Via Francigena hike from Siena to Monteriggioni: Wine tasting

Walk an ancient pilgrimage route, end with wine in a walled village

This 5-mile hiking tour from Siena follows the Via Francigena, a medieval pilgrimage route, through forests, vineyards and olive groves to the hilltop fortress of Monteriggioni. An expert guide leads the trek past castles and villages, then a local producer guides you through 3–4 organic wines in the village before you return to Siena by bus at your own pace.

The experience

The walk starts at Siena train station at 9am and follows the same route pilgrims and traders used to reach Rome in the Middle Ages. For roughly 3 hours you hike through the heart of Tuscan countryside (forests and fields, vineyards and olive groves) past the ruins and medieval villages that still dot the landscape. The guide explains what you're walking through as you go, so the history isn't something you read about later. It's the reason the path exists at all. The terrain is uneven countryside footpaths, not a paved trail, and the pace is steady rather than leisurely.

Monteriggioni appears as you crest a rise: a small fortress town built by Siena in the 1200s as a defense against Florence, its walls still intact and imposing. Once you arrive, a local wine producer takes over and walks you through a guided tasting of 3–4 organic wines made in the region, explaining each one as you taste. After the tasting, the village is yours to explore on your own. The streets are narrow, the views from the walls reach across the valley, and there's no schedule pushing you out. When you're ready to leave, a bus stop nearby has multiple return options to Siena. Your ticket is included.

What’s included

• Wine samples from the local producer.
• transport by air-conditioned minivan to the trailhead.
• a live English-speaking guide for the hike.
• return bus ticket to Siena.

Before you book

Days and timesMonday and ThursdayDeparts at 09:00

Book up toStart time

GroupUp to 16 · max 8 per booking

Live guideEnglish

Meeting point and pickupNo hotel pickup: you go to the meeting point. Ends back at the starting point.

Cancellation and refundsFree cancellation up to 24 h before the start. After that, no refund.It may be canceled due to bad weather or if the minimum number of travelers isn't reached. If that happens, you're offered another date or a refund.

Prices and times updated 10 days ago

Good to know

Moderate physical effortPets welcomePublic transport nearbyNot recommended during pregnancyNot recommended with heart problems

Operated by Tuscan Escapes by Papilio SRL

Is this one for you?The hike covers uneven ground for 3 hours at a steady pace, so it suits hikers comfortable with countryside footpaths and moderate physical effort, not a casual stroll. The early 9am start from Siena train station means an early morning, but it gets you to Monteriggioni before the afternoon crowds and leaves the evening free.

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Top questions

What happens if it rains?

It may be canceled due to bad weather. If that happens, you're offered another date or a refund. Free cancellation up to 24 h before the start.

What is the Via Francigena and why does this hike follow it?

The Via Francigena is an ancient pilgrimage and trade route that connected pilgrims and merchants traveling to Rome throughout the Middle Ages. This hike follows the same path through Tuscany, so you walk the actual route rather than a modern trail built to mimic it, passing the castles and villages that grew up along it centuries ago.

How difficult is the 5-mile hike and what kind of shoes do I need?

The trek crosses uneven countryside footpaths for about 3 hours and requires at least a moderate level of physical fitness. Comfortable, sturdy hiking shoes are essential because the ground is not paved. The operator recommends shoes you've already worn, not new ones.

What happens during the wine tasting in Monteriggioni?

A local organic wine producer guides you through a tasting of 3–4 different wines made in the region, explaining each one as you taste. The tasting takes place in the village after the hike, so you taste the wines where they're produced.

Can I spend time exploring Monteriggioni after the wine tasting?

Yes. After the guided tasting ends, you have leisure time to walk the village on your own. You return to Siena whenever you're ready by taking the bus from a nearby stop. Your return ticket is included and there are multiple departure times available.

What's included in the price and what do I need to bring?

The tour includes the minivan transport from Siena to the trailhead, the guide, wine samples during the tasting, and your return bus ticket to Siena. Bring water, snacks and sun protection. The operator does not provide food or drinks beyond the wine tasting.