Difficulty Rating : 5 Start: Chiusi Finish: Siena Daily Average: 10-16km Weekly Average: 84km Tour Type: Self Guided,Walking Teaser: This tour explores this beautiful region famous for its fine food and wine, magnificent landscapes and wonderful hilltop towns.
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This tour explores this beautiful region famous for its fine food and wine, magnificent landscapes and wonderful hilltop towns. We visit the thermal springs of Bagno Vignoni and the Val d'O with its breathtaking landscape, its Renaissance towns and its fabulous monasteries.

The tour starts with a walk towards the medieval town of Montepulciano where you spend the night. We trek through the stunning rolling hills, oak woods and pretty villages and end up in a thermal bathing place where the main square is a basin of steaming hot water! The tour meanders along vineyards and olive trees towards Montalcino, home of some of Italy's most famous wines. The stunning city of Sienna is our final destination, where you have time to explore the beautiful squares and churches that make up this historic city.

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Day 1

Arrival in Chiusi

You are met by our representative who will spend a short time going over the tour with you answering any question you may have. He will then drive you to your hotel in Montepulciano.

Day 2


From the San Biagio church (which is on the outskirts of town and certainly worth a visit) the road takes you to Montichiello - a nice little village immersed in the "Crete". You can stop there for a nice lunch or just for a cappuccino before continuing to Pienza which is one of the nicest Renaissance towns in Tuscany. Visit the town which is also an agricultural centre is well known for pecorino cheese and truffle production. Overnight in a nice hotel in the town.
(6 hrs walking time; 15 km 490 m ascent)

Day 3

Pienza/San Quirico d'Orcia/Bagno Vignoni

The walking today crosses a beautiful region of rolling hills, oaks woods, quiet villages and ends in, or close by, a thermal bathing place where the main square is a basin of steaming hot water. It is possible to swim in the thermal pool (additional charge) if you do not get there too late; according to availability, the night can be spent in Bagno Vignoni, or in an agriturismo 2 km from the town along the walking trail.
(5 hrs walking time; 15 km 415 ascent)

Day 4

Bagno Vignoni/Sant'Antimo/Montalcino

A longer walking day along dry river beds in the rather wild environment to reach St Antimo; a lovely abbey isolated in the middle of a pastoral landscape with grazing herds around which adds peacefulness to the scene. From there it is additional 10 km of a steep ascending trail to reach Montalcino, so the car with your luggage will pick you up in St Antimo to drive you to this nice medieval town. Accommodation in Hotel Montalcino.
(6 hrs walking time, 13 km 585 elevation gain)

Day 5


As Montalcino is the country of Brunello - one of the most famous wines of this region - you will be walking through vineyards and olive trees. Then the route will lead you through the beautiful “Crete” landscape. You will spend the night in a nice agriturismo 3 km from Buonconvento.
(4hrs walking time; 15km / 255 m elevation gain)

Day 6


A short day but full of ups and downs. The unpaved road will take you to Monte Oliveto Maggiore, one of the most impressing abbeys in Italy – a red brick construction in a rugged landscape. The owner of the agriturismo can collect you if walking back feels too much (if you decide to walk back, it will take approx 3 hours). You can also skip today’s walk and enjoy the Inn’s swimming pool or its beauty farm Sauna
(4hrs walking time)

Day 7

Buonconvento/Monte Oliveto Maggiore/ Siena

You will start the day with a transfer to Monte Oliveto Maggiore – you can visit the abbey before the tourist rush hours and start walking back towards your accommodation. You can stop for a light snack at Chiusure, the first village on your way back. There is a small “Alimentari” where you can enjoy a freshly made panini. Pick up your luggage and get on a train to Siena for your last night (there is a possibility of a private transfer to Siena).
(3 hrs 30 mins walking time; 16 km / 285 m elevation gain)

  • 7 nights B&B - All breakfasts
  • Needed transfers
  • Luggage transfer at each change of accommodation
  • Transfer to Montepulciano from Chiusi train station
  • Detailed road book and maps
  • One of our assistants will meet you on the first day (or the next morning if biking or hiking are not in the program for the first day) to explain the tour and answer your questions

Optional tour extension in Villa Lecchi includes:
2 nights accommodation with breakfasts and dinners, transfers as per the itinerary, maps and route notes.

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2024 Tour Price
€1150 per person sharing
€200 single room supplement ( if travelling with others )
€330 solo traveler supplement (if traveling on your own)

Self Guided Tour Information

Tour can start on any day.

Nearest airports: Rome, Pisa or Florence, then you take the train to Chiusi from where you will be transferred to Montepulciano.

When checking the flights for this trip, consider that it is quite convenient traveling from Pisa airport (the train station is at the front of the airport) to Chiusi; it takes approximately 3 hours and from Siena to Pisa airport it is a 2 hour trip. Web site on trains in Italy: www.trenitalia.it


BB Agnolo Montepulciano www.lagnolo.com


Hotel Corsignano www.hotelcorsignano.it


Albergo Le Terme Bagno www.albergoleterme.it


Hotel Dei Capitani –www.deicapitani.it


Fattoria Pieve a Salti www.pieveasalti.it


Fattoria Pieve a Salti www.pieveasalti.it


Hotel Chiusarelli www.chiusarelli.com

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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Payment Information

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.