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Tuscany Getaway: 4 Nights in Siena, Montalcino & Pienza

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  • 4 nights | 26 miles/day
  • Difficulty Level: 3
  • Self-guided from: €990
  • View Dates

Tours using road, hybrid or touring bikes:

  1. Mostly flat
  2. Flat with some gentle slopes
  3. Rolling, hilly terrain
  4. Some long and/or steep climbs
  5. Extensive climbing

Tours using mountain bikes:

  1. Mostly flat, wide trails
  2. Some gentle slopes, wide trails
  3. Rolling, hilly terrain and/or narrow trails
  4. Some long and/or steep climbs and/or technical trails
  5. Extensive climbing and/or highly technical trails
  1. Variety: Choose from more than 200 tours offered by local operators in 35 countries.
  2. Advice: Our informed advisors help you choose the trip that's right for you.
  3. Lower cost: You pay local tour company prices—less than what big American companies charge.
  4. Great exchange rates: Pay low rates thanks to the millions of dollars in foreign currency we buy each year.
  5. Convenience: We handle the full booking and payment process.
  6. Support: We’re your advocates from initial planning through final pedal stroke.
Tour Type: Guided Self-guided

Tour description

We put together this short bike tour for those who do not feel like taking a vacation entirely on a saddle, besides each day there will be a choice for short easier bike rides and more challenging ones.

Whether crowned by timeless villages, covered by vineyards and olive groves or strewn with wildflowers, the hills of Tuscany have one thing in common: they’re perfect for exploring on two wheels. Pedal to lofty hill towns, spin through broad valleys and follow sinuous country roads past cypress-lined lanes and quiet woodland.

Off your bike, discover unforgettable Renaissance art and architecture, visit winery and cellars: you will be in the heart of Brunello wine land, savor meals created from the finest local ingredients and relax in charming Tuscan retreats.

Daily program

Day 1: Welcome! Benvenuti in Toscana
Pienza the "perfect town" is a remarkable example of Renaissance-era town planning. If you have even the least appreciation for beautiful architecture, it is a treat to stroll about its cobblestone streets. Meet and Greet, we'll fit your bikes and introduce you to each day ride. First loop to San Quirico (14 miles/22 km) to test the bicycle and the equipment!

Day 2: Vino Nobile di Montepulciano (34 or 21 miles/55 or 35 km)
Loop bike tour to Montepulciano and Monticchiello. Start your day with a pleasant downhill, you’ll follow a route checkered with vineyards and cypresses. Highlight of the day is Montepulciano, which is famous for the production of Vino Nobile. Back to Pienza through Monticchiello, another hilltop village.

Day 3: Montalcino and Brunello wine (29 or 21 miles/46 or 34 km)
Today bike trip to Bagno Vignoni, a thermal spa town right before reaching the beautiful Castiglione d'Orcia. Enjoy a long downhill to the monastery of Sant'Antimo. On your way to the Etruscan village and wine town of Montalcino, where you will stay you’ll pedal through magnificent vineyards.

Montalcino is a fortified town which was used as a shelter by Siena nobles during the 16th Century, but today it is even more famous thanks to the production of one of Italian’s premier fine red wines, Brunello di Montalcino.

Day 4: Siena and Palio race (36 or 32 miles/58 or 50 km)
Ride from Montalcino to Siena. On the way you'll coast along the forested crest of a ridge, home to the famed Monte Oliveto Maggiore monastery. Stop here to visit the beautiful buildings and perhaps have lunch at the restaurant. Afterwards, you'll travel through the fascinating area called Le Crete, Tuscany's answer to the Badlands.

Easier: Start with 10 km descent and pass through Buonconvento. Heading northbound to Siena, you’ll be treated to more gorgeous cycling along secondary roads. In the village ofMurlo, you can visit the fascinating Etruscan Museum. Continue to Ville di Corsano always on a breathtaking scenery and end up in Siena arch gate Porta San Marco.

You'll have time to take a leisurely stroll around this medieval art city in the afternoon and to visit Piazza del Campo, Torre del Mangia and the famous Duomo. Piazza del Campo is famous because here it is held twice a year the disputed DzPaliodz horse race, which opposes the 17 Dzcontradedz of this fascinating city.

Day 5: End of tour
End of bike tour after breakfast.


Daily: Mar 15-Oct 31, 2018


Tour package
Per person, double occupancy
Single room surcharge (1 person/1 room)
Bike Rentals
Hybrid touring bike
Road bike
Electrically assisted bike
Please note: Instead of operating bicycle tours ourselves, BikeTours.com represents local bicycle tour operators around the world. Review the tour operator's information and terms below, then submit your booking request through BikeTours.com. The primary benefits of booking your tour through BikeTours.com include:
  • Lower cost: You pay local tour company prices—less than what big American companies charge
  • Variety: Choose from more than 200 tours offered by local operators in 35 countries.
  • Advice: Our informed advisors help you choose the trip that's right for you.
  • Great exchange rates: Pay low rates thanks to the millions of dollars in foreign currency we buy each year. Or pay in euros!
  • Convenience: We handle the full booking and payment process.
  • Support: We’re your advocates from initial planning through final pedal stroke.
Contact us with any questions about booking and paying for your tour through BikeTours.com. We look forward to serving you!

Cicloposse Terms and Conditions

In the event that you cancel your participation on the trip, the tour operator has the right to charge a penalty if the customer renounces his booking:

If cancellation occurs:

  • more than 60 days before starting date: no penalty (just handling charges of 19 euros plus .2 (point-2, not 2) percent of tour price)
  • between 60 and 45 days before starting date 30% penalty
  • between 44 and 30 days before starting date: 50% penalty
  • between 29 and 21 days before starting date: 70% penalty
  • within 20 days before starting date: 100% penalty

Cancellations by us
Scheduled guided tours with low enrollment may be subject to cancellation. Registrants will receive a forty-five day notice and full refund or option to move to another scheduled week. In very rare cases it may be necessary for the tour operator to cancel a tour. In the event of cancellation, a full refund will be sent to the client and this constitutes full settlement. The tour operator is not responsible for other expenses incurred such as pre-paid hotel reservations or non-refundable airline tickets. 

Trip Insurance
The tour operator strongly recommends cancellation and accident insurance to prevent any losses in case of illness, accident or otherwise. It is the responsibility of the client to apply directly to the insurance company. Please purchase trip cancellation insurance in case an illness forces you to cancel or depart early from a trip.

Clients are responsible for selecting a tour suitable for their athletic ability. They are responsible for reading all pre-trip materials, informing us of any medical or dietary restrictions, signing our release form prior to the start of their tour, and obeying all safe biking rules. The tour operator reserves the right to decline or withhold service to any person who, for physical or other reasons, is deemed unfit for the trip. Every care will be taken to respect your luggage at all times. However, the tour operator is not responsible for damage, loss or theft of your personal belongings


Our accommodations are in excellent four and three-star hotels and country inns. We will do everything in our power to secure you lodgings in our first-choice hotels, but it may not be possible if you are booking less than three months before traveling or during a particularly busy season. In that case we will secure you lodgings in comparable hotels. Tour prices are based on double occupancy. Additional nights can be arranged for early arrivals or late departures. Single supplements are available upon request.

Rental Bicycles
PROVIDED EQUIPMENT: 27-speed touring or race bikes, alloy frame with carbon fiber fork and equipped with Shimano high quality components; Helmet; Front handlebar bag; water-bottle & cage; Lock; Cycle computer; Repair kit, including spare tire; Pump; Toe clips.

We will ask for your measurements to insure that you get the most suitable bike possible, we strongly recommend you book as early as possible.

You will be responsible for the bicycle once you take possession of it at your first hotel. Your responsibilities include any costs for damage or theft up to the full value of the bicycle.

The tour operator and its representatives act only in the capacity of tour operators for land transportation, sightseeing and hotels which provide services included in the specified tour.

The individual tour participant agrees that the tour operator and its representatives shall not be liable for any injury, damage, loss, accident, delay, or irregularity, liability or expense to person or property due to any act of default of hotel, land transportation carrier, restaurant supplier or other contractor rendering or providing services. The tour operator and its representatives shall not be responsible for any expense or liability resulting from labor disputes, war, acts of terrorism, government restraints, weather conditions, sickness, pilferage or any other cause beyond their control. The tour operator and its representatives reserve the right to accept, or to retain or refuse any person as a participant of any tour or to cancel any program of a tour if circumstances so demand.

By submitting a booking request, I have and do hereby fully assume all risk of illness, injury, or death and hereby release the tour operator from all actions, claims, or demands for damages resulting from my participation on the trip. I agree that the foregoing obligation shall be binding upon me personally, as well as upon my heirs, executors and administrators and all members of my family, including any minors accompanying me. I have had sufficient opportunity to read this entire document. I have read and understood points above and I agree to be bound by their terms.

All photos used by permission. ©Cicloposse


Ratings Snapshot

  • 5 Star 1
  • 4 Star 0
  • 3 Star 0
  • 2 Star 0
  • 1 Star 0

Average Ratings

  • Overall


  • Difficulty level (Actual vs. expected) 3
  • Value 4
  • Included meals 5
  • Bikes & equipment 5
  • Hotels or boat 5
  • Scenery 5
  • Ease of navigation 5
  • Tour documents 5
  • Local tour company services 5
  • Route selection 5