Hiking the Pilgrim Path from Siena to Monteriggioni

Hike along the scenic and famous Via Francigena pilgrim trail from Siena to Monteriggioni. This easy trek follows ancient paths used by pilgrims since the year 800 CE. People from across Europe followed the trail on their way to or from Rome when going on a pilgrimage was the goal of a lifetime. Walk on the same paths today, but with more comfortable shoes!

Along the way, you’ll visit one of the oldest churches in the province of Siena, the Romanesque abbey of San Salvatore and Cirino. This church still displays an intricate 15th-century painting on its main altar. Continue to the little hamlet of Monteriggioni, mentioned by Dante Alighieri in his "Divine Comedy." Dante compares the giants at the entrance of the Ninth Circle to Monteriggioni’s famous towers. He writes:

Because as on its circular parapets
Monteriggioni crowns itself with towers
E'en thus the margin which surrounds the well
With one-half of their bodies turreted 
The horrible giants.

Itineraries with Hiking the Pilgrim Path from Siena to Monteriggioni

Explore Tuscany: Florence, Siena, Pisa, & Lucca - 11 Days

Explore the region that gave birth to the modern Italian language on this packed 11-day trip. Start in Florence to see Michelangelo's 'David' sculpture and other famous Renaissance works, then head to Pisa to climb the leaning tower and try the local gelato. Sample world-famous wine and local pecorino cheese in the Val d'Orcia region and see Tuscany from a hot-air balloon. End in medieval Lucca, where you'll learn how to hand make your own pasta before relaxing in a 12th-century Piazza with a cup of coffee and a good book.

Via Francigena: San Miniato, San Gimignano, & Siena - 5 Days

In 990 BCE, the Archbishop of Canterbury traveled from England to Rome to meet with the Pope. He wrote a detailed diary of the 80 stages of his journey through the United Kingdom, France, and Italy, and this path is now known at the Via Francigena (the Francigena Way), a path for religious pilgrims from Canterbury to Rome. The trail travels through Tuscany, and you can experience it on this five-day itinerary that winds through the Tuscan countryside.

Veneto and Tuscany for Active Families: Venice, Verona, Lake Garda, Siena & Florence - 14 Days

Families with teens who want to get out and explore (and find the perfect backdrop for their photos) should give this two-week itinerary through the Veneto and Tuscany a try. You'll start in Venice, where you can explore secret passages, craft your own masks, and paddle a gondola. Then head to Verona and Lake Garda, biking through both urban and natural attractions. Wrap up in the Tuscan cities of Siena and Florence with a hot air balloon ride, gelato-making, and more.

Veneto and Tuscany for Active Families: Venice, Lake Garda & Siena - 10 Days

Your whole family can fully engage with Italy on this adventurous itinerary, ideally suited for teens with energy to spare. You'll begin in Venice, where you'll craft Carnival masks and explore the secret passages of the city's famous landmarks. After a stop to wander the streets of Verona, you'll head to the park-lined shores of Lake Garda, filled with attractions for all ages. Finish the tour in the Tuscan city of Siena, your base for hot air balloon rides, hikes, and more.