Biking Tuscany Italy

San Gimignano is a treasure on the hill and jewel of Tuscany, wonderful for cycling and exploring. With its thirteen outstanding medieval towers, it’s clear why the town is on the UNESCO world heritage list. You’ll ride over clouds of sunflower fields under the Tuscan sun and along cypress lined country roads through olive groves and vineyards which produce some of the world’s finest olive oil and wine. You shall savor the flavor of these ingredients in the outstanding local cuisine. Travel to Etruscan and Roman times, from one picturesque hilltop to the next, each with its own history and charisma. Get pinched, this is the real thing.

v  San Gimignano UNESCO heritage town

v  Stay in a charming Tuscan farm house with pool

v  Quiet roads and quintessential “strade bianche”

v  Wonderful landscapes with vineyards, cypress lined roads and olive groves

v  Authentic country towns and villages: Siena, Volterra, Certaldo, Casole d’Elsa, Colle Val d’Elsa, Monteriggioni

v  Friendly people and great traditional Tuscan culinary specialties

Arrive at the farmhouse near San Gimignano and unwind as this shall be your comfortable Tuscan home for your lovely stay in Italy. Breathe in the wonderful country air as you explore the tiny medieval village of San Donato and take a stroll along the classic green rolling hills, marveling at the breathtaking views of the surrounding countryside. Immerse yourself in the tranquility.

Day 2 31.9km or 67.1km  Ulignano, Certaldo Alto, Barberino and Tavernelle

Today you will cycle through prestigious vineyards towards the charming hilltop village of Certaldo, hometown of the renowned Italian writer Boccaccio. The ascent to Certaldo is either by funicular or by a very steep climb. After visiting its ceramic-decorated main square and stunning churches, you can choose an extended ride to Barberino and Tavernelle in the Chianti Classico area, offering magnificent views.

Day 3 40.9 km   San Gimignano and Poggio del Comune

With this trip you will become familiar with the area as you make a full circle around the Poggio del Comune hill. From San Donato you go towards Castel San Gimignano passing by an unexpected sight for this very agricultural area, it is a prison. In Castel San Gimignano there is a great little bar where you can buy very good “panini” (sandwiches), then on in the direction of Volterra. Once you leave the asphalt road you enter the nature reserve which is mostly woods and some cow pastures, something rare in Italy. Leaving the forest behind you, you reach San Gimignano and you cycle straight through the old town centre stopping for a refreshing drink.

Day 4 25.5 km – (67 km  with the extentions)  Monteriggioni, and Castellina in Chianti or Siena

Today you choose the ride which suits you best. Transfer to Colle Val d’Elsa and cycle along the gentle, undulating hills of the Val d’Elsa to the perfectly preserved medieval hamlet of Monteriggioni. Continue going south in the direction of Siena or directly uphill past abundant vineyards and stimulating woods, to Castellina in Chianti, where the views are spellbinding.

Today is a rest day and we warmly suggest you go either to Siena or Florence, both of which can be easily reached with public transport

Day 6 27km   Volterra and Castelvecchio

Transfer to the magic and mysterious Ancient Etruscan city of Volterra, where you can explore its Alabaster artisan shops, Roman Theater, superb palaces and alluring city walls. Then hop on your bike for an exhilarating downhill ride into the valley, through a patchwork of wheat fields and impressive villas, followed by a delightful ascent to return to San Gimignano.

Day 7 51.1 km  . Casole d’Elsa and the Montagnola

The area between Castel San Gimignano and Casole d’Elsa is mostly open pasture used for sheep grazing in the higher parts while wheat is cultivated further below. The romantic landscape overlooking the Montagnola area is under populated, with gently undulating hills scattered with a few farmhouses and several ancient country churches. There is some traffic as you near Colle Val d’Elsa, but the rest of the route is very quiet

Overnight stay in San Donato di San Gimignano

The trip and our services end after breakfast, unless you have booked a transfer to the airport or other supplementary services.

Spend the week in the comfortable “agriturismo” (farm house) located in the hamlet of San Donato, 5 km from San Gimignano. Enjoy the swimming pool and wonderful Tuscan hospitality. Dinner is included on the first night, while breakfast is included each morning.

In this part of Italy, there are no bike lanes, so the routes follow mostly small secondary asphalt roads and strade bianche, unique Tuscan white roads paved with compacted gravel. These roads are being asphalted, so if you come across a newly asphalted stretch, please inform us so we can update our route description. You will encounter little traffic on this biking tour; however when approaching cities, along primary roads, some traffic is inevitable. Some of the routes are marked with red and white markings. You will be cycling through vineyards, wheat fields and some forests.

If you rent a bike with us, it will be delivered directly to your accommodation.

You can extend your trip by booking extra nights at the accommodation or by combining your trip with a stay in other towns and cities in Tuscany, Umbria or Lazio.

The Florence airport has both major and low cost international flights. Several low cost carriers serve Pisa and Bologna. You can also fly into Rome, although it is a bit farther away.

There is a regular bus and train service from Florence to Poggibonsi and San Gimignano, as well as connections possible from Pisa, Bologna and Rome. We can also arrange private transportation for you directly from your airport of arrival.

v  7 nights accommodations on B&B basis, at wine-and oil-producing Tuscan farm house where you will be staying, with swimming pool, 5 km from San Gimignano

v  1 welcoming 4-course dinner on the day of arrival

v  All rooms have private bathrooms. No daily maid service is available. Midweek linen change only

v  Transfer packet:

v  from San Donato di San Gimignano to Colle Val d’Elsa and from Colle Val d’Elsa to San Gimignano on the same day,

v  from San Donato di San Gimignano to  Casole d’Elsa

v  from San Donato di San Gimignano to Volterra,

v  24-hour telephone assistance, just a phone call away

v  Detailed maps and road book in English

v  Flights and public transportation

v  Bike rental 120.00 euro per bike

v  Travel insurance (mandatory)

v  Admissions and entrance fees of any kind (when not previously agreed upon)

v  Tips and gratuities

v  Personal extras and expenses such as meals, drinks, phone calls, etc.

v  Any items that have not been mentioned in the program

v  21 speed hybrid bike hire, helmet (puncture repair kit, pump, lock) Bike is delivered to accommodation

v  Airport arrival and/or departure transfers

v  Guided tour of Siena and/or Florence with a local private city guide

v  Half board service

v  Additional night/s at the farm or any other destination in Italy