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 Montisi and greeting locals as they tend their olive groves. Choose your own adventure with longer or shorter ride options that lead to our first boutique hotel, a converted estate perched on a hill outside Pienza. Relax, settle in, and enjoy a glass of wine. This evening, watch the sun set over the Val d’Orcia as the chef welcomes us with a seasonal dinner served just steps from the hotel’s garden.

Meals: Lunch / Dinner
Destinations: Pienza, Montisi
Accomplished: 23 miles / 37 km, elevation gain: 2,273 feet / 693 meters
Shorter Option: 18 miles / 29 km, elevation gain: 1,761 feet / 537 meters
Accommodations: Casa Newton

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. Marvel at the morning light in Renaissance Pienza, sip a coffee on the main square in San Quirico, and follow in the footsteps of emperors, popes, painters, and peasants as we trace the Via Cassia, an ancient Roman road to Torrenieri. This is the gourmet heart of Tuscany, where Brunello vineyards meet truffle-rich forests. Celebrate the bounty with a homemade lunch and olive oil tasting at our friend Paolo’s olive mill, then complete the loop back to the hotel. Tonight we’ll visit a local organic farm known for its flavorful raw milk sheep cheeses. Taste their tangy pecorino then sit down for a meal crafted from fresh ingredients grown and produced onsite.

Meals: Breakfast / Lunch / Dinner
Destinations: San Quirico, San Giovanni d’Asso, Castelmuzio
Accomplished: 30 miles / 49 km, elevation gain: 2,257 feet / 688 meters
Longer Option: 40 miles / 64 km, elevation gain: 3,228 feet / 984 meters
Accommodations: Casa Newton

Say goodbye to Casa Newton as we pedal out into the Crete Senesi, where the landscape turns positively panoramic. Stop to take in the Renaissance frescoes at the Abbey of Monte Oliveto before riding along a ridgeline where sheep graze and the view reveals the medieval towers of Siena in the distance. Crossing into Chianti Classico country, we’ll pedal through a green and gold landscape to lunch at a family-run winery. Afterwards, ride or transfer to the stunning Relais & Chateaux Borgo San Felice, our home for the next three nights. Get settled, relax by the pool or pamper yourself with a treatment at the spa. Tonight we’ll regather and head to a picturesque hamlet for dinner at an inviting, Tuscan osteria.

Meals: Breakfast / Lunch / Dinner
Destinations: Monte Oliveto, Asciano, Monteaperti
Accomplished: 37 miles / 60 km, elevation gain: 3,096 feet / 944 meters
Longer Option: 43 miles / 70 km, elevation gain: 3,841 feet / 1,171 meters
Accommodations: Borgo San Felice  or Castel Monastero

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. Spend a relaxed afternoon at the pool or spa before heading into Siena. Explore the cobbled streets of this UNESCO-designated medieval city and enjoy dinner on your own—your guides are happy to recommend their favorite restaurants.

Meals: Breakfast / Lunch
Destinations: Castagnoli, Gaiole, Siena
Accomplished: 25 miles / 41 km, elevation gain: 2,529 feet / 771 meters
Longer Option: 32 miles / 52 km, elevation gain: 3,483 feet / 1,062 meters
Accommodations:Borgo San Felice or Castel Monastero

Wake up to the quiet beauty of the Chianti countryside and ease into the day with a relaxed breakfast. Today’s loop ride leads us through a cycling paradise, tracing the storied roads of the famed Strade Bianche bike race. On the outskirts of Siena, we’ll visit our friend Serena, who welcomes us into her home for a memorable, home-cooked lunch inspired by her bountiful garden and passion for local cuisine. After, continue cycling back to the hotel or opt for a transfer. The afternoon is yours to spend as you wish—take a stroll through the beautiful grounds or enjoy a poolside spritz. This evening we’ll toast to our week together before a final gourmet dinner paired with renowned wines grown here on the estate.

Meals: Breakfast / Lunch / Dinner
Destinations: Castelnuovo, Pianella, Bossi
Accomplished: 32 miles / 52 km, elevation gain: 2,906 feet / 886 meters
Longer Option: 42 miles / 68 km, elevation gain: 3,874 feet / 1,181 meters
Accommodations: Borgo San Felice or Castel Monastero

On our last day, choose between a late morning at the hotel or a 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: Radda, Panzano, Florence
Optional Ride: 36 miles / 58 km, elevation gain: 2,270 feet / 692 meters
Longer Option: 48 miles / 78 km, elevation gain: 3,611 feet / 1,101 meters