Italy: Tuscany Bike Tour

Meet at the Camucia-Cortona train station mid-morning where you will be fitted to your rental bikes and briefed on route materials. Spend the afternoon cycling a leisurely route toward Montepulciano, arriving at your countryside villa late in the day. LD (Meal inclusions provided for guided trips. Self-guided trips include breakfast only)

Villa Cicolina, Montepulciano

Choose from three loops of varying distances through the hilly countryside surrounding Montepulciano. These routes avoid the biggest climbs and busiest roads in the region and allow time for relaxing by the pool and late afternoon exploration of Montepulciano, one of the most charming hilltop towns in Tuscany. Fabled to be the seat of Etruscan kings, Montepulciano was established as an important religious center and enjoyed political allegiances with Florence, bringing the wealth and splendor of some of the most important architects of the renaissance. Enjoy a quiet stroll among stone houses the many car-free streets, gaze across the surrounding farmland from one of the town’s many look-offs, or simply enjoy people-watching from one of the cafes surrounding the Piazza Grande. BL

Same lodging

You will have the chance for a final visit to Montepulciano this morning before a gradual 5km climb to the highest elevation point for the day. From here, your descent brings you a through beautiful countryside of the Val d’Orcia to Monticchiello, a small medieval town ideally located for a mid-ride break. Descend to the valley floor, and pace yourself for the climb into the UNESCO heritage site of Pienza, a lively town known for its fragrant pecorino cheese. BLD

Relais Il Chiostro Di Pienza or Hotel San Gregorio, Pienza

Your ride today starts in the heart of the UNESCO World Cultural Landscape of Val d’Orcia. Cycling along cypress-lined roads through cultivated fields of wheat and olive groves with the lava dome of Monte Amiata in the distance, you will feel as if you are in the midst of a renaissance landscape painting. Today’s climb begins just outside the foothill town of Campiglia d’Orcia and ends near Vivo d’Orcia where you will stop for lunch and enjoy long vistas over the valley. The remainder of the day will be spent descending through shady tree-lined roads along the north slope of Monte Amiata, before reaching your accommodation in the comune of Castel del Piano. After checking into your accommodation, take time to explore the warren-like narrow streets and passageways of the historic town center on foot before an independent dinner. BL

Grand Hotel Impero, Castel del Piano

A gradual morning climb heading south along the eastern foothills of Monte Amiata will give way to a long, pleasant descent through the Fiora river valley. In the small medieval town of Sovana you will have the chance to explore an Etruscan necropolis where high relief statues and burial chambers are carved from the limestone Tufa. The nearby Vie Cave is a natural passageway which was once used to reach burial grounds and later developed into more major transportation corridor. The artisan shops and cafes peppering the brick-paved main streets of Sovana are worth taking time to explore. Your ride ends with a short climb into the medieval hill town of Sorano, built upon an outcrop of volcanic tuff. BLD

Hotel della Fortezza, Sorano

Following breakfast, your ride today descends into the historic frontier town of Pitigliano. Once home to a large and flourishing Jewish community, the historic old town is still known as “Little Jerusalem”. Although the Jewish population is quite diminished, the restored synagogue remains and continues to host periodic services and is the site of a small community museum. After spending some time exploring the narrow streets, enjoy an invigorating ride through the vineyards and farms of the Fiora and Albegna river valleys. After 10km you will pass near the fortified hill town of Montemerano, a charming hamlet commissioned by the Aldobrandeschi family in the 13th century. Though a bit of a climb, the magnificent views and quiet charm make this a good lunch stop option. The remaining route will climb through vineyards of Sangiovese grapes, known locally as Morellino, the basis for the town’s most famous export, Morellino di Scansano. BD

Antico Casale di Scansano, Scansano

Enjoy a day of quiet cycling through rolling farm country as you gradually descend out of the mountains toward the Tyrrhenian coast. Forested hills and vineyards gradually give way to olive groves and fields of wheat, with views of the ocean and Monte Argentario in the distance. Your ride today ends in the picturesque hilltop village of Capalbio. BLD

Hotel Valle del Buttero, Capalbio

On your final day of riding, you will join the coast at the resort town of Ansedonia, famed for the ruins of the nearby Roman town of Cosa – a site of archaeological significance due to the extent of its excavation. The harbor of Cosa remains the earliest known Roman port in existence, with extensive masonry piers and elaborate channels cut through the limestone cliffs which are thought to have kept the main channel free of sediment. After an independent lunch in Ansedonia, a 7km ride along a sandy neck through coastal pine forests in the Feniglia natural reserve connects you with the headland created by Monte Argentario. The remaining coastal ride follows quiet roads and dedicated cycle track along an old rail bed through tunnels carved in the sea cliffs into the port town of Santo Stefano. Your day will either end in Santo Stefano or after a short van transfer up the shore to the coastal village of Talamone. BD

Albergo Belvedere, Porto Santo Stefano, or Hotel Capo d’Uomo, Talamone

After breakfast you will transfer to the train station where connections are available to Pisa, Rome, or other European destinations. Buon viaggio!