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- Going on a scenic road trip in Tuscany is absolutely a bucket list experience! With medieval hilltop towns, rolling hills, gorgeous vineyards and even enchanting hot springs, this region is one of the best places to go in Italy.
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Apr 12, 2023 · Planning an epic Tuscany road trip? This Tuscany itinerary + travel guide is designed to help your trip to Tuscany go off without a hitch!
- Florence to San Gimignano. Leave Florence, with an optional stop at Castello di Poppiano. Start your trip around the gorgeous Tuscan countryside in the morning, bright and early so that you don’t miss out on any of this trip’s glory!
- San Gimignano to Siena. Finish up in San Gimignano and (optionally) make a visit to Certaldo. Spend the morning of your second day exploring the sights you didn’t get to see in San Gimignano.
- Montalcino to Montepulciano. Make your way to Montalcino. From Siena, start driving south toward the small town of Montalcino, better known for its signature wine, Brunello di Montalcino.
- Chianciano Terme to Arezzo. Make a brief stop at the Sanctuary of the Madonna. Start your second to last day of the Tuscany road trip by visiting the Sanctuary of the Madonna di San Biagio, just outside Montepulciano.
- Day 1 – Florence or Pisa. It’s the first day of your 5-day Tuscany itinerary; welcome to Italy! You’ve likely begun your trip in the beautiful cities of Florence or Pisa, so spend at least a day exploring before heading off to Siena.
- Day 2 – Siena, Tuscany. This charming and atmospheric city, with its steep, winding, cobbled streets and dusty-colored houses, is a must-see on your Tuscany road trip!
- Day 3 – Pienza or Montepulciano. Both these beautiful hilltop towns are good options to add to your Tuscany itinerary, particularly as they’re only 20 minutes apart.
- Day 4 – Saturnia and Montemerano. Spend day 4 at the wonderful hot springs of Saturnia before spending the night in one of the most beautiful villages in all of Italy: Montemerano.
- Spend Time In Florence To Begin Your Tuscany Trip. You will begin and end your Tuscany road trip in Florence. This city is so beautiful and relaxed when compared to other larger cities in Italy such as Rome, Milan, and Venice.
- Visit Poppi For Your First Wine Tasting. Located around an hour and a half outside of Florence, Poppi is a stunning little gem of a city. This is your first taste of Tuscan wine culture.
- Get Cultured In Arezzo. Just 45 minutes from Poppi, Arezzo is a wonderful stop on your Tuscany road trip because there is so much to see and do!
- Experience Siena, A UNESCO World Heritage Site. Victoria grew up going to a Catholic Church called “Saint Catherine Of Siena.” Of course, the famous Catholic Saint is actually from Siena, Italy!
- Day 1: Monteriggioni and San Gimignano. Tuscany is famous for wonderful hilltop villages so what better way to start a road trip in this wonderful region that with two of the most scenic of all?
- Day 2: Siena and Bagno Vignoni. I recommend you spend your second day road tripping in Tuscany visiting Siena and then relaxing in the nearby thermal village of Bagno Vignoni,
- Day 3 Val d’Orcia: Pienza and Monticchiello. On this day, you get into the heart of Val d’Orcia, one of the most scenic areas of Tuscany. I recommend you start your thirds day in Tuscany visiting Pienza, a stunning hilltop village often refereed to as the ‘ideal city’.
- Day 4: Montepulciano and San Quirico d’Orcia. A short drive from Monticchiello lies the wonderful hilltop town of Montepulciano, maybe my most favorite of all!
Jul 5, 2024 · Tuscany, quite rightly, is one of Italy’s most popular destinations. A collection of historic towns and cities, beautiful countryside, thermal springs and of course incredible food. To see a bit of everything, you really need a car, as many of the best spots aren’t easily accessible by public transport.
Sep 17, 2022 · In this guide, you will find the must-see Tuscany locations and the best places to base yourself while traveling around the area. Moreover, I’ll share hidden gems to enrich your road trip to Tuscany and add a suggested itinerary for a fuller experience.
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