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Guided San Gimignano Hiking Tour

Guided San Gimignano Hiking Tour
Imagine yourself hiking in Italy, strolling through peaceful woodlands and wide open landscapes. The scenery changes constantly as you ramble past fertile vineyards, gnarled olive trees, and wildflowers. On this five day walking holiday Tuscans teach you about Tuscany. A winemaker shows you his ancient cellars where his family has been producing wine for three generations. During a cooking class you learn to make Tuscan specialties using seasonal local ingredients. We visit an abandoned 15th Century castle, a Roman theater, and an alabaster workshop. With two nights in San Gimignano and two in Volterra you have plenty of time to relax and explore.
Day 1-2 San Gimignano  We meet in Florence and shuttle to San Gimignano. Lunch is in a hilltop village and winery. We tour the wine cellars and learn the secrets of San Gimignano’s crisp white wines. Later a rolling hike takes us to a ridge with spectacular views. On day two we drive to a cooking school. We spend the morning aprons on, learning the finer points of some typical Tuscan dishes. You can hike back to San Gimignano to work off some of the homemade pasta or simply relax poolside at the cooking school.

Day 3-5 Volterra  Day three takes us through the woods to an abandoned castle and village from the Middle Ages. Records show that in 1458 the village was already in decline with a population of seven families. Five hundred years later the castle and church are still standing. We explore the archeological site and continue our off the beaten path hike. Emerging from the woods the countryside opens up with beautiful vistas all the way to Volterra. We stop for a picnic lunch before shuttling to our hotel. On day four we complete our hike to Volterra. An ancient town, Volterra features an Etruscan gate from 400 BC and a Roman Theater. Frequent busses are available for your departure on day five.

Reserve This Tour Detailed Itinerary

US$ 1,250 per person
($200 Single Supplement)

Tour prices are based on double room occupancy. A single supplement is required for single room occupancy. Please note that in Italy single rooms are frequently smaller than double rooms. Groups of three can book triple rooms and avoid the single supplement.

2018 Dates

October 11-15

5 Days, 4 Nights
Route Rating
Moderate:  3-5 miles (5-8 km) per day of hiking with some steep ascents/descents.

Meet / Finish
Florence / Volterra
  • Hands on cooking class
  • Winery tour
  • Abandoned castle archeological site
  • The hill towns of San Gimignano and Volterra
  • Picturesque villages
  • Country footpaths

What's Included
  • All lodging (3-star hotels)
  • Cooking class with lunch
  • Winery visit
  • All breakfasts
  • Two lunches
  • Private van transfer from Florence on day one
  • Van support during hikes
  • 4 beautiful hikes
  • Friendly bilingual tour guide

Cancellations: Terms and Conditions

Tour Summary
Map and Distances

Wineries and Castles
Dates don't work?
Consider one of our self-guided hiking trips. We can schedule a self-guided hiking tour whenever you want March 1 to October 31.

Have a group of four or more?
With a group of four or more we can schedule a guided tour whenever you want.