Open Travel Guide
Hiking in Siena

Siena Hiking & Trekking Guide 2026

Where to walk in Siena — from easy half-days to serious treks, with honest difficulty grades.

By Updated

Siena has 5+ hiking trails covered in this guide, led by Via Francigena: Monteriggioni to Siena (Porta Camollia), Crete Senesi Walk to Monte Oliveto Maggiore from Asciano and Monte Amiata Summit Hike. Each entry below includes the practical details — what it costs, when to go, and how to plan around it.

Siena travel guide: where to stay, what to do and where to eat in Siena, Tuscany, Italy.

Top trails

Routes worth lacing up your boots for.

  1. 1

    Via Francigena: Monteriggioni to Siena (Porta Camollia)

    About 20-21 km one wayAbout 5-6 hours walking (one source estimates 4.5 hours)Easy to ModerateGentle rolling terrain; no major climb

    The classic last stage of the Via Francigena into Siena, from the walled hamlet of Monteriggioni across countryside to Porta Camollia, the traditional pilgrim entrance to the city.
  2. 2

    Crete Senesi Walk to Monte Oliveto Maggiore from Asciano

    Roughly 10-14 km one way depending on the route chosen; marked routes and distances should be checked locally3-5 hours one wayModerateRolling clay hills; moderate cumulative climb

    Open clay hills, cypress-lined farm tracks and the Benedictine abbey of Monte Oliveto Maggiore, with its cloister frescoes.
  3. 3

    Monte Amiata Summit Hike

    Summit loops typically 8-14 km depending on start; the Anello della Montagna loop is much longer3-5 hours for a summit loopModerateSummit 1,738 m

    Walk to the summit of Monte Amiata, Tuscany's highest volcanic peak, through beech forest with wide views over Val d'Orcia and Maremma.
  4. 4

    Riserva Naturale Alto Merse Walks

    Trail lengths vary; short loops of several km are available2-4 hoursEasy to ModerateLow hills along the River Merse

    A protected river valley with woodland, gorges and swimming spots along the River Merse in southwest Siena province.
  5. 5

    Chianti Walk from Gaiole in Chianti to Badia a Coltibuono

    About 8-12 km depending on the loop chosen (approximate; verify locally)3-4 hoursModerateRolling hills; moderate cumulative climb

    A walk through Chianti Classico vineyards and woods near Gaiole, with a historic abbey nearby.

Trail difficulty levels

Pick a route that matches your fitness and experience.

Easy

Short walks on firm paths, such as village loops and the lower Merse paths.

Moderate

Full-day walks on gravel and hill tracks, such as Monteriggioni to Siena, Crete Senesi and Monte Amiata.

Hard

Long or multi-stage routes such as consecutive Via Francigena stages and winter Monte Amiata.

When to hike

Seasonal conditions in Siena.

Overview
Spring (April-June) and autumn (September-November) are the best seasons; summer is hot and exposed on the Crete Senesi, while Monte Amiata stays cooler.
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Local hazards

What to watch out for on the trail.

Medium

Hazard: Heat and lack of shade on the Crete Senesi and Via Francigena in July and August; carry plenty of water.

Medium

Hazard: Slippery clay tracks after rain, which also make paths sticky.

Medium

Hazard: Scarce water points and patchy mobile signal on rural stages.

Medium

Hazard: Fog, storms and snow on Monte Amiata; check forecasts.

Medium

Hazard: Ticks and mosquitoes in woods and river areas; use repellent. Emergency number across Italy: 112.

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