Self-Guided Trail from Florence to Siena

Difficulty range

The difficulty range for this holiday:

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What do the gradings mean?

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Traverse time-forgotten trails across the famous Tuscan wine road, ‘The Chianti’, joining Tuscany’s historic and artistic jewels: Florence and Siena. Wind your way through the rolling hills, and the famous Chianti vineyards, indulging in the delights of traditional Tuscan cuisine as you travel.

Holiday highlights

• Explore Florence - birthplace of the Renaissance, and home to some of the world’s greatest works of art
• Sample the world famous wines of the Chianti in the golden stone villages of Castellina and Radda
• Stroll through the streets of medieval Siena, with its beautiful Gothic buildings
• Join the pilgrimage along the Via Francigena, to San Gimignano

What's included

• 6 nights accommodation with breakfast
• 2 evening meals
• Maps and detailed walk notes
• Luggage transfers
• Transfers on walking days, excluding 2 public bus journeys

Price based on two people sharing.

Two weeks or more

Make the most of your European holiday by visiting two resorts

Why not combine the Florence to Siena Self-Guided Trail with Guided Walking in Bonassola? Visit the five enchanting villages of the Cinque Terre, and head away from the coast to the peaceful countryside, with abundant vineyards and olive groves.

Or perhaps you might like to combine this trail with our Pisa to Florence Self-Guided Cycling tour, and cycle along quiet country lanes through Tuscan countryside, accompanied by panoramic vistas.

You could also combine this trail with Guided Walking in San Quirico d'Orcia. Enjoy gentle countryside walks and visit the charming hill-top villages of Montepulciano, Montalcino and Pienza.