Siena: Private Walking Tour, Palio Stories & Cathedral Art

Summary

Walk Siena’s winding lanes, hear Palio legends and see cathedral art

You’ll walk Siena’s ancient streets with a local guide who knows every legend and shortcut. Hear Palio stories in Piazza del Campo, peek into centuries-old churches, and stand beneath the soaring stripes of Siena Cathedral. Choose your pace — two or three hours — and let each detail sink in as you wander.

What’s the experience like?

“You know, in Siena we don’t just cheer for a horse — we cheer for our whole neighborhood,” our guide Paola said, grinning as she led us through a narrow alley that smelled faintly of baking bread. I’d never thought much about horse races before, but in Siena it’s not just sport — it’s identity. We started outside the Basilica of San Domenico, where the stone felt cool under my hand and the air inside was heavy with incense. Paola pointed out St. Catherine’s relic (her actual head — I wasn’t ready for that), and I caught myself whispering so as not to break the hush.

We wandered past the Sanctuary of St. Catherine — her old family home now split into little chapels. There were locals lighting candles quietly; one older woman smiled at me when I fumbled with my camera strap. The streets twisted around us, sometimes opening onto sunlit squares where laundry flapped from windows. At Piazza del Campo, everything suddenly felt bigger: kids chasing pigeons, a couple arguing softly over which gelato flavor to get, and Paola explaining how each “contrada” has its own colors and animal symbol. She tried teaching me how to say “Onda” (the wave district) and laughed when I got it wrong — apparently my accent made it sound like “onda” as in “wave goodbye.”

The Siena Cathedral stopped me in my tracks — black-and-white stripes against the sky, all sharp lines and impossible details. We didn’t go inside right away; first Paola told us why they never finished building it larger (plague, money troubles… classic medieval drama). When we finally stepped in (tickets were easy to get on-site), I just stood there staring at marble floors so intricate you almost don’t want to walk on them. Michelangelo and Donatello sculptures tucked into corners like they’re just part of the furniture here. It’s funny what sticks with you — I still think about that moment when sunlight hit the mosaics near the altar.

Step-by-step itinerary

Day 1 — Explore Siena's historic landmarks

• Start at Basilica San Domenico
• See St. Catherine's relic inside
• Visit Sanctuary of St. Catherine outside
• Discover oldest private building and Siena symbol
• Admire Piazza del Campo and Palazzo Pubblico
• Learn about Palio horse race and Contrade
• View Siena Baptistery from outside
• See the Crypt from outside
• Arrive at Siena Cathedral
• Optionally visit inside Cathedral

Top questions

How long is the Siena private walking tour?

You can choose between a 2-hour or 3-hour tour with your local guide.

Does the tour include entry to Siena Cathedral?

You can visit inside if you wish; tickets are purchased onsite during the tour.

Is this walking tour suitable for wheelchairs or strollers?

Yes, it is wheelchair accessible and infants or small children can use prams or strollers.

What main sights are covered on this Siena walking tour?

The Basilica of San Domenico, Sanctuary of St. Catherine, Piazza del Campo, Palazzo Pubblico, Baptistery of San Giovanni, and Siena Cathedral.

Can I customize what we see during the tour?

Yes! You can discuss your interests with your guide and tailor the route together.

Is there public transportation nearby for this tour?

Yes, public transportation options are available near the starting point.

Are service animals allowed on this tour?

Service animals are welcome throughout the walking tour.

Can I visit a Contrada Museum during this tour?

If you’re interested in Palio tradition, your guide can include a Contrada Museum visit if time allows.

Is there anything special I should wear or bring?

Wear comfortable shoes and be ready for any weather conditions; an umbrella might help if rain is forecasted.

What’s included

Your day includes a licensed local guide leading you through Siena’s historic center at your chosen pace (2 or 3 hours). You’ll explore major sites like Basilica San Domenico, Piazza del Campo, and outside views of Baptistery and Cathedral—with flexible stops based on your interests. Entry tickets for interior visits (like Siena Cathedral) can be purchased directly onsite during your tour.