Via Classica Self Guided Cycling Holiday in Tuscany

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3 days (approximately)
Offered in: English and 1 more

Explore the enchanting landscapes of Tuscany at your own pace with the Via Classica cycling holiday. This self-guided adventure includes hand-picked local accommodations and expertly curated cycling routes that showcase the region's charm, from sprawling vineyards to picturesque hill towns. Enjoy a welcome gift of local wine, a digital guide filled with cultural insights, and 24/7 phone support to enhance your journey. Perfect for couples and comfort-seeking riders seeking an authentic experience in Tuscany.

- 2 nights with breakfast included in charming local stays
- Enjoy enhanced GPX routes with cultural points of interest
- Flexible itineraries featuring loop or point-to-point journeys
- Ideal for couples and small groups wanting a personalized cycling experience

What's Included

Accommodation with breakfast
Breakfast (Optional[2])
Breakfast
digital guide and suggestions
GPX routes and planning
lunches and dinners
transportation to and from Tuscany

Meeting and pickup

Meeting point

The meeting point is Tuscany Cycle bike shop, where you will pick up the bikes or drop off the luggage if it applies. This is a self guided cycling tour and not guide will come with you.

End point
This activity ends back at the meeting point.

Itinerary

Duration: 3 days (approximately)
    Day 1

    Florence → Pistoia → Montecatini

    1 stop
  • 1

    Riders leave the Renaissance heart of Florence and quickly transition into rolling Tuscan countryside. Expect olive groves, cypress-lined roads, and gentle hills. In Pistoia, they’ll encounter medieval piazzas, Romanesque churches, and a more local, authentic Tuscan atmosphere. The ride ends in the spa town of Montecatini Terme, known for its elegant architecture and thermal baths.

    1 hour • Admission ticket free
    • Day 2

    Montecatini → Certaldo → San Gimignano → Colle Val D'Elsa

    1 stop
  • 2
    San Gimignano

    This is the most scenic and challenging day, filled with classic Tuscan landscapes. Cyclists pass through vineyards and sunflower fields, with a stop in Certaldo—birthplace of Giovanni Boccaccio. As they approach San Gimignano, the famous towers rise dramatically on the horizon. Expect winding climbs, panoramic views, and postcard-perfect villages.

    2 hours • Admission ticket free
    • Day 3

    Colle Val D'Elsa → Florence

    1 stop
  • 3
    San Casciano in Val di Pesa

    he final day blends cultural stops with classic wine-country scenery. Cyclists descend from San Gimignano and pass through Colle Val d’Elsa, known for crystal craftsmanship. The route winds through Chianti’s vineyards, stone farmhouses, and shaded country roads. As Florence comes back into view, riders finish with a sense of completion—having experienced Tuscany’s art, history, and landscapes in full.

    30 minutes • Admission ticket free

Additional info

  • Public transportation options are available nearby
  • Not recommended for travelers with poor cardiovascular health
  • Travelers should have at least a moderate level of physical fitness
Supplied by Tuscany Bike Route

Tags

Nature and Wildlife Tours
Mountain Bike Tours
Multi-day Tours
Private and Luxury
Private Sightseeing Tours
Bike Tours
E-Bike Tours
Adventure Tours

Cancellation Policy

If you cancel at least 6 full day(s) before the scheduled departure time, you will receive a full refund.
If you cancel between 2 and 6 day(s) before the scheduled departure time, you will receive a 50% refund.
If you cancel within 2 day(s) of the scheduled departure, you will receive a 0% refund.

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