Siena
Medieval Tuscany at its most intense—the Palio, the Duomo, and the shell-shaped piazza.
About Siena
Siena is Florence's great rival—and in many ways, it wins. This medieval city of golden-brown brick is one of Italy's most perfectly preserved, centred on the extraordinary shell-shaped Piazza del Campo where the famous Palio horse race has been run twice a year since the Middle Ages. The Gothic cathedral—with its striped marble facade and Piccolomini Library—is breathtaking, and the surrounding streets are a maze of medieval contrade (neighbourhoods) that still define Sienese identity and fierce local rivalries. Siena's food reflects its Tuscan roots but with a distinct personality: pici pasta (fat hand-rolled spaghetti), ribollita, and panforte, the dense spiced cake that's been made here since the 13th century.
Best Time to Visit
April to June or September to October. July 2 and August 16 for the Palio horse race—book months ahead. Spring is perfect for the surrounding Crete Senesi landscape. Autumn brings harvest festivals.
Local Tips
- Experience the Palio fervour.
Even if you can't get Palio tickets, the contrade energy in the days before the race is electric. A local can take you to a contrade dinner (cena propiziatoria) and explain the centuries-old rivalries that make the Palio so intense.
- Explore the Crete Senesi.
The lunar landscape of clay hills south of Siena is one of Tuscany's most striking landscapes. A local knows the best viewpoints, the cypress-lined roads, and the agriturismi where you can taste pecorino and local wine.
- Climb the Facciatone.
The unfinished extension of the Duomo offers the best view in Siena—looking down into the Piazza del Campo from above. A local will time the climb for afternoon light and minimal queues.
(the local lens)
Meet the Local Experts
Your on-the-ground insiders. The ones who know the enduring favourites, the quiet corners and what’s worth your time.
Manuela
Palermo, Florence +13
Born and raised in Rome, with family roots in Sardinia, I developed a deep appreciation for Italy’s regional diversity and cultural identity from an early age. For years, I have accompanied my guests across Italy, gaining hands-on knowledge of the country’s landscapes, traditions, and local communities. My approach is rooted in authenticity, meaningful connections, and a true understanding of how Italy works beyond the surface.
Eleonora
Palermo, Syracuse +10
Hello, I’m Eleonora. I was born in Tuscany, just outside Florence, where growing up surrounded by history, shaped my curiosity and love for art. I studied Art History at the University of Florence, specializing in the Renaissance. I began guiding students early on, and it was there that I developed a passion for storytelling — because there is nothing more challenging than engaging teenagers and young adults. I later expanded my focus to the broader history of Italy, leading groups throughout the country, from Venice to Sicily. Eventually, I moved to Rome, where I now work as an expert tour guide, leading visits to the city’s most iconic sites, including the Vatican and the Colosseum, as well as off the beaten path, to some of its hidden gems. In my free time I love to drive around Italy to its myriad hilltop medieval towns, where each one is a new discovery, both architectural and natural and also, of course, culinary! Over the years, many travelers have asked me for advice and suggestions to help plan the rest of their itineraries. That is why I’m happy to connect with you even before your trip begins, sharing my insights and helping you make the most of your time in Italy.
Massimo
Florence, Pisa +3
My name is Massimo Coppo, I live in Florence, I am a tourist guide in English and French, I also work as a driver and sommelier, I have a degree in philosophy and a degree in literature, I love being able to introduce my country to those who come from far away and always learn something new.
Edoardo
Amalfi, Sorrento +11
Born and raised in Italy's Marche region, I have explored the country from north to south during travels and study periods away from home. I have lived part of my life in amazing cities such as Venice and Bologna, and have visited Rome a lot since I have family and friends there. I am an experienced trip planner for destinations all over Italy, from the breezy Cinqueterre in Liguria down to the sun kissed Amalfi coast. If you want someone to help you with all-encompassing guidance and make the best out of your trip to Italy, I will be most happy to help you!