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.
Michele
Florence, Siena +1
Hi. My name is Michele, I was born in Naples, the city of pizza, and I used to work as a bartender. After working in cocktail bars and 5-star hotels in Tuscany, I fell in love with Florence and decided to capitalize on my passion for history, art, languages, foreign cultures, and above all, my passion for creating human connections. I then became a professional tour guide. I now work primarily in Florence, Tuscany, and occasionally in Naples. I love creating personalized and unique experiences to share with my guests. What are you waiting for? If you're looking for a friend, a consultant, and an experienced guide to help you plan your trip to Italy... here I am! It will be a pleasure to plan together!
Renata
Florence, Siena +2
I am an expert local guide in Tuscany, half Italian half Brazilian with a great passion for Art! Throughout my life I have done numerous courses about art history, painters, theatre and music. I love going to museums, concerts, art galleries, theatres but also walking in the nature and relaxing on the beach. I love being around people from different cultures. I graduated in Art and Drama and I concluded a Master and a Doctorate Degree in these areas. Professionally, I've been working for 20 years as a touristic guide, a teacher and an actress. I've been living in Florence for 12 years. During this period I have taken people from all over the world to see the gorgeous landscapes in Tuscany and to visit the beautiful medieval cities such as Florence, Siena, San Gimignano, Val D'orcia, Chianti, Pisa, Lucca, Volterra and many more. Visiting the historical buildings, the museums, squares and parks with so much history is a unique experience!
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!
Heliana
Florence, Siena +3
Travel isn't just about meeting expectations— it's going beyond them, enjoying every moment without worrying about logistics. I'm a professional tour guide and driver based in Florence, Tuscany. For over 20 years, l've been helping travelers create personalized, meaningful experiences through my small travel company. Share your questions and interests you have on Florence, Tuscany & Italy and I'll help you to make your best choices based on direct experiences!