Cycling Holidays in Tuscany



Our cycling holidays in Tuscany are a paradise for lovers of food, wine and cycling. The landscape of Tuscany is one of the most beautiful and evocative in Europe, with rolling hills laced with green vineyards, and statuesque cypress trees lining the roads. You’ll ride from one incredible view to the next, getting to know the lands of so many great artists of the past, such as Leonardo da Vinci and Michelangelo. You’ll have the chance to visit the superb medieval town of Siena, as well as to admire Florence, cradle of the Renaissance. Last but not least, in this tour you’ll discover picturesque villages and be tempted by the excellent traditional Tuscan cuisine!


Saturday departures between March and June or August and October

Price - £745pp

(Based on 2 people sharing a double or twin room)



Single room supplement - £220

Single Traveller Supplement - £85

Bike hire - £95

E-Bike - £190

Helmet - £15

Extra nights in double/single room with breakfast:

in Siena - from £90/£60

in Florence - from £105/£75


Trip Code - GIROB03


Rob's Highlights

  • The historic city of Siena

  • Radda in Chianti

  • The capital of Tuscany, Florence

  • Colle Val d'Elsa

  • The famous wine of the Tuscan region

  • Greve



What's Included

24 hour emergency back up support

7 nights in small & intimate hotels or B&B's

Bed & Breakfast

Luggage transfers between hotels

Trip planner with route notes and maps

What's Not Included


Bike Hire


Lunch & evening meal


Local taxes

Train transfer from Florence to Certaldo (10 euros)


Day 1: Arrive in Pisa

Individual arrival.

The city is famous all over the world for its magic Piazza dei Miracoli, with the characteristic leaning tower, the bell tower of the city cathedral. On the UNESCO World Heritage list since 1987, besides a large number of monuments, it also boasts the friendly and lively atmosphere of a cosmopolitan university city.

Day 2: Pisa - Lucca (30/45 km)

Today you cycle northwards along the Serchio river for an easy stage. For those who wish a slightly longer itinerary, there is the option of heading towards Massaciuccoli Lake before reaching Lucca.

Day 3: Lucca - Montecatini (45 km)

Journey along a panoramic road, until reaching the little village of Collodi and the adjacent town of Pescia. In Collodi, where the author of Pinocchio spent his childhood, you can visit the famous Pinocchio’s Park -created in 1962, and the aristocratic Villa Garzoni. In Pescia you can enjoy a quiet stroll among churches, palaces, Renaissance mansions and the local flower street market.

Day 4: Montecatini roundtour (60 km)

Today’s route offers you, again, two possibilities. You can relax in one of the most famous thermal cities in Europe, strolling down the narrow lanes of the old city. Situated on a hill, it can be reached by a characteristic cable-railway. Otherwise, a picturesque itinerary will lead you among villas of the Medici family. Through shady olive groves, vineyards and traditional working farms, you’ll ride past Vinci, Leonardo’s birthplace, where a visit to the museum is a lovely way to while away some time.

Day 5: Montecatini - Florence (50/65 km)

Today you can choose either to start riding directly from Montecatini or to shorten the trip via a brief train transfer to Pistoia, rich in Romanesque and Renaissance monuments and ancient churches, and with one of the most evocative squares in Italy - Piazza del Duomo (translated as Cathedral Square). From here back into the saddle, to reach Florence.

Day 6: Florence

Free day. It will be up to you to decide how to spend your time in one of the world’s most beautiful cities!

Day 7: Florence - Empoli - Pisa (40/65 km)

Today you can choose either to start cycling directly from Florence, arriving in Pisa, via a train transfer from Empoli, or taking the train to Empoli and riding to Pisa alongside the river Arno.

Day 8: Pisa

Departure after breakfast.


Due to organisational reasons, weather conditions or provisions issued by local authorities, the itinerary may be subject to some changes before and/or during the holiday.

Along the way you may find temporary deviations (for example road works) which cannot be foreseen; in this case each rider can decide autonomously how to deal with these stretches.


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