Tuscany Countryside Holidays

Travel the world and you’ll still struggle to find anywhere quite like Tuscany – an unrivalled blend of medieval heritage and glorious countryside. Much of the charm comes from the region’s dreamy hills, which are accessorised with vineyards and hilltop towns. San Gimignano is perhaps the best known Tuscan town, home to a well-preserved collection of soaring towers and romantic piazzas, while lesser-known gem Monteriggioni is a tiny hamlet ringed by massive fortress walls. There are plenty more locations to discover, however, ranging from sophisticated spa towns, to sleepy rural hamlets.

Food and drink are a big deal in Tuscany. There’s a reason the Romans declared Tuscany the breadbasket of their empire – the famous Tuscan hills produce more ingredients than almost any other region in Italy. There are ancient vineyards with heritage grapes and rural farms that were organic long before it became fashionable. Food is kept simple here – think bread, cheese and pasta, as well as the region’s quality Florentine steaks and Chianti wines.
Destinations in Tuscany Countryside
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Cascading from the peak of a steep hillside to the Serchio River below, Barga is a patchwork of peach and cream houses, set beneath a dramatic 11th-century cathedral.
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Set on the banks of the beautiful River Arno is the picturesque hamlet of Candeli. Popular among locals for its prime location close to Florence, this village is dominated by the majestic Villa La Massa – a magnificent 16th-century Renaissance villa now operating as a luxury hotel. 
Casole d'Elsa
The historic town of Casole d'Elsa has breathtaking views of the rolling hills the Siena countryside has to offer. Surrounded by the fortress walls which are rich in history, Casole d'Elsa is a place where you can immerse yourself in culture, art, landscapes and nature.
Castelnuovo Berardenga
Situated just 15 miles from Siena, Castelnuovo Berardenga is often overlooked in favour of its mother city, but reveals a rich tapestry of culture and history to those who take a proper look.
Colle di Val d'Elsa, Tuscany / Italy: Colle di Val d'Elsa Cathedral (Concattedrale dei Santi Alberto e Marziale or Duomo di Colle di Val d'Elsa) and houses of the upper town of Colle Alta.
Colle di Val d'Elsa
Colle di Val d’Elsa, between Florence and Siena, is the perfect starting point to explore everything Tuscany has to offer.
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Limite Sull`Arno
Set downriver from Florence, Limite Sull’Arno is a petite Tuscan village tucked neatly around a corner of the River Arno.
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Holidays in Lucca take you to the beautiful Tuscan countryside in the heart of Italy. This Renaissance town is home to 16th Century architecture and historic sights, with the vineyards and rolling green hills of Tuscany just outside its walls.
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Monsummano Terme
Monsummano Terme is a charming spa town watched over by a romantic castle ruin. The town itself is formed of Monsummano Alto (Upper Monsummano) and Monsummano Bassa (Lower Monsummano), with each offering unique benefits to visitors.
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Montaione holidays bring you a taste of Tuscany’s beautiful landscapes and rich history. Surrounded by vineyards, olive groves and fragrant citrus orchards, the town is perched on a hillside, overlooking spectacular farmlands and the surrounding villages.
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Montecatini Terme
One of Tuscany’s most prominent spa towns, Montecatini Terme is an intoxicating blend of historic architecture, beautiful scenery and some great local attractions.
Old town Montepulciano, Tuscany, Italy
Montepulciano is one of Tuscany’s most picturesque sights: a beautiful hilltop town surrounded by vineyards and olive groves.
Monteriggioni is a Tuscan gem, once mentioned by Dante in his Divine Comedy and today known for its mesmerising skyline and prime hilltop position.
picturesque medieval village of Volpaia, Radda in Chianti in Tuscany
Radda in Chianti
Radda is in the heart of Tuscany's wine region famous for Chianti and is steeped in history.
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Everyone knows about Pisa’s Leaning Tower and magnificent baroque basilica, but look behind these brochure cover stars and you’ll find an array of modem museums, picturesque piazzas and exceptional restaurants vying for your attention. 
San Gimignano
San Gimignano is a remarkable medieval town and UNESCO World Heritage Site, set on a particularly high hilltop in the Tuscan countryside. This fortified marvel is the historic equivalent of a modern high-rise city, with steel skyscrapers replaced with dizzyingly high ancient towers, and noisy alleyways swapped for uneven cobbled lanes.
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San Giuliano Terme
San Giuliano Terme is a scenic spa town situated just a few miles from Pisa. Popular since the 1700s, and with a permanent population of just 3,000, this town is a great option for those seeking an authentic escape to Tuscany. 
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Holidays in Siena take you to central Italy, in the heart of Tuscany’s countryside. It’s surrounded by the emerald green hills and valleys the area is renowned for, as well as warm stone buildings and a history which stretches back to the Medieval era.

Handpicked hotels in Tuscany Countryside

Discover the real Tuscany Countryside while staying in one of our carefully selected hotels

Things to do in Tuscany Countryside

Flight Information

The majority of international flights arrive into Pisa airport (PSA). Direct flights to Pisa are available from Belfast, Bristol, East Midlands, Edinburgh, Glasgow, Leeds Bradford, Liverpool, London Gatwick, London Heathrow, London Luton, London Stansted, Manchester and Newcastle and take approximately 2 hours. 

When to go

Tuscany is predominantly a summer destination, with the main tourist season generally running from April to October. Temperatures are at their hottest in July and August, this is also when Tuscany is at its busiest. However, Tuscany also enjoys a mild climate in spring and autumn with temperatures rarely going beneath 20 degrees which makes it perfect for visiting at the beginning or end of season too. The coast has wonderful sea breezes and the hilltop towns are much cooler than the lower countryside villages. The best time to visit is during the quieter season, from April to June and September to October when the weather is good, prices are a bit lower and there are fewer crowds. There are many festivals and events throughout the year in Tuscany and Easter and Christmas are always busy.

Visa Information

At the current time, British citizens do not require a visa to visit Italy.


You don’t have to leave a tip in Italy – most Italians don’t tip for restaurant meals, bar drinks, taxi rides or hair and beauty treatments. However if you do leave a tip, you might receive quicker service.

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Our recommendations

Insider tips from our well travelled team
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Linda Kulka

I'd highly recommend spending a day in Siena. It's a stunning city, and walking around you almost feel like you've stepped back in time. The highlight is the huge main square, Piazza del Campo. where the twice-yearly Palio di Siena horse race takes place.

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What our customers think

We have been helping our customers discover the real Italy for 90 years now. Our experience and expertise, together with our attention to detail and personal touch, really does make us the leading Italian holiday specialist

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