self-guided
Cycle through wine country and sample the produce
Tuscan Wine Classic
Tour Description: Guided
(View Self-guided)
Cycle through enchanting Tuscan landscapes at your own pace. Pass the monastery where parts of The English Patient were filmed. See the Chianti vineyards, and sample the wine in the evenings. Explore beautiful villages and castles, and see local craftsmen at work.
This tour immerses you in Tuscany!
Learn more about self-guided tours.
Cycle through wine country and sample the produce
Tuscan Wine Classic
Tour Description: Self-guided
Cycle through enchanting Tuscan landscapes at your own pace. Pass the monastery where parts of The English Patient were filmed. See the Chianti vineyards, and sample the wine in the evenings. Explore beautiful villages and castles, and see local craftsmen at work.
This tour immerses you in Tuscany!
Learn more about self-guided tours.
Cycle through wine country and sample the produce
Tuscan Wine Classic
Highlights: Guided
(View Self-guided)
- Pienza Renaissance town
- Castelmuzio
- Montepulciano, the jewel of southern Tuscany
- Monticchiello, the quintessential Tuscan hill town.
- Bagno Vignoni, a miniature spa
- monastery of Sant'Antimo
- wine town Montalcino
- Monte Oliveto Maggiore monastery
- Castello di Brolio
Cycle through wine country and sample the produce
Tuscan Wine Classic
Highlights: Self-guided
- Pienza Renaissance town
- Castelmuzio
- Montepulciano, the jewel of southern Tuscany
- Monticchiello, the quintessential Tuscan hill town.
- Bagno Vignoni, a miniature spa
- monastery of Sant'Antimo
- wine town Montalcino
- Monte Oliveto Maggiore monastery
- Castello di Brolio
Cycle through wine country and sample the produce
Tuscan Wine Classic
Daily Program: Guided
(View Self-guided)
Cycle through wine country and sample the produce
Tuscan Wine Classic
Daily Program: Self-guided
Day 1: Pienza
We'll meet you at Pienza, the purest Renaissance town in the world (you will arrive by the train to Chiusi-Chianciano station, a major stop on all the Rome-Florence lines). Your charming hotel Il Chiostro is housed in a 15th-century convent in a quiet, secluded location right in the center of town. Meet us for the bike fitting session and to receive all the packages - maps, instructions, equipment - of the tour.
Overnight in Pienza.
Day 2: Pienza - Montepulciano - Pienza (31 miles/50 km)
Your tour starts with a circular ride from Pienza. Be sure to stop along the way to visit the remote convent where parts of The English Patient were filmed, and in the enchanting little hamlet of Castelmuzio. By lunchtime you'll come to Montepulciano, the jewel of southern Tuscany. After relaxing a while, return to Pienza with a stop in the village of Monticchiello, the quintessential Tuscan hill town.
Overnight in Pienza.
Day 3: Pienza - Montalcino (approx. 46 km/29 miles)
Ride from Pienza to Montalcino, with a pause in fairy-tale Bagno Vignoni, a miniature spa that is among the most unique towns in Europe. You can have lunch in Castiglione d'Orcia, then push on to the monastery of Sant'Antimo, where you might catch one of several vesper services performed each day by the monks. The famed wine town of Montalcino is your destination. Visit the fortress to see a breathtaking view of the entire valley you've just biked, then reward yourself with dinner at our favourite restaurant.
Overnight in Montalcino.
Day 4: Montalcino - Siena (37 miles/60 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, and finally arrive in Siena.
Overnight in Siena.
Day 5: Siena - Castellina in Chianti) (28 miles/45 km)
Ride from Siena to Castellina 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.
Overnight in Castellina in Chianti.
Day 6: Castellina - Greve in Chianti (25 miles/40 km)
Circular bike ride to Panzano and Greve in Chianti. Have a stop at Greve's main piazza, characterized by an original formation of irregular triangular shape, defined by beautiful long porticos.
Overnight in Castellina.
Day 7: Monteriggioni
End of tour after breakfast – optional short ride to Monteriggioni.
Departure: train and bus available to reach Firenze where extension of vacation is suggested or where you can take fast train to other town
Cycle through wine country and sample the produce
Tuscan Wine Classic
Dates: Guided
(View Self-guided)
Cycle through wine country and sample the produce
Tuscan Wine Classic
Dates: Self-guided
Daily: Mar 15-Oct 31, 2013
Cycle through wine country and sample the produce
Tuscan Wine Classic
Route Map: Guided
(View Self-guided)

Cycle through wine country and sample the produce
Tuscan Wine Classic
Route Map: Self-guided

Cycle through wine country and sample the produce
Tuscan Wine Classic
Packages and Prices: Guided
(View Self-guided)
Cycle through wine country and sample the produce
Tuscan Wine Classic
Packages and Prices: Self-guided
| Category A |
 |
|
3- and 4-star hotels |
| |
|
| Per person, double occupancy |
€1350 |
| Single room supplement (1 person/1 room) |
€300 |
|
| Category B |
 |
|
3-star hotels |
| |
|
| Per person, double occupancy |
€1250 |
| Single room supplement (1 person/1 room) |
€300 |
|
*The dollar amount is based on today's exchange rate and is subject to currency fluctuation.
Cycle through wine country and sample the produce
Tuscan Wine Classic
Included Services: Guided
(View Self-guided)
Cycle through wine country and sample the produce
Tuscan Wine Classic
Included Services: Self-guided
- Six nights in excellent four and three-star superior hotels (double room with private bath)
- Six breakfasts
- Rent of top-quality touring or race bike fully equipped
- Route notes and itineraries and sightseeing, restaurant and shopping suggestions
- All baggage transfers
- Pick-up of bikes and gear in Castellina
- Keepsake Cicloposse water bottle
Cycle through wine country and sample the produce
Tuscan Wine Classic
Hotels: Guided
(View Self-guided)
These are sample hotels and may vary based on availability.
Category A: 3- and 4-star hotels
Day 1 and 2: Relais il Chiostro, Pienza
www.relaisilchiostrodipienza.com
Il Chiostro di Pienza is housed in a 15th-century convent and sits protected and quiet right in the center of this tiny town. It has been recently renovated but all the beamed ceilings frescoed walls and ancient tile floors have been preserved. Garden and swimming pool.
Day 3: Hotel Vecchia Oliviera, Montalcino
www.vecchiaoliviera.com
The Hotel Vecchia Oliviera is situated at the gates of Montalcino in the province of Siena. This hotel has its home in a fascinating old olive oil mill that has been carefully renovated. Both its location and considerate service make it a fully relaxing place to stay.
Day 4: Chiostro del Carmine, Siena
www.chiostrodelcarmine.com
The hotel was once a 14th century Carmelite Monastry. It is situated a short distance from the Siena Cathedral and from Piazza del Campo
Day 5 and 6: Hotel Palazzo Squarcialupi, Castellina
www.palazzosquarcialupi.com
Palazzo Squarcialupi is part of the history of Castellina in Chianti. It is situated in the historical town center, on a road running along the 15th-century city wall. It has medieval origins and it has been renovated becoming a luxury palace.
Category B: 3-star hotels
Day 1 and 2: Relais il Chiostro, Pienza
www.relaisilchiostrodipienza.com
Il Chiostro di Pienza is housed in a 15th-century convent and sits protected and quiet right in the center of this tiny town. It has been recently renovated but all the beamed ceilings frescoed walls and ancient tile floors have been preserved. Garden and swimming pool.
Day 3: Hotel Giglio, Montalcino
www.gigliohotel.com
Located a few steps from the main piazza, the hotel is decorated in a rustic Tuscan style.
Day 4: Chiostro del Carmine, Siena
www.chiostrodelcarmine.com
The hotel was once a 14th century Carmelite Monastry. It is situated a short distance from the Siena Cathedral and from Piazza del Campo
Days 5 and 6: Hotel Colombaio, Siena
www.albergoilcolombaio.it
The family run hotel was converted out of a farmhouse in the Chianti region. For your enjoyment here are 13 comfortable rooms, a garden, and a swimming pool.
Interested in visiting other areas before or after your tour? Visit our hotels page to learn more about lodging options.
Cycle through wine country and sample the produce
Tuscan Wine Classic
Hotels: Self-guided
These are sample hotels and may vary based on availability.
Category A: 3- and 4-star hotels
Day 1 and 2: Relais il Chiostro, Pienza
www.relaisilchiostrodipienza.com
Il Chiostro di Pienza is housed in a 15th-century convent and sits protected and quiet right in the center of this tiny town. It has been recently renovated but all the beamed ceilings frescoed walls and ancient tile floors have been preserved. Garden and swimming pool.
Day 3: Hotel Vecchia Oliviera, Montalcino
www.vecchiaoliviera.com
The Hotel Vecchia Oliviera is situated at the gates of Montalcino in the province of Siena. This hotel has its home in a fascinating old olive oil mill that has been carefully renovated. Both its location and considerate service make it a fully relaxing place to stay.
Day 4: Chiostro del Carmine, Siena
www.chiostrodelcarmine.com
The hotel was once a 14th century Carmelite Monastry. It is situated a short distance from the Siena Cathedral and from Piazza del Campo
Day 5 and 6: Hotel Palazzo Squarcialupi, Castellina
www.palazzosquarcialupi.com
Palazzo Squarcialupi is part of the history of Castellina in Chianti. It is situated in the historical town center, on a road running along the 15th-century city wall. It has medieval origins and it has been renovated becoming a luxury palace.
Category B: 3-star hotels
Day 1 and 2: Relais il Chiostro, Pienza
www.relaisilchiostrodipienza.com
Il Chiostro di Pienza is housed in a 15th-century convent and sits protected and quiet right in the center of this tiny town. It has been recently renovated but all the beamed ceilings frescoed walls and ancient tile floors have been preserved. Garden and swimming pool.
Day 3: Hotel Giglio, Montalcino
www.gigliohotel.com
Located a few steps from the main piazza, the hotel is decorated in a rustic Tuscan style.
Day 4: Chiostro del Carmine, Siena
www.chiostrodelcarmine.com
The hotel was once a 14th century Carmelite Monastry. It is situated a short distance from the Siena Cathedral and from Piazza del Campo
Days 5 and 6: Hotel Colombaio, Siena
www.albergoilcolombaio.it
The family run hotel was converted out of a farmhouse in the Chianti region. For your enjoyment here are 13 comfortable rooms, a garden, and a swimming pool.
Interested in visiting other areas before or after your tour? Visit our hotels page to learn more about lodging options.
Cycle through wine country and sample the produce
Tuscan Wine Classic
Bike Rentals: Guided
(View Self-guided)
The bikes included with the cost of the tour are road bikes or a hybrid bike.The bikes are aluminum or scandium frame; carbon forks, components Shimano Deore 27 speed, gel saddle, upright handle bar, road wheels 28.
Equipment provided for free with all rentals are a handlebar bag (with plastic pocket for map) and a waterbottle you get to keep as a souvenir.
To insure your safety we require our guests to wear helmets. We provide state-of-art Italian helmet trade mark Limar.
We provide all equipment but if you want to bring your own helmet, pedals, and seat, that is certainly acceptable. Please do not bring your seat post.The bikes are equipped with toe clips pedals or flat pedals If you want to bring your own clipless pedals we will be happy to install them on our bike.
Cycle through wine country and sample the produce
Tuscan Wine Classic
Bike Rentals: Self-guided
The bikes included with the cost of the tour are road bikes or a hybrid bike.The bikes are aluminum or scandium frame; carbon forks, components Shimano Deore 27 speed, gel saddle, upright handle bar, road wheels 28.
Equipment provided for free with all rentals are a handlebar bag (with plastic pocket for map) and a waterbottle you get to keep as a souvenir.
To insure your safety we require our guests to wear helmets. We provide state-of-art Italian helmet trade mark Limar.
We provide all equipment but if you want to bring your own helmet, pedals, and seat, that is certainly acceptable. Please do not bring your seat post.The bikes are equipped with toe clips pedals or flat pedals If you want to bring your own clipless pedals we will be happy to install them on our bike.
Cycle through wine country and sample the produce
Tuscan Wine Classic
Surface and Terrain: Guided
(View Self-guided)
There are lots of ups and downs on rolling hills and some climbs. The terrain is rarely flat.
The tour is rated challenging and is for experienced cyclists in above average physical condition.
Cycle through wine country and sample the produce
Tuscan Wine Classic
Surface and Terrain: Self-guided
There are lots of ups and downs on rolling hills and some climbs. The terrain is rarely flat.
The tour is rated challenging and is for experienced cyclists in above average physical condition.
Cycle through wine country and sample the produce
Tuscan Wine Classic
How To Get There: Guided
(View Self-guided)
Tour start
Nearest airport:
Nearest train station:
Tour end
Nearest airport
Nearest train station:
Tips on getting to and from your tour
Cycle through wine country and sample the produce
Tuscan Wine Classic
How To Get There: Self-guided
Tour start
Nearest airport:
Nearest train station:
Tour end
Nearest airport
Nearest train station:
Tips on getting to and from your tour
Cycle through wine country and sample the produce
Tuscan Wine Classic
Weather: Guided
(View Self-guided)
Weather Underground offers information on average and record temperatures at many destinations throughout the globe. Type a destination in the search box and enter a travel date range to learn about seasonal weather patterns.
Get weather information.
Cycle through wine country and sample the produce
Tuscan Wine Classic
Weather: Self-guided
Weather Underground offers information on average and record temperatures at many destinations throughout the globe. Type a destination in the search box and enter a travel date range to learn about seasonal weather patterns.
Get weather information.
Cycle through wine country and sample the produce
Tuscan Wine Classic
More About Italy: Guided
(View Self-guided)
Of all European countries, none draws visitors over and over again like Italy. A peninsula extending into the Mediterranean Sea, Italy consists of 21 diverse regions of rolling hills, vineyards, mountains, lakes, cliffs and islands. Each region has its unique charm, but all share the ‘Italian’ view that life should be taken at a slow pace with time to enjoy conversation, food and drink. Together, Italy’s regions boast the highest number of UNESCO World Heritage Sites in the world. Rome, Florence, Venice, Assisi and Pisa are a few of the country's renowned cities along with Italy’s 95,000 monumental churches, 40,000 forts and castles and 5,600 museums and archaeological sites. Whether you ride a gondola through Venice’s Grand Canal, stroll along Lake Como or visit the Coliseum in Rome, the opportunities are endless when visiting Italy.
More on bicycling in Italy >
View all Italy bike tours >
Cycle through wine country and sample the produce
Tuscan Wine Classic
More About Italy: Self-guided
Of all European countries, none draws visitors over and over again like Italy. A peninsula extending into the Mediterranean Sea, Italy consists of 21 diverse regions of rolling hills, vineyards, mountains, lakes, cliffs and islands. Each region has its unique charm, but all share the ‘Italian’ view that life should be taken at a slow pace with time to enjoy conversation, food and drink. Together, Italy’s regions boast the highest number of UNESCO World Heritage Sites in the world. Rome, Florence, Venice, Assisi and Pisa are a few of the country's renowned cities along with Italy’s 95,000 monumental churches, 40,000 forts and castles and 5,600 museums and archaeological sites. Whether you ride a gondola through Venice’s Grand Canal, stroll along Lake Como or visit the Coliseum in Rome, the opportunities are endless when visiting Italy.
More on bicycling in Italy >
View all Italy bike tours >
Cycle through wine country and sample the produce
Tuscan Wine Classic
Tour Company Background: Cicloposse: Guided
(View Self-guided)
Where are you located?
Pienza and Siena, Italy
In which countries do you offer tours?
Italy
How many years has your company been in business?
Since 1994 - 18 years
How many employees do you have in your office?
3 employees
From which countries do most of your clients come?
From the USA and Canada
About what percentage of your clients are from English-speaking countries?
99%
Cycle through wine country and sample the produce
Tuscan Wine Classic
Tour Company Background: Cicloposse: Self-guided
Where are you located?
Pienza and Siena, Italy
In which countries do you offer tours?
Italy
How many years has your company been in business?
Since 1994 - 18 years
How many employees do you have in your office?
3 employees
From which countries do most of your clients come?
From the USA and Canada
About what percentage of your clients are from English-speaking countries?
99%
Cycle through wine country and sample the produce
Tuscan Wine Classic
Terms and Conditions: Cicloposse: Guided
(View Self-guided)
Cancellations.
In the event that you cancel your participation on the trip, CICLOPOSSE 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 CICLOPOSSE to cancel a tour. In the event of cancellation, a full refund will be sent to the client and this constitutes full settlement. CICLOPOSSE is not responsible for other expenses incurred such as pre-paid hotel reservations or non-refundable airline tickets.
Trip Insurance.
CICLOPOSSE 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.
Responsibility.
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. CICLOPOSSE 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, CICLOPOSSE is not responsible for damage, loss or theft of your personal belongings
Accommodations.
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.
Responsibility:
Cicloposse 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 Cicloposse 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. Cicloposse 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. Cicloposse 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.
Release:
By submitting a booking request, I have and do hereby fully assume all risk of illness, injury, or death and hereby release CICLOPOSSE 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.
Cycle through wine country and sample the produce
Tuscan Wine Classic
Terms and Conditions: Cicloposse: Self-guided
Cancellations.
In the event that you cancel your participation on the trip, CICLOPOSSE 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 CICLOPOSSE to cancel a tour. In the event of cancellation, a full refund will be sent to the client and this constitutes full settlement. CICLOPOSSE is not responsible for other expenses incurred such as pre-paid hotel reservations or non-refundable airline tickets.
Trip Insurance.
CICLOPOSSE 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.
Responsibility.
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. CICLOPOSSE 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, CICLOPOSSE is not responsible for damage, loss or theft of your personal belongings
Accommodations.
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.
Responsibility:
Cicloposse 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 Cicloposse 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. Cicloposse 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. Cicloposse 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.
Release:
By submitting a booking request, I have and do hereby fully assume all risk of illness, injury, or death and hereby release CICLOPOSSE 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.