Pienza to San Gimignano Bike Tour

This 8-day guided bike tour is a deep dive into Tuscany’s most picturesque landscapes and timeless towns. Beginning in the Renaissance gem of Pienza and finishing beneath the medieval towers of San Gimignano, you’ll cycle through the heart of the Val d’Orcia, past cypress-lined hills, world-famous vineyards, and ancient fortresses.

With expert guides leading the way and full van support throughout, this moderate-level bike tour is as rewarding as it is scenic. Expect meaningful stops at cheese farms, wine estates, and historic hill towns, plus charming boutique stays and memorable dinners each night.

Day 01 :

Arrival in Pienza - 20 km

Welcome to southern Tuscany! After settling into your hotel in Pienza, you’ll meet your guides and fellow riders for a bike fitting and trip overview. Spend the evening exploring this stunning Renaissance town before enjoying your first group dinner at a local trattoria.

Accommodation: Hotel Corsignano or Hotel San Gregorio Pienza

Dinner

Day 02 :

Pienza Loop to Radicofani - 70 km

Start the day with a scenic downhill cruise through peaceful countryside en route to Radicofani, a hilltop village crowned by a dramatic fortress. After exploring its winding streets, continue riding through cypress-lined roads to a pecorino cheese farm for a tasting and light lunch. Finish with a satisfying climb back into Pienza for a well-earned rest.

Accommodation: Hotel Corsignano or Hotel San Gregorio Pienza

Breakfast + Dinner + Lunch

Day 03 :

Pienza to Montalcino - 48 km

Ride north through rolling farmland and olive groves toward Montalcino, home of the legendary Brunello wine. The route includes sweeping views and optional wine stops. After arriving and checking into your hotel, explore the historic center or simply relax before a group dinner in town.

Accommodation: Hotel Il Giglio Montalcino

Breakfast + Dinner

Day 04 :

Montalcino to Siena - 50 km

Today’s ride brings you into the Crete Senesi, a surreal landscape of soft clay ridges and quiet farmland. Arrive in Siena by late afternoon and settle into your hotel just steps from the city’s historic centre. The evening is free to explore — visit the famous Piazza del Campo, or grab dinner at one of Siena’s lively osterie.

Accommodation: Hotel La Villa Siena

Breakfast + Dinner

Day 05 :

Free Day in Siena

Take a break from the saddle and immerse yourself in the culture of Siena. Wander its medieval streets, climb the Torre del Mangia, or relax at a café with a caffè shakerato. Your guides are on hand for optional suggestions or bookings.

Accommodation: Hotel La Villa Siena

Breakfast

Day 06 :

Siena to Castellina in Chianti - 65 km

Ride into the heart of the Chianti Classico region. Rolling vineyards and forested trails lead you to Castellina in Chianti, a charming hilltop town known for its wine, stone archways, and laid-back pace. Dinner tonight is a group celebration of your final full ride.

Accommodation: Hotel Palazzo Squarcialupi Castellina C.

Breakfast + Dinner

Day 07 :

Castellina to San Gimignano - 40 km

Your final ride winds through vineyards, olive groves, and sleepy hamlets before reaching San Gimignano, with its famous medieval towers. After arriving and soaking in the views, enjoy a farewell toast with the group before your journey comes to a close.

Accommodation: Fattoria Poggio Alloro San Giminiano

Breakfast + Dinner

Day 08 :

Arrivederci

Today is our last chance to savour the scenery together before departing. We’re always sad to part, but we know the friendships we make in Tuscany will continue to enrich our lives in the years ahead!

Breakfast