visitors join in.
- Scenic drive: Radda to Castellina, with sweeping vineyard views.
5. Maremma: Tuscany’s Coastal Secret
For something unexpected, head to Maremma in southern Tuscany. Here, fall colors meet olive groves, wild beaches, and medieval hill towns.
- Must-stop: Massa Marittima, with its stunning cathedral square.
- Autumn highlight: Olive oil harvest festivals in November.
- Scenic drive: SP60 from Scarlino to Gavorrano with sweeping sea views.
Where to Stay on Your Road Trip
Autumn is the best time to book an agriturismo (farm stay). You’ll wake up surrounded by vineyards or olive groves, enjoy homemade meals, and often meet locals who share insider tips.
Recommended options:
- Val d’Orcia: Agriturismo Il Rigo (rustic farmhouse with views)
- Casentino: Borgo Corsignano (luxury cottages near forests)
- Chianti: Castello di Verrazzano (historic wine estate with tastings)
Many of these stays are available on Booking.com and Airbnb.
What to Eat and Drink Along the Way
Fall is Tuscany’s richest culinary season. Be sure to taste:
- Porcini mushrooms: Found in risotto, pasta, or grilled.
- Chestnuts: Roasted or in cakes (castagnaccio).
- Truffles: Especially white truffles in San Miniato (November).
- New wine & olive oil: Fresher than you’ll ever find outside Tuscany.
Don’t miss stopping at local trattorias along your route—this is where Tuscany’s autumn flavors shine.
Helpful Apps for Your Road Trip
- Google Maps / Maps.me: Download offline maps before you drive.
- Rome2Rio: For backup if you need to connect buses or trains.
- The Fork: To reserve tables at restaurants, especially in smaller towns.
- GetYourGuide: For booking harvest tours, wine tastings, or guided walks.
Safety & Practical Tips
- Drive during daylight: Rural Tuscan roads can be winding and dark at night.
- Plan ahead for festivals: Locals greatly enjoy the autumn harvest events.
- Pack layers: Days can be warm, but nights drop quickly in temperature.
- Fuel stations: Some countryside towns have limited hours—fill up in advance.
Sample 5-Day Fall Foliage Road Trip Itinerary
Here’s a balanced itinerary to cover Tuscany’s hidden gems in autumn.
Day 1–2: Val d’Orcia
Explore Pienza, Montalcino, and the Bagno Vignoni hot springs.
Day 3: Casentino Valley
Drive to Poppi, hike in Foreste Casentinesi.
Day 4: Chianti Hills
Wine tastings along SR222, overnight in Greve.
Day 5: Maremma Coast
Finish with Massa Marittima and coastal drives.
Final Thoughts
Tuscany in the fall is a dream. The crowds vanish, the landscapes transform, and the food and wine are at their peak. By choosing under-the-radar foliage road trips, you’ll see Tuscany in a way few travelers do.
Ready to plan your trip? Start by booking your rental car here [affiliate link], and map your autumn adventure across Tuscany today.
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