Tuscany Italy Cycling

Tuscany Italy Cycling

Tuscany Italy Cycling

tuscany - Guided

Pedal across the Tuscan countryside

Tuscany is the stuff of fairy tales!
Given to warm climates and warmer people, lush vineyards that spill onto the hillsides, and a poetic charm that stays with us.
To see this area from the seat of a bike is legendary. Our journey takes us to the finest hill towns in Tuscany to savor traditional cuisine and taste wines as we ride among centuries-old fortified towns, villas and palazzi.

wow moments

  • Explore the lush hillsides of Tuscany on a fully-supported bike tour
  • Pedal past scenic vineyards, Renaissance towns, and beautiful pastures
  • Enjoy fresh cuisine and taste Italy’s famed wines
  • Ride up to 43 miles a day, with ample opportunity to explore and soak in the views

unforgettable 6-days journey

Our destinations range from the Renaissance town of Pienza, to the tree-lined hills of Crete Senesi and, finally, to lively Siena.
We bike approximately 40 miles a day through rolling hillsides, our views filled with forests and cypress trees. Our local guides show us Italy’s most authentic side, leading us through charming villages to local artisans, and providing us with historical background along the way.
Cycling along the countryside is the perfect opportunity to enjoy the best of Tuscany.


From lovely Pienza to charming Bagno Vignoni.

Our trip begins in Chiusi, Italy. Situated on the main line from either Florence or Rome, the Chiusi train station is a convenient place to meet your guide and fellow travelers for the group transfer to Pienza, a lovely renaissance town conceived by Pope Pius II. Our hotel occupies a 15th century convent located in the center of town. After checking into our rooms and changing into cycling clothes, our guides conduct a bike-fitting session. Time permitting, a warm up ride takes us to Bagno Vignoni, a thermal village located in the Val d’Orcia Artistic, Natural and Cultural Park. The village is famous for its thermal spa, which has been in use since Roman times. This evening we enjoy a welcome dinner in a local trattoria where we have the chance to taste homemade pici pasta. Dinner included.

Cycling: 19 miles (2–3 hours, paved road), Elevation gain/loss: +1,300 / -1,300′; Van transfer: 1 hour


Past landscapes that inspired Renaissance painters

We begin our day with a loop ride into the rolling countryside of the Val d’Orcia, A UNESCO World Heritage Site. The distinctive landscape, with its flat chalk plains interspersed by conical hills topped by fortified settlements, inspired the Sienese artists Daccio and Lorenzetti. Their paintings illustrate the beauty of Renaissance agricultural landscapes where inhabitants are depicted as living in harmony with nature. The first several miles out of Pienza are mostly downhill with some gently rolling hills along quiet country roads. We then climb to reach Castiglione d’Orcian, an enchanting medieval commune with a landmark rocca (castle) dating back to 1250. It is one of the most impressive fortresses in Tuscany, with extraordinary views over the Val d’Orcia and the surrounding region. We descend to the Abbey of Sant’Antimo, a monastery originally constructed during the reign of Charlemagne; there may be an opportunity to hear the resident monks chanting. En route to the Etruscan village of Montalcino, we pass through magnificent vineyards that produce several of Italy’s most notable wines, including the world-renowned Brunello di Montalcino. This afternoon we have time to explore the narrow cobblestone streets of this medieval town before cycling back to our hotel in Pienza. Breakfast and lunch included.

Cycling: 43 miles (5–6 hours, paved road), Elevation gain/loss: +4,329 / -4,329’


Traverse the Crete Senesi lunar-like landscape.

Our ride begins with a fun descent from Pienza, pedaling through the picturesque villages of Castelmuzio and Trequanda. We soon roll into a postcard Tuscan landscape rich with olive groves, geometrical vineyards and slender cypress trees. Cycling through the Crete Senesi area, the verdant hills give way to a lunar-like landscape of chalk cliffs and gullies. These Tuscan badlands consist of strange rock formations and lone farmhouses flanked by cypress trees. We arrive in Lucignano, a well preserved hill-top village that is a remarkable example of medieval urban planning. The village is known for its agricultural and artisan traditions. Its most well-known products include extra-virgin olive oil, honey, ceramics, and sandstone used in architecture and sculpting. Breakfast and dinner included.

Cycling: 37 miles (4–5 hours, paved road), Elevation gain/loss: +3,491 / -3,392′


Arrive in Chianti, famed for its wine.

Pedaling north, we pass two charming southern Tuscan towns before making a stop at Castelnuovo Berardenga, the gateway to the Chianti Classico region. Continuing on, the vineyards of the acclaimed wineries Castello di Bossi and San Felice provide a rich landscape to our cycling route. The Castello di Brolio winery, one of the oldest wineries the world, is where Chianti wine was born. The Ricasoli family, owners of the Castello di Brolio since 1167, is responsible for the special blending of grapes we now consider Chianti Classico. We’ll stop for lunch in Gaiole, a lively town located along the river Massellone and home to the annual l’Eroica vintage (pre-1987 steel frame) bicycle race. A few more miles bring us to Castellina in Chianti. Castellina’s medieval street, the Via delle Volte, was originally open to the sky, but over the years houses and shops have encroached on the ancient city walls, covering the street and providing an intriguing underground home for shops and restaurants. This afternoon we taste the region’s famed wine and learn about its production at a Chianti classic winery. Breakfast and dinner included.

Cycling: 43 miles (5–6 hours, paved road), Elevation gain/loss: +3,804 / -3,631′


Marvel at San Gimignano’s Medieval Towers.

A full day is spent further exploring the Tuscan countryside. This morning we pass Monteriggioni, a small hilltop town whose medieval towers inspired Dante. We continue cycling through a vibrant landscape of rolling hills, vineyards, and sunflower fields until reaching San Gimignano. This walled medieval hill town is famous for the fourteen medieval “skyscrapers” that dominate its skyline. Affluent families erected these towers in the 12th-century to display their wealth and power. You’ll have time this afternoon to explore the town’s narrow cobblestone streets and wide piazzas before returning to Castellina in Chianti. This evening we dine at a tavern overlooking the endless vineyards in the valley below. Breakfast and dinner included.

Cycling: 36 miles (4–5 hours, paved road), Elevation gain/loss: +2,898 / -3,765′;


Pedal hills blanketed with vineyards and forests to Siena.

The previous days have prepped our legs for the ride through the famed hills of Chianti! The first stretch crosses an unbelievably scenic clutch of hills blanketed with vineyards and thick forests. It’s breathtaking, and so is the ride. We bike along a winding panoramic road to Radda in Chianti, home to many important archaeological finds hinting at its ancient past. The gothic towers of Siena materialize on the horizon as we continue our ride towards this medieval city. We’ll share a final celebratory lunch on the outskirts of Siena and toast a great cycling adventure before saying our goodbyes at the train station in the mid-afternoon. Hop on a train to your next destination or better yet, extend your stay in the enchanting city of Siena. Breakfast and lunch included.

Cycling: 34 miles (4–5 hours, paved road), Elevation gain/loss: +2,616 / -3,642′

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single file on bikes
fantiwinetour scaled Tuscany Italy Cycling
Tour start in Pienza
Tour end in Siena

italy tuscany cyclin map



best period Spring & Fall

DIFFICULTY medium to challenge



Tour Reviews

6 July 2022

Hi Giuliana,
We are back home in the US now for about a week and a half, after finishing a glorious trip (Tuscany Italy Cycling) with Cicloposse. Everything about the trip was perfect, and we wanted to thank you and your family for making our trip so memorable. There were so many things that we are grateful and thankful for, which included (to name just a few):
• Your allowing us to do the tour with just the six of us.
• The historic places that were chosen for our lodging. They were all spotlessly clean, comfortable and full of history. We enjoyed them all, especially Castello di Gargonzo where the owner gave us a tour.
• The maps!
• The bikes (the best ever)!
• The coffee breaks (and the towns that were chosen for our coffee breaks)
• The excellent guidance and company provided by Marco, Tomaso and Panos.
Fidelma (Cycle West Ireland), had so many nice things to say about Cicloposse, and we were very happy to make your acquaintance, well as Marco, Tomaso and Panos. Maybe we will meet Mathilde as well sometime in the future.

We have so many happy memories of our trip, and please thank everyone for all that they did to make the trip so wonderful. We have already recommended your company to friends and are already thinking about a way to make a future trip with Cicloposse happen for our family.

Kind Regards to All,

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Price & Inclusions


Cost: Euro 2750  per person in double occupancy
single room supplement euro 750


Five nights in superior hotels with private bath and breakfast
Four dinners, two lunches & two wine tastings
Snacks and drinks along the way
All maps, trip notes and detailed route directions
GPS: offline maps, and voice navigation with ridewithgps app
All Shuttles and technical assistance
Van Support, all baggage transfers
Experienced English speaking guides
Cicloposse water bottle
Sales taxes

Not included

Airfare to Italy, train to Chiusi, 3 lunches, 1 dinner, beverages, gratuities, travel insurance, laundry expenses and items of a personal nature.

Bike Rental for entire tour
Hybrid bike   euro 180
Race bike, Gravel, E-bike        euro 250

Relais Il chiostro di Pienza

This 15th-century convent in Pienza’s heart exudes tranquility and heritage. Its preserved beamed ceilings, frescoed walls, and a serene garden overlooking Val d’Orcia captivate visitors.

Castello di Gargonza

Immerse yourself in the tranquillity of a thirteenth-century fortified village within medieval walls. Wander through carefully restored houses, preserving the simplicity of rural life and offering forest trails to explore

Palazzo Squrcialupi – Castellina

Steeped in medieval history, Palazzo Squarcialupi resides in Castellina’s historical town center. Surrounded by spacious gardens and featuring a charming swimming pool, this palace underwent a luxurious renovation.

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