This is an itinerary I’ve put together and am hoping to do soon! This trip consists of making a 6-day road trip loop in Tuscany – exploring classic Tuscan hilltop towns, vineyards and restaurants along the way. The photos I’ve included are from when I studied abroad in Florence and did a bit of traveling around Tuscany in 2005 which has really fueled my desire to go back and spend more time exploring Tuscany.
DAY 1 /Arrive Florence
DAY 2 / Florence
- Some of the fun stuff in this itinerary: Florence
DAY 3 / Rent Car and Drive to Volpaia
- Late Morning: Check into Hotel Podere Terreno
- Afternoon:
- Explore grounds of hotel and relax
- If you feel like leaving, explore nearby towns of Chianti region:
- Greve
- Wine taste at Enoteca Falorni
- Radda
- Greve
- Dinner: Make sure you’re a carnivore before arriving at Officina della Bistecca in nearby Panzano (20 minutes from hotel)
DAY 4 / Wine and Cheese Tasting on the way to Panicale
- Late Morning: Drive to Montalcino and explore the town
- Wine Tasting: Castello Banfi / Castello di Poggio alle Mura
- Open 7 Days a week, Winery Tours available by appointment
- Wine Tasting: Castello Banfi / Castello di Poggio alle Mura
- Afternoon: Cheese Tasting and Explore Pienza
- Podere Il Casale Cheese Farm – Visit the Farm and do cheese tasting
- Bagni di San Filippo – Outdoor hot spring which can be found by walking on a beautiful trail into the woods, and enjoying the warm pools (free of charge!).
- Late Afternoon/ Evening: Arrive and Explore Panicale
- Dinner at slow-food-style restaurant : Lillo Tatini
- Accommodations: Pre-Book AirBnb or VRBO within the city.
DAY 5 / Panicale and Day trip to Montepulciano
- Late Morning: Drive 45 min from Panicale to Montepulciano
- Explore Montepulciano
- Wine Tasting at: Avignonesi at Fattoria La Capezzini
- Lunch Break: Fattoria Pulcino
- More Wine Tasting: Poliziano
- Afternoon: Return to Panicale
- Evening: Dinner in Panicale at Masolino
DAY 6 / Make your way back to Florence with a stop in Bucine
- Bucine:
- Wine Tasting Stop at Poggio Molina
- Lunch: Cucina Donna Luisa Restaurant at Il Verreno
- Evening: Overnight in Florence
DAY 7 / Travel Home
The drive will look a bit like this:
bikesandbordeaux.com 
First, let s see the list of the beautiful villages I recommend; among them the ones you shouldn t miss are San Gimignano, Monteriggioni, Pienza, Montepulciano and possibly Pitigliano, though this last one is a bit further away considering your route from Tuscany to Rome. The map in this recent post about the most scenic drives in Tuscany can help you give an idea on your possible road itinerary through the region up to Rome. While this interesting road trip from Rome to Tuscany and back can give further ideas of special places to visit.
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