Rail Holidays to Tuscany & Umbria

With their verdant, ethereal landscapes and stunning, art-packed cities, the regions of Tuscany and Umbria are top of the list for a rail holiday to uncover the ‘real’ Italy. Enjoy visits to beautiful Renaissance cities like Florence, Siena, Assisi and Perugia with grand piazzas and al fresco restaurants. Or head out for a drive into undulating countryside carpeted with vines.

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Our favourite rail holidays in Tuscany & Umbria

Grand Tour of Europe by Rail

33 days

From £3199pp

Discover Tuscany & Umbria by rail

In the heart of central Italy, Tuscany and Umbria offer a captivating blend of Renaissance art, medieval history, beautiful countryside and outstanding food and wine. These neighbouring regions share a rich cultural heritage but have distinct personalities, making them particularly rewarding to explore together.

Tuscany is home to Florence, birthplace of the Renaissance and a treasure trove of art, architecture and historic landmarks. Beyond the regional capital, discover Siena's remarkable Piazza del Campo, the medieval towers of San Gimignano, Pisa's famous Leaning Tower and the charming walled city of Lucca. The rolling vineyards of Chianti and the cypress-lined landscapes of the Val d'Orcia provide a picturesque backdrop to the region's historic towns and villages.

Often described as Italy's green heart, Umbria offers a quieter atmosphere, with wooded hills, olive groves and beautifully preserved medieval settlements. Assisi is renowned for its association with St Francis and its extraordinary basilica, while Perugia combines Etruscan history with a lively cultural scene. Orvieto, perched dramatically on a volcanic plateau, is another highlight, with its richly decorated cathedral and fascinating underground passages.

Both regions are known for their regional cuisine, local wines and traditional festivals. With rail services linking many of their principal destinations, Tuscany and Umbria can be combined in a leisurely multi-centre holiday, perhaps alongside Rome, Bologna or Venice.

Cities and places to visit in Tuscany & Umbria

Travelling by rail in Tuscany & Umbria

Travelling through Tuscany and Umbria by train offers a delightful combination of historic cities, rural landscapes and slower journeys through the Italian countryside. Florence is the principal rail hub, with high-speed services connecting it to Bologna, Rome and other major Italian cities, while regional trains provide access to Siena, Pisa, Lucca and Arezzo.

Some of Tuscany's most appealing railway journeys follow quieter routes through the countryside. The line from Siena towards Chiusi passes through rolling hills, vineyards and traditional towns, including Asciano and Rapolano Terme. Another scenic journey connects Siena with Grosseto, crossing the rural landscapes of southern Tuscany, while the coastal railway from Pisa towards Rome offers glimpses of the Tyrrhenian Sea. Further north, the historic Porrettana Railway winds through the wooded hills and valleys of the Apennines.

In Umbria, regional trains connect destinations including Perugia, Assisi, Spoleto and Orvieto, making it possible to combine several historic towns within one holiday. Some hilltop centres require a short onward journey by bus, funicular or taxi.

For an exceptional luxury experience, the Venice Simplon-Orient-Express offers selected journeys to Florence aboard its beautifully restored vintage carriages. La Dolce Vita Orient Express provides another way to experience the region, with exclusive itineraries through Tuscany combining elegant onboard accommodation, fine dining and carefully curated excursions.

Whether you prefer high-speed connections between cities, leisurely regional journeys or an indulgent luxury train experience, we can incorporate the most suitable routes into your tailor-made holiday.

Why book your Tuscany & Umbria rail holiday with us?

Placeholder text. Every holiday is planned by a rail specialist who knows the routes first hand. We arrange your trains, hotels and transfers, and stay on hand throughout your journey.

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Questions about rail holidays in Tuscany & Umbria

Frequently Asked Questions About Tuscany & Umbria

Yes. Both regions can be reached by rail from the UK, travelling by Eurostar and onward European trains through France, Switzerland or northern Italy. Florence is a convenient starting point for exploring Tuscany, while Perugia, Assisi and Orvieto can be reached using Italian rail connections. We recommend allowing time for an overnight stop en route, perhaps in Paris, Switzerland or northern Italy. We can also arrange holidays beginning elsewhere in Europe.

Spring and autumn are particularly attractive, with comfortable temperatures for sightseeing and beautiful countryside. April, May, September and October are popular choices, while autumn brings grape harvests, truffle festivals and seasonal food specialities. Summer is ideal for outdoor events, including Siena's Palio and Umbria Jazz, although temperatures can be high, particularly in the cities. Winter offers a quieter atmosphere for cultural visits, with fewer crowds at many major attractions.

Yes. Tuscany and Umbria are renowned for their wines, olive oils and regional cooking, making food and wine experiences a natural addition to a holiday. Vineyard visits and tastings can be arranged in areas such as Chianti and Montepulciano, while Umbria offers opportunities to discover traditional olive oil production, local wines and seasonal truffles. As many rural estates are away from railway stations, private transfers or organised excursions are often the most convenient way to visit.

Many of the principal destinations are accessible by train, including Florence, Pisa, Lucca, Siena, Perugia, Assisi and Orvieto. However, some of the most picturesque hilltop towns and rural areas are not directly served by rail. Local buses, taxis, private transfers and organised excursions can help you explore beyond the railway network. And if you'd prefer the added freedom of car hire, we can certainly arrange this as part of your package.

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