There isn't one way to walk Tuscany. You can follow the Via Francigena through medieval towns and pilgrimage landscapes, cross the Apennines into Florence on the Via degli Dei, walk through the vineyards of Chianti and the Val d'Orcia, or leave the familiar inland scenery behind for the coast and the island of Elba. The question is not whether Tuscany is good for walking. It clearly is. The question is which Tuscany you want to walk through.
This guide covers all the self-guided walking routes we offer in Tuscany, with enough practical detail to help you compare and enough honesty to point you toward the one that actually suits you.
If you’re looking for inspiration for your next Camino, or want help choosing the itinerary that best matches your needs,
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Best for: History lovers, pilgrimage atmosphere, iconic Tuscan scenery, first-time long-distance walkers
The Via Francigena is Tuscany's great pilgrimage road. It enters the region from the north through the Apennine Pass of Cisa, descends into the Lunigiana, and then unfolds southward through some of the most recognizable landscapes in the world.
From Lucca's medieval walls to the shell-shaped Piazza del Campo in Siena, the route strings together a sequence of remarkable places: the towers of San Gimignano appearing on the horizon after a long morning's walk, the fortified village of Monteriggioni rising from the hills, and then the Val d'Orcia, where the road stretches south toward Rome through rolling clay hills and isolated farmhouses.
Pontremoli to Lucca - Lunigiana, Statue Stele, Versilia coast. Historical, varied terrain.
Lucca to Siena - San Gimignano, Monteriggioni, Colle Val d'Elsa. Classic, iconic, well-serviced.
Siena to Viterbo - Val d'Orcia, Radicofani, Lake Bolsena. Dramatic, remote, meditative.
The Lucca to Siena section is our most requested and a natural starting point for first-timers. The path is well-marked and towns appear regularly throughout.
For a gentler version, our Easy Via Francigena from Siena to Orvieto covers the Val d'Orcia at a slower pace, with shorter daily stages and some private transfers on the more demanding stretches.
Best for: Nature lovers, Apennine forests, walkers who want to arrive in Florence on foot
The Via degli Dei crosses the Apennines on a route that passes through mountains named after ancient deities: Monte Venere, Monte Luario, Monte Giunone. It connects Bologna to Florence through forests of beech and chestnut, along ancient Roman roads and ridge paths.
This is a different kind of Tuscany. There are no vineyard panoramas here, no medieval towers on the horizon. Instead, there are long green ridges, military cemeteries deep in the woodland from the Second World War Gothic Line, and the gradual descent toward Florence that ends with a view of the city from the hills of Fiesole.
You reach Florence having walked there through the mountains, and the city looks completely different because of it.
Key facts:
Total distance: approximately 130 km, divided into 5 or 6 stages
Our trip: 8 days (including arrival and departure days), stages of 20-25 km
Terrain: Apennine ridges, forest tracks, some steep ascents and descents
Difficulty: moderate to challenging
We also offer a shorter 5-day version covering the heart of the route, and an easy version with transfers on the harder sections.
From Florence, walkers can continue south along the St. Francis Way through the Casentino forests toward La Verna, linking the Via degli Dei into a longer Tuscany journey.
Best for: Nature seekers, walkers who want forested terrain and a strong sense of pilgrimage history
The St. Francis Way connects Florence with some of the places most closely associated with Franciscan history in Tuscany, including the La Verna Sanctuary, where Francis is said to have received the stigmata. It then continues south through Tuscany and into Umbria toward Assisi and Rome.
The Tuscan section covers different ground from the Via Francigena. The path moves through chestnut and fir forests, past hermitages and small Casentino villages, with less urban infrastructure and more natural landscape.
What makes it different from the Via Francigena:
Forested Apennine terrain rather than open Tuscan hills
Fewer large towns along the route
Connects naturally to Umbria for walkers who want to continue south
Stronger sense of pilgrimage atmosphere throughout
The La Verna Sanctuary is a complex of medieval buildings perched on a rocky promontory in the forest, still an active Franciscan community, and one of the most historically significant sites on the route.
We offer the Tuscan section as a standalone trip: Florence to La Verna (8 days), or as part of the complete Florence to Rome journey.
Best for: Food and wine lovers, couples, travelers who want iconic Tuscan scenery without demanding terrain
Tuscany's wine country is one of the most walked landscapes in our catalog, and for good reason: the terrain is gentle, the towns are beautiful, and the food and accommodation along the way are genuinely excellent. We offer two routes in this territory, depending on how much ground you want to cover.
This is the longest and most complete Tuscany walking holiday we offer: 14 days from Florence to Rome, covering 97 km on foot across Chianti, Siena, and the Val d'Orcia, with a final train connection to Rome.
The walking stages range from 8 to 21 km, with several private transfers built into the programme on non-walking days. You start in Florence with a walk through the hills above the city to Fiesole, then spend three days in the Chianti Classico zone around Greve and Radda, before a transfer to Siena for a full leisure day. The walking then continues south along the Via Francigena through the Crete Senesi to Buonconvento and on to Montalcino, with a rest day there before the train to Rome. Suitable for beginners, with the option to add guided days in Florence and Siena.
A shorter, self-contained trip focused entirely on the Chianti Classico zone: 5 days, 40 km, based in Greve in Chianti and Radda in Chianti before ending in Siena. Daily walks range from 8 to 17 km and are mostly loop routes, so your luggage stays at the hotel while you walk. Rated suitable for beginners and can be extended with extra days in Florence or Siena.
Both routes suit:
Travelers who prioritize food, wine, and accommodation quality alongside the walking
Those who want beautiful scenery without technical terrain
Couples and small groups
Tuscany has more walking itineraries than most people realize. These routes sit alongside the Francigena and the Via degli Dei in our catalog, and each one covers a genuinely different part of the region.
The Via Lauretana runs from Siena to Cortona through the Crete Senesi, the clay hills south of Siena: bare, rolling, dotted with isolated farmhouses and cypress groves.
From Rapolano Terme the route continues south through Sinalunga and the Valdichiana before climbing to Cortona, the hilltop town that looks out toward Umbria. The SloWays trip covers 91 km over 6 walking days, with stages ranging from 14 to 20 km.
This route follows the traces of the Etruscans through the most ancient layers of Tuscan history. From Buonconvento, it moves through the Val d'Orcia, the ideal city of Pienza, the wine estates of Montepulciano, and on to Chiusi, a town with a remarkable Etruscan past: necropoli, underground tunnels, and one of the finest Etruscan museums in Italy.
Best for: travelers with a passion for archaeology, ancient history, and the southern Val d'Orcia landscape.
The Cammino di San Jacopo is a Tuscan pilgrimage route with deep historical ties to the Santiago de Compostela tradition. It runs from Florence through Prato, Pistoia, Pescia, Lucca, and Pisa to Livorno, covering around 170 km across northern Tuscany. Pistoia became an important centre of Jacobean devotion in the Middle Ages, after a relic attributed to Saint James arrived from Santiago de Compostela in the 12th century.
The route passes through Prato, where the Pecci Center for Contemporary Art is worth a visit, and through a stretch of Tuscany that feels very different from the wine country and pilgrimage roads further south.
Best for: travelers drawn to the Jacobean pilgrimage tradition, or anyone wanting to explore the art cities of northern Tuscany on foot.
We also offer a walking holiday on the island of Elba. While most visitors come for the beaches, the island has a varied interior: granite ridges, chestnut forests, coastal paths with views across to the mainland, and the remains of the mining history that shaped the island for centuries. Napoleon spent his first exile here. It's a Tuscany that has nothing to do with vineyards or pilgrimage roads, and that's exactly the point.
Here's a simple way to narrow it down:
Medieval towns + classic pilgrimage route - Via Francigena, Lucca to Siena
Val d'Orcia + longer pilgrimage journey south - Via Francigena, Siena to Viterbo
Apennine forests + arrival in Florence on foot - Via degli Dei
Forest landscapes + Franciscan heritage - St. Francis Way
Vineyards + food and wine + gentler countryside - Grand Tour Chianti & Val d'Orcia or Chianti Hills
Archaeology + Etruscan heritage - Etruscan Way, Buonconvento to Chiusi
Crete Senesi + historic pilgrimage landscape - Via Lauretana, Siena to Cortona
Art cities of northern Tuscany + Jacobean heritage - Cammino di San Jacopo
Coastal and island landscapes - Elba Island
On timing: spring (April to June) and autumn (September to October) are the best seasons for most Tuscany routes. Summer is possible on all routes, though exposed sections of the Via Francigena south of Siena can be very hot in July and August. The Via degli Dei and St. Francis Way, being more forested, are more comfortable in summer. The Chianti and Via Lauretana routes are available April to October.
On fitness: daily walking distances vary significantly by route. The Chianti Hills trip has stages of 8-17 km, suitable for beginners. The Via degli Dei has stages of 20-25 km and requires a good base level of fitness. Most routes sit between these two, with stages of 14-21 km. We offer easier versions of the Via Francigena with shorter stages and transfers on the harder sections.
Still not sure which Tuscany route suits you? Get in touch with the SloWays team. Tell us how many days you have, the distances you're comfortable walking each day, and the kind of landscape you're looking for, and we'll help you compare the options before you commit to anything.
Contact us or call (+39) 055 234 0736.
Written by the SloWays Team
Nominee Best Specialist Tour Operator 2026
