From Val d'Orcia to the Tyrrhenian Sea: Get a taste of quintessential Southern Tuscany, where the extraordinary beauty of daily life never fails to delight. And enjoy an introduction to the endless rolling wheat fields, ancient woodland, marvelous medieval villages of maremma and end at sandy beaches and seaside enclaves of the coast in Talamone.


Day One: Pienza

We'll meet you at Pienza, the purest Renaissance town in the world (you will arrive by the train to Chiusi-Chianciano station, a major stop on all the Rome-Florence lines). Fitting of bikes.
Your charming hotel Il Chiostro is housed in a 15th-century convent in a quiet, secluded location right in the center of Pienza - itself is a rare masterpiece: entirely rebuilt between 1459 and 1462, it was the brainstorm of Pope Pius II.
Lodging at hotel Relais Il Chiostro di Pienza


Day Two: San Casciano dei Bagni
Length: 45 km.
Today is a completely country ride: for the first 15 km you will ride downhill and after easy gentle rolling hills. you will see Radicofani medieval and enchanting village with a 1200 dating Rocca. After lunch at the hill town continue to Celle sul Rigo and San Casciano Bagni hot spring. The spa is very old and in town there is impressive town hall of renaissance time.
Lodging at hotel Sette Querce in San Casciano Bagni


Day Three: Sorano
Length: 51 km.
Today the ride is more challenging crossing minuscule villages and borgos.
Sorano is barely more than a handful of ancient homes gathered around the fortress which is partly occupied by the Fortezza: Erected in the 16th century by the Orsini family, the castle is one of the best surviving examples of Tuscan military architecture. As we all know, the main function of any fortress is to protect against marauding invaders - because of this, we can see for miles from any window in the hotel, across the valley of the Etruscans.
Lodging sovana hotel resort


Day four: sovana & amiata
Length: 50 km.
Some short steep uphill await for you today! You will pass small village on border with Amiata mountains. But enjoy Sovana! This hill town is now a village with little more than a single street running from the castle ruins to the cathedral. As time marched on, so did history sweep through the Maremma. The Romans came, saw and conquered, then built settlements atop the ruins of their vanquished enemies. These, in turn, later served as the base for medieval villages. Today, almost every town in the area clearly shows traces.
Lodging sovana hotel & resort


Day Five: Scansano & Pitigliano
Length: 45 km.
Breakfast at the hotel. Soon you will arrive at Pitigliano: a pristine warren of elegant palaces and surprisingly broad cobble-stoned streets, it is nicknamed Tuscany's Little Jerusalem in honor of extremely active Jewish community that lived here for centuries. Two of the town's most interesting attractions are its wonderfully restored Synagogue.
Our accommodation is the Antico Casale, a 200-year-old stone farmhouse converted to a small hotel, you will find true Tuscan hospitality. Dinner at restaurant of hotel: taste Morellino di Scansano wine.
Lodging at Antico Casale in Scansano.


Day six: Talamone
Length: 45 km.
Departure from Scansano town you will cycle into Magliano in Toscana a real hidden treasure of maremma. today the ride is really easy only downhill and flat. You will reach Talamone, a small fishermen village extended along a promontory overlooking the sea, dominated by an ancient sienese castle, hemmed in by the Natural Park of Maremma . The breathtaking view from the belvedere near lighthouse takes the whole coast from the Argentario to Punta ala. Highlight is to enjoy seafood in a restaurant in town.
Lodging at hotel Baia di Talamone


Day Seven
End of tour after breakfast – Departure: With a direct train from Talamone Station you will easily reach the Roman stations where you can catch the connection for Fiumicino Airport. If your next destination is an European location, International connections are also available reaching Grosseto or Civitavecchia


Duration: 7 days / 6 nights;


Tour Departures:
Any date between 15th March to end of October
This is a self-guided touring and offers total freedom of dates - you can choose whatever dates you wish. We can accommodate small parties of 2 persons up to large groups.