Rural Tuscany Holidays

Holidays to rural Tuscany are a food and wine paradise filled with medieval soul and breathtaking countryside.

Imagine hiding away in an 11th-Century converted monastery with menus overseen by Gordon Ramsay and Ferrari’s on hire to explore Chianti vineyards and chestnut forests. Or waking up in an ancient Tuscan villa breakfasting over Italianate gardens before a guided tour of ancient wine cellars where old oak barrels and centuries old machinery are still in place.

If you fancy walking through fairytale villages barely changed since the 1400’s, dream of driving past cypress trees and silvery olive groves to medieval towns or want to step inside castles that almost touch the clouds, rural Tuscany holidays are a spellbindingly good place to start. Leave behind a world of Botticelli masterpieces and Medici history in Florence for a treasure chest of different jewels – a seemingly never-ending land of Veronese green hills and times gone past where stone walls hide huge wine cellars and hilltop villages give way to medieval abbeys and monasteries.

We’ve been to this part of Italy many times and know the most picturesque ancient roads, the best enotecas for tasting sweet reds from grapes once loved by Napoleon and the most extraordinary perches for panoramic views with a picnic of pecorino, bread and olives. To experience the true enchantment of holidays to rural Tuscany we’ll tell you to take evening apertivo in Siena’s heralded scallop-shaped Piazza del Camp after exploring the city’s jaw-dropping marble Duomo, to walk inside the ancient walls of San Gimignano with its vivid fresco-filled Collegiata and to visit the whimsical hilltop town of Montepulciano and Leonardo di Vinci’s birthplace in the foothills of Montalbano.

If you’re intrigued to find out more about our handpicked rural Tuscany holidays, give one of our Personal Travel Experts a call.

Read more

Rural Tuscany Hotels

Our recommendations for the best places to stay in Rural Tuscany

Villa Casagrande

A wonderful mix of old meets new in this former farmhouse which is characterised by pure Tuscan s...

Grand Hotel Continental Siena

A luxury boutique hotel housed in a 17th-century palazzo right in the heart of Siena’s ancient ce...

Castello di Casole, A Belmond Hotel, Tuscany

Go all out with a special stay at this boutique hotel on a sprawling 10th-century castle estate a...

Torre a Cona

In the peaceful countryside close to Florence, this historic wine-making estate is an idyllic bas...

Castellare di Tonda Resort & Spa

A collection of farmhouses on a 900-acre estate resort in the Tuscan countryside.

Borgo Pignano

Action-packed break or pure relaxation – you decide how things go in this refined and blissful es...

Villasanpaolo Spa Resort

Surrounded by olive groves and the Tuscan countryside, this is a picture-perfect spot for a wellb...

You may also like

  • Rating {{ ratingFilters.length }} chevron down
    • 4 Stars{{ratingsCountWith('4 Stars')}}
    • 5 Stars{{ratingsCountWith('5 Stars')}}
  • Holiday type {{ holidayTypeFilters.length }} chevron down
    • Boutique{{holidayTypeCountWith('Boutique')}}
    • Honeymoons{{holidayTypeCountWith('Honeymoons')}}
    • Luxury{{holidayTypeCountWith('Luxury')}}
    • Spa & wellness{{holidayTypeCountWith('Spa & wellness')}}
    • Sustainability{{holidayTypeCountWith('Sustainability')}}
    • Villas{{holidayTypeCountWith('Villas')}}
    • Wellness{{holidayTypeCountWith('Wellness')}}
  • Price 1 chevron down
  • chevron down
    • Kuoni recommended
    • Name (A-Z)
    • Rating (High to Low)
    • Rating (Low to High)
    • Price (High to Low)
    • Price (Low to High)
  • {{ filter.text }}
  • Clear all

Get to know Rural Tuscany and those important practicalities when planning your perfect holiday.


GMT +1 hour




Pisa: 2¼ hours


Christianity (Roman Catholic)



Where is Rural Tuscany
The hilly areas of central Italy’s Tuscany are what define rural Tuscany, with the Valdelsa area near Florence and the Chianti hills extending from Siena to Arezzo and on to the Tiber Valley.

Read more

San Gimignano
Medieval UNESCO-listed San Gimignano has 14 lofty square towers which combine to create a striking skyline that can be seen framing the surrounding hills from miles away. Visit the Torre Grossa tower, Palazzo Comunale, Piazza della Cisterna and the Cathedral of San Gimignano. Rich in works of art, spectacular piazzas, fine shops and vibrant restaurants, San Gimignano’s serenity and beauty have made this place one of the most popular destinations in Tuscany.

Read more

The Chianti region, made famous by the wine of the same name, is dotted with historic cities, towns and villages, including the riverside city of Gaiole which is surrounded by striking castles and churches. Wine tasting is a must (make sure to book ahead) as is a visit to the doorway of Chianti, Greve, and the immense castle and underground series of roads in Castellina.

Read more

Located in the heart of Tuscany, Siena is one of Italy’s best-preserved medieval towns filled with fine examples of Gothic architecture. If you’re visiting during July or August then don’t miss the chance to attend the Palio in Siena – the most famous bareback horserace in history – where the riders and their steeds strut past the crowds in colourful finery.

Read more

Exploring Tuscany
One of the joys of a trip to rural Tuscany is driving through the wilder parts of the region between tiny wine towns, ancient hilltop villages, Renaissance churches and active monasteries. Travel due west from Siena and you will reach the charming and unique settlement of Casole d'Elsa where centuries-old Romanesque churches and striking defensive buildings sit along the spine of a hill. One of our favourite destinations is the commune of Rignano sull'Arno where tiny hamlets are joined by winding rivers and rolling agricultural lands.

Read more

Getting around
We recommend hiring a car to make the most of exploring the region as scenic drives take you to smaller towns and villages and enable you to reach the hidden corners of rural Tuscany. Parking can be difficult, and driving is not allowed in historic centres, so we advise parking outside the city limits and either walking or catching a bus into villages and towns.

Read more

Food & drink
Enotecas and restaurant menus are packed with local specialities, and you’ll find plenty of wood oven pizzerias and cafés inside the hilltop town’s central piazzas. Pore over extensive wine lists in al fresco restaurants. Dine in the middle of the Chianti hills with panoramic views and in medieval vaults under the Duomo in Siena. Try handmade rolled spaghetti, Tuscan bread and tomato salads and pici in rabbit sauce.

Read more

Rural Tuscany Weather

Apr - Oct


Rural Tuscany Weather by Month