Bike and wine: Bolgheri cycling tour

€890 (from) / Per person

Bike and wine: Bolgheri cycling tour

Bike through the two most spectacular wine regions in Tuscany: Chianti, which produces some of the oldest & most notable wines in Europe, & Bolgheri, whose position between the mountains & the Mediterranean Sea provide the perfect conditions for producing deep, complex reds. Your journey will begin in the enchanting town of San Gimignano, a UNESCO World Heritage Site. From there you’ll travel through the sun-kissed vineyards from one historic town to the next, stopping along the way to taste the exquisite wines, explore medieval castles, or admire the stunning panorama of the rolling hills. This tour can be done as an escorted group or as a self-guided tour.

  • 7 Days
  • Age 15+
  • Tuscany 


  • San Gimignano and Volterra
  • Populonia
  • Bolgheri Wines
  • Castagneto Carducci
  • Etruscan Necropolies


Day 1 – Poggibonsi 

Day 2 – Poggibonsi 

Day 3 – Siena 

Day 4 – Buonconvento 

Day 5 – Montalcino 

Day 6 – Montalcino Loop 

Day 7 – Montepulciano 

How does it work

We transfer your luggage

Just leave it at the reception desk with your name tag & you will find it at your next accommodation.

We book your hotels

We will book double rooms with private bathrooms in 3- or 4-star hotels, boutique B&Bs, or agritourism estates. You will find the vouchers to each hotel in your welcome package.

We supply detailed route notes & maps

The route notes can be in English, Italian, or French. All maps have GPS tracking.3

Destination:San Vincenzo
  • 7 nights (in 3/4 stars accommodation)
  • All breakfast (dinners on demand)
  • Emergency number 24/7
  • Gps files available
  • Luggage transfer
  • Road book & maps
  • Dinners
  • Tips

Our rental bikes

Our bikes are equipped with plastic water bottle, rear pannier, lock, kit repair, spare tubes, GPS available on demand.

Tour Plan


Day 1: Arrival and settling in

Arrival in Poggibonsi, where you will be met by our representative who will drive you to your villa in in San Gimignano which is a Vernaccia producing agriturismo.


Distance 45 km

Day 2: San Gimignano - Colle Val d'Elsa - San Gimignano

Departing from your villa, first you encounter Colle Val d’ Elsa and its glass blowing artisans, then the fortified town of Monteriggioni, its round distinctive shape dominating the surrounding plain; return to San Gimignano with its towers the visit of which will request a certain time and a couple of hours of window shopping. Aperitif with Vernaccia at a nearby agriturismo.


Distance 35 km

Day 3: Volterra

Today we start our way towards the sea with a first stop in Volterra, a beautiful town often forgotten; the main production is alabaster which you will find in an unbelievable number of shapes in the many boutique of the town centre. Along the way we will stop for an oil tasting light/ lunch at a oil mill “Frantoio”.


Distance 49 km

Day 4: Monteverde - Sassetta (Resort La Bandita)

The landscape changes and become more rugged while we pass the hills that bar the road to the sea. Along the way we will stop at a wine producing farm for a tasting /lunch before starting our descent. The landscape changes again and we find new vineyards. Soon we catch the first glimpse of the Mediterranean Sea. Night in a superb property.


Distance 28 km

Day 5: La Bandita - Castagneto Carducci - Bolgheri - La Bandita

Altitude: 170 mt – Level: easy. It’s a very interesting route which allows you to discover the Bolgheri shire and its vineyards with its famous wines, possibly the most expensive Italian wines, Sassicaia. During your excursion discover Bolgheri medieval center and its castle where we have a wine tasting lunch that will surprise you. Their red wine is superb! Same accommodation.


Distance 25 km

Day 6: La Bandita - Accattapane - Poggio Rosso

Day of transfer by bike from your villa to a wine producing resort t through the Wine Routes of Val di Cornia . After passing San Vincenzo continue for few kilometers “the Vecchia Aurelia” to proceed to the Accattapane. Enjoy the typical Tuscan countryside among vineyards and centuries old olive trees. Altitude: insignificant – Level: medium


Distance 39 km

Day 7: Poggio Rosso - Baratti and Populonia - San Vincenzo

A route to discover the secrets of the Etruscans the mysterious inhabitants of this area before the Romans. It is an amazing road that links Populonia to the sea, with views over the Gulf of Baratti and the village itself. Beside the Etruscan archaeological site that you can visit, Populonia main road is lined with small, artisan’s shops selling typical products, restaurants and of course a cafés.


Day 8: Possible transfer to Pisa airport

Price per groups vary according to number of people and type of accommodation.

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