Tuscany Italy Cycling

Trip Length 6 Days
Group Size 4-12
Activity level
Starting from
$3,499 for REI Members
$3,899 for non-members
Departures May 2021-Oct 2022

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

Tuscany is the stuff of fairytales; 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.

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Trip Highlights

  • 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


This trip is rated Moderate Plus [3-4]. Participants should have cycling experience and be comfortable in the saddle for 4-6 hours per day. Rides consist of a both moderate and more vigorous cycling days covering 35-43 miles. Terrain is predominantly hilly with some long, steep climbs. Daily rides have total elevation gains and losses ranging from 1,100' - 4,400' with hill grades averaging 4-8% and with short pitches up to 15%. Participants should be comfortable riding on a variety of surfaces including paved roads, cobblestone streets, city streets with vehicle traffic and country backroads. Vehicle support is available when needed.

The countryside in Tuscany is very hilly with few flat sections, so a conditioning program beginning at least 3-6 months prior to departure is strongly recommended.

  • Road Cycling
  • Cycling

What's Included

Five nights accommodation; meals as noted in the daily itinerary; wine with included dinners; Day 1 group transfer from Chiusi train station to Pienza; choice of hybrid bike or road bike with map holder, and bicycle computer; skilled bi-lingual cycling guide; vehicle support while cycling; maps, trips notes and detailed route directions; luggage transfers; two wine tastings.


Hotels, 5 nights

Your wheels for the journey

Every great tour begins with a great bike, and our top-flight fleet has been carefully curated for your cycling adventure.

Want to bring your own bike?  You can do that too.

Your Adventure Itinerary

Day 1

Our first ride takes us 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

Day 2

A loop ride takes us 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’

Day 3

Traverse the Crete Senesi’s unusual, 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'

Day 4

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'

Day 5

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

Day 6

Pedal hills blanketed with vineyards and forests en route 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'

Gear List

The key to staying comfortable while on an active trip is layering. To get maximum comfort with minimum weight, you need versatile layers that mix and match to create the right amount of insulation, ventilation and weather protection. Try to bring only what is necessary—this will help you and the field staff.

Collection of selected R E I Co-op cycling merchandise and snacks laid out to pack for a bike tour

What to pack

Contact Us

Feel free to give us a call at 800-622-2236 should you have any questions regarding the gear list. The staff at our stores and Direct Sales (800-426-4840) will also be happy to help you with gear questions. Or check out REI Expert Advice , which has great information to help you prepare for your trip.