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Pedal Ventures

7-Day Grand Tour of Tuscany

Tuscany, Italy • Pisa, Italy • Florence, Italy
  • 6 nights
  • Self-guided
  • Bed & breakfast
  • Bike hire available
  • Luggage transfer

Overview

A one-way taste of the Grand Tour of Tuscany, starting in Pisa and finishing in Florence. The route runs through the thermal town of Casciana Terme, the medieval hill towns of San Gimignano and Monteriggioni, historic Siena, and the vineyards of Chianti.

Tour Highlights

  • Medieval villages one after another: Casciana Terme, San Gimignano, Monteriggioni
  • The rolling vineyards and olive groves of Chianti and the Val d'Elsa
  • Florence, the cradle of the Renaissance, to finish

Tour difficulty

Best for active riders prepared for longer days in the saddle and regular rolling hills. These routes offer a noticeable physical challenge while remaining achievable for cyclists with good fitness levels.
Moderate

Perfect for

  • Vineyards

  • Food & Wine


Itinerary

  1. Day01

    Pisa

    Individual arrival and overnight in Pisa, home to the Leaning Tower and the Piazza dei Miracoli.

  2. Day02

    Pisa to Casciana Terme

    31 miles (50 km)
  3. Day03

    Casciana Terme to San Gimignano/Colle Val d'Elsa

    31 miles (50 km)
  4. Day04

    San Gimignano/Colle Val d'Elsa to Siena

    28 miles (45 km)
  5. Day05

    Siena to Greve in Chianti

    34 miles (55 km)
  6. Day06

    Greve in Chianti to Florence

    25 miles (40 km)
  7. Day07

    Florence

We recommend flying to Pisa and returning from Florence.


Bike hire


How to get there

Getting to Pisa

By plane: Pisa Galileo Galilei Airport (PSA) has direct flights from UK airports with Ryanair (London Stansted and others) and easyJet (London Gatwick). The airport is right on the edge of Pisa city centre, a 10-minute walk or short taxi ride.

By train: Pisa Centrale station has frequent connections to Florence (around 1 hour).

Getting home from Florence

By plane: Florence Peretola Airport (FLR - Amerigo Vespucci) has direct UK connections with British Airways and Ryanair, and is around 20 minutes from the city centre by tram.

By train: Florence Santa Maria Novella is a major hub, with fast trains back to Pisa (around 1 hour) if your return flight departs from there instead.


What's included

Included

  • Bed & breakfast
  • Luggage transfer
  • Roadbook, maps and GPS tracks via app

Not included

  • Flights
  • Transfers
  • Travel insurance
  • Bikes (available to hire)
  • Cycling helmets (available to hire)
  • Tourist taxes (15-20 EUR per person)

FAQs


Other tours in Tuscany, Pisa and Florence