Biking Tuscany

Posted in Biking Italy, Chianti, Tuscany and Umbria, Go Active, Italy, Italy, Trips, Women's Destinations

Highlights of Biking Tuscany Trip

  • Stay in Renaissance Pienza, rebuilt to its current beauty by Pope Pius II.
  • Cycle through rolling vineyards, golden wheat fields and chalky white hills.
  • Savor pecorino cheese, homemade pasta pici, and fruity olive oils.
  • Sip Tuscan wines including the famed Brunello and Nobile.
  • Experience the essence of Tuscany where history and beauty fill the heart as water fills a well.

There are hills to climb, but your efforts will be well rewarded with a sunny Mediterranean ambiance and a spirited hospitality. Tuscany nourishes the soul and leads you to rejoice in the earthly pleasures of daily life.These selected routes will take you along tranquil country lanes, between farmland crowned by walled villages, past ancient monasteries in secluded valleys, and to medieval forts.

Departure dates

These trips can be arranged year-round. Prices are based on a minimum of 4 people in the same group. We can arranged personal departure dates for smaller groups or price for upgraded hotels as desired. We offer certain group departure dates. Watch for our newsletter.

Trip Length 5 days/4 nights
Start/Finish Chiusi /Chiusi (transfers to or from Florence and Rome available upon request*
Walk Rating Moderate to challenging
Included Accommodations, all breakfasts, 3 dinners, 2 lunches, transfers during the tour, 1 wine tasting, full time guide.
Hotels Relais Il Chiostro. Premier accommodations
Price $2,895
Single Supplement $600



DAY 1: Pienza

Our guides meet you in Pienza, the purest Renaissance town in the world. Upon arrival in Pienza, begin with a biking fitting. Cyclists can enjoy an optional test ride to San Quirico. There is time to freshen up and enjoy the surroundings before our welcome dinner at La Bandita. (D)

Accommodations: Relais Il Chiostro or equivalent, Il ChiostroI is housed in a secluded 15th-century Franciscan monastery in the center of Pienza
Cycling distance: 20 kms. – easy terrain

DAY 2: Montepulciano & Vino Nobile

Your tour today starts with a circular ride that starts in Pienza. We stop along the way to visit a remote convent in the Hamlet of Castelmuzio where parts of The English Patient were filmed. We continue to to Montepulciano, the jewel of southern Tuscany. In Montepulciano you will be given time to wander around the town and stop for lunch before returning to Pienza. Along the way, there is a stop in the village of Monticchiello, the quintessential Tuscan hill town. Dinner tonight at the Baccus Lodge in your hotel. (B, D)

Accommodations Relais Il Chiostro or equivalent
Cycling distance: 50 km – moderate terrain.

DAY 3: Montalcino & the land of Brunello

Special event : wine tasting and cellar lunch

Ride from Pienza to Montalcino. Pause in the fairy-tale town of Bagno Vignoni, a miniature spa that is among the most unique towns in Europe. Continue to the monastery of Sant’Antimo, where you might catch one of several vesper services performed each day by the monks. The famed wine town of Montalcino is your destination. Visit the fortress for some breathtaking views of the Val d’Orcia and taken in the awe-inspiring scene that you have just biked through. Reward yourself with wine tasting and lunch at Corte Pavone. Back to Pienza by van or by bike for the very ambitious. Dinner tonight on your own. (B, L, wine tasting)

Accommodation:  Relais Il Chiostro.
Cycling distance: 46 km – moderate to challenging terrain.

DAY 4:  Radicofani & Val d’Orcia

Special event: Pecorino cheese tasting

Today’s circular bike ride takes you into the Val d’Orcia, a UNESCO world heritage region. Here you’ll see an exceptional reflection of the way the landscape was re-made during the Renaissance times to reflect the ideals of good governance. The aesthetically pleasing and picturesque landscape was in fact created and man-made into what we recognize today as the iconic and quintessential idea of Tuscany. The ride is along quiet and hilly country roads. There is one long downhill before concluding with a long climb to reach Radicofani, an enchanting medieval village dating back to the 1200s. After a stroll around the stately town of Rocca, head back into the countryside, along some of those winding cypress-lined roads for a roller coaster ride to Contignano. On the way back to Pienza, stop at cheese factory for a tasting of the famed “Pecorino” sheep milk cheese and a well-deserved lunch. Back on the saddle (or in the van if you prefer) for the last 12 kilometers to Pienza. Dinner tonight in la Foce. (B, cheese tasting, L, D)

Accommodation: Relais Il Chiostro or equivalent
Cycling distance: 66 kms.- moderate to challenging terrain


After breakfast it is time to say our good-byes. Our guide will help you with a transfer to your next destination.

Satisfaction guaranteed. Arrivederci!!!!

INCLUDED: Full time certified local bike guide during the trip, full van support, transportation during above itinerary, luggage transportation, 4 nights premiere accommodations, hotel tips and taxes, all breakfasts, 2 lunches, 3 dinners, wine tasting, specialty cheese tasting, fully equipped hybrid or racing bike rental, route notes, maps, elevation gain and Pienza city map, paid entrances to all included activities, all land transfers during the tour, all taxes and service charges at hotels and restaurants, travel guidance for pre/post-tour activities.

NOT INCLUDED: Airfares, airport taxes, travel insurance (mandatory), pre and post trip arrangements, personal purchases, mini-bar services, alcohol unless specifically included, OPC, gratuities for guide and driver.

B= breakfast included, L=lunch included, PicL=picnic lunch included, D=Dinner included
All bookings through Garth Allen Marksted Travel, Quebec License.

* Price does not include transfers from Florence, Rome or other cities. Price based on transfers from Chiusi train station and on class of accommodations listed. Contact us for pricing for luxury accommodations, personalized itineraries, other hotel choices, or for specialty groups. Routes are subject to change based on festivals and harvest season.