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7 Day Guided Bike Tour in Tuscany, Italy

Wellness Center Casanova Hotel, S.P. 146, 6/c, San Quirico D'Orcia, Province of Siena, Tuscany, Italy

Remarkable Bike Tour in Italy

Discover by bike all that Tuscany has to offer, with the people who know it best. Enjoy a real cycling adventure in Tuscany and experience the rolling hills and medieval hilltop towns! Led by guide born and raised in Tuscany, you will cycle through the paradise of the Tuscan landscape as you explore the region including Val d’Orcia, Pienza, Montalcino, and Chianti. Learn the secret of Tuscan cuisine and taste the fantastic Tuscan dishes and world famous wines! This Tuscany bike tour is a perfect mix of bike, history, wine tasting, and cooking class for an unforgettable holiday.

Key information

  • Trip type: guided biking
  • Lodging: point-to-point
  • Terrain: hilly with some climbs
  • Difficulty: Challenging (Cyclist needs to have a high level of fitness, must be an active rider, the terrain includes really challenging climbs / or 46 - 80 or more miles per day)
  • Total distance: 163 miles / 262 kilometers
  • Type of bike: road bike, hybrid bike, or E-bike
  • E-bike: available to rent for 40 EUR per day or 220 EUR per week


  • 5-day bike tour
  • Tuscan dishes cooking class
  • Climbing up to Montalcino, the town of Brunello wine
  • An unforgettable ride surrounded by the views of the Crete Senesi
  • A supported van and baggage transportation
  • Transfer from and to train station / airport
  • 5 breakfasts, 5 lunches, and 6 dinners
  • 6 nights' accommodation


5 days with instruction
Airport transfer included: Perugia San Francesco d'Assisi – Umbria International Airport
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During this bike tour, you will be accommodated at Wellness Center Casanova Hotel on the first to the third night. On the fourth night, you will be staying at Villa Curina Resort. For the fifth and the last night, your overnight stay will be at Borgo di Pietrafitta. All of them are in Tuscany, Italy.

Wellness Center Casanova Hotel

Along the Via Cassia, one of the most important consular roads that connects Rome to Siena, on its most spectacular stretch between Montalcino and Pienza, you find the Val d’Orcia, where water is its leitmotif, from the hot springs healing water of Bagno Vignoni and Bagni San Filippo to that which has carved the ravines and, finally, the water that would move the millstones of the Mill Park of San Quirico d’Orcia. Nestled within this unique panorama of art, history, and nature is the Wellness Center Casanova Hotel. What comes to your attention when you arrive is a typical Tuscan structure that blends in perfectly with the nature that surrounds it, where absolute peacefulness is perceived and that offers an all-round panorama of the valley and the medieval village of San Quirico d’Orcia at just a short distance from the hotel.

Villa Curina Resort

Deep in the peaceful countryside, surrounded by rolling Chianti hills, and a few kilometers from Siena, arises Villa Curina Resort. This little sixteenth-century village is full of history and fascination where a refined holiday full of charm awaits you. Elegant rooms, a staff always at your disposal, a restaurant with local, and avant-garde cuisine but always respectful of Tuscan tradition and a beautiful Italian garden - little jewel from the 1700s - make this an ideal place for an unforgettable stay. Breathtaking sunsets with Siena as the backdrop will frame your holiday and turn it into a dream which, once back home, you will want to share with the ones you love most.

Borgo di Pietrafitta Relais

Imagine the unique feeling of staying in a small perfectly renovated medieval village in Tuscany, in which to enjoy the peace and quiet where every interior is designed right down to the smallest detail to ensure you have a memorable stay. This is Borgo di Pietrafitta Relais, where the green hills are full of vineyards and olive groves in a one-of-a-kind and suggestive setting. It will give you an experience which involves all five senses in the heart of the Tuscan countryside.


Day 1: Welcome to Tuscany

You will meet the staff at Chiusi train station and head to the Hotel Casanova, located at San Quirico d’Orcia in the heart of Val d’Orcia, by private transportation. Otherwise, you can join the hotel on your own. During your stay, you can take a relaxing break from the cycling journey and enjoy the spa light package, a hydrotherapy circuit in salted water with natural micro-components, from 09:00 to 20:00. You will get a briefing and delicious dinner in the typical restaurant in San Quirico d’Orcia.

  • Accommodation: Wellness Center Casanova
  • Included meals: dinner in a typical restaurant

Day 2: Pienza, Montepulciano, and Monticchiello

You will bike through the landscapes of the Val d'Orcia region, one of the most beautiful places in Tuscany and UNESCO world heritage site. Afterward, you will visit Pienza, the ideal city of the Renaissance time which is also famous for its Pecorino cheese. You will make a quick stop at Montepulciano, with its winding streets and squares. Monticchiello is a small medieval and charming town. You will have light lunch with Pecorino cheese tasting in a typical farm and dairy. Take a relax break from the cycling journey and enjoy the spa before dinner.

  • Distance: 56 kilometers
  • Elevation gain: 910 meters
  • Accommodation: Wellness Center Casanova
  • Included meals: breakfast and dinner
  • Activities: light lunch with cheese tasting

Day 3: Montalcino and Bagno Vignoni

You will be climbing up to Montalcino, the town of Brunello wine, then visiting Montalcino, a medieval town surrounded by vineyards and beautiful view on the valley, followed by visiting the Abbey of Sant’antimo, one of the most beautiful Romanic churches in Italy. You will climb again towards Castiglione d’Orcia and Rocca d’Orcia. Those beautiful landscapes will compensate the challenging ascent.

You will have lunch in Bagno Vignoni, a cute medieval town where the main square of the village is a big thermal pool which contains the original source of thermal water. Take a relaxing break before a cooking class where you can discover the secret of Tuscan dishes. During the lesson, you will make a complete menu and, in the end, dinner is served with what has been prepared during the lesson.

  • Distance: 51 kilometers
  • Elevation gain: 990 meters
  • Accommodation: Wellness Center Casanova
  • Included meals: breakfast
  • Activities: lunch in Bagno Vignoni and cooking class with final dinner

Day 4: The Crete Senesi

You will take an unforgettable ride surrounded by the views of the Crete Senesi to the edge of the Chianti. The Crete Senesi region is where badlands and biancane characterize the landscape in this part of Tuscany. You will take a short break at Asciano with its churches and museums. Your lunch with wine tour and tasting in a Chianti winery will be located at Castelnuovo Berardenga while your dinner and overnight accommodation will be at Villa Curina Resort.

  • Distance: 56 kilometers
  • Elevation gain: 700 meters
  • Accommodation: Villa Curina Resort
  • Included meals: breakfast and dinner
  • Activities: Chianti wine tour and tasting with lunch

Day 5: Chianti Region

You will have a chance to discover Castelnuovo Berardenga and its landscape museum, Villa a Sesta, and San Gusmè, a cute town in Chianti. The journey will continue to The Castle of Brolio, the symbol of Chianti and good wines to taste. Afterward, you will continue to Gaiole, the town where L’Eroica was born in 1997, followed by the trip to Radda in Chianti with its small street and a wonderful view of the vineyards. Your dinner and accommodation will be at Borgo di Pietrafitta.

  • Distance: 50 kilometers
  • Elevation gain: 1,080 meters
  • Accommodation: Borgo di Pietrafitta Relais
  • Included meals: breakfast and dinner
  • Activities: Lunch in typical osteria

Day 6: Monteriggioni And San Gimignano

You will ride your bike to Castellina in Chianti, the most medieval of the Chianti towns and Monteriggioni with its walls and the ring of towers that dominate the hill. You will then climb up to San Gimignano, the towers of the town that can be seen for miles around and the UNESCO World Heritage historic site. You will have light lunch and taste Vernaccia wine before the transfer back with the van. The dinner and accommodation will be at Borgo di Pietrafitta

  • Distance: 49 kilometers
  • Elevation gain: 630 meters
  • Accommodation: Borgo di Pietrafitta Relais
  • Included meals: breakfast and dinner
  • Activities: Light lunch and Vernaccia wine tasting

Day 7: Arrivederci or optional tour to Florence

Today, you will check-out and be back to the starting point of the tour or join an optional tour to Florence (hotel of the city center, train station, or airport).

Active rider

This tour is for a cyclist who rides a bike regularly, two times or more a week, comfortable with rides of two hours or more, and who loves a physical challenge. The rider can ride in all terrain, paved and unpaved roads, with hills and some medium climbs. The average daily ride is 50 - 100 kilometers per day, with around 1,000 meters of climbing. During the tour, you’ll be riding during a part of the day, giving you the chance to visit the places along the path, to try some activities on your daily ride, and alternating physical challenge to relax.


This bike tour will take place in Tuscany, Italy. On the first part of the week, you will cycle surrounded by the beautiful landscape of Val d’Orcia, protected UNESCO site, and you can visit some nice towns including Pienza, Montepulciano, and Montalcino. On the second part, you will cycle through the Crete Senesi region to Chianti, which is famous for its wine. On the last day of this bike tour in Italy, you can also decide to go home or join to Florence by bike, extend your stay in Tuscany, and visit the beautiful city.


You will be provided with five breakfasts, five lunches which include a light lunch with cheese tasting, two lunches with wine tastings, and another two lunches, as well as six dinners, one of which is along with the cooking class.

The following meals are included:

  • Breakfast
  • Lunch
  • Dinner
  • Snacks
  • Drinks

The following drinks are included:

  • Water
  • Alcoholic beverages

The following dietary requirement(s) are served and/or catered for:

  • Regular (typically includes meat and fish)
If you have special dietary requirements it's a good idea to communicate it to the organiser when making a reservation

Things to do (optional)

Optional tour to Florence

You can decide to join Florence by bike, where you can add more day at your stay and discover this beautiful city. On this tour, the stage is completely set in the Chianti Fiorentino. It highlights Panzano in Chianti and Cecchini steak as well as the triangular square of Greve in Chianti, with the arched loggias that line its three sides. Then, you will enjoy triumphant arrival at Florence’s Piazzale Michelangelo, the last highlights of the Tuscany bike tour. Your rides finish in Florence, where you can extend your stay and visit this beautiful city.

  • Distance: 55 kilometers
  • Elevation gain: 800 meters

Optional activities for non-riders

  • Cooking classes
  • Horseback riding
  • Trekking
  • Wine tours

What's included

  • 5-day bike tour in Tuscany
  • Exploring medieval cities in Tuscany
  • Tuscan dishes cooking class, wine tours, and cheese tasting
  • Services of an expert bike guide
  • Van support each day with water, fruits and power bars
  • Maps and information for your daily stage
  • Baggage transportation between the hotels
  • Medical / baggage insurance
  • Private transfer on day one and seven
  • 5 breakfasts, 5 lunches, and 6 dinners
  • 6 nights' accommodation

What's not included

  • Bike rental (hybrid, road bike, or electric bike)
  • Activities for non-cyclist (cooking classes, wine tours, truffle hunting, horseback riding, trekking, etc.)
  • Flights
  • Drinks
  • Tourist city tax
  • Discount for private transfer on day one if you arrive with your car

How to get there

Recommended Airports

Arrival by train

You can take the train and arrive at Chiusi-Chianciano Terme train station. Anima Toscana Bike Tour will pick you up and transfer you to Casanova Hotel. The pickup service is included in the price.

Airport: Perugia San Francesco d'Assisi – Umbria International Airport Airport transfer included: Perugia San Francesco d'Assisi – Umbria International Airport No additional charges. You can request this in the next step.

Cancellation Policy

  • A reservation requires a deposit of 25% of the total price.
  • The deposit is non-refundable, if the booking is cancelled.
  • The rest of the payment should be paid 30 days before arrival.
7 days / 6 nights
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Arrival: Wednesday October 14, 2020
Departure: Tuesday October 20, 2020


This vacation is available all year round, from March to November, please select an arrival date below.

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