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Favorite Moment
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.
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!
Play Around
Explore Tuscany with 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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Start Planning
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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.
Guidester Favorites
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.
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.
Montepulciano
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 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.
Pitigliano
The hilltop town of Pitigliano has a unique geology thanks to its volcanic rock-bed, which has resulted in some interesting underground caves. Visitors can ask the Tourist Office for more information if they are interested in visiting these underground spaces.
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.
Castello Verrazzano
The Castle and Winery of Verrazzano is located in Greve in Chianti, in the heart of the Chianti Classico area, between Florence and Siena. The expansive vineyards, reimplanted by Cappellini Family starting from 1958, remain unchanged for centuries.
Castello di Ama
This leading vineyard produces high-quality Chianti.
Visitors can tour the area for an in-depth look at the
winery, its cellars, the chapels, the 18th-century Pianigiani and Ricucci and villas, and the estate’s gardens.