This exclusive bike tour of Tuscany is fully guided by professional Italian cycling guides, includes a rental bike, and is available from April to October for private groups of four or more.  The accommodations are definitely premier level, and all of your breakfasts, dinners, and three lunches are included as well!  You’ll have a support van and luggage transfers, even your arrival and departure transfers from Pisa or Florence airport.  Truly a luxury cycling holiday in one of the most idyllic landscapes on earth!
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8 Days

This journey brings together two of Tuscany’s most distinctive cities: Pisa, with its inspiring Piazza dei Miracoli, and Siena, with its “shell shaped” Piazza del Campo, an elegant and harmonious space in the heart of the city. Getting to know these two Tuscan treasures, and the timeless land between, is a gratifying experience that will not disappoint…
The surrounding countryside is distinguished by the Castelvecchio nature reserve and its great variety of plant-life, featuring rocky outcrops, overhanging rock faces, and unique local fauna. fauna. In fact, the cliffs on which the ruins of Castelvecchio stand are an ideal habitat for the rare peregrine falcon.
Cycling around Siena we will find another unique spot, the village of Monteriggioni…a place where time seems to stand still. The tiny fortified hamlet is encircled by its elliptical city walls, featuring 14 towers and 2 gateways. From the walkways on the walls you can almost hear the voices of the past and the sounds of ancient battles as you admire the magnificent countryside of the Chianti and the Valdelsa and enjoy the view of the village from this unusual vantage point.
Of course, the area does not want for excellent local dishes, such as the thick, handmade spaghetti-like pici served with mallard sauce or fried breadcrumbs, and the hearty ribollita soup made from cavolonero cabbage and cannellini beans. The unique flavors and aromas of this area will stay with you long after your journey is over. This is the authentic side of Tuscany, a region that promises to seduce and delight.

Let us lead you into this corner of Tuscany with its wealth of history and traditions, its verdant countryside, stunning medieval towns and wonderful local produce.

Best of all, after an exciting day exploring the countryside, you will find yourself relaxing at some of Tuscany’s premier accommodations:
Vicarello di Volterra is a 15th-century village in the heart of the tranquil Tuscan countryside where history, culture and art form a natural setting.Situated in the centre of the Era valley, the historic residence is surrounded by landscapes synonymous with Tuscany: low hills covered in Mediterranean vegetation, vineyards, and olive groves, rows of tall cypress, farmhouses and fortified medieval villages.
The village offers all the amenities necessary to make your stay a unique and unforgettable one, including a wellness centre with jacuzzi, sauna, Turkish bath, multi-sensory shower, and gym, and an open-air swimming pool with sun terrace.
Fattoria San Donato is a small medieval hamlet set among the green hills around San Gimignano and the Castelvecchio nature reserve. The hamlet grew up on the Via Francigenapilgrim route around a smallRomanesque church and has maintained its original architecture: the fortified villa with itscenturies-old park, the farm houses, and the guard tower which has been converted into a tavern for guests. The cuisineis based on homemade dishes and reflects Tuscan traditions.

Tour Dates & Pricing

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Day 1Below the Leaning Tower of Pisa.

Plan to arrive in the Pisa airport today, where you're private driver will meet you for the transfer to your 4* hotel. Tonight you''ll meet your guide for the week, have an in-depth tour briefing, and then sit down to a sumptuous Tuscan meal, complete with some of the best vintages in the world!

Day 2Cycling through the Land of Bocelli

Our tour will start from the Piazza dei Miracoli in Pisa, where we will climb the Leaning Tower, visit the Cathedral and tour the Monumental Cemetery. Afterwards we'll transfer by private vehicle to the luxury residence of Borgo Vicarello di Volterra, a village originating from the 15th century. From here we will cycle along country roads through an undulating landscape of vineyards and olive groves. Guided tour of the winery followed by wine tasting.

On our return we will have time to unwind at the hotel spa and, on request, take advantage of the wellness treatments available.

Technical details for day 2:

Environment: Slightly undulating, typically Tuscan landscape featuring vineyards, olive groves and woodland.

Grade: Easy

Terrain: An easy short stage characterized by dirt tracks and one ascent leading to Lajatico. 20% surfaced roads, 80% dirt tracks.

Distance: 20 km

Elevation gain: 150m

Meals: Breakfast, lunch, dinner.


Day 3The Theatre of Silence...BorgoVicarello diVolterra

After a breakfast of fresh fruit and organic produce, we will set off by bike for Lajatico. Travelling along paths of the cycle track network of the upper Cecina valley, we will observe many species of the Mediterranean flora such as the strawberry tree, lentisk, maritime and domestic pine, and come across quaint medieval churches. A country path through magical scenery will lead us to the entrance to the Theatre of Silence where a local guide will reveal the history of the theatre. Our journey will continue to the center of Lajatico where we will be able to visit Andrea Bocelli’s home.

Technical details for day 3:
Environment: slightly undulating typically Tuscan landscape, vineyards, olive groves, Mediterranean scrub, medieval hamlets

Grade: Moderate

Terrain: An undulating route along dirt tracks and surfaced roads (30% surfaced roads, 70% dirt tracks and mule paths)

Distance: 40km

Elevation gain: 200m

Meals: Breakfast, lunch, dinner.


Day 4From the Etruscans to the Middle Ages...Volterra to San Donato

Today’s tour will start from Volterra which we will reach by private transfer. After a visit to the Etruscan Museum, you will be able to enjoy some free time to explore the town on your own. After lunch we will take to the saddle once more to cycle through beautiful landscapes to the Castelvecchio nature reserve. We will reach the famous hamlet of San Gimignano where we will have a short tour of the town and then cycle onwards to the San Donato Farm. Here we will rest and enjoy a tasting of some local organic food, wine and olive oil.

Technical details for day 4:

Environment: Slightly undulating typically Tuscan landscape, vineyards, olive groves, Mediterranean scrub, medieval hamlets

Grade: Moderate

Terrain: An uneven route along dirt tracks and surfaced roads (20% surfaced roads, 80% woodland and tracks, 20% dirt tracks)

Distance: 30km

Elevation gain: 400m

Meals: Breakfast, dinner.


Day 5Around the Towers of San Gimignano

A leisurely ride through the woods will bring us to San Gimignano where we will visit the town, its towers and museums. Gourmet lunch at one of the most celebrated local restaurants. Spend the afternoon exploring the town on your own and afterwards return to San Donato to enjoy some rest time and perhaps a dip in the pool.

Technical details for day 5:

Environment: Slightly undulating typically Tuscan landscape, vineyards, olive groves, woodland

Grade: Easy
Terrain: a short stage along a variety of terrain: dirt tracks, surfaced roads and paths (20% surfaced roads, 80% woodland and tracks)

Distance: 15 km

Elevation gain: Insignificant

Meals: Breakfast, lunch, dinner


Day 6The Via Francigena, San Donato to Siena

After breakfast at the farm we will ride along the famous Via Francigena, with the towers of San Gimignano in the background. We will cycle mostly along dirt tracks on gently rolling terrain, taking in the surrounding Tuscan countryside. We will proceed towards Colle Val d’Elsa, passing through Montalto, and then on to the heart of Monteriggioni where we will stop to visit this compact medieval town and enjoy a light lunch. We will then continue our ride to Siena.

Technical details for day 6:

Environment: Slightly hilly landscape, vineyards, olive groves, Mediterranean scrub. Most of this stage is along the old pilgrim route, the Via Francigena .

Grade: Moderate

Terrain: Fairly easy terrain of dirt tracks and woodland (15% surfaced roads, 85% woodland and tracks)

Distance: 41 km

Elevation gain: 690 m

Meals: Breakfast, lunch, dinner


Day 7Urban biking or Urban Walking

After breakfast, the morning will be dedicated to an urban biking tour of Siena. A local tour guide will accompany us by bike through the most characteristic streets and places of this splendid city of art.

We will have lunch at an exclusive trattoria in Siena, where we will taste modern reinterpretations of typical Tuscan dishes accompanied by a selection of the area’s best-known wines.

Afternoon at leisure for shopping or relaxation.

Dinner and overnight stay at the hotel.

Meals: Breakfast, lunch, dinner

Day 8 – Departure

Private transfer to Pisa or Florence Airport.

Meals: Breakfast.


What´s Included

Accommodation, food, transport

  • 7 nights included in luxury hotels and hotels of charm
  • spa facilities, where specified
  • 7 breakfasts, 3 lunches at restaurants (beverages excluded) and selected Tuscan trattorias, all dinners (wine included)
  • private transfer from Pisa or Florence Airport to the beginning of the tour
  • private transfer from the end of the tour to Pisa or Florence Airport
  • All transfers during the tour
  • Transfer, loading and unloading of suitcases

    Technical equipment and nutrition

  • Cannondale bike
  • Urban bike
  • MTB for the last stage
  • bike helmet
  • heart rate monitor
  • downloadable GPS Files
  • back up vehicle, rescue support
  • Back-up nutrition
  • Personalized data sheet
  • Certificate of attendance

    Museum and winery visits

  • Entrance fees and guided tours
  • Wine and olive oil tasting at San Donato Estate.
  • Guided tour and wine tasting at Marcampo Estate.
  • What´s not Included

  • Flights and public transportation
  • Lunches and beverages where not specified
  • Transfers to airport other than Pisa or Florence at the end of the tour
  • Trip Interruption/Cancellation and Medical Insurance (strongly recommended, call for details)
  • Tips and gratuities
  • Any items that have not been mentioned in this program

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