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Check out Guidester’s favorite Tuscany experience.
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.






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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 Baumann
Hi, my name is Jack Baumann, and I have a passion for helping independent travelers unlock the wonders of Europe. I founded Guidester - we build personal mobile guidebooks sourced from local experts - so travelers could cut through the noise and dive deeper into the wonders of Europe. I hope you enjoy my stories and tips!

Jack Baumann
Hi, my name is Jack Baumann, and I have a passion for helping independent travelers unlock the wonders of Europe. I founded Guidester - we build personal mobile guidebooks sourced from local experts - so travelers could cut through the noise and dive deeper into the wonders of Europe. I hope you enjoy my stories and tips!
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Wander around Siena's Piazza del Campo
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Local Tips
Wine touring here is not about a five-minute tasting at a roadside wine bar, but rather it's an immersive experience.
At any of Tuscany’s wineries, you won’t just be served a glass of wine, you will learn about the history, culture, and innovations behind that wine while surrounded by the landscapes that inspired some of the world’s greatest artists.
In Tuscany, you typically need to telephone the day before to book your tour. Tours last about one hour and cost around $10–$15 per person.
You will often finish in a tasting room where, with expert guidance, you’ll develop a better appreciation for the fruit of the vine.
If you’re paying for a wine tasting, you aren’t obligated to buy. But, if a winery is doing a small tasting just for you, they’re hoping you’ll buy a bottle or two.
Tuscany is awash in picture perfect views over nearly ever hilltop. If you want the best views you need elevation and a great way to get a birds eye view is to climb the Torre del Mangia in Siena for unobstructed 360 views of the city and surrounding countryside.
The best way to really immerse yourself in Tuscany is by car. If you’re willing to brave the Italian roads it’s so worth it, but even if you don’t want to go the hassle you may consider hiring a driver for select days to show you around.
There is a different rhythm to life in Italy and to enjoy your visit, you have to accept this. It’s slower, more relaxing, and gives you time to enjoy life. In Italy happiness comes from taking time to stop and enjoy the small moments of life. Sit down. Enjoy a snack. Soak in the day. Don’t stress. If you don’t do it today, you can do it tomorrow. Have a coffee. Don’t worry about it.
Additionally, Italians appreciate people who are well-dressed and give them more respect and attention. Dark neutrals such as black, gray, and brown will help you blend in.
Be sure to check if the service charge is included (it often is). Tip is “mancia”, and should only be given for service rendered. Italians usually leave a few Euros, just the loose change from the bill, as a tip for extra service.
The menu should be posted outside the restaurant stating both the service charge if any, and the ‘Pane e Coperto’ is a table charge. Service charges vary but may be as much as 15% whilst the Pane e Coperto is only a few euros, typically between 1 and 5 euro per person.
Where To Stay
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.
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Siena
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.
Local Eats

Dining in Tuscany...

La Taverna di San Giuseppe
- Art & History
- Foodie
- Outdoorsy

Buonconvento
A medieval village, Buonconvento has plenty of
museums and majestic buildings for you to explore, and when a place is named as one of Italy’s most beautiful towns, you have to take a look! Visit the Museo della Val d’Arbia (Val d’Arbia Museum) and the Museo di Arte
Sacra (the Museum of Sacred Art), Palazzo Ricci, the church of San Pietro e Paolo (Saint Peter and Saint Paul) and the Oratorio di San Sebastiano (the Oratory of Saint Sebastian).
Tip: Only those with a pre-paid admissions ticket will be let in. You can find the booking/ticket office in the basement.

San Gimignano
The walled, medieval village of San Gimignano dates back to the 12th century when it was an Etruscan village. Today it attracts thousands of visitors thanks to its city wall and fourteen unique towers that exude an aura of traditional Italy. A place not to be missed for that taste of the past. There are several museums and galleries and is a varied and cultured Tuscan town.
Tip: Another must see is the Basilica of Santa Maria del Popolo, famous for its Renaissance art by some of the greatest artists ever to work in Rome: Pinturicchio, Raphael, Carracci, Caravaggio, and Bernini.

Radda in Chianti
Radda in Chianti is a beautiful medieval town in the Chianti region enclosed by large defensive walls. Located up on a hill between the valleys of Arbia and Pesa, the town has ancient origins. Inhabited since the 9th century, Radda features stone facades that add to the medieval feel characterized by narrow streets and towers.

Montepulciano Wine Tour
The first citizens arrived to Castle Hill in the 13th century after the Mongolian invasion, seeking protection in the hills of Buda and the first royal castle was built around this time. The golden age of Castle Hill was in the 15th century, following the marriage of King Matthias Corvinus and Beatrix of Naples in 1476. Today, Castle Hill is recognized as a World Heritage Site, and has many must-see attractions, Gothic arches, eighteenth-century Baroque houses and cobblestone streets.

Fattoria Viticcio
In the prestigious area of Chianti is the vineyard of Fattoria Viticcio, owned by the Landini family for several generations. With 40 hectares of organically run vineyards, the majority being Sangiovese, we produce 300,000 bottles of excellent quality wine. This is a family-run winery, so most likely you’ll find a family member guiding you on the journey into the world of wine, starting from their vineyards to the winery before moving on to the tasting of their wines.