Tuscany hill town the best of Senza titolo 2 Short Escape Tuscany 4-night


We put together this short bike tour- 3 full days of cycling and one half day – for those who do not feel like taking a vacation entirely on a saddle, besides each day there will be a choice for easier and short 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, savour meals created from the finest local ingredients and relax in charming Tuscan retreats.

You can choose between  Carbon frame race bike, hybrid, high-end E-bike and Gravel… to enjoy at the best pace!


  • 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 soup, Panzanella Tuscan Salad, fresh pastas as pici  and delicious pastries of Siena
    Enjoy gracious hotels with distinct regional and charming style.


Same place to stay but 7 nights with more loop: have a look at southern Tuscany bike tour

At A Glances:

Day one

Welcome To Pienza!


Arrival Pienza on your own. Meet you: fitting of bikes and Orientation Pienza

Hotel Relais Il chiostro

Day two
Distance: 50 km/31 miles
Loop Pienza to Sant’Anna in Camprena, Castelmuzio, Montepulciano, Montichiello Pienza

Hotel Relais Il chiostro

Day three
Distance: 48 km/30 miles
Bike ride Pienza to Montalcino, via Bagno Vignoni and Sant’Antimo Abbey Montalcino

Hotel Giglio

Day four
Distance: 52 km/32,5 miles
Bike ride from Montalcino to Siena, via Murlo e Ville di Corsano. Siena

hotel  Villa di STR

Day five Arrivederci End of Tour after Breakfast

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

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

Montalcino Brunello land

Today’s ride will take you to Bagno Vignoni, a thermal spa 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 several vesper services performed each day by the monks.. 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.
Visit the fortress to see a breathtaking view of the entire valley you've just biked, 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

Siena, Etruscan and Palio race

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 of Murlo, 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 “Palio” horse race, which opposes the 17 “contrade” of this fascinating city.
Option A: Moderate to strenuous Distance: 58 km/36 miles
Option B: Moderate distance 50 km /32 miles


End of bike tour after breakfast
Short Escape Tuscany bike tour
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Hotel Il Chiostro di Pienza
Il Chiostro di Pienza is housed in a 15th C convent and sits protected and quiet right in the center of this tiny town. It has been renovated but all the beamed ceilings frescoed walls and ancient tile floors have been preserved, nice garden overlooking val d’Orcia with pool. www.relaisilchiostrodipienza.com
Hotel Giglio - Montalcino
A charming retreat in the heart of town, hotel Giglio, family-run, in a warm and quiet building, facing a gorgeous landscape, the best part is the view of the cliff-clinging houses of Montalcino to your left and the rumpled patchwork of green valleys stretching out below. Plus a great restaurant where enjoy gourmet tuscan dinners.
Chiostro Carmine - Siena
Il Chiostro del Carmine has been meticulously restored from a XIV century Carmelite Monastry, place of history and holiness, remained intact in the centuries, with its delightful and quiet courtyard. It is situated a few hundred metres from the Siena Cathedral and from Piazza del Campo
Luxury upgrade in Siena: Relais Campo Regio -
More of a boutique guest house than traditional hotel, Campo Regio Relais’ 6 rooms are centrally positioned in the heart of Siena’s historic centre, allowing guests to easily reach the most important monuments of the city; the main square, Piazza del Campo, the Duomo, and the museums that house the masterpieces of Sienese art.
Luxury upgrade in Pienza: Bandita townhouse
La Bandita Townhouse is a luxury boutique hotel tucked inside the historic center of Pienza. The building is a rambling Renaissance-era palazzo where nuns have lived for over 500 years. the property itself blends in completely with the Renaissance character, is a comfortable, and stylish place www.la-bandita.com

Short Escape Tuscany

Price & Inclusions 

Cost: Euro 1030 per person in double occupancy
Single room supplement eEuro 300
Solo Traveller Supplement Euro 380

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, Gravel  euro 130

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

Renting GPS for 4 days – 50 euro
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!


Tour Reviews

28 Novembre 2019

Although it has been months since our cycling trip, I remember it vividly! It is one of the best organized trips I have ever been on!!
We had a fantastic time! The weather was beautiful and scenery spectacular!
The cycling routes you set up were low traffic and very scenic. Tuscany is every bit as beautiful as the movie! The route distance was perfect (30 to 40 miles). There was enough time to get started at a leisurely morning time and back to relax for a wonderful Italian dinner and some wonderful wine. The first day we had a little rain, but this was the shortest day so this worked out well. The GPS maps and the tourist information with recommendations was great and provided useful information. Yes, the course was a little hilly, but anything is hillier than central Illinois! The bikes provided were all in excellent condition and were great road bikes! Your pump worked perfectly and there were never any issues.
The hotels were all 4 or 5 stars and had great meals included. They were all located in excellent places, walking distance to sightseeing, restaurants, grocery stores, or laundromats. The hotels were accommodating with our bikes and very friendly and great hospitality! Our luggage was picked up from the hotel and was always at our new location.
Thank you to the gentlemen (I’m sorry, I do not remember his name) who picked us up from the train station, fitted our bikes, gave us the maps etc. He did a great job with the bike fitting and getting everyone individual attention!
I have recommended your outfitter group to another group from Central Illinois. I bet they will have a wonderful time too!

Thank you for your attention to detail and being such wonderful ambassadors to cycling and Italy!!

17 Ottobre 2016

Hi, Giuliana! We had a wonderful trip. Everything went smoothly and it was the trip of a lifetime! We are now in Florence for a few days and home on Sunday. Again, we had an amazing time and will recommend Cicloposse to our friends. I did post a recommendation for Cicloposse on Trip Advisor, and also on my blog, http://www.europe2wheels.blogspot.com Grazie.

17 Ottobre 2016

Giuliana and Marco, I just wanted to send you a note to let you know how much we enjoyed the Cycling Trip in Tuscany!! EVERYTHING was wonderful, the hotels, the maps, the suggestions on restaurants and where to visit and especially the cycling. We had such a wonderful time and will definitely be back someday to ride even more!!

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