Epic One Day Road-Trip in Chianti Tuscany Itinerar...

Epic One Day Road-Trip in Chianti Tuscany Itinerary

Radda in Chianti Tuscany Italy Road Trip Wine Road

Road-Trip Chianti, Tuscany

Chianti Road Trip Tuscany Italy Landscape

I recently embarked on a Tuscan road-trip, drove through the rolling hills of Chianti in a quintessential Italian car – in this case, a Fiat – and stopped at one-too-many spots to frolick in the vast vineyards under the Tuscan sun. It was my dream for the longest time. I’m happy that I have finally checked that off my bucket list! It may sound cliché, but it was every bit as dreamy as I have imagined it.

My journey began in Florence where I arrived at the Santa Maria train station from Milan. I made my way by taxi – you can also take the bus – to the car rental by the airport. I rented an automatic Fiat 500 with Sicily Car despite their alarming reviews. Fortunately, everything went smoothly with them. I also picked up a hotspot device at the Sicily Car rental – lifesaver! And off I went to the Tuscan villa.

Fiat Tuscany Road Trip Chianti

As a driver in Miami, I was somewhat prepared for the chaos that it is to drive in Florence. But oh, boy, if it wasn’t horrifying – keep in mind, it was also my first time driving abroad. The nerve-wracking drive out of Florence eased as soon as the Tuscan scenic landscape started to emerge -the tall trees and the narrow roads led me to my home away from home. I couldn’t believe I was finally doing it – Road tripping in Tuscany. As I entered the town San Casciano in Val di Pesa where the villa is, I spotted from afar the peach color building on top of the hill amid its vineyard. I couldn’t resist but to stop and snap a few photos.

Chianti Tuscany Villa Mangiacane Tuscan Villa Luxury Hotel in Tuscany

Tip – You don’t need to rent a car in Tuscany.You can hire a private driver, go on tours, or take public transportation – I do not recommend the latter as buses run few in between especially during school break.

Chianti is located within the region of Tuscany, occupying the territory between Florence, Siena, and Arezzo. Simply put, it’s the heart of Tuscany. If you are a wine lover, you will know that Chianti is also synonymous with excellent wine. The town San Casciano in Val di Pesa is located near the border of Chianti, 30 minutes away from Florence.

Villa Mangiacane

Villa Mangiacane Chianti Tuscany

The Tuscan villa is not only beautiful but also rich in history. The Machiavelli family built the property in the 15th century and designed with the help of Michelangelo.

Villa Mangiacane – Luxury Villa in Chianti

15th Century Tuscan Villa

As I drove past the gate, I couldn’t believe how beautiful the place was. After exploring the Tuscan villa’s beautiful olive garden and vineyard, I had dinner at their restaurant. I was planning to explore San Casciano in Val di Pesa and find a local restaurant, but the chef lured me in with his enticing truffle menu. I gave the chef carte blanche and prepared a 4-course menu with locally sourced ingredients, making sure that black truffle was the star of each dish.

Villa Mangiacane Luxury Villa in Chianti Tuscany |

Villa Mangiacane Luxury Villa in Chianti Tuscany |

Villa Mangiacane Restaurant – Menu

Villa Mangiacane Luxury Villa in Chianti Tuscany |

Fresh pecorino
Black truffle with honey
Locally sourced
Paired with Villa Mangiacane Chianti Classico 2013

Fresh pasta with white Truffle paste and black truffle
Paired with Villa Mangiacane Chianti Classico – Riserva 2012

Veal Pancetta
Zucchini tomato
Black truffle
Paired with Villa Mangiacane Aleah

Mascarpone semifreddo with rosemary and orange peel
Paired with Villa Mangiacane Il Cardinale Vin Santo del Chianti Classico

Tip – If you are looking for the best Chianti wine in the region, look for the Consorzio Chianti Classico’s seal of approval – or the famous black rooster symbol.

Day Trip in Chianti Tuscany

Chiantigiana Tuscany Chianti Tuscan Town

The Chiantigiana highway

The via Chiantigiana – the road connecting Florence to Siena or SR 222 – is one of the most scenic routes in Italy. Driving through acres of vineyards, idyllic towns, historical abbeys, and churches, will make you fall in love with Tuscany – if you haven’t yet. Road tripping on such a scenic route made it almost impossible to stick to a schedule.

Chianti Tuscany Road Trip Chianti Wine Road

Tip – If you are embarking on a road-trip, make sure to have a navigation system. Roads can be tricky to navigate. I rented a pocket Wi-Fi device, and Google Map was a lifesaver.

You could easily do the Chiantigiana road-trip in one day if you start early. But if you are like me, stopping every chance I got to enjoy the Tuscan landscape and stroll through the medieval streets – can you blame me?- consider adding a few extra days to your itinerary.

Greve in Chianti

Greve in Chianti - Tuscany - Chianti Road Trip

The main attractions of this charming town are the monastery and the main plaza. As soon as I arrived, I parked the car up a hill and made my way down while contemplating the beautiful scenery. The town, although small, is full of charm. I enjoyed walking around it as the locals go about their day.

Every year, Greve hosts the Chianti Classico Wine Festival in September. Local merchants showcase their products and tasting is free! All you need is to purchase a glass. If you are around the area, make sure to stop by the event.

Greve Chianti Tuscany Italy Road Trip

Greve Chianti Tuscany Italy Road Trip

Greve in Chianti - Tuscany - Italy

Tip – If you have extra time, pack a picnic basket and stop at one of the many scenic locations and enjoy the breath-taking Tuscan landscape.

Radda in Chianti 

Radda in Chianti Tuscany Italy Road Trip Wine Road

Radda was my favorite place in Chianti. A large defensive wall surrounds the beautiful medieval town. With the area enclosed, the quaint alleys, and tall medieval buildings, the charming place transports you back in time. While the town is a little off the main road, it’s worth the small detour.

If you are looking for a midpoint between Florence and Siena, Radda makes a good option. It’s close to restaurants, major sites, and the main road.

To get there, exit the Chiantigiana road and take the SR429.

I didn’t have time but If you do, you can also add hot air balloon to your itinerary. I guess that’s a great excuse for me to go back!

Radda in Chianti Tuscany Italy Road Trip Wine Road

Tip – If you want to visit a few of the renown Chianti wineries, there are many located on the road SR 222 – most of them take walk-ins. If you would like a tour of the cellars, I highly recommend booking in advance.

Wineries and wine tasting

VITICCIO (Greve in Chianti)

CASTELLO DI BROLIO (Gaiole in Chianti)


TORRE A CONA (Rignano sull’Arno)


IL TREBBIO (S. Brigida)


Did you know?

For a wine to qualify as Chianti wine, it must be produced with at least 80% Sangiovese grapes.

Villa Mangiacane Luxury Villa in Chianti Tuscany |

Where to Dine in Chianti

Il Caminetto del Chianti
Ristorante Villa Bordoni
Dario Cecchini

When in Tuscany, you MUST try:

Truffle dishes
Pecorino Fresco
Ossobuco – Ox Tail
Bistecca Alla Fiorentina

Italy Truffle season:

White Truffle: October – December
Black Winter Truffle: December – March
Black Summer Truffle: May – September

Tuscany was certainly one of the most beautiful places I have ever been. The rolling hills, delicious food, medieval towns, make the Italian region a must on your bucket list. Have you ever been to Chianti or Tuscany? Let me know 🙂

Pin it if you liked this post or would like to visit Tuscany one day!


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  1. KRisten

    12 August

    Ummm this is SOOOOOO epic! Love all of your imagery too! Thanks for sharing! I’ll be bookmarking this for when I visit, So helpful!

    • Diana

      24 August

      Thank you Kristen!! Hope you get to visit soon! 😀 It’s breathtaking!

  2. Victoria

    12 August

    This looks amazing. I totally feel uneasy driving in different countries. It’s something about the being responsible in a place where you don’t really speak the language makes me nervous. Lol more power to you! Thanks for the tips

    • Diana

      24 August

      Thank you Victoria! haha yes, it was an interesting experience. Hope you get to visit soon!

  3. Carolina

    12 August

    Love truffle!
    Can relate to the drivning, bicycled there last year and went around in cars with friends. To hit the cars next to you when you park they called touching and was apperently nothing to care about😂😬

    • Diana

      24 August

      Me too! I could eat anything with truffle sprinkled on it lol hahaha that’s so true!

  4. Your photos are absolutely beautiful, Diana! You are giving me a serious case of travel bugs and I honestly can’t think of a more scenic place to do a road trip. Was it easy to find automatic rentals in Europe tho? I hear they mostly drive manuals there and it’s rare to find automatic cars.

    • Diana

      24 August

      Aww thank you so much!! It was not hard but they do cost a little more but I say, totally worth it. I hope you get to visit because it’s STUNNING! and the foooodddddd 🤤

  5. Ana

    13 August

    I am totally in love with Italy. Tuscany is still missing from my travels, but it is on priority right now. Lovely post, and the pictures… they took me right there. Ahh.. bella Italia!

    • Diana

      24 August

      Thank you Ana! oh yeah, make sure to make Tuscany a priority because is GORGEOUS! and the food! OMG 🤤

  6. Oh how I love Tuscany! I studied abroad in Florence for a summer in college and absolutely fell in love with Italian culture and wine. It sounds like you had an amazing experience! xo

    • Diana

      24 August

      Ahh you are so lucky! I wish I could spend a few months in Tuscany. Florence is so beautiful and full of history and delicious food and wine 🤤🤤🤤

  7. Oh wow you’re photos are truly wonderful! I’m thinking of heading to Florence later this year and think now I must try head out to the country side for a day or two, Tuscany looks so beautiful… Especially that pink villa 🙂

    • Diana

      24 August

      Thank you Rachel! yes, definitely add a few of the smaller towns. The drive there is worth it! It will also give you a little escape from busy Florence. Can’t wait to read all about it!

  8. Mihaela

    17 August

    You really managed to transport me there with your post! So well documented as usual! I am now obsessed with this Villa Mangiacane after all your stories and pics!!! and I mis Tuscany! PS: you even took a black car??

    • Diana

      24 August

      Thank you Mihaela!! You should definitely go back! It has everything you like: Great Wine LOL It’s gray but I wanted a pink or a red one lol

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