Walking in the Crete Senesi: The Gladiator Trail from Pienza

South of Siena, the Crete Senesi is a landscape of clay hills, cypress trees, and golden fields. Autumn is the perfect time for walking here, with cooler air and harvest colors. The “Gladiator Trail” near Pienza is a scenic highlight.

Crete Senesi from the Gladiator Trail

Why Go?

This area is quieter than Chianti but just as beautiful. It’s classic “film Tuscany,” with wide horizons and winding roads.

A bit of History

The Crete Senesi was shaped by erosion, leaving a moonscape admired since medieval times. Pienza was redesigned in the 15th century as the “ideal Renaissance city” under Pope Pius II.

What to Expect

• Gentle hiking trails through farmland and cypress avenues.

• Views used in Ridley Scott’s Gladiator.

• Quiet villages and abbeys.

5 Things to Do and See

1. Stroll Pienza’s streets, UNESCO-listed for Renaissance planning.

2. Walk the Gladiator Trail loop into the countryside (2–3 hours).

3. Visit the Cathedral and Piccolomini Palace in Pienza.

4. Explore Abbey of Monte Oliveto Maggiore, with Renaissance frescoes.

5. Sample pecorino cheese, Pienza’s specialty.

Food Culture

Expect pecorino, pici pasta, and local wines like Brunello di Montalcino and Vino Nobile di Montepulciano.

Where to Eat

• La Bandita Townhouse (Pienza) – Modern dining with Tuscan ingredients.

• Trattoria Latte di Luna (Pienza) – Family-run trattoria, famous for pici all’aglione.

• Antica Osteria da Divo (Siena) – Atmospheric dining in ancient caves.

Where to Stay

• La Bandita Townhouse Hotel (Pienza) – Chic boutique stay in a converted convent.

• Hotel Corsignano (Pienza) – Comfortable, friendly, with countryside views.

Off the Beaten Track

Cycle the gravel roads (strade bianche) of the Crete Senesi, a favorite of cyclists.

How to Get There by Train/Bus

Train to Siena, then bus to Pienza (approx. 1h). Trails start just outside the town.

Pienza