Via FrancigenaSan Gimignano to Siena
Cover over 50 km in 4 days, exploring the rolling hills, vineyards, and medieval towns that make this region so unique.
Your journey begins in San Gimignano, a hilltop town famous for its medieval towers and rich history. From there, you’ll follow scenic trails through olive groves and vineyards, soaking in the beauty of the Tuscan countryside. With a stop in Colle Val d’Elsa, the route becomes much more manageable and suitable for all walkers, allowing you to enjoy the experience at a relaxed pace. As you approach Siena, the landscape transforms, leading you to one of Italy’s most captivating cities.
A Journey to Savor
This route takes you straight into the heart of Tuscany’s wine country, where every turn offers a postcard-perfect view. Along the way, you’ll have time to enjoy local flavors, discover hidden gems, and take in the region’s timeless atmosphere.
With carefully selected accommodations, luggage transfer, and full support throughout the trip, all you have to do is take in the scenery and enjoy the experience at your own pace.
If you want to add 1 night in Siena click here
If you want to walk in just 2 days click here
Walk the Via Francigena in good company
- Overnight stays according to your needs
- Luggage Transport each day Door to Door
- Our Maps
- Airport or Station Shuttle
- Assistance every day from 8:30 am to 7:00 pm all the information from the specialists of the Via Francigena!
We take care of everything!
Via Francigena Walking, from San Gimignano to Siena is a relaxed walking trip, to enjoy in a weekend.
A highly variable route, with easier and shorter stages, and others with decent climbs and descents.
The route is very well marked and has no objective difficulties.
Assistance along the way if you don’t want to walk we will take you to your next hotel.
Difficulty: 3/5
Arrival Airport: Pisa Airport or Florence Airport
Arrival Train Station: San Miniato or Siena
Departure Train Station: Siena
- 4 nights with overnight and breakfast formula
- Luggage transport EVERY DAY from Hotel to Hotel
- Detailed route with our Original Virtual and Paper Maps
- Telephone support from 8:30 to 19:00
- Transfer to reach the places of arrival and departure
- Lunches and dinners (You can add to your package HB formula on request where available)
- Visits and entrances to museums and attractive clubs
- Tourist taxes in hotel facilities
- Anything not specified under “the fee includes”
In case of any cancellation of your booking, the following charges are expected:
More than 30 days before Departure date – deposit = 20%
29 – 20 days before Departure date – 30% of the total cost
19 – 15 days before Departure date – 50% of total cost
Less than 14 days before Departure date – 100% total of cost
Itinerary
DAY 1: Arriving in San Gimignano
DAY 1
San Gimignano
Where the Journey Begins
Your adventure starts in San Gimignano, a medieval town where history lingers in every stone. Walking through its winding streets, you’ll pass beneath the towering silhouettes that define its skyline. The Piazza della Cisterna is the heart of the town, the perfect spot to pause and take it all in. Before setting off, enjoy a glass of Vernaccia, the local white wine. This is the first step into an unforgettable four-day experience along an ancient path.
DAY 2: San Gimignano to Colle Val d’Elsa
DAY 2
San Gimignano to Colle Val d’Elsa Distance to Cover: 13 Km Walk Time: 3/4 hours
Between Stone Towers and Crystal Waters
Leaving San Gimignano, the trail winds through a patchwork of vineyards, olive groves, and golden fields. The path follows the Foci Valley, with gentle ups and downs that make the walk both peaceful and engaging. Cypress-lined routes lead past quiet farmhouses and ancient churches, where history and nature blend seamlessly. As you approach Colle Val d’Elsa, the sound of flowing water welcomes you—this town, famous for its crystal production, holds a unique charm. The day ends strolling through medieval streets before resting in a place shaped by centuries of craftsmanship.
DAY 3: Colle Val d’Elsa to Monteriggioni
DAY 3
Colle Val d’Elsa to Monteriggioni Distance to Cover: 15 Km Walk Time: 4/5 hours
Tracing History Through Countryside Paths
Leaving Colle Val d’Elsa, the trail weaves through a landscape of rolling fields, oak forests, and quiet country roads. Along the way, you reach the Romanesque church of San Martino di Strove, a timeless landmark where centuries of pilgrims have passed before you. As the journey continues, the silhouette of Monteriggioni’s medieval walls slowly emerges on the horizon. Stepping through its ancient gates, you enter a perfectly preserved stronghold—a place where history lingers in every stone.
DAY 4: Monteriggioni to Siena
DAY 4
Monteriggioni to Siena Distance to Cover: 21 Km Walk Time: 5/6 hours
A Timeless Welcome
Leaving Monteriggioni, the trail gently winds through woodlands and open countryside, following ancient paths once traveled by countless pilgrims. With each step, the distant silhouette of Siena grows clearer, its medieval towers and grand city walls standing proudly against the sky. Entering through its historic gates, you’re welcomed by a city where Gothic architecture, lively piazzas, and centuries of tradition create an unforgettable atmosphere. In Piazza del Campo, the journey ends, but Siena’s timeless beauty ensures the experience lingers far beyond the final step.
Silver Package
Bed and Breakfast Formula
in 2-stars Hotel/B&B
Gold Package
Bed and Breakfast Formula
in 3-stars Hotel/Agritourism
Platinum Package
Bed and Breakfast Formula
in 4/5-stars Hotel/Agritourism
Services
Hotelsalong the paths
Single and Double Room package
with BB formula in Hotels,
B&B and Farmhouses along the path.
Triple Room package on request
(where available)
Would you like to schedule an appointment with one of our Assistants to talk about your next trip on the Via Francigena?
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