Pienza to Castelnuovo Berardenga Bike Tour

Overview

This 7-day guided bike tour is a full-immersion ride through the rolling hills, vineyard-covered valleys, and cultural gems of southern Tuscany. Beginning in the Renaissance town of Pienza and ending in the wine-rich countryside of Castelnuovo Berardenga, this bike tour blends cycling, history, food, and wine into one unforgettable journey.

Along the way, you’ll visit iconic villages like Montepulciano, Montalcino, Gaiole, and Radda, stay in a restored medieval castle, and ride the same scenic roads featured in The English Patient and Gladiator. With expert guides, full van support, curated tastings, and beautiful boutique accommodations, this is Tuscany the way it was meant to be experienced.

Highlights

Arrival in Pienza
Stay in Pienza the ideal renaissance Town.
Magical stay at a real medieval castle Gargonza.
Riding through scenic landscapes where “English Patient” and “Gladiator” were filmed.
A private tour of the cantina of Brunello in Montalcino, one of the older winery Costanti.
Enjoy Chianti resort with wine and food focus.

Day 01 :

Arrival in Pienza

Your bike tour begins in Pienza, often called the “ideal Renaissance town.” After a transfer from Chiusi, meet your guides, get fitted for your bike, and join the group for an optional warm-up ride to Bagno Vignoni, a thermal village along the ancient Via Francigena. In the evening, enjoy a welcome dinner at La Bandita Townhouse, where handmade pasta and local wine set the tone for the week ahead.

Dinner

Day 02 :

Pienza Loop to Montepulciano & Monticchiello - 55 km

Ride through landscapes so scenic they’ve been featured in classic films. You’ll pedal past Castelmuzio, Petroio, and the vineyards of Montepulciano, where you can explore medieval streets and visit the town’s oldest wine cellar. Return to Pienza via the hilltop village of Monticchiello, taking in panoramic views the entire way.

Breakfast + Dinner

Day 03 :

Pienza Loop to Montalcino & San Quirico - 68 km

Cycle downhill into the Val d’Orcia, then climb toward Castiglione d’Orcia and visit the historic Sant’Antimo Abbey. Continue through Brunello vineyards to Montalcino, where you’ll enjoy a private tasting at the renowned Ciacci Piccolomini winery. Return to Pienza via San Quirico, with a stop to explore the Horti Leonini Gardens. Dinner is on your own tonight — plenty of great options nearby!

Breakfast

Day 04 :

Pienza to Castello di Gargonza - 57 km

Today you’ll ride through the Crete Senesi, Tuscany’s wild and lunar-like “badlands.” Pass through the villages of Castelmuzio, Trequanda, and Lucignano, before arriving at your destination: the incredible Castello di Gargonza, a restored medieval castle where you’ll dine and stay like royalty.

Breakfast + Dinner

Day 05 :

Gargonza to Castelnuovo Berardenga - 50 km

Enter Chianti country with a scenic ride north through olive groves and vineyards. Visit the historic town of Castelnuovo Berardenga, then continue past hamlets and vineyards to Castello di Brolio, home of the Ricasoli family and the birthplace of Chianti Classico. In the evening, enjoy a Chianti tasting at Fèlsina Winery, followed by dinner at your countryside resort.

Breakfast + Dinner

Day 06 :

Chianti Loop Ride to Gaiole, Radda & Castello di Ama - 62 km

On your final ride, visit the “Chianti Alliance” villages of Gaiole, Radda, and Ama, pedaling along quiet roads, past ancient abbeys and hidden wineries. Stop for lunch in Gaiole, home of the vintage L’Eroica bike race, and return via the scenic Via dei Castelli with a visit to Castello di Ama. Relax by the pool before your farewell dinner and final toast.

Breakfast + Dinner

Day 07 :

Departure from Castelnuovo Berardenga

After breakfast, you’re free to transfer to Siena or onward destinations. Grazie and arrivederci — you’ve experienced Tuscany like never before.

Breakfast