Self guide short escape Tuscany bike


Tuscany hilltown the best of self guided tour.

Self guide short escape Tuscany bike tour put together three full days of cycling and two half days.

For those who do not want to take an holiday entirely on the saddle, every day there will be possibility to choose for easier or shorter bike rides.

If you like a self guided more challenging ones just ask it!!!

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 and, savory meals created from the finest local ingredients and relax in charming Tuscan retreats.

The self guide short escape Tuscany bike tour is all this and something more but you can discover it only on cycling.

Highlights of Self guide short escape Tuscany bike:

  • Scenic cycling through the stunning landscape of the Val d’Orcia
  • Taste the splendid wines Brunello of Montalcino, Vino Nobile di Montepulciano
  • Delight in hearty Ribollita soupe, Panzanella tuscan Salad, fresh pastasas pici  and delicious pastries of Siena
  • Enjoy gracious hotels with distinct regional and charming style.


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 around its cobblestone streets.
Gift hunters will also be enthralled.
Pienza is also a veritable gastronomic paradise.
Meet and Greet, we’ll fit your bikes and introduce you to each day ride.
First loop to San Quirico to test the bicycle and the equipment! Stop in the village at Horti Leonini Garden, the top attraction of town. Total Distance 22 km.
Your charming Hotel Il Chiostro is housed in a 15th-century convent in a quiet, secluded location right in the center of Pienza.
Entirely rebuilt between 1459 and 1462, itself is a rare masterpiece: it was the brainstorm of Pope Pius II

Day 2 – Montepulciano & Vino Nobile

Loop ride to Montepulciano and Monticchiello.
Start your day with a pleasant downhill, you’ll follow a route that winds through a scenic landscape checkered with vineyards, cypresses, and medieval villages…
Among the sites you’ll ride through meet the hilltop villages of Castelmuzio and Petroio.
Today’s ride will take you to Montepulciano, which is famous for the production of Vino Nobile di Montepulciano.
Visit one of the typical wine cellars in town, the oldest one in town is situated under the Ricci Palace.
Back to Pienza through Monticchiello… another hilltop village.
Option A : Moderate to challenging
Distance: 55 km/ 34 miles
Option B: easy to moderate
Distance: 35 km /21 miles

Day 3 – Montalcino Brunello land

Today’s ride will take you to Bagno Vignoni, a thermal town that dates back to Roman times right before reaching the beautiful Castiglione d’Orcia. 
Enjoy a long downhill to the monastery of Sant’Antimo, where you might catch one of vesper services performed each day by the monks.
On your way to the wine town of Montalcino, where you will stay, you’ll cycle 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.
Visit the fortress to see a breathtaking view of the entire valley, then reward yourself with dinner at our favourite wine cellar.
Option A: Moderate to challenging 
Distance: 46 km/28, 5 miles
Option B: Easy to Moderate
Distance: 34 km / 21 miles

Day 4 – Siena Etruscan and Palio race

Start with 10 km descent and pass through Buonconvento. 
Heading northbound to Siena, you’ll be treated to more gorgeous cycling along secondary roads.
On the way you’ll coast along the forested crest of a ridge, home to the famed Monte Oliveto Maggiore monastery. 
Perfect for a coffe time,  here you can visit the beautiful buildings.
Afterwards, you’ll travel through the fascinating area called Le Crete, the moon land!!!
Continue to Asciano, always on a breathtaking scenery and end up in Siena.
You have time to take a leisurely stroll around this medieval art city in the afternoon, visit Piazza del Campo, Torre del Mangia and the famous Duomo.
Piazza del Campo is famous because the contested “Palio” horse race takes place here twice a year, with the 17 “contrade” of Siena
Option A: Moderate to strenuous
Distance: 58 km/36 miles
Option B: Moderate
Distance: 50 km /32 miles

Day 5 Arrivederci

End of bike tour after breakfast.

Price & Inclusions


Cost: Euro 1250 per person in double occupancy

Single room supplement Euro 250


Four nights in excellent three-star superior hotels

Four breakfasts Route notes, maps, elevation gain and city map

Sightseeing, restaurant and shopping suggestions in handbook

All Baggage transfers

Pick-up of bikes and gear in Siena

Sales taxes

Not Included

Bike Rental per entire tour

Hybrid bike  euro 105

Race bike  euro 120

E-Bike  euro 120

City Tax  each village charge a tax per each day between euro 0,70 to 4,00


Renting GPS for 4 days – 50€

We can rent you a Garmin Edge Touring.

It works like the GPS navigator you use in your car, only with maps and features specifically designed to help you find your way by bike.

We will upload all the route notes and you will have really no problems in finding your way to the next town!



Self Guided



Rolling hills

Best Time

Any time from March to October











contact us and book the tour

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Based on 96 reviews
Manuel König
Manuel König
I rented the Canyon Gravel bike for the Strade Bianche and felt I had made the optimal choice. The booking process was very easy, Luigi is extremely kind, knowledgeable and helpful, the bikes are beautiful, perfectly maintained and adjusted to your needs and the price is more than fair compared to competitors. 5/5 stars. I would come back any time.
Silvia Dagnoli
Silvia Dagnoli
Top! Professionalità e disponibilità al 100%. Ho preso una Canyon Gravel a noleggio, mi sono trovata molto bene.
Very friendly, speaks good english. The bikes themselves are great. The bikes are nog insured by default.
Matthew Ng
Matthew Ng
We had 5 excellent days of gravel riding (self guided Tuscany tour). The routes that Luigi provided us were a good mix of paved and gravel, and of course hills! The bikes (Canyon Grizl) were very nice and the luggage was always waiting for us at the next hotel. Luigi was accomodating, modifying the routes based on my requests. I would definitely recommend doing a trip with this company.
Robert Head
Robert Head
The route was wonderful, with amazing scenery and history at every turn. Our guides, Sarah and Gigi were the best. They are both very accomplished and personable riders, provided interesting history of Tuscany during the tour, and emphasied safe riding while keeping everyone within sight. They are also great dinner companions!
James Twidale
James Twidale
Luigi and BikeRiding Tuscany were an absolute pleasure to deal with. The bike was in incredible condition, delivered to my hotel and Luigi even arranged for a local mechanic to help with a small mechanical issue after my first ride. The experience from start to finish was brilliant. The communication friendly and quick. Simona was equally helpful on collection of the bicycle. I would love to join Luigi for a cycle tour as he seems very knowledgeable about the area and a good rider. I would recommend this company to anyone looking to explore Tuscany or Siena.
Mark Gatha
Mark Gatha
Exceptional self guided tour. I highly recommend for all levels (but especially for a road cyclist). This is the tour company to book with! Bikes - excellent high end bikes. I rode a Canyon Ultimate CF SL Ultegra - light and fast and we'll tuned with new tires. My wife road the e-mountain bike which she really enjoyed. Routes - beautiful. We did 50-60km a day. Rapolano de Terme, Pienza, Montalcino, Siena and Castellini in Chianti. Varied terrain, vineyards, great climbs and beautiful medieval towns. Extremely well thought out. All on quiet roads. Hotels - all 3 and 4 stars with loads of character. The ones with pools were our favourites. All of the hotels were able to let us check in very early (it was hot so we rode as early as we could manage). Hotels all came with breakfast. Really great. Service - Luigi was a gem. Easy to contact, quick to communicate (before we came and during the tour) and passionate about cycling. He gave us a lot of great recommendations to help maximize our tour. I cannot say enough positive things about this trip and Bike Riding Tuscany. This was truly memorable. Highly recommended.
Bruce Jenkins
Bruce Jenkins
I was on a trip around the world and stopped in Italy. A friend recommended BikeRidingTuscany to me for an unforgettable experience and it didn’t let down. They planned a custom 1 day gravel ride for me that took us from Rapolano Terme to Sienna and back. The pace was perfect and they were gracious with any requests for breaks or stops for water/food. I enjoyed myself so much that I extended my stay to do a run on the gravel amongst the beautiful sunflowers. If you’re adventurous, and seeking some safe fun riding, this is your team
greg luckos
greg luckos
Great rental service! Nothing is a problem for Luigi. All bikes are set up tubless. Thank you

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