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Homepage > Italy > Pisa to Siena

Duration: 4 Nights
Difficulty: Level 2-3
Tour Type: Self Guided
Availability: Saturdays from 28th March to 10th October
Location: Pisa

Cycling from Pisa to Siena

Tour Details

This classic cycling holiday in Tuscany follows the historic Via Francigena from Pisa to Siena, combining gentle riverside riding with rolling hills, vineyards and some of Italy’s most iconic medieval towns. From UNESCO-listed Pisa to the elegant streets of Siena, this Tuscany cycling tour offers a perfect blend of culture, scenery and local gastronomy.

Starting Location

Pisa

Price Includes

4 nights bed and breakfast
3 and 4 star accommodation
Information Pack
Navigation by Smart Phone App
Luggage transfers
GPS Files on request

Price Excludes

Transport before and after tour
Single Rooms
Flights
Tourist Tax
Hybrid Rental
E-Bike Rental
Travel Insurance

Trip Info

Travel Insurance

It is a requirement of booking this tour with Hooked on Cycling that you have suitable travel insurance which covers you for the chosen activity and for emergency evacuation and hospital care.

Itinerary

Day 1Arrival in Pisa

Individual arrival in Pisa and overnight stay. The city is world-famous for the magnificent Piazza dei Miracoli, home to the iconic Leaning Tower, the Cathedral and the Baptistery — a UNESCO World Heritage Site since 1987.

Beyond its historic monuments, Pisa also offers the lively and welcoming atmosphere of a university city, making it an excellent starting point for your Italy cycling holiday.

Day 2Pisa – Casciana Terme 31miles 50km, +290 m / -180 m

Cycling along the River Arno, you leave Pisa and ride towards Pontedera, a modern town known for its industrial heritage and nearby wine estates. The route then leads through peaceful olive groves and vineyards, offering a first real immersion into the Tuscan countryside.

Your destination is Casciana Terme, a historic thermal spa town with Etruscan origins. The healing waters were discovered in the 12th century by Countess Matilda of Tuscany, and the town remains a relaxing highlight of this cycling in Tuscany experience.

Day 3Casciana Terme – San Gimignano / Colle Val d’Elsa – 31miles 50km +755 m / -545 m Alternative: 70 km, +1000 m / -980 m

Today you follow stretches of the ancient Via Francigena, cycling through vineyards and rolling hills towards one of Tuscany’s most celebrated hill towns. San Gimignano rises on the horizon with its distinctive medieval towers, earning it UNESCO World Heritage status and worldwide fame.

Spend the evening enjoying the town’s excellent local cuisine and wines. Alternatively, overnight accommodation is available in Colle Val d’Elsa for those choosing the longer and more challenging stage.

Day 4San Gimignano / Colle Val d’Elsa – Siena – 27.9 miles 45km +740 m / -675 m From Colle Val d’Elsa: 25 km, +445 m / -242 m

Continuing along historic paths of the Via Francigena cycling route, today’s ride offers memorable views of Mount Maggio and the impressive fortress of Monteriggioni — immortalised by Dante in The Divine Comedy.

Your journey ends in Siena, one of Italy’s most beautiful medieval cities. Recognisable by its warm brick buildings and the soaring Torre del Mangia, Siena is the crowning highlight of this Tuscany cycling holiday.

If starting from Colle Val d’Elsa, the stage is shorter but still scenic.

Day 5Departure from Siena

Departure after breakfast, marking the end of your unforgettable cycling tour in Tuscany.

Day 8Departure

Depart after breakfast.

Map

Travel

How to get there

Fly to Pisa with Ryanair or with British airways and then by bus or taxi to your hotel

Book Now

2026 Prices – For complete tour price breakdown please click the book now button and select your holiday tour date. Prices will then be listed.

Tour Code	Prices From (per person)	Book Now
PSiena (4 Nights)	from £628	Book Now

Tour Images

Pisa to Siena