Castiglion Fiorentino Palio dei Rioni: A Local Tuscan Festival You Can Reach by Train

If you love the idea of Siena’s Palio but want something more intimate, more local, and far easier to enjoy as an independent traveler, the Palio dei Rioni in Castiglion Fiorentino is one of Tuscany’s best-kept secrets. Held each June, this historic festival combines deep-rooted tradition, fierce neighborhood pride, and a thrilling horse race—without the overwhelming crowds of Italy’s most famous events.

Set in eastern Tuscany between Arezzo and Cortona, Castiglion Fiorentino is perfectly placed for travelers exploring Italy by rail, making it an ideal cultural highlight on a car-free itinerary.

What is the Palio dei Rioni?

The Palio dei Rioni is Castiglion Fiorentino’s annual competition between the town’s three historic districts, known as rioni. Each rione fields a horse and jockey to compete for the Palio banner, following days of ceremonies, parades, drumming, and flag-throwing that bring the entire town into the streets.

The three districts are:

• Cassero

• Porta Fiorentina

• Porta Romana

This is not a staged performance for visitors—it is a living tradition that locals grow up with, argue about, and passionately defend. The result is an atmosphere that feels authentic, emotional, and deeply connected to place.

When does it take place?

The Palio dei Rioni is traditionally held on the third Sunday of June, with celebrations building throughout the preceding week. The race itself usually takes place in the afternoon, following a morning religious ceremony and the blessing of the horses and jockeys.

If you want the full experience, plan to arrive at least the day before race day to catch the buildup and feel the town’s energy as rivalries intensify.

Why it’s special

What makes Castiglion Fiorentino’s Palio so appealing—especially for international visitors—is its scale. You can see the race clearly, move around the town easily, and still feel part of the crowd rather than overwhelmed by it. It offers the drama and symbolism of a Palio event, but with a warmth and accessibility that larger festivals often lose.

Getting to Castiglion Fiorentino by train

Castiglion Fiorentino is easy to reach by rail, making it ideal for travelers avoiding car hire.

• From Florence or Rome, travel by train to Arezzo, then take a short regional train (around 10 minutes) to Castiglion Fiorentino.

• From Bologna or Venice, travel south via Florence or Bologna to Arezzo, then continue onward.

The train station sits just below the historic centre; taxis are readily available, or you can walk uphill if traveling light.

Where to eat during Palio weekend

Restaurants fill quickly during Palio week, so booking ahead is highly recommended—especially for Saturday night and Sunday lunch.

Da Muzzicone

A classic local favourite serving traditional Tuscan dishes in a relaxed, welcoming setting. This is the kind of place where Palio loyalties are openly discussed at neighbouring tables.

Website: https://www.damuzzicone.it

Sillas Bistro

A more contemporary option offering refined plates and good local wines, ideal if you’re looking for something slightly lighter or more modern.

Website: https://www.sillasbistro.it

Pizzeria Il Gallo Nero

Casual and friendly, perfect for an easy meal during a busy festival weekend.

Website: https://www.ilgallonero.net

Where to stay in and around Castiglion Fiorentino

Accommodation books up early for Palio weekend, particularly in June, so advance planning is essential.

Agriturismo Agrisalotto

A beautiful countryside agriturismo just outside town, well known for its excellent restaurant as well as its rooms. Ideal for travelers who want to combine the Palio with a slower, food-focused Tuscan stay.

Website: https://www.agrisalotto.it

Hotel Park

Located close to the train station, this is one of the most convenient choices for travelers arriving by rail and planning a short stay.

Website: https://www.hotelparkcf.it

Casa Fiordalisi

A private four-bedroom house about ten minutes’ drive from town, ideal for families or groups who want space and countryside privacy while still being close to the Palio events.

Website: https://www.casafiordalisi.com

Other things to do while you’re there

Beyond the Palio itself, Castiglion Fiorentino rewards slow exploration. Wander the historic centre at golden hour, enjoy views across the Valdichiana, and use the town as a base for easy train day trips to nearby Arezzo or hill towns such as Cortona.

Other Palio-style events across Italy (all reachable by train)

If the Palio dei Rioni sparks your interest, there are several other lesser-known Palio-style festivals worth building into a rail itinerary:

Palio di Asti (Piedmont, September) – One of Italy’s oldest Palios, with a strong medieval atmosphere.

Palio di Ferrara (Emilia-Romagna, May) – Renaissance costumes, parades, and multiple competitions in a beautifully preserved city.

Palio di Legnano (Lombardy, late May) – A powerful historical commemoration near Milan.

Palio dei Somari, Torrita di Siena (March) – A lively and humorous donkey Palio in southern Tuscany.

Palio di San Ranieri, Pisa (June 17) – A historic rowing Palio on the River Arno.

All of these destinations are accessible by regional or high-speed trains, making them ideal additions to an independent Italy-by-rail journey.

For travelers looking to experience Italy’s living traditions without the stress of driving or large-scale tourism, the Palio dei Rioni in Castiglion Fiorentino offers something rare: authenticity, accessibility, and a powerful sense of place—best enjoyed slowly, and by train.

For a full guide to Touring Italy by Train grab your copy here: https://mybook/TouringItalybyTrain