Overview & Brief History

Tuscany beautifully combines breathtaking scenery, history, and some of Italy’s best made wines. In this enchanting landscape of rolling hills and winding roads, you’ll find glorious sunflower fields, ancient olive groves, medieval ruins, walled cities, wild forests, and of course, world-class vineyards.


A Brief History

The origins of Tuscany trace back to the Etruscans, a pre-Roman civilization that thrived in the area between the 8th and 4th centuries BC. The Etruscans left behind a legacy of art, architecture, and a unique cultural identity. As Rome expanded, Tuscany became part of the Roman Republic and later the Roman Empire, contributing to the empire’s economic and agricultural prosperity.


Following the fall of the Roman Empire, Tuscany experienced a period of political fragmentation. City-states like Florence, Siena, and Pisa emerged as powerful entities, engaging in both cultural and economic competition. The Renaissance, which began in the 14th century, marked a golden age for Tuscany. Florence, in particular, became a leading center for art, literature, and intellectual pursuits, with figures like Leonardo da Vinci, Michelangelo, and Galileo Galilei making groundbreaking contributions to their respective fields.


The 16th century saw Tuscany becoming a grand duchy under the rule of the Medici family, who left an indelible mark on the region’s artistic and architectural landscape. In subsequent centuries, Tuscany experienced various political changes, including being part of the Grand Duchy of Tuscany, the Kingdom of Italy, and the Italian Republic after World War II.


Today, Tuscany is renowned for its picturesque landscapes, historic cities, and cultural treasures, making it a timeless destination that reflects the enduring legacy of its Etruscan, Roman, and Renaissance past.

Things to See & Do


Siena epitomizes a classic medieval city with its Gothic appearance acquired between the 12th-15th centuries which has all been well-preserved. Head to Torre del Mangia for views across Piazza del Campo and if you’re feeling adventurous climb up 400 steps to the top of the tower for a 360 degree view of the surrounding countryside.

Badia a Coltibuono

Located in the heart of the Chianti region, Badia a Coltibuono has for 1,000 years been an important farm and its land has been producing excellent wines and oils for centuries. The historic winery was originally a monastery dating to the 11th century which was then converted into a vineyard owned by a local family.

Castellina in Chianti

Castellina in Chianti is a small town in the heart of the Chianti region with a lovely medieval closed walkway. The city’s origins go back to Etruscan times which you can experience with the local archaeological museum.

San Gusme

The picturesque town of San Gusme is a true gem and stands untouched by time. The quaint hilltop village sits perched atop a hill that provides beautiful panoramic views of the surrounding Tuscan countryside and gives off a down to earth Italian charm vibe.

Castello Brolio

Castello Brolio is a picturesque castle and winery set in the stunning Chianti region of Tuscany. With its gentle hills, valleys, and thick woodlands of oaks and chestnuts, the 1,200 hectares of property include almost 240 hectares of vineyards and 26 of olive groves.


Located in the southern part of Tuscany, Montepulciano is a medieval town full of Renaissance architecture where the influence of the great Medici family can still be felt. The architecture is so authentic that no major building works have been carried out here since the late 1500s.

Local Dining

Dining in Tuscany…

Both lunch (“pranzo”) and dinner (“cena”) usually consist of several courses; the pasta course (“primo”) takes the place of a soup course, not a main dish, followed by the meat dish (secondo) then a desert if you have it in you.


La Taverna di San Giuseppe

This typically Tuscan location dates back to 1100 – and is situated in the heart of the historic center of Siena, 400 meters from the famous Piazza del Campo. In the evening the tables are lit by candle light creating a magical dining atmosphere.

Insider Tips

Siena has always been a personal favorite as a base to explore Tuscany. Siena is nearly smack in the middle of the region, has a town with all the amenities you will need, and is a beautiful city to discover in its own right.

Another option for a more intimate experience is to find a villa or winery to stay for a few days. There are thousands of small villas and wineries that double as a B&B, which would allow you to really immerse yourself in the Tuscan countryside.

Virtual Tours

Tuscany: Hilltop Villages

Luxury Villages in Tuscany

Tour of Pitigliano

The Wines of Tusdany

Siena, Italy Walking Tour

What to Eat in Tuscany

Jack’s Favorite Moment

Hilltop Winery in Tuscany

Nestled in the heart of Chianti region in the rolling hills of Tuscany is the most picture perfect winery you’ll ever see. Badia a Coltibuono has for 1,000 years been an important farm and its land has been producing excellent wines and oils for centuries. I took a tour group here June 2019 for a private tour and tasting and ‘wow’ was on the tip of our tongues the entire experience.

The historic winery was originally a monastery dating back to the 11th century which was then converted into a vineyard by a local family that still owns the estate to this day.

The history of Badia a Coltibuono is a fascinating one which is interwoven in Italian and wider world history.

Keep Reading

In 1051 a monk named Giovanni Gualberto received a donation from a powerful local aristocratic family, the church of San Lorenzo a Coltibuono, with the order to build a monastery to host the monks and a hospice for the pilgrims.


The original Latin name ‘Badia a Cultus Boni’, means “good culture”, “good agriculture”, or “good harvest”. A monk’s document from Coltibuono, dated from the 12th century, mentions for the first time ever the word Chianti referring to this area.


In short time the property gained a preeminent religious, political, social, and economic role. The estate thus gained a considerable property that was not dispersed or split up during the following centuries, which was unique to other estates of the day. You will also find priceless works of art and artifacts sitting about, such as an original grinder and seed separating machine invented by Leonard DaVinci himself. 


For generations the family strives to safeguard and transmit the values over centuries, cultivating the land of the countryside. They have maintained excellent organic wines, extra fine olive oil, savory foods, culture, art and beauty.

A visit to the winery is an experience to understand history, fine local foods, and Chianti wines. We had a behind the scenes tour of the property, the underground cellar, their private wine collection (with wine dating back to the 1930s), the gorgeous gardens, and capped it all off with a private tasting of their very finest wines. A perfect day! The property also has villas for rent, which means you could spend your days in an ancient monastary/winery.


Badia a Coltibuono is truly a charming destination on the hillside of the Monti del Chianti which is reached via small windy roads. While it feels secluded, the estate is easily accessible from Florence, Siena, or Arezzo, and is a place that will leave an unforgettable impression on every visitor.


Jack Bauman

Founder of Guidester


Interactive Maps

Wander around Siena’s Piazza del Campo​​

Explore the medieval village of Montepulciano​

Wander around Castello di Brolio winery

Explore the village of San Gimignano


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