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Siena Rail Tours & Holidays

The medieval city of Siena is remarkably well preserved and boasts a mix of narrow streets, pretty open spaces and magnificent buildings focused around the great central Campo, a shell-shaped piazza. This Tuscan hill town initially developed under the Etruscans, before coming under the control of the Romans in about the first century BC. The Lombards then invaded the area around Siena and re-routed some of the region's major roads, so that they passed through the city. Countless pilgrims and traders on their way to Rome then came through Siena, cementing its position as a wealthy trading post. By the early 14th century Siena was one of Europe's richest cities, whose wealth funded the construction of many of the city's greatest buildings.

Art, architecture and history
In 1348 the Black Death arrived, and decimated the population. With only a quarter of its previous population, Siena lost much of its influence, and was absorbed into the Medici's Grand Duchy of Tuscany in 1557. Over the next few centuries the role of Siena became ever more provincial, and as a result it was untouched by either of the World Wars. Soon after this time the city was discovered by tourists, and was in such a good state of preservation that its historic centre - largely dating back to the 14th century - was designated a UNESCO World Heritage site. One of the city's most famous and celebrated buildings is the spectacular Duomo. Built from alternating strips of black and white marble, the striped cathedral is one of Italy's greatest, and houses statues by Donatello, Bernini and Michelangelo as well as a unique and elaborate mosaic floor.

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4 results matching: Escorted Rail Tours to Siena

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FlorenceFlorenceFlorenceFlorenceFlorence
Save up to £400pp
2026Oct
2027AprMayJunAugSepOct

Enjoy a holiday that captures the essence of Tuscany, travelling to and from the Tuscan spa town of Montecatini Terme by rail. This UNESCO World Heritage site is an ideal base for exploring this scenic and cultural region. From the grand Renaissance art and architecture of Florence to the fantastic shell-shaped Piazza del Campo and medieval...

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Save up to £400pp
9 days from
£1,599 pp £1,499 pp
per person
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ClassicClassic
Highlights of TuscanyHighlights of TuscanyHighlights of TuscanyHighlights of TuscanyHighlights of Tuscany
Save up to £400pp
4.4 stars(335 reviews)
2026Oct
2027AprMayJunAugSep...

Savour the glorious colours, aromas and flavours of Tuscany on a holiday highlighting the true beauty of this beloved region. Discover the great Renaissance city of Florence, visit a historic family estate for a tour and dinner, and marvel at the iconic monuments of Pisa, including the Leaning Tower. Explore the stunning sights of Siena, the...

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Save up to £400pp
10 days from
£2,099 pp £1,999 pp
per person
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ClassicClassic
VeniceVeniceVeniceVeniceVenice
Save up to £400pp
4.4 stars(67 reviews)
2026Oct
2027AprMayJunSepOct

From the Alpine foothills to the island of Sicily and all that lies between, uncover the best of Italy. Travelling the country's length, we delve into the history and culture of Italy's remarkable destinations, including Venice, Florence and Rome. Bask in the beauty of the Amalfi Coast and marvel at the remains of ancient Pompeii before venturing...

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Save up to £400pp
16 days from
£5,299 pp £4,999 pp
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LuxuryLuxury
Venice, ItalyVenice, ItalyVenice, ItalyVenice, ItalyVenice, Italy

After two wonderful days taking in the sights, sounds and tastes of Rome, your journey on the La Dolce Vita Orient Express begins with a sumptuous meal curated by 3-Michelin starred chef Heinz Beck. As the train travels northwards, disembark for time in magical Venice, followed by an evening of cocktails and live music that creates a sophisticated...

7 days from
£6,705 pp
per person
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Our customers love our Siena tours
Treasures of Tuscany
16/Sep
Martin Goodman
4 stars
“Great holiday. Very well organised but sometimes too many locations squeezed into a single day. Hotel room facilities minimal. Not 4 star . Advertised spar facility shut.
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Top to Toe of Italy
6/Jul
Shirley Brown
4 stars
“The dinner in Rome was underwhelming! Small appetizer, small pasta bland dish and small dessert - tiramisu or pancetta. Service was very slow and cursory. All tour guides were excellent. Our tour leader, Georgina was excellent.
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