guided
Nature, culture, and cuisine in Tuscany
Essence of Tuscany
Tour Description: Guided
Join us on this total immersion into Tuscany. Our back roads head into rolling hills and through the fortified medieval villages of an untouched Toscana. Goal of the bike trip is also enjoy the genuine Tuscan cucina: fruity olive oil, pecorino sheep-milk cheese and classic best Tuscany wine: Brunello (which has made Tuscany so famous), Chianti and Nobile. You will taste a selection of our favorite producers during our special events.
Traveling with a small group of fellow adventurers and Tuscany's leading biking guide, you'll enjoy a wonderful combination of nature, culture, cuisine and fun.
Learn more about guided tours.
Nature, culture, and cuisine in Tuscany
Essence of Tuscany
Tour Description: Self-guided
(View Guided)
Join us on this total immersion into Tuscany. Our back roads head into rolling hills and through the fortified medieval villages of an untouched Toscana. Goal of the bike trip is also enjoy the genuine Tuscan cucina: fruity olive oil, pecorino sheep-milk cheese and classic best Tuscany wine: Brunello (which has made Tuscany so famous), Chianti and Nobile. You will taste a selection of our favorite producers during our special events.
Traveling with a small group of fellow adventurers and Tuscany's leading biking guide, you'll enjoy a wonderful combination of nature, culture, cuisine and fun.
Learn more about guided tours.
Nature, culture, and cuisine in Tuscany
Essence of Tuscany
Highlights: Guided
- Tuscan wines: Brunello, Chianti, and Nobile
- Tuscan cuisine including oilve oil and pecorino cheese
- Orcia valley
- Montepulciano, known as the Pearl of the Sixteenth Century
- Monteriggioni, a town-in-a-castle
Nature, culture, and cuisine in Tuscany
Essence of Tuscany
Highlights: Self-guided
(View Guided)
- Tuscan wines: Brunello, Chianti, and Nobile
- Tuscan cuisine including oilve oil and pecorino cheese
- Orcia valley
- Montepulciano, known as the Pearl of the Sixteenth Century
- Monteriggioni, a town-in-a-castle
Nature, culture, and cuisine in Tuscany
Essence of Tuscany
Daily Program: Guided
Day 1: Pienza
Meet at Chiusi-Chianciano train station (a stop on all major Florence-Rome lines).
Transfer to Pienza, the most perfect Renaissance town in the world.
Check into your rooms at our hotel, which occupies a 15th century convent in the center of town. Meet your guide during a bike-fitting session and Get to know the rest of the group. First short ride to San Quirico: there are barely more than a dozen streets in this tiny town, but they are all actually paved with real terra cotta, and there's also a magical baptistery. Dinner in a wonderful local trattoria Le botte Pienza where you will taste the special Pici pasta.
Overnight in Pienza hotel Relais Il chiostro.
Day 2: Montepulciano & Orcia valley (41 miles/66 km)
Circular bike ride into Orcia valley: is a completely country ride and for the first 20 km we will ride downhill and very easy gentle rolling hills. Then the gentle climb to reach Radicofani, a medieval and enchanting village with a 1200 dating Rocca. After a stroll around the stately old town, we'll head back into the country, along some of those winding cypress-lined roads. We will go to Montepulciano, known as the Pearl of the Sixteenth Century, and visit ancient wine cellar and taste nobile wine for aperitif. Free dinner in town
Overnight in Pienza hotel Relais Il chiostro.
Day 3: Montalcino (29 miles/46 km)
Special event: brunello wine tasting
Today we'll start out on a long descent into the rolling green pastures of the Val d'Orcia, followed by a hearty uphill stretch that takes us to our reward: picturesque Bagno Vignoni. It's probably the only town you've ever seen where the main square is actually a thermal pool! Refreshed, we continue on to a secluded country Sant’ Antimo Abbey, where we might be in time to hear the monks sing vespers. Five miles later we'll be pedaling through the fortress walls into Montalcino. Wine tasting at cellar of the famed Brunello at Altesino winery. Afterwards we'll have plenty of time to visit the town, and perhaps purchase a couple of bottles to take home. Dinner at il Leccio in the little hamlet –discrict of Sant’Angelo in colle. Overnight in Montalcino hotel Vecchia Oliviera.
Day 4: Siena (34 miles/55 km)
Pedaling north, we'll whisk past a pair of typical southern Tuscany towns and make a stop at Monte Oliveto Maggiore, one of the most important Benedictine monasteries in Italy. We'll traverse the famous Crete region. This is Tuscany's answer to the Badlands, with strange rock formations and lone farmhouses flanked by twin cypress trees. In Siena, we'll check into our rooms at a lovely garden hotel. Free dinner Overnight in Siena at Palazzo Ravizza.
Day 5: Chianti (31 miles/50 km)
Special event: Chianti wine tasting
The previous days have prepped our legs for the famed hills of Chianti, which await us today! The first stretch crosses an almost impossibly scenic clutch of hills blanketed with vineyards and thick forests. It's breathtaking, and so is the ride! We'll rest our legs in Borgo San Felice and Castello di Brolio, where is possible also visit the castle’s garden - home of Baron Ricasoli and his world-renowned wine.
Back in the saddle, we continue along the same winding panoramic road to Radda in Chianti and then to Castellina in Chianti. In Castellina we'll check into our rooms at our hotel Palazzo squarcialupi, which occupies a historic palace with garden. Tonight Italian Pizza cooked in wood Owen. Overnight in Castellina at hotel Palazzo Squarcialupi
Day 6: San Gimignano (37 miles/60 km)
More vineyards await us today, but you'll be amazed at how different they look once we get into the district of San Gimignano. Our route includes two stellar hill towns. First there's Monteriggioni, literally a town-in-a-castle. Barely two hundred yards across, its eighty residents all reside within the picture-perfect round turreted walls that crown the hilltop visible for miles around. Also seen in the distance are the seventeen towers of San Gimignano. We'll have plenty of time to wander through the cobblestoned streets, window shop and buy a few last-minute Tuscan mementos for our friends and...why not, for ourselves too! Shuttle back to Castellina in Chianti. Our dinner will be at Tenuta Casanova, an organic farm outside the town - a short cooking lesson and then farewell dinner.
Overnight in Castellina at hotel Palazzo squarcialupi
Day 7: Departure
Departure after breakfast. End of the tour .
Nature, culture, and cuisine in Tuscany
Essence of Tuscany
Daily Program: Self-guided
(View Guided)
Nature, culture, and cuisine in Tuscany
Essence of Tuscany
Dates: Guided
Fridays: May 24, Jun 14; Sep 13; Oct 18, 2013
Nature, culture, and cuisine in Tuscany
Essence of Tuscany
Dates: Self-guided
(View Guided)
Nature, culture, and cuisine in Tuscany
Essence of Tuscany
Route Map: Guided

Nature, culture, and cuisine in Tuscany
Essence of Tuscany
Route Map: Self-guided
(View Guided)

Nature, culture, and cuisine in Tuscany
Essence of Tuscany
Packages and Prices: Guided
| Tour package (guided) |
 |
|
|
| |
|
| Per person, double occupancy |
€2150 |
| Single room supplement (1 person/1 room) |
€390 |
| Touring/hybrid bike rental |
€140 |
| High-end race bike rental |
€170 |
|
*The dollar amount is based on today's exchange rate and is subject to currency fluctuation.
Nature, culture, and cuisine in Tuscany
Essence of Tuscany
Packages and Prices: Self-guided
(View Guided)
Nature, culture, and cuisine in Tuscany
Essence of Tuscany
Included Services: Guided
- Six nights in superior hotels with private bath and breakfast
- Four dinners, one lunch & two wine tasting
- Snacks and drinks along the way
- Bikes (race or hybrid) and all gear
- All maps, trip notes and detailed route directions
- All Shuttles and technical assistance
- Support Van, all transfer baggage
- Services experienced guide
- Water bottle
Nature, culture, and cuisine in Tuscany
Essence of Tuscany
Included Services: Self-guided
(View Guided)
Nature, culture, and cuisine in Tuscany
Essence of Tuscany
Hotels: Guided
These are sample hotels and may vary based on availability.
Days 1 and 2: Relais Il Chiostro, Pienza
www.relaisilchiostrodipienza.com
The hotel is in a15th-century convent in a quiet, secluded location right in the center of Pienza. It is a was entirely rebuilt between 1459 and 1462, and was the brainstorm of Pope Pius II.
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: Palazzo Ravizza, Siena
www.palazzoravizza.it
The hotel is decorated in the style of a 1920’s mansion. Each of the rooms is decorated differently and provides all the needed conveniences.
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.
Nature, culture, and cuisine in Tuscany
Essence of Tuscany
Hotels: Self-guided
(View Guided)
These are sample hotels and may vary based on availability.
Days 1 and 2: Relais Il Chiostro, Pienza
www.relaisilchiostrodipienza.com
The hotel is in a15th-century convent in a quiet, secluded location right in the center of Pienza. It is a was entirely rebuilt between 1459 and 1462, and was the brainstorm of Pope Pius II.
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: Palazzo Ravizza, Siena
www.palazzoravizza.it
The hotel is decorated in the style of a 1920’s mansion. Each of the rooms is decorated differently and provides all the needed conveniences.
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.
Nature, culture, and cuisine in Tuscany
Essence of Tuscany
Bike Rentals: 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.
Nature, culture, and cuisine in Tuscany
Essence of Tuscany
Bike Rentals: Self-guided
(View 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.
Nature, culture, and cuisine in Tuscany
Essence of Tuscany
Surface and Terrain: Guided
The itinerary is on secondary asphalted roads. Tuscany is a hilly area, and the route that the tour follows has some generally rolling or hilly terrain.
The tour is rated moderate and is for cyclists in good physical condition.
Nature, culture, and cuisine in Tuscany
Essence of Tuscany
Surface and Terrain: Self-guided
(View Guided)
The itinerary is on secondary asphalted roads. Tuscany is a hilly area, and the route that the tour follows has some generally rolling or hilly terrain.
The tour is rated moderate and is for cyclists in good physical condition.
Nature, culture, and cuisine in Tuscany
Essence of Tuscany
How To Get There: Guided
Tour start
Nearest airport:
Nearest train station:
Tour end
Nearest airport:
Nearest train station:
- Castellina in Chianti-Monteriggioni
Tips on getting to and from your tour
Nature, culture, and cuisine in Tuscany
Essence of Tuscany
How To Get There: Self-guided
(View Guided)
Tour start
Nearest airport:
Nearest train station:
Tour end
Nearest airport:
Nearest train station:
- Castellina in Chianti-Monteriggioni
Tips on getting to and from your tour
Nature, culture, and cuisine in Tuscany
Essence of Tuscany
Weather: 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.
Nature, culture, and cuisine in Tuscany
Essence of Tuscany
Weather: Self-guided
(View 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.
Nature, culture, and cuisine in Tuscany
Essence of Tuscany
Tour Company Background: Cicloposse: 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%
Nature, culture, and cuisine in Tuscany
Essence of Tuscany
Tour Company Background: Cicloposse: Self-guided
(View 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%
Nature, culture, and cuisine in Tuscany
Essence of Tuscany
Terms and Conditions: Cicloposse: 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.
Reservations and payments.
A deposit of Euro 300 per person is required at the time of booking. Full payment is due 60 days prior to departure. If the balance is not received by the due date, Cicloposse will consider the reservation canceled and our cancellation policy, as outlined below, will apply.
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 1-9 above and I agree to be bound by their terms.
Nature, culture, and cuisine in Tuscany
Essence of Tuscany
Terms and Conditions: Cicloposse: Self-guided
(View 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.
Reservations and payments.
A deposit of Euro 300 per person is required at the time of booking. Full payment is due 60 days prior to departure. If the balance is not received by the due date, Cicloposse will consider the reservation canceled and our cancellation policy, as outlined below, will apply.
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 1-9 above and I agree to be bound by their terms.