Tantalize your taste buds on a blissful bike tour of Tuscany

Embark on an irresistible bike tour through Tuscany, one that combines breathtaking bicycle routes with captivating cookery classes designed to give you an authentic overview of some of Tuscany's most tantalizing dishes.

La Cucina Toscana is simplicity in its purest form. Tuscan cooks enjoy having the freshest seasonal ingredients right at their disposal, including sumptuous olive oil, gorgeous wines, and flavorsome cheeses - Tuscan cuisine is natural, fresh, and spectacularly appetizing. Most days of your wonderful cycling tour will include a hands-on cooking class or a delicious food tasting provided by a local artisan. You'll also enjoy special dining out opportunities at a simple osteria, family trattorias, and elegant restaurants.

As a cyclist, you'll explore magical loop rides in beautiful Val d'Orcia, visiting the highlights of Pienza, Montalcino, and San Quirico, amongst other attractions. The routes will cross Val di Chiana, pass through stunning Cortona and Crete Senesi, and lead you onwards to sublime Siena.

You'll return home inspired, carrying not only a new recipe book, but the enthusiasm to incorporate these dishes into your everyday lifestyle!

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Highlights

• La Cucina Toscana
• Traditional Tuscan cooking classes
• Olive oil, cheese, and wine tastings
• Bagno Vignoni Roman spa
• Sant'Antimo Abbey
• Montalcino
• Pienza
• Montepulciano, the 'Pearl of the 16th Century'
• Val d'Orcia
• Spa day in San Casciano dei Bagni
• Radicofani, medieval fortress village
• Cortona
• Siena
• Etruscan architecture
• Monticchiello, the quintessential Tuscan hill town

Learn More

Learn more about our guided trips or see more bike tours in Italy.

Interested in adding to your itinerary? Take a look at our cycling day tours in Rome, Florence, and Pisa.

Daily program

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.

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Dates & Prices

Questions about pricing or options? Call +1-215-613-0874 to talk to a Tour Advisor now.

Included services

• 6 nights accommodations
• Breakfast each morning; 6 dinners and 2 lunches
• All maps, trip notes, and detailed route directions
• All shuttles and technical assistance
• Support van
• Services of an experienced guide
• 2 cooking classes
• 2 wine tasting and 1 cheese tasting
• Water bottle
• Transfer on Day 1 from Chiusi train station
• Transfer on Day 7 to the Chiusi train station
• Sales taxes

Local hotel taxes are not included and are to be paid directly to each hotel (approximately €1-5 per person/night).

Tour Company

Map

Maps are for information purposes only and reflect typical routes between overnight locations. They may not reflect your actual route.

Surface and terrain

You’ll be riding at an easygoing pace—typically between 9–12 mph (15–20 km/h)—and covering around 18–45 miles (30–70 km) each day. There are a few hills (this is Tuscany, after all!), with the biggest climb reaching up to 4,389 feet (1,338 m) of elevation gain. But don’t worry—it’s not about speed; it’s about soaking in the scenery (and enjoying the wine).

On two days, the route includes gravel sections. That means quieter country roads, fewer cars, and stunning views—truly some of the most memorable parts of the ride.

You can choose the bike that suits you best: an e-bike, a hybrid, or a gravel bike. And if you ever feel like skipping a ride to relax at the villa or explore something else, that’s completely up to you. A support vehicle is always nearby, so you can hop in whenever you like.

Prefer a more challenging ride? No problem. Stronger cyclists are welcome to follow the route at their own pace using a GPS app, while the guide stays with the main group.

And if you’re not planning to ride at all, that’s totally fine too. Non-cycling guests are more than welcome, with optional daily activities like wine tastings, local sightseeing, or simply lounging by the pool.

How to get there

Tour start and end
Nearest airport: Florence, Italy (FLR); Rome, Italy
Nearest train station: Chiusi-Chianciano

From Fiumicino Airport, the Leonardo Express train (around 30 mins) departs each half hour to Termini Station.

From Fiumicino Airport to train station: the first trains at 07.37, 08.07, 08.37, the last at 22.37.

From Termini Station to airport: the first trains at 06.51, 07.21, 07.51, the last at 21.51.

From Florence Peretola, bus or cab to Florence train station.

To get into Chiusi by train, there are many trains from Rome and Florence. Check the timetable (English version) on the official website: https://www.trenitalia.com/tcom-en. Some trains are marked IC (intercity: faster) or R (regional: slow).

The tour company will transfer you to and from the Chiusi train station. On Day 1, the tour company will meet you around 1:00-1:30 pm. On Day 7, you will be transferred to the train station after breakfast. This service is included in the cost of the tour package.

Tips on getting to and from your tour.