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7 Day Self Guided Bike Tour in Tuscany, Italy
This listing has no upcoming availability. Check out these similar experiences

This listing has no upcoming availability. Check out these similar experiences

(No availability) 7 Day Self Guided Bike Tour in Tuscany, Italy

Wellness Center Casanova, SP 146 Località Casanova 6/c, San Quirico d'Orcia, Province of Siena, Tuscany, Italy

Unforgettable Bike Tour in Italy

Discover all that Tuscany has to offer by bike with the people who know it best! During the tour, you will experience the rolling hills and medieval hilltop towns. You will cycle through the paradise of the Tuscan landscape as you explore the region including Val d’Orcia, Pienza, Montalcino, and Chianti. The Tuscany bike tour is a perfect mix of bike, history, and local product for an unforgettable bike holiday.

Key information

  • Trip type: Self-guided
  • Lodging: Point to Point
  • Terrain: Hilly with some climbs
  • Difficulty level: Moderate (Cyclist needs to have a good level of fitness, terrain is mostly hilly or unpaved but they will ride on flat terrain sometime,31-45 miles per day)
  • Total Distance: 195 Miles / 314 Kilometers
  • Vacation type: Leisure biking
  • Type of bike: Road bike, hybrid bike, or E-bike
  • E-bike: Available to rent / 220 EUR per week


  • 5-day biking with beautiful views
  • Exploring medieval cities in Tuscany
  • A perfect Tuscany bike tour for active riders
  • Technical assistance and GPX tracks for GPS system
  • Baggage transportation between the hotels
  • Maps and information for your daily stage
  • 5 breakfasts and 4 dinners included
  • 6 nights' accommodation


6 days with instruction
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During this bike tour, you will be accommodated at Casanova Wellness Center for the first and second night, Fattoria Pieve a Salti for the third night, Hotel Athena Siena for the fourth night, CDH Hotel Radda for the fifth night, and you can choose to stay in a three-star hotel in Florence or Hotel Leon Bianco for the last night.

Casanova Wellness Center

The Casanova Hotel Wellness Center is set in the unique panorama of art, history, and nature, in one of the most evocative places in Tuscany; Val d'Orcia. The Casanova Wellness Center offers its customers various types of rooms. The sober and elegant furniture recalls the warm atmosphere of Tuscan homes with precious woods, terracotta floors, and the cozy fabrics of curtains and tapestries. All rooms and apartments have a private bathroom with hydromassage bath or shower, hairdryer, courtesy set, minibar, safe, satellite TV, telephone, internet connection, and air conditioning. Some comfort rooms have been created on the ground floor and equipped also for disabled guests in order to make the stay more pleasant and versatile.

Fattoria Pieve a Salti

Fattoria Pieve a Salti is a farmhouse with restaurant, spa, riding stables, outdoor swimming pool, indoor pool, convention center, tennis, biking, and truffles of the famous white truffle of the Crete Senesi. The rooms are cozy and comfortable, furnished in a typical Tuscan rustic style with wrought iron beds, terracotta floors, and ceiling beams. The rooms are equipped with bathroom and shower, air conditioning, LCD satellite TV, minibar (not served), telephone, hairdryer, courtesy line, and linen.

Hotel Athena Siena

The rooms at the Hotel Athena are the greatest expression of their own philosophy of hospitality. With furnishings by local artisans, colors that echo the tones of the Tuscan landscape, and the many comforts available, Hotel Athena wants to welcome you and make you feel completely at home / at ease, surrounded by the warmth of a welcome you will always remember. To make you feel at home, Hotel Athena offers for your use a free fridge bar and smart TV.

CDH Hotel Radda

Nestled among the rolling hills, impregnated with fine grapes and combed with generous vines, the four-star CDH Hotel Radda is born in the heart of Chianti in Radda, cradle of the Chianti Classico Consortium. The CDH Hotel Radda is equipped with all the services a guest may need, the "De Gustibus" Restaurant with typical Tuscan cuisine, the wine bar, the "My Wellness" spa with massage cabins and relaxation path, the outdoor swimming pool overlooking the on the suggestive hills of Chianti, ample outdoor parking reserved for guests, and boasts breathtaking views from anywhere in the hotel. Free Wi-Fi in all areas of the hotel allows you to stay connected at any time.

Hotel Leon Bianco

The elegance of a three-star hotel and the charm of the medieval palace, the Hotel Leon Bianco welcomes you in the main square of San Gimignano, Piazza della Cisterna. The intimate atmosphere of the 26 rooms, the authentic hospitality of the past, and the pearls of Tuscany all around you are just the prelude of an unforgettable journey back in time. Wrapped in the romantic colors of the furnishings and with a view of the rolling hills or Piazza della Cisterna, your holiday in Tuscany will be a break from the world, back in time.



Day 1: “Benvenuti in Toscana”

You will arrive at Casanova Wellness Center located in San Quirico d’Orcia, in the heart of Val d’Orcia. There will be a briefing and delicious dinner in a typical restaurant in San Quirico d’Orcia.

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

Day 2: Pienza, Montepulciano, and Monticchiello

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

  • Distance: 56 kilometers
  • Elevation gain: 910 meters
  • Accommodation: Casanova Wellness Center
  • Included meals: Breakfast and dinner
  • Optional activities: Light lunch with cheese tasting

Day 3: Montalcino and Bagno Vignoni

Bagno Vignoni is a cute medieval town where the main square of the village is a big thermal pool which contains the original source of thermal water. You will be climbing towards Castiglione d’Orcia and Rocca d’Orcia, the beautiful landscapes that will compensate for the challenging ascent.

The cycling will continue to the Abbey of Sant’Antimo, one of the most beautiful Romanic church in Tuscany. You will be climbing up again to Montalcino, a town of Brunello wine. Montalcino is a medieval town surrounded by vineyards and a beautiful view of the valley. You will then go downhill surrounded by Chianti vineyards direction Buonconvento, a nice town in Val d’Arbia. You will enjoy dinner and stay at Fattoria Pieve a Salti, a typical Tuscan agriturismo with spa, horse riding, and restaurant.

  • Distance: 52 kilometers
  • Elevation gain: 1,030 meters
  • Accommodation: Fattoria Pieve a Salti
  • Included meals: Breakfast and dinner
  • Optional activities: Brunello wine tour and tasting

Day 4: Crete Senesi and Siena

You will experience 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 have a short break at Asciano with its churches and museums. You will continue the tour to Siena on the horizon. The visit to this beautiful city will make your experience in Tuscany unique. You will enjoy a free dinner and stay at Hotel Athena Siena.

  • Distance: 54 kilometers
  • Elevation gain: 890 meters
  • Accommodation: Hotel Athena Siena
  • Included meals: Breakfast
  • Optional activities: Cooking class with dinner

Day 5: Chianti region

Today, you will explore Castelnuovo Berardenga and its landscape museum; Villa a Sesta and San Gusmè, a cute town in Chianti; the Castle of Brolio, a symbol of Chianti and good wines to taste; and Gaiole, the town where L’Eroica was born in 1997. Dinner and overnight stay will be at CDH Hotel Radda in Chianti with its small street and a wonderful view of the vineyards.

  • Distance: 48 kilometers
  • Elevation gain: 910 meters
  • Accommodation: CDH Hotel Radda
  • Included meals: Breakfast and dinner
  • Optional activities: Chianti wine tour and tasting

Day 6: Select the most suitable itinerary

Option 1: Panzano and Greve in Chianti on the road to Florence

Today's biking stage completely set in the Chianti Fiorentino. The highlights include Panzano in Chianti, Cecchini steak, and the triangular square of Greve in Chianti with the archived loggias that line its three sides. Finally, you will arrive at Florence’s Piazzale Michelangelo, last highlights of the Tuscany bike tour. Free dinner and accommodation will be in a three-star hotel.

  • Distance: 55 kilometers
  • Elevation gain: 800 meters
  • Accommodation: A three-star hotel in Florence
  • Included meals: Breakfast

Option 2: Monteriggioni and San Gimignano

You will cycle to Castellina in Chianti, the most medieval of the Chianti towns. One of the highlights is 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 historic town center and is a UNESCO World Heritage Site. Free dinner and accommodation will be at Hotel Leon Bianco.

  • Distance: 49 kilometers
  • Elevation gain: 630 meters
  • Accommodation: Hotel Leon Bianco
  • Included meals: Breakfast
  • Optional activities: Light lunch and Vernaccia tasting

Day 7: “Arrivederci”

You will check out and depart to your home. Optional transfer is available on request.

Level: Active ride

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 climb. 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.


On the first part of the week, you will cycle surrounded by the beautiful landscape of Val d’Orcia, Italy, UNESCO protected 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 Siena and the Chianti region, famous for its wine. You can decide to finish the Tuscany bike tour in San Gimignano or Florence where you can add more days to visit this beautiful city.


The following meals are included:

  • Breakfast
  • Dinner

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 activities for riders

  • Day 2: Light lunch with Pecorino cheese tasting in a typical farm and dairy
  • Day 3: Brunello wine tour and tasting
  • Day 4: Cooking class with dinner
  • Day 5: Chianti wine tour and tasting
  • Day 6 (option 2): Light lunch and Vernaccia tasting

Optional activities for non-riders

  • Cooking classes
  • Horseback riding
  • Trekking
  • Wine tours

What's included

  • 5-day biking with beautiful views
  • Exploring medieval cities in Tuscany
  • Maps and information for your daily stage
  • GPX tracks for GPS system
  • 1 intervention of technical assistance along the route (parts not included)
  • Baggage transportation between the hotels
  • Pick-up of everything you bought during your daily stage (wine, gift, and more)
  • Anima Toscana phone assistance
  • 6 nights' accommodation
  • 5 breakfasts and 4 dinners

What's not included

  • Bike rental (hybrid, road bike, or electric bike)
  • Activities for non-cyclist (cooking classes, wine tours, horseback riding, trekking, etc.)
  • Flights
  • Transfer on arrival and departure day from the airport, train station, or hotels
  • Drinks
  • Medical baggage insurance
  • Tourist city tax

How to get there

Recommended Airports

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.
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