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.
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.
Maria
Florence, Siena +1
I design personalized journeys in Florence and throughout Tuscany for travelers who want to experience Italy with depth, beauty, and ease. From handpicked boutique hotels and exceptional restaurants to private cultural experiences and seamless logistics, every detail is thoughtfully curated around your style and rhythm. Whether it’s exploring masterpieces at the Uffizi Gallery, admiring the Duomo di Firenze, or escaping to the Tuscan countryside, I craft experiences that feel authentic, elevated, and effortlessly Italian. Florence is my home — designing meaningful stays here is my passion. Let’s create your unforgettable Italy. MARIA
Rosa
Florence, Pisa +13
5.0(1)Hi, I’m Rosa - your local Italy travel planner based in Florence. I live in Florence, in the heart of Tuscany. Italy is not just where I live, it's what I love sharing with others. Over the years, I've explored many cities like Bologna, Milan, Venice, Rome Naples, Sicily, Sardinia, Puglia and many more. Each region has its own flow, flavors and traditions, and understanding these differeces is what makes a trip truly special. I help travelers experience Italy beyond the typical tourist path. From selecting the perfect area to stay, to reccomending authentic restaurants, wineries and hidden villages. I desing trips that feel personal and deeply Italian. If you want to experience Italy with local insight and thoughtful planning, I’ll help you create a journey you’ll never forget.
Mike
Rome, Florence +7
5.0(2)I’m Mike from Rome with Mike, an American who’s called Italy home since 2003. I help travelers plan relaxed, unforgettable Roman holidays—at a local’s pace. Think hidden corners, underground sites, and experiences not everyone gets to see. No rushing, no tourist traps—just smart planning and insider insight. Whether you’re here for art, history, or food and wine, I’ve got you covered. Let’s slow it down and make Rome feel like home. The goal is simple: to help you experience Rome not as a tourist, but as a Roman.
Barbara
Rome, Cinque Terre +13
5.0(2)As a certified Tour Leader, I've had the incredible privilege of guiding groups from all over the world across Italy and Europe. I adore my country, and over the years, I've realized that my favorite role is being a bridge between travelers and the true soul of a place. Today, I invite you to experience this through my eyes. Whether you need a customized itinerary for your trip or a cultural deep-dive anywhere in Italy, I am here to help you live the best experience of your vacation. I’m waiting for you! Let’s plan something beautiful together.