Tuscany Backroads Guided

tours / Cycling

Tuscany Backroads Guided information and booking

  • Duration
    8 days
  • Group size
  • Difficulty
    moderate - challenging
Check prices & availability

Schedule Details

  • 7 nights 3 to 4 star hotels
Equipment Required
Wet weather gear, sunscreen, bike helmet and sun hat. (A comprehensive gear list is included in the pre-departure information provided on booking).


  • Cycling through the beautiful Tuscan countryside
  • Experiencing fabulous towns such as Pisa, San Gimignano and Vinci
  • Shopping for regional specialties such as ceramics and leather goods in the markets of Florence
  • Enjoying the fantastic cuisine of the region
  • Exploring the renown Tuscan centres of Siena and Florence

Tour description provided by World Expeditions

Follow the backroads on this bicycle journey of Tuscany's highlights. Discover Leonardo da Vinci's birthplace, see the Leaning Tower of Pisa and indulge in the ancient thermal resort of Casciana Terme. Wind your way through vine-covered countryside to San Gimignano, a beautifully preserved medieval city where only 14 of the original 72 towers remain. Explore the enchanting and classic Tuscan city of Siena with its Gothic architecture. Cycle through the vineyards and olive groves of the Chianti region, the centre of Tuscany's world famous wine industry. This journey which is offered as a guided cycle concludes in Florence where an incredible concentration of attractions complete our journey.

What's included

  • 7 breakfasts – continental breakfasts are served and usually consist of breads, jams, coffee, tea and juices
  • 5 dinners – 3 courses, often in typical restaurants
  • 7 nights accommodation in 3 to 4 star hotels
  • Bicycle, 21 speed with pannier
  • Luggage transfer, and bus and train transfers as per the itinerary
  • Company of a trained travel guide and an accompanying support vehicle throughout the tour
  • All entry fees and guided tours according to the program
  • Sightseeing tours in vinci – leonardo museum, lucca and san gimignano, detailed city tours in florence and siena and a short city tour in pisa
  • Information kit including detailed maps, sightseeing references & welcome briefing


Day 1 Join Montecatini Terme
The trip begins at the first hotel in Montecatini (details to be provided closer to departure). Later in the afternoon / early evening a briefing will be held. Montecatini, located at the foot of the Pisoian Mountains, is famous for the therapeutic qualities of its spa waters and the baths/spas found in the town date back to the 14th century. It is a great town to watch the world go by and offers excellent cuisine. We recommend taking the historic funicular railway train to Montecatini Alto.
Day 2 Round trip cycle to Vinci, Leonardo da Vinci’s birth place (55km)
Today we cycle along small paths, through the olive groves of Montecatini Terme to Vinci (Leonardo da Vinci’s birth place) returning to Montecatini Terme for the evening. The town of Vinci is set around a Romanesque castle (Conti Guidi) which is home to the Leonardo da Vinci museum. Here you will find a collection of his drawings (mostly copies) and working models based on the drawings including a clock, flying machine, underwater exploration device and a tank. We visit the museum before returning to Montecatini Terme.
Day 3 Train to Lucca and cycle to Pisa for city tour (50km)
This morning we take the train to the former capital of Tuscany, Lucca. This is the only walled town in Italy and the old town has an impressive Romanesque cathedral. We take a tour of the wide shaded ancient ramparts by bike and may visit the Puccini museum before continuing to the Lake of Massacciuccoli (also known as lake of Giacomo Puccini), near the town of Viareggio. The lake is part of the Migliarino, San Rossore and Massacciuccoli Nature Park and in the lakeside town of Torre del Lago Puccini is the birth home of the great composer Giacomo Puccini (1858-1924). From the lake, the cycle route continues to the much visited city of Pisa, where amongst many highlights resides the famous ‘Leaning Tower of Pisa’. Overnight Pisa. A short tour of Pisa’s special sites at the Court of Miracles is included.
Day 4 Cycle to spring town Casciana Terme (40km)
From Pisa the cycle route follows the Arno River before joining country lanes to the idyllic spa town, Casciana Terme. Set in classic Tuscan countryside, there is ample opportunity to relax in town, enjoy a spa treatment or explore the countryside further.
Day 5 Cycle through vineyards to San Gimignano (55km)
The route takes us through vineyards and traverses rolling hills to reach the hill town of San Gimignano. The town dominates the Elsa Valley below with its imposing towers, which date back to the 11th and 13th centuries. The architecture has been influenced by neighbouring Siena and Florence, and we tour the highlights. You are now in the north of Siena province, between the Chianti area and val D' Elsa. Overnight stay in San Gimignano.
Day 6 Cycle to Siena (45km)
Today is a particularly scenic day with the Tuscan landscape at its best. Rolling hills, vineyards and Tuscan villas are characteristic of the day, and the architectural wonder of Siena is our destination. We will cycle through Monteriggioni where you will feel as though you were in the Middle Ages. There will be a sightseeing tour of Siena in the evening and during the tour we will explore this enchanting medieval town with its gothic buildings such as the Palazzo Pubblico, and the rich art history contained in its churches. The centre of town is Il Campo, a huge square, which acts as a meeting point for locals and tourists alike. Il Campo is also the location of the colourful horse race which occurs twice a year (2 July & 16 August). It is worth climbing the bell tower at the lower point of the square for a view of the town and surrounding countryside. There will also be time to wander the many side streets and take a look inside the duomo, one of Italy’s great gothic churches.
Day 7 Cycle via Chianti-region and bus to Florence (50km)
Today is our last day of cycling and we spend it pedalling through the hilly and picturesque Chianti-region, where the “Chianti Classico” comes from. As we cycle to Greve, there are some interesting hilltop towns including Castellina in Chianti. The steep climbs up to these towns are well worth the effort. From Greve we take a bus to Florence.
Day 8 In Florence, city tour then trip concludes
A tour of Florence including the famous duomo is included this morning, after which the trip concludes.