Cypress trees in Tuscany Italy at sunset

A Taste of Tuscany: Self-Drive Itinerary for a Day Trip from Florence to Chianti and Val d’Orcia

Looking for a fun day trip from Florence? Immerse yourself in the dreamy Tuscan landscape surrounding Val d’Orcia and Chianti!

If you are a regular Yoga, Wine & Travel reader then you’ll know that I can occasionally get carried away and slightly overambitious when it comes to itinerary planning. There’s so much of the world to see, and so little time to see it all! So it should come as no surprise that I once again went a little overboard during our latest trip back to Italy.

Val d'Orcia landscape in Tuscany Italy with text overlay Val d'Orcia landscape with rows of cypress trees in Tuscany Italy with text overlay Vineyards in Chianti Italy with text overlay Castle in Chianti Tuscany Italy with text overlay

Though I had been to Florence a handful of times, I had yet to see the rolling hills and vineyards in the heart of Tuscany. So what does one do when faced with the choice between embarking on a day trip from Florence to Chianti or a day trip from Florence to Val d’Orcia?

Vineyards in Chianti Italy

What any insane, overly ambitious person would do: choose both! Is it ideal? Probably not, but we were short on time and had a full day (and full hearts) to spare in Florence.

Rolling hills in Val d'Orcia in Tuscany Italy

Though you may only get a tiny taste of Tuscany, driving from picturesque town to town, eating delicious Italian fare and drinking mouthwatering Tuscan wine is a fantastic way to spend 1 day if you’re looking for a fun day trip from Florence. If you’re looking for an easy-to-follow itinerary through Chianti and Val d’Orcia, read on!

Italy may be compact and easy to travel around, but each region is unique in its own way – you’d need a lifetime to experience everything it has to offer! Read more on what to know about Italy before you visit here.

Where is Chianti? Where is Val d’Orcia?

View from Panzano in Chianti Italy

Chianti and Val d’Orcia are two famous regions within Tuscany. Florence, Tuscany’s capital city, is one of the most popular destinations in Italy and renowned for its Renaissance art, architecture and culture. Both Chianti and Val d’Orcia are located south of Florence, with Chianti being most well-known for the ruby-red wine from the region, and Val d’Orcia for its UNESCO-listed landscape.

Sangiovese grapes in Chianti Italy

Chianti is located approximately mid-way between Florence and Siena and encompasses a number of small towns including Greve, Panzano, Castellina, Radda and Gaiole. It is home to several world-class wineries and vineyards, most of which have restaurants or cellar doors that you can visit.

Val d’Orcia is located even further south, about 2 hours away by car from Florence. The main towns in the region include San Quirico, Castiglione, Pienza, Monticchieloo and Montepulciano. The landscape features iconic rolling hills, farmhouses, cypress trees and even fortresses.

Most of the time, people visiting Chianti or Val d’Orcia will choose to spend a few nights in either region (at the very least), and venturing out to wineries for meals and wine-tasting, or to other towns for sightseeing. For those of you who want to have your lasagne and eat it too, read on for how to visit both Val d’Orcia and Chianti in 1 day!

Love visiting wine regions around the world? Here are some stunning wine regions that will spark your wine-derlust!

How to get around Tuscany

Rental car in Tuscany Italy

You could go an organized Chianti tour from Florence (and there are tons of Tuscany tours from Florence) where transportation is taken care of, but if you enjoy the flexibility that comes with having your own car then I highly recommend renting a car to drive to the vineyards near Florence and explore the greater Tuscany region. However, driving in Italy comes with some, shall we say, unique issues.

If you Google “renting a car in Florence” you will see tons of information about the “ZTL” restricted traffic zone. This type of traffic zone is not uncommon across Italy, especially in busy cities with small historic centres – they are designed to limit the amount of vehicle traffic as streets can be narrow, and there are often many pedestrians out and about. In order to drive in Florence’s ZTL area you must have a special permit, or the car rental agency has to make arrangements to report the rental vehicle’s license plate to the police so that you don’t get slapped with a fine.

When we looked into renting a car in Florence we read horror story after horror story of people accidentally entering the ZTL and receiving a fine of a few hundred Euros in the mail months after their trip. In addition, the car rental offices within Florence’s city centre had, quite frankly, horrific reviews, and parking can be expensive or a bit tricky as most places ask that you leave the keys so that they can move your car around the garage if needed. If there’s any damage they are unlikely to assume responsibility. So, what is your best option if you only need a car for the day in Florence? Rent from outside the city to avoid the ZTL zone and penalties.

Driving in Tuscany Italy

Here’s what we did to rent the car from Florence Airport, about 20 minutes by bus from the SMN train station downtown:

  • Take the airport bus from the bus terminal at 17 Via Santa Caterina da Siena. Location here. Buses leave every 30 minutes and cost 6 Euros each way – buy your ticket directly from the driver. Alternatively, you can take a taxi which will cost approximately 22 Euros (with surcharges for luggage and/or rides between 10 PM and 6 AM).
  • Follow the signs at the airport to the car rental shuttle bus which will take you to the car rental depot near Florence Airport.
  • We rented our car from B-Rent and paid 40 Euros for the day + 30 Euros extra to reduce the excess to $0 (AKA deductible). The B-Rent guys were truly fantastic and upgraded us to a slick new Mercedes Benz as well. As the rental was for a full 24 hours, we just dropped the car off in the evening and left the keys in their dedicated key drop-off box. Click here to check current rental car prices – bookings can be cancelled or amended if your plans change!
  • If you plan on stopping at some wineries make sure the driver limits their intake or have a designated driver, as the BAC limit in Italy is very low.
  • The road conditions are great with limited toll stops, and the speed limit is anywhere from 40-90 KM/hour on smaller roads or 90-130 KM/hour on highways.
  • If you are prone to motion sickness you’ll definitely want to pop a dramamine!
  • You may also need an international driving permit.
  • The cell signal is patchy through Tuscany’s wine country, so I recommend downloading offline maps.

Where to stay in Florence

Duomo reflection in wineglass in Florence Italy

Florence is an incredible city in its own right, but also a fantastic base for day trips out to Siena, Pisa, Cinque Terre, Lucca, Chianti or Val d’Orcia. Here are some tried-and-tested places to stay in Florence!

Hotel Calzaiuoli is a 2-minute walk away from the Duomo Complex and one of the best luxury hotels in Florence. The staff are extremely friendly and accommodating, the rooms are bright, comfortable and spacious, and the location just can’t be beat if it’s your first time to Florence. Click here to book your stay at Hotel Calzaiuoli!

La Tana Dei Leoni is a small guesthouse right in front of the Ponte Vecchio. The rooms and bathrooms are extremely spacious, and the value for money is fantastic given its convenient location. Some rooms even offer a small private balcony overlooking the Ponte Vecchio. Click here to book your stay at La Tana Dei Leoni!

Agnolo is a 2-bedroom apartment in the Santa Croce district of Florence. It is perfect if you are traveling with friends or family as the apartment has a kitchen, 2 bedrooms and 2 bathrooms as well. Click here to book your stay at Agnolo in Florence or check out some other accommodation options in Florence here.

For even more Italy accommodation recommendations head on over here.

1 day Florence to Chianti and Val d’Orcia Itinerary

Vineyards in Chianti Italy

The Tuscan landscape can only be described as dreamy. Warm tones fill every corner of your eye, and you won’t even know where to look as the road winds and weaves ahead of you. Is it possible to visit Chianti and Val d’Orcia in 1 day? Yes, but this itinerary requires a bright and early start to pick up your rental car from Florence International Airport, and will get you back home late in the evening.

To give you an idea, we left the apartment at 8 AM in the morning and didn’t get back until about 11 PM. This itinerary will give you an idea of where to go and where to stop, but feel free to make modifications as needed.

Note: Staying in Siena? You can also use this itinerary for ideas on where to go in Chianti and which towns to visit in Val d’Orcia! It’s also possible to visit both Chianti and Val d’Orica from Siena in 1 day if you limit the number of stops – you can expect to cover approximately 200 kilometres and spend around 3-4 hours on the road in total.

1. Head towards Greve in Chianti

Castello di Verrazzano near Greve in Chianti Italy

Once you’ve picked up the rental car from Florence Peretola Airport, drive 45 minutes or so towards Greve in Chianti. I recommend heading straight to Castello di Verrazzano near Greve for lunch.

Walking among vineyards in Chianti Italy

The elegant castle was once an Etruscan settlement before it became a Roman one, and wine-making has been a longstanding tradition over the past few centuries. It is surrounded by lush Chianti vineyards that this postcard-perfect region is famous for.

Castello di Verrazzano Hosteria near Greve in Chianti Italy

Verrazzano offers guided tours or you can stop by for lunch and a wine flight of your choosing – bookings are essential if you want a table in their stunning dining room!

2. Explore Greve

Greve in Chianti Tuscany Italy

Greve is sometimes described as the “Gateway to Chianti” and is one of the larger towns in the Chianti region. From Verrazzano, the drive will take you no longer than about 10 minutes – you can park your car in a parking lot just outside the main square.

Shops in Greve in Chianti Italy

Piazza Matteotti is the main square in Greve with a handful of local cafes, bakeries and boutiques. Though small, it is an easy-to-visit and charming town that is representative of Italian life in the region. We stopped for just under an hour to try out some handmade pastries and a much-needed cappuccino.

Not keen on Greve? You can also make a quick pit stop in Radda or Castellina.

3. Check out the view from Panzano

View from Panzano in Chianti Italy

Head south from Greve towards Panzano, about 15 minutes away by car. Panzano is a hilltop town in Chianti that, much like Greve, is compact but convenient with its own town square, supermarkets, butcher shops and so on. Its strategic location overlooking the valleys of vineyards makes it a perfect photography stop for views like this.

View from Panzano in Chianti Italy pano shot

It goes on for days.

Vineyards and landscape in Tuscany Italy

No seriously, you’re going to need to pick your jaw up off the floor.

4. Check out San Quirico d’Orcia

San Quirico d'Orcia in Tuscany Italy

Next up is the beginnings of your time in Val d’Orcia. From Panzano, the drive to San Quirico will take 90 minutes or so, so strap in and enjoy the scenic ride. Free parking is available just outside the town square.

Horti Leonini in San Quirico d'Orcia in Tuscany Italy

San Quirico features an enchanting historic centre and Renaissance-era gardens (Horti Leonini), as well as the beautiful Church of Santa Maria Assunta.

Church of Santa Maria Assunta in San Quirico d'Orcia ITaly

Our time in San Quirico was short but sweet, and I’ve made a mental note to head back to explore more of this town on a future trip!

5. Visit the Cappella della Madonna di Vitaleta

Cappella della Madonna di Vitaleta in Tuscany Italy

This tiny chapel might possibly be the most-photographed chapel in the world. It is located just outside of San Quirico d’Orcia, and is believed to be built upon the spot where the Virgin Mary appeared to a shepherdess. The chapel can be reached by foot from parking lots on either end – the stroll should take no longer than a few minutes’ time.

Cappella della Madonna di Vitaleta in Tuscany Italy

If you are on schedule, you should be able to visit the Cappella just as the sun is beginning to set – the effervescent glow that streaks across the Tuscan sky makes for a perfect backdrop against the iconic chapel!

Valleys in Val d'Orcia in Tuscany Italy

6. Finish the day in Montepulciano

Valleys in Val d'Orcia in Tuscany Italy

By this time you should be getting ready to wrap up your day in the Tuscan countryside. Make your way towards Montepulciano, another landmark town within the Val d’Orcia region. The drive from the Cappella della Madonna di Vitaleta to Montepulciano will take just over 30 minutes, which gives you just enough time to work up an appetite for dinner. The drive along the SP146 road is probably one of the most scenic drives of the region, so enjoy the ride!

Montepulciano Piazza Grande in Tuscany Italy

Montepulciano is a medieval fortress-esque hilltop town that features a commanding tower, palazzo, duomo and cobblestone walking paths. The car-free town offers several parking areas just outside the city centre – we parked for free in this parking lot – parking within the white lines is for visitors, and those within the blue lines is for residents.

Streets of Montepulciano in Val d'Orcia Italy

Treat yourself to a tasty Tuscan dinner at Trattoria di Cagnano, just steps away from the Piazza Grande. This charming restaurant has a diverse menu that will please even the pickiest of eaters – try the hearty vegetable soup and fresh pasta!

Truffle tortellini in Val d'Orcia Tuscany Italy

After dinner, slowly mosey back towards Florence to drop off your rental car. Have more time? Turn this into a multi-day itinerary by spending 2 nights in Chianti and 2 nights in Val d’Orcia!

Ready to plan your epic day trip through this stunning wine region? If you are staying in Florence I recommend staying at Hotel Calzaiuoli, a 2-minute walk away from the Duomo Complex and one of the best luxury hotels in Florence. Click here to book your stay at Hotel Calzaiuoli! Traveling with friends or family? Check out Agnolo, a 2-bedroom apartment in the Santa Croce district of Florence. The apartment has a kitchen, 2 bedrooms and 2 bathrooms as well. Click here to book your stay at Agnolo in Florence or check out some other accommodation options in Florence here.

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I hope this Tuscany itinerary helps you to plan a perfect trip to some of its most picturesque regions! As with any travel guide, this is designed to give you some ideas and suggestions – feel free to modify it to better suit your travels. If you found this helpful please share it with friends or family, or pin it for later!

This article contains affiliate links. If you choose to book using these links, I will earn a small commission at no extra cost to you. Thank you for supporting my website by using these links, I only recommend products or services that I have personally used & hotels I have stayed at and loved.

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