Tuscany Bike Tour: What Locals Love Beyond Siena and Florence

Meet our guides at the Chiusi train station for a transfer to Pienza, a Renaissance town in the heart of Tuscany’s Val d’Orcia. Check into our boutique hotel and tuck into lunch before we set off for our first ride into the countryside. You’ll feel as though you’ve traveled back to the 13th century while pedaling on the cobbled streets of tiny Petroio and greeting locals as they tend their olive groves. Choose your own adventure with longer or shorter ride options. This evening, watch the sun set over the Tuscan hills as we dine al fresco on the terrace of a local organic farm.

Accomplished: 17 miles / 28 km, elevation gain: 1,630 feet / 497 meters

Longer Option: 24 miles / 38 km, elevation gain: 2,303 feet / 702 meters

Set off riding through the Val d’Orcia, an area so beautiful that UNESCO designated it a World Heritage Site—you may also recognize it from the movie Gladiator’s famous wheat field scene. Climb up to the craggy medieval fortress of Castiglione for a coffee stop (a key component of Italian cycling culture), then enjoy an endless downhill through the olive groves. The final push brings us to our favorite Brunello winery, where the reward for our efforts is a gorgeous tasting lunch. Spend the afternoon relaxing by the pool or getting pampered at the spa of our five-star castle hotel. This evening we’ll head into Montalcino for a cooking class and dinner in the 15th-century home of our friend Lina.

Accomplished: 24 miles / 39 km, elevation gain: 2,247 feet / 685 meters

Longer Option: 38 miles / 62 km, elevation gain: 3,487 feet / 1,063 meters

Today’s loop ride begins with a climb to Montalcino, followed by a downhill section through vineyards into the Asso Valley (home to some of Italy’s finest truffles). Pedal along the valley floor, then follow a scenic ridgeline to our friend Paolo’s olive mill for lunch cooked by his mother and a tasting of organic olive oil. After lunch, revel in majestic views towards the dormant volcano of Monte Amiata as we pedal to medieval San Quirico. From here, complete the full loop ride or opt for a quick shuttle back to the hotel. This evening, treat yourself to some rest and relaxation at the hotel before another satisfying dinner.

Accomplished: 33 miles / 53 km, elevation gain: 2,893 feet / 882 meters

Longer Option: 50 miles / 81 km, elevation gain: 4,497 feet / 1,371 meters

Say goodbye to the Castello di Velona as we ride through the mystical morning light that bathes the Romanesque Abbey of Sant’Antimo. Pedal across the Brunello region before we stop for a visit of the Renaissance frescoes at the Abbey of Monte Oliveto. After a picnic lunch, continue riding along the open ridges of this scenic landscape. Opt for an earlier van transfer or continue cycling all the way to our final hotel. Tonight, head into the medieval city of Siena to explore and dine there, or stay close and delight in dinner at the hotel.

Accomplished: 29 miles / 46 km, elevation gain: 2,083 feet / 635 meters

Longer Option: 48 miles / 77 km, elevation gain: 3,972 feet / 1,211 meters

Olive and cypress trees surround us as we ride deep into the hills of Chianti. We’ll see plenty of fortified hamlets and castles—relics of Florence and Siena’s 300-year struggle for regional dominance and ownership over the birthplace of Chianti Classico wines found in ancient cellars around the area. Pedal past countless estates as we weave our way through forests and vineyards to lunch with our friend Max at his innovative bistro. After lunch, opt for a longer ride or a straight shot back to the hotel. We’ll regroup in the evening for a tasting of San Felice’s famous wines and a festive final dinner.

Accomplished: 31 miles / 50 km, elevation gain: 2,673 feet / 815 meters

Longer Option: 39 miles / 63 km, elevation gain: 3,132 feet / 955 meters

Accomplished: 29 miles / 46 km, elevation gain: 2,083 feet / 635 meters

Longer Option: 48 miles / 77 km, elevation gain: 3,972 feet / 1,211 meters

On our last day, choose between a late morning at the hotel or ride all the way across Chianti for a triumphant finish in Florence’s Piazzale Michelangelo. Whether you rode here or took a transfer, we say our goodbyes with the stunning Florentine skyline as our backdrop as guides see you off to your next adventure.

Optional Ride: 32 miles / 52 km, elevation gain: 2,470 feet / 753 meters

Longer Option: 43 miles / 69 km, elevation gain: 3,477 feet / 1,060 meters