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Highlights

This self-guided tour covers a small but stunning part of Tuscany ! Discover the beauty of Montepulciano, Pienza, Montalcino and its famous Brunello wine, and Siena, as well as many little medieval villages on your ride every day. This is a relaxed tour with 2-night stays in 3 different towns, so you are not always packing. If you wish to take a day off from riding you can sightsee, have a wine tasting, and walk along beautiful paths. Food and wine are highlights of this trip! You will have the opportunity to taste the local homemade pasta pici, the local cheese pecorino, as well as typical appetizers bruschetta and crostini, while sipping great wine !

To see

Embark on a trip through the enchanting landscapes of Tuscany, starting with the Horti e Leonini Garden in San Quirico d'Orcia and the historic town of Montepulciano. Continue to the thermal spa town of Bagno Vignoni, leading to the picturesque Castiglione d'Orcia with its imposing Rocca A Tentennano. Explore the renowned Brunello vineyards in Montalcino, visit the truffle village of San Giovanni d'Asso, and immerse yourself in the cultural richness of Siena, all while traversing the scenic Chianti hills.

Gastronomy

Ribollita, Pappa al Pomodoro, Pecorino Toscano, Crostini di Fegatini, Panzanella, Ossobuco

Wine

Alta Valle della Greve, Colli della Toscana centrale, Costa Toscana, Montescastelli, Toscana, Toscano, Val di Magra

Feedbacks

5/5

PROGRAM

J-1

Pienza


Arrival at Chiusi Chianciano train station in the morning/ early afternoon and transfer on your own to the first hotel in Pienza, your home for the next two nights. The 'perfect town' almost entirely built between 1459 and 1462, Pienza 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. Gift hunters will also be enthralled, and Pienza is a veritable gastronomic paradise.

If you arrive early enough, the first loop is to San Quirico to test the bicycle and the equipment! Stop in the village at Horti e leonini Garden, the top attraction of town.

Distance : 22 Km (14 mi)


Accommodation : Relais Il Chiostro di Pienza**** - Pienza show
Included : phone not provided,mobile guidance application,roadbook,travelbook,Orientation with a local guide,luggage transfer,bedroom and breakfast the next morning

J-2

Pienza - Monastery of Sainte-Anne - Castelmuzio - Petroio - Montepulciano - Monticchiello - Pienza


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. This is where 'the English Patient' was filmed. Among the sites you'll ride through there are 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. After a stroll about the medieval streets of this village, you can stop to visit one of the typical wine cellars in town, the oldest one which is situated under the Ricci Palace. Back to Pienza through Monticchiello another hilltop village !

Distance : 52 Km (32 mi).

Elevation: 1058m


Accommodation : Relais Il Chiostro di Pienza**** - Pienza show
Included : bedroom and breakfast the next morning

J-3

Pienza - Bagno Vignoni - Castiglione d'Orcia - Montalcino


Bike ride to Montalcino . 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, with the imposing Rocca A tentennano. Enjoy a long downhill to the monastery of Sant Antimo, your next stop: if you have luck, you will hear the monks chanting. On your way to the Etruscan village and wine town of Montalcino, where you will stay for next three days, you'll pedal through magnificent vineyards. It 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 Italy's premier fine red wines, Brunello di Montalcino.

Distance : 44 Km (27 mi).

Elevation: 856m


Accommodation : Hotel Il Giglio**** - Montalcino show
Included : luggage transfer,bedroom and breakfast the next morning

J-4

Montalcino - Monte Oliveto Abbey - San Giovanni d'Asso - Montalcino


Your detailed directions will take you through typical postcard scenery of Tuscany, Italy’s most photographed region—for good reasons. Following a picturesque crest road, you’ll ride by Monte Oliveto Maggiore Abbey , a Benedictine abbey built in the 13th century and famous for its frescoed cloister and stunning setting.

Afterwards, you'll travel through the fascinating area called Le Crete, Tuscany's answer to the Badlands. Here the verdant hills give way to little domes of clay and Tuscany reveals another face of its identity, an unusual, almost lunar landscape of chalk cliffs and gullies soaked in a primeval atmosphere. Back via San Giovanni d’Asso, the truffle village in Tuscany.

Distance : 46 Km (29 mi).

Elevation: 695m


Accommodation : Hotel Il Giglio**** - Montalcino show
Included : bedroom and breakfast the next morning

J-5

Montalcino - Buonconvento - Murlo - Siena


Start with 10 km descent and pass through Buonconvento, Heading northbound to Siena, where more gorgeous cycling on secondary roads. In the village of Murlo, you can visit the fascinating Etruscan Museum, one of the highlight of the day.

Continue to Ville di Corsano always on a breathtaking scenery up to Siena arch gate Porta San Marco. Often described as Italy's best preserved medieval city, Siena rivaled Florence for dominance in Tuscany during the 1300s. You'll have time to take a leisurely stroll about 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.

Distance : 55 Km (34 mi).

Elevation: 857m


Accommodation : Hotel la Villa Di STR*** - Siena show
Included : luggage transfer,bedroom and breakfast the next morning

J-6

Siena - Radda in Chianti - Gaiole in Chianti - Castello di Brolio - Castelnuovo Berardenga - Siena


Loop Ride from Siena to Gaiole and Radda in Chianti. Along the way you can visit Castelnuovo Berardenga, a medieval town that marks the gateway to Chianti country. Not far away is Castello di Brolio, a castle that you can visit. There's also the chance to shop at a first-class ceramics workshop just before Radda in Chianti. Back to Siena via chiantigiana road.

Distance : 55 Km (34 mi).

Elevation: 936m


Accommodation : Hotel la Villa Di STR*** - Siena show
Included : bedroom and breakfast the next morning

J-7

Departure from Siena


Today is departure day, you can take your time getting started in the morning, have breakfast and depart at your leisure from Siena. From Siena, you will find directs trains to Rome (3 h) and Florence (1h45). According to your program, we can arrange accommodations and transportation. (Depart on your own).


Included : breakfast

CUSTOMIZED
TOUR

This is a catalog tour, it can be modified as you wish : add extra nights, extra activities (wine tastings, visits, transfers...).

ARRIVALS & DEPARTURES

To get to the start of your Tour (Pienza), the easiest airport are Rome Fiumicino and Florence Peretola.
Fiumicino aiport (Roma) take the train “Leonardo Express” to Roma train station (about 30min, start each half hour and is direct). From Roma to Chiusi you willfind many trains (about 2h00). Then take a taxi to your hotel in Pienza (about 60eur).
From Florence Peretola (Florence) take a bus or a cab to Florence train station. Then Take a train from Florence train station to Chiusi (about 1h45). To reach Pienza, take a taxi to your hotel (about 60eur).

Your tour ends in Siena.
The train station is very close to Siena. You will find direct trains to Roma (3h00) and Florence (1h45)

BIKES


included

Hybrid Bike - Standard

More info

We put together the disc brake for the stability and the reliability of braking and the compact gear with 42 teeth in the back, an advanced gearing concept that helps maintain rider efficiency.

About disc brake we have the advantage of the power – it generate an incredible amount of stopping power, usually far more than is necessary to adequately stop a road bicycle and Reliable, all weather braking.

For the rest is an hybrid with straight handlebars, lightweight with hybrid wheels ad narrow tires for low rolling resistance allowing for greater speed and less exertion when riding on paved road.

Included with your bike rental :

• 1 new bottle

• Helmet

• Odometer

• Lock

• Pump frame

1 Handlebar bag with rain cover containing : Tire levers / 2 Spare tubes / Toolkit

• Pedals are included, flat by default or toe straps on request. If you want to use your bike shoes, you should bring your own pedals + pedal wrench : we will be happy to install them on your bike.

Note: "Please notice that every bike change during the trip may cause an extra cost."




optional

Electric Assisted Bike - Standard

More info

The electric pedal assisted bike is a amazing invention around bike world, electric bikes are regular pedal bikes that provide electric assistance whenever you want it.

We selected the model E-sub cross 10 as the best for our tours: The SCOTT E-SUB Cross 10's newly developed frame ePowered by a new 500wh Bosch Internal battery, will get you where you are going faster and more comfortably than ever before. Throw in wider rims and 47c Smart Sam tires and the result is one sleek speedy and well equipped Cross E-Bike.

Included with your bike rental :

a Big saddle bag & a Handlebar bag containing : Helmet / Lock / pump / Spare tube / Toolkit

• 1 water bottle

• Odometer

• Bike charger

• Pedals are included, flat by default or toe straps on request. If you want to use your bike shoes, you should bring your own pedals : we will be happy to install them on your bike.

Note: "Please notice that every bike change during the trip may cause an extra cost."




optional

Road Bike - Standard

More info

With drop handlebars, these bicycles are built for traveling at higher speeds on paved roads, sometimes referred to as racing bikes. Our race bikes are all brand-new, reliable, and well maintained for your ideal cycling experience of Italy. Extremely efficient, incredibly smooth to ride and will take you everywhere with stability after a professional bike fitting session. Race bike with drop handle bar is strongly suggested if you use regularly those bikes !

Included with your bike rental :

• Helmet

• Odometer

• Pump

• 1 new bottle

• lock

• Spare Tubes / Toolkit / Tire levers

• Map holder

NB: "Chaque changement de vélo pendant le voyage peut entraîner des frais supplémentaires."




optional

Gravel Bike - Standard

More info

Bike rental description

New Scott Addict Gravel 20 with drop handle bar, a cyclocross touring oriented , disc brake and wider tires to enjoy the classic strade bianche in Tuscany: Eroica itinerary and Francigena path. Our gravel bikes are all brand-new, reliable, and well maintained for your ideal cycling light off-road experience of Tuscany. Lightweight because of carbon fiber frame, hydraulic disc- brake,these bikes can perform on both the road and off the road.

Included with your bike rental :

• Helmet / Lock / pump / Spare tube / Toolkit

• 1 water bottle

• Odometer

• Pedals are included, flat by default or toe straps on request. If you want to use your bike shoes, you should bring your own pedals : we will be happy to install them on your bike.

Note: "Please notice that every bike change during the trip may cause an extra cost."

Details

Included


ACCOMODATIONS

- 6 nights of accomodation in charming hotels with private shower and/or bath

MEALS

- Daily breakfast at each hotel

BIKES

- Hybrid bike rental included

GEAR

- Complimentary Discover France Gear (including water bottle, drawstring bag)
- Guidance Applicaton (phone not provided)

SUPPORT

- Orientation in person with our local guide
- Detailed ROAD BOOK, including detailed maps, touristic information, step by step itinerary and cue sheets
- Comprehensive trip literature
- Technical and emergency support available at all times
- Concierge service available to assist you for your requests during your trip (taxi transfer, restaurant, activities...)

TRANSFER

- All luggage transfers

Not included


  • Airfare to and from the trip
  • Lodging before and after the trip
  • Drinks
  • Some meals are not included in each destination, which gives you the opportunity to explore regional cuisine on your own. You will find all information needed with our team support in your roadbook
  • You have to pay local taxes each day (0.70 to 2.50 eur) in cash to each hotel (tourist administration tax)
  • Multirisk travel insurance

Other questions?

See our FAQs page for answers to common questions.

FAQ

Rates

Tour rates vary based on hotel availability and specific start date

PRICE FROM / PER PERSON
STANDARD HOTEL ACCOMODATION
Double occupancy *
1865 €
Single supplement **
450 €
Solo traveler ***
1890 €

* Please contact us for triple hotel rates. ** Traveling with a group. *** Traveling alone.

Upgrade your bike

From / Per person

Electric Assisted Bike - Standard
315€
Road Bike - Standard
265€
Gravel Bike - Standard
315€

CANCELLATION INSURANCE

Cancellation insurance 6%

STANDARD HOTEL ACCOMODATION FROM

Relais Il Chiostro di Pienza**** - Pienza

The Relais Chiostro di Pienza is a former Franciscan Convent dating back to the 13th century, located in an enviable position, in the centre of the magnificent hamlet of Pienza, in the heart of the Val d'Orcia. The Relais, in addition the charm of antiquity and history which has literally "passed" through its rooms, hides a wonderful surprise: the panoramic terrace with garden set in the romantic Sienese hills. The Relais Il Chiostro di Pienza is today an elegant and tranquil location, offering comfortable and stimulating accommodation due to its uniqueness together with the functionality of its rooms and facilities.
http://www.relaisilchiostrodipienza.com/

Relais Il Chiostro di Pienza**** - Pienza

The Relais Chiostro di Pienza is a former Franciscan Convent dating back to the 13th century, located in an enviable position, in the centre of the magnificent hamlet of Pienza, in the heart of the Val d'Orcia. The Relais, in addition the charm of antiquity and history which has literally "passed" through its rooms, hides a wonderful surprise: the panoramic terrace with garden set in the romantic Sienese hills. The Relais Il Chiostro di Pienza is today an elegant and tranquil location, offering comfortable and stimulating accommodation due to its uniqueness together with the functionality of its rooms and facilities.
http://www.relaisilchiostrodipienza.com/

Hotel Il Giglio**** - Montalcino

Just a few steps from the main Piazza, in the heart of medieval Montalcino, the “Il Giglio” have just 12 rooms, each one with cast-iron bed frames, painted ceiling and travertine stone bathrooms in a harmonious blend of rustic Tuscan style and classical elegance. The breathtaking panorama through the windows contributes to create an atmosphere that can only be experienced, never described.
http://www.gigliohotel.com/en/

Hotel Il Giglio**** - Montalcino

Just a few steps from the main Piazza, in the heart of medieval Montalcino, the “Il Giglio” have just 12 rooms, each one with cast-iron bed frames, painted ceiling and travertine stone bathrooms in a harmonious blend of rustic Tuscan style and classical elegance. The breathtaking panorama through the windows contributes to create an atmosphere that can only be experienced, never described.
http://www.gigliohotel.com/en/

Hotel la Villa Di STR*** - Siena

The Villa of Str, Located just outside the old city walls of Siena, The Villa is a charming liberty style residence dating from the early years of the twentieth century and within easy walking distance from the historic centre of Siena. Offering solutions for all needs, whether as a family, a couple, with friends or even with your pets, all our rooms are tastefully decorated with respect for the aesthetic and historical origins of the building. Whatever your reasons for visiting Siena, our hotel will prove welcoming, stylish and comfortable, a great base from which to explore the medieval town of Siena.
http://www.lavilladistr.it/en/home

Hotel la Villa Di STR*** - Siena

The Villa of Str, Located just outside the old city walls of Siena, The Villa is a charming liberty style residence dating from the early years of the twentieth century and within easy walking distance from the historic centre of Siena. Offering solutions for all needs, whether as a family, a couple, with friends or even with your pets, all our rooms are tastefully decorated with respect for the aesthetic and historical origins of the building. Whatever your reasons for visiting Siena, our hotel will prove welcoming, stylish and comfortable, a great base from which to explore the medieval town of Siena.
http://www.lavilladistr.it/en/home