A Path Through History | Tuscany, Italy

Walk through one of the most vibrant landscapes on earth under the Tuscan sun.

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  • Tuscany
  • Tuscany village
  • Tuscany view of vineyards
  • Tuscany bridge
  • Vineyard in Tuscany

Trip Highlights:

  • Visit some of the most classic historic sites in Europe
  • Walk the Roman road which Caesar constructed to link the North Sea and Rome
  • Travel to Monteriggioni, where there is an opportunity to spend the night within the castle’s walls
  • Enjoy all of the classics of Italian cuisine, including local meats and cheeses and fresh pastas

The Tuscan sun has nurtured one of the most vibrant landscapes on earth. Thick forests of low lying Mediterranean foliage, sweeping sunflower and lavender fields, historic vineyards, and castle- dotted ridges will mark your progress across this pastoral land. There are few places more peaceful than Tuscany. This unique opportunity to see it on foot will bring you through both rarely visited villages and some of the most classic historic sites in Europe.

Our route primarily follows the most remote and walkable section of the Via Francigena, one of the great historic pilgrim’s routes. The trail follows the imprint of the Roman road which Caesar constructed to link the North Sea and Rome. On many sections of the route the old road is still visible, with the original cobblestones poking through the soil. The Via Francigena is perhaps the best pilgrim’s trails to hike as, of the historic routes across Europe, it is among the least disturbed by modernity and construction.

The hike begins in San Gimignano, fondly referred to as the Manhattan of the Middle Ages due to its unique spires and towers. San Gimignano is an excellent entry point to the Via Francigena because of both its density of medieval architecture, and the stunning views back towards the historic village as you depart.

From San Gimignano you travel to a farm-house hotel just outside the Colle di Val d’Elsa and spend a day walking along the river into the village proper, where one may visit its multiple landmarks. The Colle di Val d’Elsa itself has multiple cathedrals and a historic “upper city,” while our location outside of it allows for the chance to experience a slice of rural Tuscan living.

From there, the route travels to Monteriggioni, a beautifully preserved and highly fortified medieval castle, where there is an opportunity to spend the night within the castle’s walls. Monterigionni is essentially a living renaissance fair, with vendors, artisans, and performers coming to set up shop in the castle walls.

Finally, complete your journey by walking into the historic landmark city of Siena. The last day of walking has you exploring the dense forests and scattered villages as the pilgrims route approaches one of its primary stops and the location that devout wanderers have traveled to for generations. Siena has become legendary over the years for its Gothic cathedrals and winding alleyways, representing one of the densest and most intact old towns in all of Europe.

Tuscan food and accommodations are a joy. Modern amenities lie hidden amongst the medieval streets, while every corner has another cafe or trattoria to explore. Expect to enjoy all of the classics of Italian cuisine, including local meats and cheeses and fresh pastas, all heartily seasoned with regional herbs.

Overall the trip features reasonably gentle walking with some longer distances on the more remote sections of the pilgrim’s trail. Ascent and descent are usually unsustained as the you proceed through the rolling landscape, where farm roads and trails dive in and out of forested gullies and broad fields.

Trip Itinerary

Choose from our standard itinerary or customize the trek by adding or subtracting days.

Arrive in San Gimignano by either bus or taxi. We recommend that you arrive through Florence with the opportunity and time to visit its world class Gothic cathedral and vibrant student and art scene.

Begin your trek out of San Gimignano to a farm-house hotel outside of Colle di Val d’Elsa. This will be your first leg along the legendary Via Francigena, as it passes through oceanic sunflower fields, local farms, and remote Tuscan villages.
12 miles, 500 ft ascent and descent.

Distance: 12 miles. Elevation gain/loss: 1000/1200 ft.

Enjoy a shorter walk into Colle di Val d’Elsa along a popular river trail, which passes low lying waterfalls and jubilant swimming holes. Spend the afternoon in the Val d’Elsa upper village with the opportunity to visit the village’s cathedral and multiple medieval palaces. Return either by bus or along the river to your hotel.

Distance: 5 miles. Elevation gain/loss: 175/325.

Walk from the Val d’Elsa to the unique castle-town of Monteriggioni. The relaxing hike wanders past local castles, nunneries, and vineyards before arriving at Monteriggioni where a living renaissance fair will greet you.
8 miles, 1000 ft ascent and descent.

Distance: 8.2 miles. Elevation gain/loss: 800/625 ft.

The final leg of the trek takes you directly into the untouched-by-time medieval alleyways of Siena. This last leg along the Via Francigena will provide the true pilgrims experience, emerging from the Tuscan wilderness into one of the true meccas of Medieval Europe. Once again, we recommend scheduling extra time to see the magnificent cultural landmarks of Siena after the tour.

Distance: 14 miles. Elevation gain/loss: 1225/1000 ft.



Tuscany, Italy | A Path Through History

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