Siena Area

“A living, breathing UNESCO World Heritage Site.” - Reviewed by Deborah

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  • Deb says: “Siena was such a delightful surprise. You think you’ll never be blown away again after visiting Florence, but Siena is in a class of its own.”

While historians recount how Siena and its surroundings were first inhabited around 900-400 BCE by the Etruscans, it is the city’s medieval legacy that truly captures the imaginations of the thousands of visitors who snap photos of its streets and attractions each year. The medieval walled city is like a treasure trove of historical wonders and fabulous places to enjoy a cheeky spritz of an afternoon.

Guidebooks would have you believe that Tuscany aficionados tend to fall into one of two camps: Florence fans or Siena buffs. Travellers usually develop a fondness for one city over the other – somewhat reminiscent of the historical rivalry that persisted between the two communities during the medieval period.

The course of history certainly had a hand in shaping the architecture of these two cities. Florence is a perfect example of progress and the embodiment of the Renaissance due to the undeniable influence and investment of the Medici family. On the contrary, Siena retains its authentic Gothic beauty because of its decline following a plague that crippled the city and left only a third of its population standing. As a result, Florentine Cosimo I de’ Medici took control of Siena and curbed its development and power – which means that today we get to enjoy the city’s gothic architecture virtually unadulterated.

Siena is most famous for Il Campo, a huge piazza that fans out from the Palazzo Pubblico on a gentle gradient like an amphitheatre. It is also known for the totally mind-blowing Siena Cathedral which, unlike Florence’s Duomo, can be fully appreciated from a good enough distance away that photos of it are truly amazing – even without a professional camera or wide lens.

If you are in the area around the time of the annual Il Palio event, celebrated on 2nd July and 16th August, you are sure to be left with your jaw-dragging on the ground as you watch the colourful medieval pageantry that engulfs the city and the bareback horse race that sees the different communities in Siena defend their banners.

The charms and beauty of Siena can easily be appreciated while staying in villas and homes in the surrounding area. Not only are views of Siena dominating the hilltop impressive from afar, but the roads to Siena are easy to navigate if you are planning to rent a vehicle. Just be sure to park before entering the medieval city walls in one of the many car parks available.


  • Tuscany, central Italy
  • 80 minutes to Florence International Airport
  • 2 hrs 40 mins to Rome International Airport
  • 20 minutes by car to Chianti wine region
  • 60 minutes to San Gimignano
  • 70 minutes to Arezzo


  • Sightseeing – There are plenty of sights to enjoy in Siena. The city centre itself is a UNESCO World Heritage Site.
    • Piazza del Campo
    • Siena Cathedral
    • Palazzo Comunale
    • Orto de’ Pecci
  • Museums – Some great museums to explore which feature all kinds of art ranging from religious artefacts to Byzantine and Gothic paintings to sculptures.
    • Museo dell’Opera del Duomo
    • Museo Civico
    • Pinacoteca Nazionale
    • Complesso Museale Santa
  • Walking and cycling tours – The whole city is easily walkable or you can rent bicycles and join a tour.  There is no shortage of expert polyglot guides.
  • Gastronomy – Discover the many local and regional dishes with hundreds of restaurants to suit every taste and budget.
  • Wine Tastings – So close to both Chianti and Montepulciano, you will be spoiled for choice for wine tasting tours, with options for days tours and even wine classes.
  • Shopping – Boutiques and speciality shops selling everything from local designer clothing and unique Italian commodities such as leather items, silk ties, ceramics, handmade stationery and jewellery.

Special dates

  • Il Palio
    Pageants and horse race – 2nd July and 16th August
  • Music Festivals
    • Classical Concert Series by the Academia Musicale Chigiana
    • Micat in Vertice – Nov to April
    • Settimana Musciale Sense – July
    • Estate Musicale Chigiana – July to August.