Crete Senesi to Montalcino Cooking & Bike Tour

This 7-day guided cooking and bike tour is a celebration of Tuscany’s greatest pleasures — rolling hills, medieval villages, Brunello wine, handmade pasta, and the joy of riding through it all. Beginning and ending in Rapolano Terme, this loop-style journey blends scenic cycling with three immersive cooking classes designed to send you home with new skills and unforgettable flavours.

Each day offers a carefully balanced mix of physical adventure and culinary indulgence. You’ll ride through iconic landscapes like the Crete Senesi, visit hill towns like Pienza, Cortona, and Montalcino, and return each evening to warm hospitality, delicious food, and the kind of Italian camaraderie that lingers long after the last glass of Chianti is poured.

Day 01 :

Arrival & Warm-Up Ride - 20 km

After checking into your countryside villa near Rapolano Terme, you’ll meet your guides and get fitted for your bike. Ease into the rhythm of Tuscany with a warm-up ride to Asciano, then climb the scenic Pecorile Road back to the villa. Tonight, you’ll roll up your sleeves for your first cooking class — and then enjoy the results at your welcome dinner.

Lunch

Day 02 :

Loop Ride to Pienza & Val d’Orcia - 63 km

Begin with a ride to Pienza, then continue through San Giovanni d’Asso, Torrenieri, and San Quirico d’Orcia, following parts of the ancient Via Francigena. Stop for gelato and breathtaking views of the UNESCO-listed Val d’Orcia before riding quiet roads past Castelmuzio and Petroio. Return to the villa through the countryside made famous by The English Patient.

Breakfast + Dinner

Day 03 :

Loop Ride through Crete Senesi - 55 km

Today’s ride drops into the Crete Senesi, Tuscany’s surreal clay hills often compared to a lunar landscape. Cycle to Asciano and tackle the scenic Lauretana Road, with big climbs and even bigger views. After a relaxed lunch stop in Rapolano Terme, return to the villa for your second cooking class — featuring traditional recipes and local ingredients.

Breakfast + Dinner

Day 04 :

Ride to Siena + City Tour - 65 km

Ride through the Chianti foothills en route to Siena, one of Italy’s most beloved medieval cities. Pedal past vineyards and olive groves before arriving in the historic Piazza del Campo, home of the famous Palio horse race. Enjoy a guided walking tour, then return to your villa by van for a free evening.

Breakfast + Dinner

Day 05 :

Ride to Cortona & Final Cooking Class - 53 km

Cycle through sunflower fields and forested climbs to reach Cortona, the hill town made famous by Under the Tuscan Sun. After lunch at a local trattoria and time to explore its medieval lanes, return by van to the villa. Tonight’s final cooking class is a celebration of everything you’ve learned — and everything you’ve eaten!

Breakfast + Dinner

Day 06 :

Ride to Montalcino & Brunello Tasting - 62 km

Your final ride takes you through Chiusure, past the majestic Abbey of Monte Oliveto Maggiore, and into the wine capital of Montalcino. Climb through Sangiovese vineyards and finish with a guided Brunello tasting at one of Tuscany’s oldest wineries. Return to the villa for a farewell dinner and one last toast with your fellow riders and chefs-in-training.

Breakfast + Dinner

Day 07 :

Farewell & Transfer to Siena

Enjoy one last breakfast together before transferring to Siena Station. You’ll leave with new recipes, stronger legs, and memories that taste as good as they feel.

Breakfast