Classic Tuscany Bike Tour

Meet your guides at the Chiusi train station for a transfer to the tiny village of Montefollonico. Here, an authentic Tuscan welcome awaits with lunch on the scenic terrace of a centuries-old olive mill. After, get fitted on your bike and set off on a ride through the classic Tuscan countryside—you’ll feel as though you’ve traveled back to the 13th century 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 that lead to our boutique hotel in the heart of Pienza, tucked in amongst the town’s Renaissance architecture. This evening, watch the sun set over the Tuscan hills as we dine al fresco on the terrace of a local organic farm.

Meals: Lunch / Dinner
Destinations: Pienza, Petroio
Accomplished: 19 miles / 29 km, elevation gain: 1,919 feet / 585 meters
Shorter Option: 14 miles / 22 km, elevation gain: 1,332 feet / 406 meters
Accommodations: La Bandita Townhouse

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.

Meals: Breakfast / Lunch / Dinner
Destinations: Montichiello, Castiglione d’Orcia, Montalcino
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
Accommodations: Castello di Velona

Today’s loop ride begins with a climb to Montalcino on a route lined with prestigious vineyards. Follow in the footsteps of Roman legions, popes, and emperors as we pedal along the ancient Via Cassia into medieval San Quirico. Soak up the atmosphere in the main piazza before continuing along 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, enjoy a relaxed spin into the Asso Valley (home to Italy’s rare white truffles). From here, complete the full loop ride or take a quick shuttle back to the hotel. This evening, treat yourself to some rest and relaxation at the pool and spa before another satisfying dinner.

Meals: Breakfast / Lunch / Dinner
Destinations: Montalcino, San Giovanni d’Asso, Castelmuzio, San Quirico
Accomplished: 38 miles / 61 km, elevation gain: 2,893 feet / 1,032 meters
Longer Option: 50 miles / 81 km, elevation gain: 4,720 feet / 1,439 meters
Accommodations: Castello di Velona 

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 to visit the Renaissance frescoes at the Abbey of Monte Oliveto. Crossing into Chianti Classico country, the views turn positively panoramic, and we’ll pedal through the wide-open landscapes of the Crete Senesi to a well-earned lunch at a family-run winery. Tonight, spend the evening in Siena as you wish: dine on your own, explore the medieval city, or have dinner right at our hotel. 

Meals: Breakfast / Lunch
Destinations: Buonconvento, Monte Oliveto, Asciano, Siena
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
Accommodations: Borgo San Felice or Le Fontanelle

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, completing our loop for lunch back at the hotel. Enjoy a relaxed afternoon at the pool or spa before regrouping for a final dinner with our friend Serena featuring top wines and generous Tuscan hospitality.

Meals: Breakfast / Lunch / Dinner
Destinations: Castelnuovo, Brolio, Castagnoli
Accomplished: 31 miles / 50 km, elevation gain: 2,673 feet / 815 meters
Longer Option: 40 miles / 64 km, elevation gain: 3,575 feet / 1,090 meters
Accommodations: Borgo San Felice or Le Fontanelle

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.

Meals: Breakfast
Destinations: Panzano, Greve, Florence
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