Cycling and Cooking in Tuscany

Day 1: Welcome to the villa, Pienza

Arrive at the Chiusi train station (a major stop on all the Rome-Florence lines) at 14:00. A private van transfer will transport you to the farmhouse, just a short drive from Pienza. You'll check in to your room, meet your guides, and start the bike fitting session. Once everyone is set up with a bike and equipment, there'll be a short test ride in the valley.

At 6:00, you will have an introduction of the weeks activities and meet with chef Paolo - a perfect way to get to know your fellow travelers during which you will enjoy a cheese and olive oil tasting! After a rest, you'll share the table and savor a tasty dinner.

Day 2: Montalcino and Brunello
25 miles/40 km

Saddle up for a 40 km cycling journey through landscapes that look like they’ve been painted during the Renaissance. The first half of the ride to Montalcino is about 80% gravel, taking you past Sangiovese vineyards (from Sangue di Giove). Explore Montalcino, a town rich in medieval history, with its battles between Florentine and Sienese city-states and its towering 14th-century fortress. Take time to wander its charming piazzas and visit the fortress.

Enjoy a gentle downhill ride to Castelnuovo dell’Abate to visit the Abbey of Sant’Antimo, followed by a wine tour and light lunch at Tenuta Fanti winery.

For the return to La Pieve, there are two options:

• A relaxed ride back, or

• A more challenging 48 km route, rewarding for those who want an extra adventure.

Dinner:
Tonight, savor a meal at 13Gobbi in Montefollonico, featuring the specialty Pici Cacio e Pepe.
Elevation gain +698 m | +2290 ft/elevation loss -817 m| -2680 ft

Day 3: Pienza
24 miles/38 km

Venture out on a 38 km bike ride that includes a visit to Pienza, the epitome of Renaissance architectural perfection envisioned by Pope Pius II. Explore the meticulously designed Piazza Pio II, adorned with a loggia, Palazzo Piccolomini, and the impressive Duomo.

Cycle through picturesque villages such as Castelmuzio, Montisi, and Trequanda along quiet secondary paved roads. Stop in Pienza for a visit and lunch on your own. Complete your ride with the last 4 km along scenic gravel roads before returning to La Pieve by 16:30.

Evening:
Get ready for your first hands-on cooking session with Chef Paolo! Prepare fresh pasta as a primo piatto, then enjoy a rest with an Italian Spumante Metodo Classico sparkling wine as an aperitif. Finally, gather with all guests to share the table and savor the dinner you’ve helped create.

Elevation gain +763 m | +2503 ft / Elevation loss -763 m | -2503 ft

Day 4: Le Crete & Monte Oliveto Abbey (38 miles/62 km)

After breakfast, departure by bike from the villa:

Following a picturesque crest road, you’ll ride past Monte Oliveto Maggiore Abbey, a 13th-century Benedictine abbey famous for its frescoed cloister and stunning setting. Afterwards, you’ll travel through the fascinating area known as Le Crete, Tuscany’s answer to the Badlands. Here, the verdant hills give way to little domes of clay, revealing a more unusual side of Tuscany — an almost lunar landscape of chalk cliffs and gullies, steeped in a primeval atmosphere.

Tonight: Pizza Party at the Villa!
No food & wine vacation in Italy would be complete without dedicating an evening to gourmet pizza. Sample a variety of delicious pizzas, and prepare to be surprised by the perfect wine pairings.
Elevation gain +1338 m | +4389ft / elevation loss -1338 m | - 4389 ft

Day 5: Monticchiello & Bagno Vignoni & spa day
18 miles/28 km

Embark on a bike ride to Monticchiello, a charming village whose medieval character has been beautifully preserved through the ages. Continue to Bagno Vignoni, famous for its ancient thermal pool. Enjoy a picnic lunch before soaking in the therapeutic waters that have drawn travelers along the Via Francigena pilgrimage route for centuries. Stroll through the village and explore its fascinating history of healing.

Dinner:
Savor a meal at Restaurant La Terrazza del Chiostro.

Elevation gain +387 m | + 1269 ft / elevation loss -529 m | – 1735 ft

Day 6: Radicofani and the Legend of Ghino di Tacco
34 miles/54 km

Enjoy another terrific day of cycling through gentle climbs and rolling hills leading to the medieval village of Radicofani. Explore its impressive fortress, offering extraordinary panoramic views over the Val d'Orcia, Mount Amiata, the Apennines, and Lakes Trasimeno and Bolsena. Discover the legend of Ghino di Tacco, the charismatic gentleman bandit who once roamed the Via Francigena and was even mentioned in Dante’s Divine Comedy. Stroll through Radicofani’s stately old town before returning to the villa.

This evening:
Get ready for another hands-on cooking lesson with Chef Paolo, followed by a festive farewell dinner. All you need is an appetite and an apron!
Elevation gain +877 m | + 2877 ft / elevation loss -1007m | -3303 ft

Day 7: Individual departure

After a farewell breakfast all together, you'll be transferred to the Chiusi train station between 9:00-10:00 am (on request, transfers can be arranged for a different time).

Don't want the adventure to end? Consider taking a cycling day tour in Rome, Florence, or Pisa to top off your holiday.