TakeTours > Europe > Italy > 8-Day Tuscany around Siena and Chianti Bike Tour from Siena

8-Day Tuscany around Siena and Chianti Bike Tour from Siena Tour Code: 634-6919

From USD$951  
Daily (3/1 - 10/15)
Siena, Italy
8 7
Visit Asciano, Casole d’Elsa, Certaldo, Colle Val d’Elsa, Gaiole in Chianti, Montalcino, Monteriggioni, Murlo, Pienza, San Gimignano, San Giovanni d'Asso, San Quirico d'Orcia, Siena, Volterra.
  • Cycle with an expert guide along some of the most beautiful and genuine landscapes of Italy and appreciate a real contact with the surrounding nature
  • Discover incredible art cities off the beaten path such as L'Aquila, Teramo and Chieti
  • Taste some of the best local wines directly from their producers
Price (/person)
    Single $1204
    Double $951
    3rd Person
    Adult $951
    Child $951
    4th Person
    Adult $951
    Child $951

Pricing Policy

  • Child rates:�Child rates apply to those who are 0-12 yrs old. Children sharing a room with 2 adult passengers pay the same price as a third or fourth adult. Please note that each hotel room can only accommodate up to 4 guests of any age.
  • To display prices, please mouse over the date on the calendar; the relevant cost-per-person will be displayed.
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* Please note the Tour Map is subject to change.

Day 1: Siena

Today guests will arrive at Sienna. Guests will have the chance to explore this town by yourselves. The informative material, road maps, and the itinerary will be provided as you arrive at the hotel.
Note: the bikes will be delivered to the hotel in the evening.
  • Siena, ITALY

    Famous for its cuisine, art, museums, medieval cityscape, and the Palio, an annual horse race, Siena is a city in Italy, and one of the country's most visited tourist attractions. Its historic center is a UNESCO World Heritage Site.
Standard Hotel: Hotel in Siena or similar

Day 2: Siena - Castle of Brolio - Castelnuovo Berardenga - Asciano (46 km)

After breakfast, we will start the bike tour. Today we will cycle among Chianti hills with its wine and woods. Take your time to visit Brolio Castle, the hamlet of Villa a Sesta and the town of Asciano. Last we will arrive at Asciano and overnight in the hotel.
  • Gaiole in Chianti, ITALY

    The city of Gaiole in Chianti is an important city within the Chianti Classico region, located along the river Massellone and on the road connecting Chianti to Valdarno. It has proven to be rich in artifacts from ancient people's making it their home.

    Castello di Brolio

    Castello di Brolio
    Castello di Brolio was remodeled with Gothic turrets and towers in the mid-19th century by Bettino Ricasoli, two-time prime minister of Italy and the man responsible for introducing Chianti wine to the world.
  • Asciano, ITALY

    Asciano is a centuries-old town located in the heart of the Crete Senesi. The town still vaunts a typically medieval plan, which makes walking a pleasure. Asciano is dense with priceless architectural features, worth discovering at a leisurely pace.
Standard Hotel: Hotel in Asciano or similar

Day 3: Asciano - Monte Oliveto - San Giovanni d'Asso - Pienza (20 km)

After breakfast, we will set off by bike in the morning. Today we will bike from Chianti to the wild Orcia Valley. We will see the monastery of Monte Oliveto, the medieval town of San Giovanni d'Asso, the monastery of Sant'Anna in Camprena and Pienza, the jewel city of the Renaissance. Last we will arrive in Pienza and have a rest in the hotel.
  • Asciano, ITALY

    Asciano is a centuries-old town located in the heart of the Crete Senesi. The town still vaunts a typically medieval plan, which makes walking a pleasure. Asciano is dense with priceless architectural features, worth discovering at a leisurely pace.

    Abbey of Monte Oliveto Maggiore

    Abbey of Monte Oliveto Maggiore
    It is situated in a beautiful position between typical forms of eroded soil and a forest of cypresses and oaks. The Abbey was founded in 1313 by Sienese Bernardo Tolomei who retired in this isolated place, after he converted to Benedictine order. The structure as you see it today has been completed during the following centuries.
  • San Giovanni d'Asso, ITALY

    San Giovanni d'Asso, ITALY
    The village takes its origins from an ancient Longobard parish, built in the dawn of Christianity in Italy, on which was erected a castle. It's about a 25-mile drive southeast of Siena in the rolling hills of Tuscany's Crete Senesi region.
  • Pienza, ITALY

    Pienza enjoys a strategic position standing high atop a hill, dominating all the Orcia Valley with extraordinary views. This charming village is widely known as the "ideal city of the Renaissance".

    The monastery of Sant'Anna in Camprena

    The monastery of Sant'Anna in Camprena
    The monastery of Sant'Anna in Camprena stands in the middle of a beautiful oasis of green. Steeped in history and spirituality, this place has bewitched some great artists. Now it's was chosen for filming some of the most famous scenes of "The English Patient".
Standard Hotel: Hotel in Pienza or similar

Day 4: Pienza - S.Quirico - Montalcino - Buonconvento - Murlo (30 km)

After breakfast, we will continue discovering the Orcia Valley - famous for its renowned red wine Brunello di Montalcino. Don't miss a walk in the historical center of San Quirico, a glass of Brunello in the town of Montalcino, and to take a picture in the medieval hamlet of Murlo. Overnight in Murlo.
  • San Quirico d'Orcia, ITALY

    San Quirico d'Orcia is a peaceful little town perfect for a relaxing stroll and a peek at the portals of the beautiful Romanesque Collegiata church. It is located in one of the most enchanting parts of Tuscany, the idyllic Val d'Orcia famous for its picture-perfect views.
  • Montalcino, ITALY

    Montalcino has remained practically unchanged over the centuries, with its 13th-century defense walls and historic centre dominated by the 14th-century fortress. Renowned for its world-famous Brunello di Montalcino, it's also a fairy-tale place to spend a day immersed in Tuscany's history and countryside.
  • Murlo, ITALY

    Murlo is a charming circular village encircled by its ancient walls. It is untouched by modern development and industry, making it a true open-air museum of medieval architecture, and a beautiful place to wander.
Standard Hotel: Hotel in Murlo or similar

Day 5: Murlo - Monteriggioni - Colle Val d'Elsa (8 km)

Passing through Radi and Sovicille by bike, we will reach the walls of Monteriggioni - a real jewel historic center of Colle Val d'Elsa. Overnight in Colle Val d'Elsa.
  • Monteriggioni, ITALY

    This comune in the Italian province of Siena is a walled medieval city that rises on a hill above the surrounding area. It was referenced in Dante's Divine Comedy and is a playabel locatin in Assassin's Creed II.
  • Colle Val d’Elsa, ITALY

    Colle val d'Elsa is a quaint townwhose antique origins sit on the top of the hill, presiding over the border separating it from the renowned Chianti territory. Today Colle Val d'Ela is famous for the production of crystal items.
Standard Hotel: Hotel in Colle Val d'Elsa

Day 6: Colle Val d'Elsa - Casole d'Elsa - Ulignano - Volterra (26 km)

Today we will bike among the beautiful hills of Chianti Senese and visit the ancient villages of Casole d'Elsa and Volterra. After that we will arrival in Volterra and overnight.
  • Casole d’Elsa, ITALY

    Casole d’Elsa, ITALY
    The territory of the present hamlet of Casole d'Elsa, Tuscany, has been an important place since the primordial times not only for the exploitation of natural resources, but also for the location along important communication routes between the various areas of the Tuscany center -west and inward penetration.
  • Volterra, ITALY

    Volterra, ITALY
    Volterra has an unmistakable Medieval character, where the atmosphere of an ancient village can still be felt and whose authenticity is protected by the relative isolation that has limited the development of the city center in the industrial era, safeguarding the city from urban speculation.
Standard Hotel: Hotel in Volterra or similar

Day 7: Volterra - Il Castagno - San Gimignano - Certaldo - Siena (184 km)

Arrive in San Gimignano first, the city of the hundred towers. We could go for a walk in the historic centre where we will find artisan shops, wine cellars, and food producers. Here we can stop for lunch and taste local cuts and the white wine Vernaccia di San Gimignano. Afterwards we continue our journey and get to the historic center of Certaldo. Then we will transfer to Siena by train and stay in a Siena hotel for the night.
  • San Gimignano, ITALY

    San Gimignano, ITALY
    This small, walled medieval city sits on a hill in the Italian state of Tuscany. It is most notable for its well-preserved medieval architecture, evidenced by the tower houses that still stand.
  • Certaldo, ITALY

    The hilltop medieval town of Certaldo has always been one of the favourite destinations of history lovers, who enjoy the stroll with a taste of the Middle Ages through the old town centre boasting unique features.
Standard Hotel: Hotel in Siena or similar

Day 8: Siena

After breakfast we will check out and return back home.

Price Includes

  • 7 nights hotel accommodations with breakfast
  • Luggage transfer from hotel to hotel
  • Road book, maps, tourist information in English
  • Telephone service hotline

Price Excludes

  • Transfer between your city and departure point and return
  • Attraction entrance fees
  • Meals and beverages
  • Rental bike (21 speed bike with free wheel) + 1 pannier bag and 1 tool kit €150/person, Rental E-bike €260/person, Helmet €10/person.
  • City tax (to pay on the spot)
  • Tips and personal expenses
  • Everything not listed under item "Inclusion"

Additional Note

  • Typical landscape of the Tuscan countryside is the hill: the routes are almost always wavy with easy ups and downs; Sometimes there will be some steep slopes. There are 5-15 km of dirty road every day.


  • All purchases are subject to re-confirmation within 2-3 business days after booking. Please do not book airline tickets until you have received the confirmation.


  • You will receive an confirmation email (e-ticket) after your order is received. Complete operator information, including local telephone numbers at your destination, are included on your e-ticket. You must print the e-tickets and take them along on your trip; they are your proof of purchase.

Terms & Condition

  • All purchases are subject to re-confirmation within 2-3 business days after booking.
  • Changes to Reservations: A fee may be charged for any revision or alteration made to a reservation after the booking is confirmed. Name changes or corrections may be treated as a cancellation and cancellation fees will apply. A change of tour date or tour itinerary will be treated as a cancellation, and normal cancellation fees will apply.
  • Cancellation penalties per person
    (Notification day and departure day are not counted)
    45 days or more prior to departure - fully refund
    44-30 days prior to departure - 20% of total purchase amount.
    29-20 days prior to departure - 50% of total purchase amount.
    19-15 days prior to departure - 75% of total purchase amount.
    Within 14 days prior to departure - 100% of total purchase amount.
    Day of departure or no show - 100% per person.
    Unused features are non-refundable. No shows forfeit entire payment.
    Trips require a minimum number of participants to avoid cancellation. We reserve the right to cancel a schedule trip to fully refund affected customers although tour companies will make every efforts to maintain the normal operation.
    The refund amount will be credited directly to your TakeTours wallet as credits for future use. Or the refund can also be forwarded directly to your credit card with a 6% handling fee.
  • Prices may vary subject to availability/season/weekend/holiday.
  • We reserve right to cancel a schedule and fully refund affected customers, although we will make every effort to maintain the regular operation.
  • We reserve the right to modify the tour arrangements for smooth operation of the tour.
  • We are not responsible for any other travel arrangements affected due to our cancellations.

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