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Pedal Ventures

Pisa to Siena via Tuscany

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

Overview

A short taste of Tuscany for those with less than a week to spare, riding from Pisa to Siena through vineyards and olive groves, with medieval villages including Casciana Terme, San Gimignano and Monteriggioni along the way.

Tour Highlights

  • The hills of the Val d'Elsa, among vineyards and olive groves
  • San Gimignano's medieval towers and Monteriggioni's walls
  • The medieval centre of Siena and the Torre del Mangia

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

  • Short break


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

We recommend flying to Pisa and returning from Siena.


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 across Tuscany.

Getting home from Siena

By plane: Siena has no airport of its own, so most visitors travel back to Florence Airport (FLR) or Pisa Airport (PSA) by bus or train (both around 1.5-2 hours, usually with a change) to catch a flight home. Florence is generally the more frequent and direct connection.

By train: Regular trains and coaches run from Siena to both Florence and Pisa; services can involve a change, so allow extra time before an early flight.


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 (approx. 10 EUR per person)

FAQs


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