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San Gimignano & Chianti Cycling Holiday

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Cycling self-guided tour of Tuscany

Tuscany, Italy
5 Days
€ 550 combadi price


Save €20 to €50 when booking via Combadi

Holiday Type
Open dates
Running Period
March to November

The Combadi Insight:

Experience all the magic of the Chianti region and don't miss a thing with this well planned and carefully selected itinerary and accommodation. The pool at the restored farm house has exquisite views and is the perfect place to relax your muscles after a day of cycling and enjoy the wine that the region is famous for.

Holiday Code: AY3

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Discover the very best of Tuscany's Chianti wine region on this stunning cycling holiday. Everyday, experience breathtaking views of Tuscan hills as you cycle through its country side and its medieval towns. Relax while enjoy authentic Italian food and the most delicious olive oil and wine that the region is famous for. This cycling holiday in Tuscany will delight all the senses and challenge you with moderate to strenuous cycling routes.

You will be staying at a wonderful Tuscan estate, just outside San Gimignano, which produces its own wine and olive oil. Each day you set off to discover the delights of Chianti on your bike; Roman and Etruscan sites, boutique vineyards, olive oil producers, cypress lined roads, medieval towns, the fourteen towers of San Gimignano and perfect Tuscan countryside.

Cycle on quiet roads over rolling hills through the heart of Tuscany, perhaps stopping for a long lunch at a local vineyard, medieval town or just a roadside field where you can kick back and enjoy an afternoon snooze.

Each day’s cycle explores a different part of Chianti. The daily distance varies between 22 and 42 km, with extensions to 67 km possible. The riding is graded moderate to strenuous and there is between 500 & 1000m of climbing each day due to the rolling terrain.

DAY 1 Arrive in San Gimignano

We recommend flying to Rome, Florence, Pisa, Perugia or Bologna airports. Connections are possible by bus and train to San Gimignano.

After arriving at your comfortable Tuscan farmhouse near San Gimignano unwind, breathe in the wonderful country air and explore the tiny medieval village of San Donato. Take a stroll in the Tuscan hills or perhaps just relax and soak up the warm sunshine, enjoying the magnificent views from the pool.

Overnight: San Donato de San Gimignano

You will be staying at Fattoria Voltrona for the duration of your trip. A wonderful Tuscan wine and olive oil producing estate in San Donato, which is less than five km outside San Gimignano.

The accommodation is comfortable Tuscan style. All rooms are en suite, the restaurant specializes in authentic home cooked Tuscan cuisine and the swimming pools has views to die for. You will experience the real Tuscan way of life on a family farm, surrounded by the tranquil Tuscan countryside.

DAY 2 Cycling in Chianti A day of tough choices as you have to decide which ride through the perfect countryside of Chianti suits you best. Perhaps something that is best done over a freshly brewed cappuccino?

Decision made, we will transfer you to Colle Val d’Elsan where your ride begins. Cycle through the undulating hills of the Val d’ Elsa to the perfectly preserved medieval hamlet of Monteriggioni. A great spot for a coffee, chat and relax in the sun.

Continue uphill, past endless rows of vines, tranquil woods and towards Lilliano or up to Castellina in Chainti, where the view seems to encompass the whole of Chianti. Your ride continues to Colle Val d’Elsa, where our driver will meet you to whisk you back to your hotel.

Ride: 40 Km or 67 Km with extensions

DAY 3 Vineyards of Ulignano, Certaldo Alto & Barberino

Today you will cycle through impeccable vineyards towards Ulignano and the charming hilltop village of Certaldo, hometown of the renowned Italian writer Boccaccio.

The ascent to Certaldo is by funicular or a very steep climb if you are feeling energetic. Visit the ceramic-decorated main square, marvel at the stunning churches and enjoy a drink on the piazza while you debate the extended ride to Barberino and Tavernelle in the Chianti Classico area. The panaoramic views of Chianti are worth every ounce of the extra effort!

Ride: 42 Km or 67 Km with extensions

DAY 4 Volterra to San Gimignano

We will transfer to the ancient Etruscan city of Volterra first thing. Explore its Alabaster artisan shops, Roman Theatre, palaces and Etruscan city walls.

Then hop on your bike for an exhilarating ride through a patchwork of wheat fields and Tuscan villas down to the valley.

The inevitable climb back up to San Gimignano follows. But you really can’t complain when the scenery is this good and a glass of chilled wine is waiting.

Ride: 22km or 35km with extension

DAY 5 Onward Travel

Included - 4 Nights accommodation at a wine and olive oil producing farmhouse with swimming pool, 5 km from San Gimignano - 5 breakfasts - 1 welcome dinner at the farm (drinks excluded) on arrival day - Mid week linen change - Delivery of hire bikes to farm on arrival day - 5 Days self guided cycling - Pickup of bikes from the farm at the end of the tour. - People & bike transfer to Colle Val d’Elsa, Volterra and Casole d’Elsa as per itinerary. - Emergency telephone support from our local representative & UK office in the event of a problem. (puncture repair and basic bike repair not covered)

Excluded - Bike Hire - Travel to/from San Donato. - Daily room cleaning service. - Lunches, dinners (other than day 1), snacks and drinks. - Travel Insurance. - Admissions or entrance fees. - Public transport or additional transfers.

Optional Extras - Trek Electric E-bikes or 21 speed hybrid bike hire, helmet, puncture repair kit, pump, lock,front bag with map holder and rear side bag - Additional night/s at any of the accommodation on the way or other destinations in Italy - Sightseeing tour of Florence and or Siena with a English speaking guide - Cooking class in Siena or Florence - Arrival and departure transfers to airports or train stations


  • The 14 medieval towers and cultural treasures San Gimignano.
  • Spellbinding views of the perfectly formed Tuscan landscape.
  • Authentic food and accommodation on a Tuscan Estate. Enjoy view of Tuscan rolling hills from the pool.
  • Enjoying a glass of Vernaccia di San Gimignano at the pool.
  • Great cycling routes through beautiful Chianti.


Fattoria Voltrona Agriturismo Fattoria Voltrona, enjoys a wonderful position just outside San Gimignano. The rooms are in restored authentic Tuscan Farm buildings at the heart of the estate, which produces wine and olive oil. The restaurant spills out of the barn onto the terrace and specializes in local Tuscan dishes. There is a perfectly situated swimming pool, horse riding available and plenty of easy walking available.


The cycle routes are not marked but we supply detailed maps and route notes so you will have no problems following the route each day.


The rides are along surfaced country lanes, secondary roads with little traffic, and 1/3 of the time on good dirt roads. Near larger towns, the roads are busier. Grade Moderate to strenuous on hilly terrain, some shade on the roads (Daily climb between 500—1000 meters.)

Solo Travellers & Single Rooms

This trip is suitable for solo travelers although there is a solo supplement payable. Single rooms are available. A single supplement is payable.


The delicious Tuscan food and wine is undoubtedly a highlight of this holiday. The price of your holiday includes breakfast each morning and dinner at the farm on your arrival day. All other lunches and dinners are not included. The farm has an excellent restaurant or you can eat in nearby San Gimignano.

Bike Hire (Not included)

Bike hire is available as an optional extra. Choose from a Trek Electric E-bike or 21 speed hybrid bike. A helmet, puncture repair kit, pump, lock, front pannier with map pocket and near side pannier are included.

Recommended Reading

Tuscany & Umbria—Lonely planet Regional Guides. Walking and Eating in Tuscany and Umbria—James Lasdun and Pia Davis

Payment terms

30% deposit to be paid on booking Remaining amount to be paid 8 weeks prior to departure.


How fit do I need to be?

This cycling holiday is graded moderate to strenuous and involves 21 to 42 km of cycling each day with extensions to 67km. You should enjoy an active lifestyle to get the most from this holiday.

What happens if I can’t cycle one day?

You can cycle as much or as litte as you wish. If you would prefer to take a day off there is plenty to see and do in the surrounding area.

What happens if I have a problem with my bike?

You are expected to be able to take care of minor repairs and punctures. In the case of a major mechanical problem we would send our representative to assist.

When is the best time of year?

Spring in Italy is sublime and April, May and June are absolutely lovely. Autumn is probably my favourite time of year as the landscape is made up of a gold and red pallet so September and October are unmissable. July and August can be very hot so you will have to start early to miss the heat of the day, although the towns and villages are buzzing which is great. You can view weather details for the region here.

How far in advance do I need to book?

We suggest you book as soon as your plans are finalised. Tuscany is extremely popular especially during July/August. You will find up to date availability on our website and we will always try and accommodate your plans so just ask.

What personal equipment do I need?

You will need normal cycling clothes, waterproof jacket and trousers and some warmer cycling clothes in early spring or autume, a full detailed kit list will be included in your info pack.

Which is the best airport? Either Perugia, Florence, Pisa, Bologna or Rome are convenient and you can reach San Donato by train/bus and taxi in a few hours.

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