This popular route takes you to impressive medieval hilltop towns and  thermal spa villages. Begin your journey in San Casciano dei Bagni – a popular destination of the Siennese nobility. The first travel day passes through the unspoiled Tuscan towns of Contignano and Radicofani en route to the spa town of Bagno Vignoni. Enjoy the relaxing thermal baths before you carry on.

Cycle to Pienza, famous for its Pecorino cheese and as the setting for Felini's "Romeo and Juliet'  Pedal through popular filming countryside including "The English Patient" and "The Gladiator".There are countless fields of wild flowers, rolling vineyards and impressive chalky white hills, the scenery just keeps getting better and better. Stop somewhere for a gourmet  picnic. Then off to the famous town of Montalcino overlooking both the Val d’Orcia and the Siennese heartlands. Sample some of Italy's finest wines including the Brunello di Montalcino and settle into our charming hotels and private villas.

Well deserved thermal baths and hotel pools await you at most of the places encountered.

• Medieval hilltop towns of Montalcino and Pienza.
• Charming 3 star hotels
• Superb thermal baths in San Casciano dei Bagni and Bagno Vignoni.
• Enchanting medieval city of Siena.
• Impressive Abbey of Sant’ Antimo and monastery of Monte Oliveto Maggiore.

Flavors of the region: Settle into our charming hotels and private villas and savor the famous Tuscan cuisine. Take advantage of some of Italy's finest wines, including the Brunello di Montalcino.

Click to See: Tour Price - Departure Days - What's Included - Reserve this tour Request Newsletter

Day 1 - Arrival day  

Transfer from Rome airport to Chiusi by train. Pick up by our rep in minibus and transfer to San Casciano dei Bagni (2 hrs).

Day 2 - Active Free Day - you choose:

• Walk to Mount Cetona through beautiful pine forests.
• Walk to the tiny medieval village of Piazze.
• Treat yourself to the hot spring waters in the outdoor spa complex or visit the medieval town.

Day 3 - San Casciano dei Bagni to Bagno Vignoni

Cycle to the spa village of Bagno Vignoni passing by timeless Radicofani and Contignano. (48km/30 mi)

Day 4 - Active Free Day - you choose:

Walk to the impressive tower of Rocca d’Orcia.

Stroll to the neighboring village of San Quirico d’Orcia.

Day 5 -  Bagno Vignoni to Montalcino

Cycle to the renaissance town of Pienza then to the famous town of Montalcino.(40km/25 mi)

Day 6 - Active Free Day - you choose:

Day 7 -   Montalcino to Buonconvento 

Descend through the vineyards and olive groves to the fortified village of Murlo and then finishing at the charming villa overlooking Siena.(40km/25 mi)

Day 8 - Active Free Day - you choose:

The  day brings you through wonderful scenery to the towns of Asciano and Montisi.        (32 km/19 mi).

• Visit the impressive stone castle of medieval Trequanda with its lovely outdoor swimming pool.

• Pedal across to the charming village of Casteimuzio and the monastery of Sant' Anna.

Transfer to Chiusi by minibus and train to Rome airport (3 hrs).

SELF- GUIDED INN TOUR

Tour # ITM-1702/77 - 7 DAYS - $1690

Joins tour in Montalcino on Day 5 and continues to the end on day 11

Price includes all breakfasts and dinners except 2 dinners that are not included in Montalcino

Price includes all breakfasts and dinners except 2 dinners that are not included in Montalcino

Tour # ITM-1702/117 - 11 DAYS - $2090

Begins in San Casciano dei Bagni on Day 1

Price includes all breakfasts and dinners except 2 dinners that are not included in Montalcino

Departure dates: Every day from 1 April to 31 October

Accommodation: 3 star quality hotels.

The Bicycles: 24 speed Italian Bianchi touring bikes or our own tandem bikes equipped with bike computers, water bottle, panniers, spare inner tube, transparent map case, pump, bike lock and a puncture repair kit.

We also provide children's bikes, trailer bikes and tag along bikes for the youngsters

Price Includes:

Detailed briefing from the overseas representative with information on the tour                             Top of Page

Return transfers from airport

Luggage transfers daily from hotel to hotel.

Bike Hire and equipment (panniers, water bottle and pump, spare inner tube, puncture repair kit and levers, lock, map case)

Detailed route notes and maps and information packs.

Backup assistance and personal service

All nights accommodation with breakfasts. Dinners included at all destinations, except for 2 dinners in Montalcino.

Price Includes: Airport transfers and luggage transfers, Bike Hire and equipment (panniers, water bottle and pump, spare inner tube, puncture repair kit and levers, lock, map case) with detailed route notes and maps. All nights accommodation with breakfasts. Dinners not included are 2 at Montalcino and 2 at Montisi. All the rest are on a B&B basis.

Exclusions: Lunches, beverages, items of a personal nature such as phone calls and laundry, anything not specifically mentioned as included.

In Case of Breakdown - We do not intervene for flat tires. However, should any breakdown occur that prevents the completion of the days journey we will make repairs on the road. A phone number will be provided. All other types of necessary repairs that do not make cycling impossible will be repaired at the hotel each night.