Tuscany Villa Bike Tour

We’ll arrange a private transfer from Rome or Florence deep into the Tuscan countryside. First order of business: a fresh, nourishing lunch at a historic rural restaurant designed to power us through our first ride to the villa. After a bike fitting and safety talk, pedal up and down the panoramic ridges, stopping to explore the cobbled streets of the sleepy medieval hill town of San Quirico. Pedal all the way to our villa and take a dip in the pool while a private chef works some magic on our first Tuscan dinner.

Non-riders can visit the natural thermal baths here in the Val d’Orcia or head straight to the villa after lunch to settle in and enjoy the pool.

Meals: Lunch / Dinner
Destinations: San Quirico, Pienza
Accomplished: 20 miles / 33 km, elevation gain: 1,247 feet / 382 meters
Longer Option: 30 miles / 50 km, elevation gain: 2,096 feet / 639 meters
Accommodations: Luxury Tuscan Villa

Today we celebrate the humble olive; an integral part of the surrounding landscape and agricultural history of the area. Rooted deeply in the local culture and cuisine, these trees grow up and down the hillsides throughout Tuscany. Ride through some of the top olive-oil producing villages to a local olive mill where we’ll meet our friend, Paolo. Taste his diverse range of oils over a home-cooked farm lunch before pedaling back to the villa. This evening we’ll keep with the farm theme and head to a nearby organic cheese farm that produces goat cheese to dine at their farm restaurant.

Non-riders can relax in the morning, go for a walk or horseback ride, and join the group for lunch at the olive mill. In the afternoon visit the organic cheese farm before dinner.

Meals: Breakfast / Lunch / Dinner
Destinations: Trequanda, Montisi, Castelmuzio
Accomplished: 27 miles / 43 km, elevation gain: 2,952 feet / 900 meters
Long Option: 38 miles / 62 km, elevation gain: 3,788 feet / 1,155 meters
Accommodations: Luxury Tuscan Villa

Today we’ll head up the most iconic road in the area: the switch-backed climb out of Montichiello. The cypresses here grace countless postcards and the view from the top is magnificent. Continue on to Montepulciano and the Renaissance church of San Biagio. Opt to head up into town to explore the village or continue riding. Our destination is Pienza, refashioned in the 1400’s into the ideal Renaissance town by a local pope. Stop for lunch with a view at our friend Maurizio’s restaurant, hidden in a cloister. This evening we’ll make a special visit to our friend Vittorio’s home and winery. Sip his incredible vin santo and watch the sunset over the Val di Chiana before heading to a lively local trattoria for dinner.

Non-riders can explore shops and cafés in the hill towns of Montepulciano and Pienza before meeting the riders for lunch.

Meals: Breakfast / Lunch / Dinner
Destinations: Montichiello, Montepulciano, Pienza
Accomplished: 21 miles / 34 km, elevation gain: 2,040 feet / 622 meters
Longer option: 39 miles / 63 km, elevation gain: 2781 feet / 848 meters
Accommodations: Luxury Tuscan Villa

Take a day off the bikes, instead relaxing at the villa or exploring nearby Siena, Cortona, or another charming hill town on your must-see list. Immerse yourself in the Italian way of life—whether it’s browsing shops, wandering the historic cobbled streets, or lingering over lunch paired with a bottle of wine. If you prefer, we can arrange a private tasting and lunch at a local winery, a cooking class at a local home, or an exclusive tour of the countless castles, towns, or Etruscan ruins in the villa’s radius. For the ambitious cyclists who want to keep up with their daily miles, the option is on the table to conquer the climb up Mt. Amiata for some serious bragging rights. Venture into town to enjoy dinner on your own this evening.

Meals: Breakfast
Destinations: Siena, Cortona, Mt. Amiata, and beyond
Accomplished: Optional riding
Accommodations: Luxury Tuscan Villa

Another day, another beautiful ride through the backdrops of Tuscany. Our destination is the gourmet hamlet of San Giovanni, one of the few places where white truffles grow. Meet our friend Paolo and his faithful truffle dog to hunt for the perfect morsel, which we’ll taste at our friend Donatella’s cozy osteria—right here in town. After lunch, continue riding over to the Renaissance Abbey of Monte Oliveto to visit the incredible frescos preserved here. This evening, cook dinner with our private chef at a relaxed cooking class where we’ll bond over local food and wine.

Non-riders can spend the day at the villa, visit the Monte Oliveto frescoes, go horseback riding, and/or join the riders for the truffle hunt.

Meals: Breakfast / Lunch / Dinner
Destinations: San Giovanni, Chiusure, Buonconvento
Short Option: 29 miles / 46 km, elevation gain: 2,132 feet / 650 meters
Long Option: 48 miles / 77 km, elevation gain: 3,874 feet / 1,181 meters
Accommodations: Luxury Tuscan Villa

This morning will find us pedaling to the perched town of Montalcino. Nearly abandoned during the post-war economic boom, Montalcino has enjoyed a renaissance due to the popularity of Brunello wines that, by law, can only be produced here. We’ll ride the entire length of this now-famous wine region and pause for a tasting lunch with a renowned producer. After lunch, choose to shuttle back to the villa or complete the full loop by bike. Tonight, the final dinner with your guides celebrates a successful week—did someone say pizza oven?

Non-riders can go for a vineyard walk, spend the day at the natural thermal hot springs of Bagno Vignoni, visit a local Brunello producer for a tasting, or do all three!

Meals: Breakfast / Lunch / Dinner
Destinations: Montalcino, Castiglione d’Orcia, San Quirico
Short Option: 25 miles / 40 km, elevation gain: 2,200 feet / 675 meters
Long Option: 45 miles / 72 km, elevation gain: 4,234 feet / 1,291 meters
Accommodations: Luxury Tuscan Villa

Enjoy a final breakfast here at the villa, then depart in a private transfer back to Rome, Florence, or the nearby Chiusi train station.

Meals: Breakfast