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A beautiful holiday in Chianti and beyond

Castellare in Chianti is about 8 km from the town of Gaiole in Chianti, a small Tuscan village with bars, restaurants, pizzerias, hairdressers, a supermarket and a pharmacy.
Chianti is one of the most beautiful hilly areas of Tuscany and perhaps of Italy. Famous worldwide for the production of Chianti wine, this region of Tuscany extends between the provinces of Florence and Siena. The landscape is characterized by vineyards, olive groves, fortified villages, castles, and picturesque hamlets, each overlooking its splendid panorama.
There are many locations to visit to make your stay at Castellare in Chianti even more enjoyable. Here are some recommended places (distances and travel times are calculated from the town of Gaiole in Chianti).

The medieval villages of historic Chianti

In one day you can visit Radda in Chianti, Castellina in Chianti, and Gaiole in Chianti, small Tuscan villages located in the Chianti Classico area, which historically formed the Chianti League, created by the Republic of Florence in the 14th century and active until 1774.

- Radda in Chianti (11 km/12 minutes)
- Castellina in Chianti (22 km/25 minutes)
- Gaiole in Chianti (8 km/10 minutes)

Siena

Siena is one of the most beloved and visited cities in Tuscany, a place rich in history and art, but also in strong traditions, primarily tied to the districts and the famous Palio of Siena. Located in the center of Tuscany, Siena can be easily reached from other cities in the region by car, train, or bus, depending on the transportation that suits you best. Keep in mind that the historic center is closed to private vehicles, so you'll need to get around on foot or by public transport.
One day in Siena is certainly not enough to experience all the city's nuances or to visit all its treasures. However, with a little planning, you will undoubtedly manage to see Siena's main attractions in a day and enjoy its charm and atmosphere, leaving with the desire to return as soon as possible.

San Gimignano and Monteriggioni

San Gimignano, a small fortified town halfway between Florence and Siena, is famous for its architecture and beautiful medieval towers that make the town's skyline truly unique. During its heyday, the wealthy families of San Gimignano built as many as 72 towers as a symbol of their wealth and power. Of these, 14 remain today, which add to the charm of the town's atmosphere. Declared a UNESCO World Heritage Site in 1990, San Gimignano is one of the small gems of the Siena province and also offers excellent local products such as saffron and the white wine called Vernaccia di San Gimignano.
The village of Monteriggioni is small with few streets, but the impression that remains in memory lasts forever. You realize you have discovered a magical place, almost an enchanted castle like those known in childhood fairytales. Arriving at the village in the evening, when the outer walls are illuminated by yellow lights, Monteriggioni almost seems like a mirage in the middle of the Tuscan hills: the circle of walls and the 14 evocative towers embrace it as if in a hug. They are still intact, just as they were when built in the Middle Ages to protect and safeguard the inhabitants.

Val d’Orcia

Medieval castles, rolling hills, old villages, beautiful agriturismi, isolated farmhouses, cypress-lined avenues, fabulous vineyards and olive groves, and golden wheat fields: these are just some of the elements that make up the fantastic and harmonious landscapes of the Val d'Orcia! Very few other places are capable of impressing visitors so deeply. It is a land with a surreal, suspended atmosphere, which has also given rise to some of the most precious and appreciated Italian wines: Brunello di Montalcino, Nobile di Montepulciano, Rosso Orcia, and other DOCG wines. The beautiful landscapes of Val d'Orcia, which inspired many Renaissance painters, are dotted with small villages, castles, abbeys, and towns, each with its incredible history. Time flows slowly here.

Crete Senesi

Tuscany, out of time. The protagonist of the four weeks of “Crete d’autunno” is this evocative area nestled between the Orcia, Chiana valleys, and the city of Siena. Five municipalities where white truffle has been protected like a rare animal for years, where new youth entrepreneurship finds life in the customs of a peasant society that no longer exists, and where the Cinta Senese or olive oil, “returning myths” of food and wine tourism, have never ceased to be part of the usual food basket.

Firenze

Florence, the capital of Tuscany, is a special destination visited every year by millions of people because it has so much to offer and there is never enough time to visit it all. Florence is intriguing for first-time visitors, wonderful for those who become more familiar with it. Not just the canonical routes, but also the more peculiar and less-traveled paths have a charm that leaves a lasting impression. Florence reached its peak during the Renaissance era: its historic center and urban planning faithfully reflect this historical journey. The main attractions of the city are all within walking distance, perhaps planning a few stops between one destination and another. Request an itinerary designed to ensure you miss nothing of the city's main monuments.