Difficulty Rating : 6 Start: Siena Finish: Cortona Terrain: There are a number of climbs on this tour Daily Average: 40km Weekly Average: 234km Tour Type: Self Guided Teaser: Tuscany is justifiably famous for its fine food and wine, magnificent rolling landscapes and medieval walled hilltop towns
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Justifiably famous for its fine food and wine, magnificent rolling landscapes and medieval walled hilltop towns, Tuscany is a classic destination for cyclists.

Our Safari begins in the heart of the Tuscan landscape where we are staying in a typical Italian villa for two nights. Our first day's cycle takes us amongst the vineyards of the Chianti Classico region to the magnificent San Gimignano where we can indulge in an ice cream in the cobbled town square. The next day we move on to the UNESCO world heritage city of Siena with its incredible piazza where we spend the night within this walled city.

A beautiful patchwork of neat vineyards, dark green olive groves, cypress trees unfold before us as we head towards the medieval towns of Montalcino and Montelpulciano, two of the best examples of walled towns in the region. We stay in them both to soak up their atmosphere whilst enjoying their excellent local food and wine, a wonderful end to a perfect week!

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Day 1

Arrival in Poggibonsi

You will be met by our representative at the train station in Poggibonsi and driven to your villa in Staggia near Castellina in Chianti (10 km – 20 min by car), where you will enjoy an excellent Italian supper.

Villa Lecchi is a typical Italian villa perched on top of a hill with lovely panoramas of the surrounding Tuscan countryside.

Day 2

Colle Val de’Elsa, San Gimingnano, Lecchi 35 km

Departing from Villa Lecchi, you cycle to the fortified town of Monteriggioni with its round distinctive shape dominating the surrounding plain. Your journey continues to Colle Val d'Elsa and its glass blowing artisans, before arriving in the beautiful walled town of San Gimignano with its lovely towers which will require more time and a couple of hours of window shopping before heading back to Villa Lecchi.

Day 3

Villa Lecchi, Castellina in Chianti, Siena 52 km

Your cycle winds its way through Chianti, in a landscape of vineyards and superb wineries. Castellina in Chianti is your first stop, well known for its links with the Chianti Classico wines bearing the famous black rooster symbol. The classical walled town of Monteriggioni which sits on top of a hill dominating the surrounding landscape awaits before arriving at the magnificent world heritage site of Siena with one of the most famous squares in Italy: Piazza del Campo.

Day 4

Siena, Buonconvento 32 km

A lovely day cycling through quiet Chianti roads watching the landscape change from luscious vineyards to the more linear cypress-crested hills of the "Crete" near Buonconvento. Murlo is a nice little village on your way to the beautiful farm where you are spending the night. You will be glad to get a refreshing dip in the swimming pool or a relaxing massage and a sauna at their beautiful farm.

Day 5

Buonconvento/Montalcino 46 km

You cycle a gentle 8km climb to reach the Monte Oliveto monastery, located in the heart of the “badlands” of the Crete Senesi.The monastery traces its foundation to 1313 and has three 15th century cloisters. The route then brings you through S. Giovanni d’Asso before you tackle the last climb of the day to reach our lovely hotel in Montalcino, the Brunello homeland, where you spend two nights.

Day 6

Sant’Antimo Abbey

A chance to relax and enjoy the beautiful town of Montalcino from the fortified walls and bastions with a 360° view. The castle is almost intact and is built into the walls of the town. A small and pleasant detour is to follow the descending trail that will lead you to the beautiful and peaceful church of Sant’Antimo where you may be able to listen to Gregorian chants.

Day 7

Montalcino, Pienza/Montepulciano 45 km

You cycle to Bagno Vignoni to Pienza, the renaissance jewel redesigned by the Pope Pio II to become a "liveable" town. Onwards to Montichiello, a lovely little village immersed in the "Crete". You can stop there for lunch or a cappuccino before continuing to Montepulciano one of the nicest Renaissance towns of Tuscany. A town famous not only for its wine but also well known for pecorino cheese and truffle production.

  • 7 nights in village hotels
  • All breakfasts
  • Road books and maps
  • Luggage transfer
  • 24-hour help line
  • Transfers as per the itineraries

Bike rental is not included in the tour price. This is an additional:
€140.00 Hybrid Bike
€240.00 Electric Bike
€175.00 Road Bike

All your accommodation is booked. Your luggage is transported from hotel to hotel. You are given a map with a fully researched route. You will also have a hotline number should you need any assistance in any way.

Bike hire is not included in the tour package. However it is of course possible to rent a touring bike which Hybrid BIANCHI - Camaleonte 4 Aluminium frame ( sizes 43/ 58 cm) Shimano gear system Sora ( triple front chain) 27 speeds 1 side bag on the rack water bottle carrier repair kit.
Electric Bikes are also available to rent. Please email us for more details on this

The daily distance is approxminately 45km

If you cant cycle for any reason you can get a lift with the person who will transport your luggage. There may be a small fee you can pay to the driver. you will need to let them know the day before if possible.

We very much enjoyed this trip, though getting up some of those hills didn’t feel that ‘easy’! The bikes were brilliant - very light and well-geared, which helped a lot. Michele was extremely helpful in explaining the routes; the directions were accurate and easy to follow. All the accommodation was of a high standard. We weren’t quite so keen on the agriturismo at Pieve a Salti but their swimming pool did make up for that.
We got a good feel for Tuscany - both the scenery and the lovely small towns we stayed at. The steep climbs to reach them were worth it!
All in all a really good experience, our first with Irish Cycling Safaris. So many thanks to you for organising it.

Barbara Lamplugh (Tuscany Easy June 2018)

We had a wonderful time on our Tuscany biking trip. The accommodations were perfect! Our favourite was the hotel in Montalcino with a view of the Tuscan Hills from our small terrace, but each had its own unique characteristics. Beppe and his staff there took great care of us.
The maps and instructions for the self-guided biking were perfectly clear. The food was very good, local rep gave us good restaurant recommendations in Montalcino.

Jennifer & Dwight (Tuscany Easy self guided June 2016)

€1090 per person sharing
€190 for single supplement (if travelling with others)
€300 for solo traveller supplement (if travelling alone)

€980 per person sharing
€190 for single supplement (if travelling with others)
€300 for solo travellers supplement (if travelling alone)

€1090 per person sharing
€190 for single supplement (if travelling with others)
€300 for solo travellers supplement (if travelling alone)

Self Guided Tour Information

Start any day from 1 April to 31 October


How to get to the start point in Siena: 

Closest airports to fly to: Pisa or Florence (both approx 1hr45mins), Rome(approx 4 hrs).

Trains to Siena TrenItalia 

As always please contact us in the office for more information (info@cyclingsafaris.com).

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Tour Date Options

Red = booked out / not available, Blue = Limited Availability, Green = available

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We require you to have Travel Insurance when you book the tour. It is important that you are covered in case of cancellation due to injury as the deposit is non refundable

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For single travellers, we organise accommodation on a twin sharing basis. Please note it may not be possible on all our tours and a single supplement will be applied.

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If you have been on a previous tour, there is a €50.00 discount on our week long tours in Ireland (unfortunately this discount does not apply to other European trips)

A €250.00 deposit is required for each person booking on a holiday. The Balance payment is required two month prior to the starting date. The deposit is forfeited in the event of a cancellation of your booking. The balancing payment is also non-refundable in the event of the cancellation occuring within 14 days of the tour starting date. All transactions are taken in Euro.

We will contact you to confirm your booking and payment details.

Please ensure that you have read the terms and conditions before proceeding.

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Booking Conditions

Irish Cycling Safaris Ltd (“the Company”) accepts bookings subject to the following conditions:

  • The contract is between the Company and the client, being any person travelling or intending to travel on a tour operated by the company. The contract, including all matters arising from it, is subject to Irish law and the exclusive jurisdiction of the Irish courts. A booking is accepted and becomes definite only from the date when the company sends a confirmation. It is at this point that a contract between the company and the client comes into existence. Before your booking is confirmed and comes into existence the company reserves the right to increase or decrease brochure prices. The company or their agents reserve the right to decline any booking at their discretion.
  • To secure a booking the Company or their agent requires a completed booking form and the necessary deposit. (Full payment if travel within 60 days). The first named client must be over 18 years of age. Clients booking by telephone, by website/E-mail or fax will be deemed to have signed the booking form and read and accepted our terms of booking. The person signing, or being deemed to sign, the booking form warrants that he/she has full authority to do so on behalf of all persons whose names appear thereon, and confirms that all such persons are fully aware of and accept these conditions.
  • The balance of all monies due, including any surcharges applicable at the time, must be paid to the company or their agents not later than 60 days before departure. In the case of non-payment of the balance by the due date the Company reserves the right to cancel your booking and cancellation charges will apply. If any cheque is dishonoured we reserve the right to charge €25 to cover administration costs.
  • Travel Insurance is mandatory for all clients whilst on a tour organised by the Company. Clients are wholly responsible for arranging their own insurance. Clients are responsible for ensuring that they are in possession of private Travel insurance with protection for the full duration of the tour in respect of at least medical expenses, injury, death, repatriation, cancellation and curtailment, with adequate cover.
  • An administration fee of €25 per booking plus any additional costs incurred will be charged if a confirmed booking is changed or transferred to a different departure date or tour, up to 60 days prior to departure. Thereafter all changes will be treated as cancellations and subject to the relevant charges. Changes are subject to availability. For an administration fee of €25 you may request a credit voucher. This must be redeemed within 12 months of issue and must be used against a new booking. The voucher is non transferable and cannot be exchanged for cash. In certain circumstances, which the Company considers reasonable, the booking may be transferred to another suitable person; however the tour arrangements must remain the same and will only be allowed if all suppliers agree to accept the name change. If a transfer is allowed an administration charge of €25 per person will be charged plus any extra charges levied by suppliers.
  • Should the client wish to cancel, cancellation charges will be imposed. These are calculated from the day written notification is received by the company or their agent as a percentage of the total tour price, including surcharges as follows:

    > 60 days before departure – retention of deposit

    60-14 days before departure – 50%

    < 14 days before departure – 100%

  • Clients are responsible for arranging, and must be in possession of, a valid passport and any visas and vaccination certificates required for the whole of their journey. Information about these matters or related items (climate, clothing, baggage, personal items etc) is given in good faith but without responsibility on the part of the company.
  • Should the client have a reason to complain, you must immediately notify our representative and the relevant supplier. If the client’s complaint is not dealt with satisfactorily at the time, they must write to us with full details of the complaint within 28 days of the end of the tour. Failure to notify complaints entirely within accordance of this clause will diminish or extinguish the client’s ability to claim compensation.
  • The company provides all services on a “ground only” basis. The client is responsible for arranging their own travel to the designated start points of each tour. The company cannot accept any liability for any delay/cancellation in your transportation and cannot offer any refunds for lost holiday time.
  • Clients agree to accept the authority and decisions of the Company’s employees, tour leaders and agents whilst on the tour with the company. If in the opinion of such persons the health, level of fitness or conduct of a client at any time before or after departure appears likely to endanger the safe, comfortable or happy progress of a tour the client may be excluded from all or part of the tour without refund or recompense. In the case of ill health the company may make such arrangements as it sees fit and recover the costs thereof from the client. If a client commits an illegal act the client may be excluded from the tour and the Company shall cease to have responsibility to/for them. If you are affected by a condition, medical or otherwise, that might affect you or affect other people’s enjoyment or active participation of the tour, you must advise us at the time of booking. No refund will be given for any unused services.
  • The Company will use its best endeavours to operate all tours as advertised. However, it reserves the right to change any of the facilities, services, prices or itineraries described in our brochure/website. If a major change is necessary or deemed advisable, the company will advise the client as soon as reasonably possible, if there is no time before departure. A major change does not apply to a change of transport or named accommodation, but is usually considered a major change in itinerary or change in duration of a client’s holiday. If advised of a major change before departure, the client will have the choice of accepting changes (at additional cost if applicable), purchasing another available tour from the company, or cancelling the tour with a full refund.

    Provided that the major change is not as a result of situations outside the company’s control or consolidation, compensation will be paid as follows:

    Notification Period Given / Compensation Per Person

    More than 30 days: Nil

    14-30 days: €40

    Less than 14 days: €50

  • Force Majeure. We regret we cannot accept liability or pay any compensation where the performance or prompt performance of our contractual obligations is prevented or affected by reasons of circumstance amounting to “force majeure”. In these conditions “force majeure” means any event which we the supplier of services in question could not, even with all due care, foresee or avoid. Such events include war or threat of war, riot, civil strife, industrial dispute, terrorist activity, natural or nuclear disaster, fire or adverse weather conditions, epidemics or health risks and all similar events outside our control.
  • The company reserves the right to cancel a tour in any circumstances but will not cancel a tour less than 4 weeks before departure except for “force majeure”, consolidation, or the client’s failure to pay the final balance. Unless the client fails to pay the final balance, the company, upon cancellation will return all monies paid to it, or offer the client an alternative holiday of comparable standard if available (if less expensive than original we will refund the difference, if more expensive, the client will have to pay the difference). Compensation will not be payable (1) where the company is forced to cancel as a result of unusual and unforeseeable circumstances beyond our control, the consequences of which we could not have avoided even with all due care or (2) where an insufficient number of people book the clients chosen holiday and we notify we are cancelling for this reason not less than 28 days before departure. In all cases our liability is limited to offering the above choices and the compensation payments (where applicable) set out in clause 11. No compensation is payable if we notify you of cancellation more than 8 weeks before departure. We cannot be held responsible for any costs or expenses you may have as a result of cancellation.
  • Client’s bookings are accepted on the understanding that they appreciate the risks inherent in adventure travel and that they undertake the tours featured in our programme at their own volition. Our obligations, and those of any suppliers providing any service or facility involved in any travel arrangements you book with us, are to provide services and facilities with reasonable care and skill. Facilities will be provided to the realistic minimum standard recommended by the regulatory authorities responsible.
  • Bike Hire: The equipment including all accessories supplied is let out on hire. The equipment remains the property of the company and the Client will not sell, hire out or otherwise part with the possessions thereof.

    The Client undertakes not to misuse the equipment and to return it with all accessories in the same condition as when received (ordinary wear and tear accepted). The company shall be entitled to charge the client for any damages caused to equipment during the period of hire. In event of a breakdown, other than a result of the Clients misuse, the company will use its best endeavours to repair or procure repair of the equipment.

    The company will not be liable for any damage or loss whatsoever, through breakdown or other defect in the equipment or other circumstances beyond the company’s control. The Client shall indemnify the company with respect to all costs, claims, expenses and demands suffered or incurred which arise directly or indirectly out of the use of the equipment during the period of hire. The company reserves the right to charge the client for partial or full settlement of any claim. In the event of the equipment being stolen or lost, the company reserves the right to call upon the client to indemnify the company the replacement of the equipment. However, should the equipment subsequently be returned in a satisfactory condition, the company undertakes to refund the clients indemnity within 14 days.

    The Client will ensure that the equipment is adequately secured when not in use, will not use the equipment whilst under the influence of drink or drugs and will immediately notify the company in the event of breakdown or loss of equipment.

  • Clients bringing their own bikes do so on the proviso that their equipment is in a suitable condition for participation in a tour. Responsibility for maintenance of bicycles brought by clients rests with the client. The company will endeavour to accommodate such clients, but cannot guarantee that correct tools and spares will be available, given the wide range of possibilities that exist.