Senza titolo 2 Tuscany Italy Cycling

Pedal across the Tuscan countryside on this unforgettable 6-day journey.

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.

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.

  • 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

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 lunch 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'; Van transfer: 1.5 hours

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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rei adventure tuscany cycling
rei adventure tuscany cycling
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rei adventure tuscany cycling
rei adventure tuscany cycling
rei adventure tuscany cycling
rei adventure tuscany cycling
rei adventure tuscany cycling
rei adventure tuscany cycling
rei adventure tuscany cycling
rei adventure tuscany cycling
rei adventure tuscany cycling
rei adventure tuscany cycling
Relais 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.
Castello di Gargonza
Castello di Gargonza is a thirteenth- century fortified village. Enclosed inside the medieval walls, the careful restored houses have retained the simplicity of rural life.Forest trails, relax in the Limonaia garden, sit at our bar with view of medieval tower and the woods surrounding the village
Palazzo Squrcialupi - Castellina
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 XV century City Wall. Set in the spacious garden, in a most suggestive position, is the swimming-pool. The palazzo has medieval origins and it has been renewed becoming a luxury palace

Essence of Tuscany

Price & Inclusions 

Cost: Euro 2,450 per person in double occupancy
single room supplement euro 450

Five nights in superior hotels with private bath and breakfast
Four dinners, three 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
Bike Rental per entire tour
Cicloposse water bottle
Sales taxes

Not included
Airfare to Italy, train to Chiusi, 2 lunches, 1 dinner, beverages, gratuities, travel insurance, laundry expenses and items of a personal nature.


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