Chianti Travel Guide: Everything You Need to Know About The Land Of Vineyards

Chianti Travel Guide: Everything You Need to Know About The Land Of Vineyards

Embark on a journey through the picturesque landscapes of Chianti; only a few regions can offer such a beautiful and rich panorama. Find yourself surrounded by rolling green hills, vineyards, olive groves, ancient villages and winding roads that lead to breathtaking views.

Immerse yourself in natural beauty, rich history, and world-renowned wines, whilst enjoying a bike ride or a walk among the numerous castles and learning about the history of this region: the heart of Tuscany awaits!

Chianti Classico Villages

Castellina in Chianti: aerial view

Although the area of production of Chianti wine is actually quite large, people usually identify Chianti with the Chianti Classico wine zone. This picturesque, oval-shaped territory situated between Florence and Siena, includes the municipalities of Greve, Panzano, Radda, Gaiole and Castellina.

These cities and villages saw their brightest time during the Middle Ages which thanks to their strategic position, played a central role in the conflict between Florence and Siena. Centuries-old tradition and stunning landscapes are what characterise these villages, which are definitely worth visiting.

Greve in Chianti is considered the gate into Chianti. This lively town is famous for its triangular shaped piazza, with large porticos on the side. This square has hosted the local market since the Middle Ages.

Panzano in Chianti is the most populous town in Chianti, and from the 12th century the town played an important defensive role for Florence and its county. But even more relevant, thanks to its strategic position, was Castellina in Chianti. Confirming this glorious past, the massive Rocca (castle) stands proudly over the city. When in Castellina, we also recommend you visit the Archaeological Museum of Sienese Chianti, where many archaeological findings, particularly Etruscan, are displayed.

Radda in Chianti is a well-preserved mediaeval town, with ancient walls that defend the centre and maze-like streets. Gaiole in Chianti also dates back to the  medieval period, when it used to be an important marketplace in the area. In the surroundings there are many castles and fortified towns that deserve a visit, keep reading if you want to know more.

A perfect way to discover the many gems scattered in the Chianti area is to take the SS222 Route, also known as Chiantigiana. This beautiful panoramic road goes from north to south through the Chianti hills, crossing numerous inhabited centres and vineyards.

Chianti Castles

Monteriggioni: aerial view

The castles of Chianti are the clearest evidence of this area as a borderland, disputed by the powerful cities of Florence, Arezzo and Siena during the Middle Ages .

Very important to discover from both an architectural and historical point of view, various Chianti manors can also be visited following a route called the Strada dei Castelli del Chianti. The route is divided into 6 itineraries:

  • Brown Route: Pieve di Spaltenna, Vertine, Uliveta, S. Donato in Perano, Vistarenni
  • Red Route: Tornano, Morelline, Cacchiano, Monte Lodoli
  • Yellow Route: Gaiole, Barbischio, Capannelle, Cancelli, Castello di Montegrossi, Badia a Coltibuono
  • Purple Route: Vertine, Meleto, Rietine, Castagnoli, Starda, Monte Luco della Beraredenga, Montecastelli
  • Orange Route: Campi, San Sano, Monteluco di Lecchi, San Polo in Rosso, Galenda, Le Selve
  • Blue Itinerary: San Giusto a Rentennano (alle Monache), Lucignano, La Torricella, Castello di Brolio




All of these routes can be travelled on foot or by bicycle, which is a great opportunity to fully appreciate the Chianti landscape and nature. Furthermore, some of these castles are wine producers, perfect if you want to combine sightseeing and wine tasting - more to come on the next section.

Among the numerous options, we suggest visiting Monteriggioni, a walled village, Castello di Volpaia and Castello di Fonterutoli, both wine producers. If you need help in organising your visit, whether that be a travel itinerary specially tailored to you, or simply bicycle rental to explore the Chianti landscape, please don’t hesitate to contact our team; we will be happy to support you.

Chianti Classico Wine

Cellar and wine barrels: internal view

The Chianti region is characterised by a combination of almost perfect weather and soil that produces a precious wine, considered one of the best wines in the world.

The tradition of cultivating vines in Chianti goes back a long time in history to the Etruscans that inhabited the area before the Roman Empire. Today Chianti wine is produced in several areas in the region, and the area of production determines the denomination:

  • Chianti Classico, also called “Gallo Nero'' is the more well-known of the Chianti wines and is produced in the area between Florence and Siena.
  • Chianti Colli Aretini, produced in the hills towards Arezzo.
  • Chianti Colli Fiorentini, produced in the hills around Florence.
  • Chianti Colli Senesi, produced in the hills around Siena.
  • Chianti Colline Pisane, produced in the hills towards Pisa.
  • Chianti Montalbano, produced in the Montalbano hills around Pistoia.
  • Chianti Montespertoli, produced in the Montespertoli, near Florence.
  • Chianti Rufina, produced in the hills near Rufina, to the east of Florence.

While enjoying your dream vacation in Chianti, you can’t miss taking a wine tour and tasting the region's delicacies. Here’s our dedicated article on The Best Chianti Vineyards You Must Visit where you will find all you need to start planning your tour.

L’Eroica: a vintage bike race

Vintage bycicles: details

Last but not least, Chianti is also the homeland of Eroica, a unique cycling event.

L'Eroica was born in 1997 in Gaiole in Chianti, and it combines challenging routes (hence the name, the Italian for “heroic”), magnificent Tuscan landscapes, and a love for vintage. In fact, all the participants ride vintage bikes and wear old fashion garments accordingly.

It is inspired by Coppi and Bartali, two of the greatest Italian cyclists, who had a heroic approach to sport and life. In addition to his legendary career - and rivalry with Coppi - Bartali is also known for playing an active role in helping the Jewish community during WW2, carrying documents and passport photos inside the bicycle frame, to help Jewish refugees escape.

From the original event in Gaiole, Eroica has grown into a global movement, a network of events attracting tens of thousands of cyclists and fans of all ages around the world. It has become a real lifestyle for locals and tourists alike.

Chianti offers the best of Tuscany countryside, encompassing stunning landscapes and historic castles with wine tasting and vintage cycling routes, the perfect combination for your dream holiday. Don’t wait any longer and start planning your perfect stay, contact us to find out more about our range of villas with a private pool to rent in Chianti.

The Salogi Team of local experts will be happy to support you in tailoring your dream vacation. Please feel free to contact us to discuss your next Italian adventure today.

You May Also Like

travel-italy.jpg

Travel Guides

Our tips to discover Tuscany. Here you will find our recommendations from places to go and things to do, from restaurants to where to park your car, etc.

Tuscany-dinner.jpg

Food and Wine

The Tuscan cuisine and wine are well known around the world. There are countless wineries and restaurants in the region, in this section you will discover Salogi's selection.

passeggiate-a-cavallo-in-toscana.jpg

Activities, Day Trips & Attractions

There is an extensive list of things you can do in Tuscany, we have selected some we believe should not be missed when exploring the region

Piero-della-Francesca-Arezzo.jpg

History & Culture

Learn about Tuscan history and its people. Find out what's unique about the region's traditions and customs to best explore Tuscany during your holiday

bkg-camporempoli-md.jpg

Salogi News & Travel Information

This section of our magazine contains articles to support you in booking your perfect home. It can be useful when planning a holiday in Tuscany.

Maremma-sea-village.jpg

Maremma Guide

Maremma is the wildest area of Tuscany. Etruscan and mediaeval villages, vineyards and woods, sandy beaches and blue sea characterise this region

chianti-vineyards.jpg

Chianti Guide

Only a few regions can offer such a beautiful and rich panorama as Chianti: green hills sketched by miles and miles of vineyards and olive groves, ancient walled villages, panoramic curvy roads.

Lucca_walls.jpg

Lucca Guide

Everything you need to know about visiting Lucca, Tuscany written by our local experts.

lorenzo-berti-_9ozSwFt8Ig-unsplash.jpg

Florence Guide

Everything you need to know about visiting Florence, Tuscany written by our local experts.

podere-bernasca-tuscany.jpg

Search by Categories

Get inspired by our articles about activities, places and suggestion, to make your holiday in Tuscany and Italy a memorable experience.