Siena, Italy. The History of the City, a Travel Guide for Tourism. Vacation Packages. Does any country boast as many holiday destinations as Italy? The majesty of Rome, the beauty of Naples, the romance of Venice; all must-visit cities at some point in one's life. But even beyond the more storied names, Italy offers much to stir the soul. The small city of Siena, with a population of barely 50,000, is a classic hidden gem. Siena is most famous for its biannual horse race, the Palio. A forthcoming documentary on the Palio should heighten British interest in a truly unique event. If possible, time your visit around either the July or August races. However, even if you can't make the Palio, you'll find much to treasure. Siena is a truly beautiful city, all cobbled streets and tall, ancient buildings. The city is split into 17 districts all with their own names and colours and, as you walk the streets, you'll notice the flags change depending on which district you travel through. Unlike certain global megacities, Siena has a strong sense of identity. It will stay with you long after you depart. Siena is a city where the architecture soars, as do the souls of many of its visitors. Effectively a giant, open-air museum celebrating the Gothic, Siena has spiritual and secular monuments that have retained both their medieval forms and their extraordinary art collections, providing the visitor with plenty to marvel at. The city's historic contrade (districts) are marvellous too, being as close-knit and colourful today as they were in the 17th century, when their world-famous horse race, the Palio, was inaugurated. And within each contrada lie vibrant streets populated with artisanal boutiques, sweet-smelling pasticcerie (pastry shops) and tempting restaurants. It's a feast for the senses and an essential stop on every Tuscan itinerary.