Tuscany Cycling

Tuscany Cycling Itinerary:

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• Day 1 Our first ride through the Tuscany takes us from Pienza, a lovely renaissance town, to San Quirco, on the edge of the Val d’Orcia.

  Your 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. A warm up ride to San Quirico, a charming walled town on the northern edge of the Val d'Orcia, allows you to test ride the bike. There are barely more than a dozen streets in this tiny town, and they are all paved with real terra cotta. This evening we enjoy a welcome dinner in a local trattoria where we have the chance to taste homemade pici pasta. Dinner included.

  Driving: ~1 hour; Cycling: 12.5 miles; Terrain: Rolling hills; Elevation gain and loss: ~840'.

• Day 2 Our loop ride from Pienza to Radicofani takes us through landscapes that inspired Renaissance painters.

  After breakfast we begin a loop ride into the rolling countryside of the Val d'Orcia. 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 expansive, sweeping countryside makes for a visually stunning ride. The first several miles out of Pienza are mostly downhill with some gently rolling hills along quiet country roads. We then climb to reach Radicofani, an enchanting medieval village with a landmark rocca (castle) dating back to 987. It is one of the most impressive fortresses in Tuscany. From its tower there is an extraordinary view over the Val d'Orcia and the surrounding region. After a stroll around the stately old town, we head back into the country along winding cypress-lined roads. This evening we visit a farm to learn how pecorino cheese is made from sheep's milk. We sample the flavors this area is known for, including truffle, red pepper, and black pepper aged in nut leaves. Overnight in Pienza. Breakfast included.

  Cycling: 41 miles; Terrain: Rolling hills then ~1400' climb; Elevation gain: ~3,335'; Elevation loss: ~3,445'. Optional: 20 extra miles; more challenging.

• Day 3 Ride across Val di Chiana to Montelpulciano, famous for its Vino Noble, before riding to Cortona, a city whose roots lie in legend.

  Our ride begins with a fun descent from Pienza. Riding rolling hills across Val di Chiana, we reach Montepulciano, a medieval and Renaissance hill town sitting high on a limestone ridge. It is world-renowned for its Vino Nobile, a red wine that is considered among Italy's best by wine enthusiasts. Montepulciano is also a known for its pork, cheese, pici pasta, lentils and honey - all tempting options for lunch today. We can take time to explore a few of Montepulciano's famous sites, some of which date from the 16th century, such as the Piazza Grande with its duomo (cathedral), the wine cellar Cantina Del Redi in the beautiful Palazzo Ricci, and the magnificent Temple of San Biagio. Following our explorations we begin a pleasant five mile descent through vineyards where the only sound is the spinning of our wheels. After a brief climb, we pass through the town of Valiano. We then begin a long, slow climb towards Cortona, the delightful hill town made famous by Frances Mayes in her bestselling novel Under the Tuscan Sun. It is the main cultural and artistic center of the Val di Chiana. We dine this evening at a lovely restaurant in a 12th century building overlooking the central square. Breakfast and dinner included.

  Cycling: 35 miles; Terrain: Hilly until Montepulciano then relatively flat ending with a ~2.5 mile climb to Cortona; Elevation gain and loss ~3,050'. Optional: 25 extra miles on hilly terrain.

• Day 4 Pedal through olive groves and vineyards to the medieval town of Trequanda, set on a hill between Val di Chiana and the Val d' Asso.

  Leaving Cortona, there is an pleasant descent to the valley floor where we pedal through olive groves, vineyards, and depending on the time of year, fields of brilliant sunflowers. Continuing on, we ride up to Montisi, an ancient borgo (small village), situated on the ridge of hills separating the broad Val di Chiana and the unique landscape of Crete Senesi. The village is home to a diverse and highly talented group of artisans as well as some of Italy's most highly prized olive oil producers. The area is rich with colorful farms, hamlets and castles reminiscent of a Renaissance painting. Our final stop is the medieval village of Trequanda, one of the most unspoiled areas in the province of Siena. Crowned by the remnants of the ancient Cacciaconti castle, it is situated on a hilltop between the Val di Chiana and the Val d' Asso. Tonight we sleep in a country inn just outside the village where we can sample their wine and dine on locally produced fare. Breakfast included.

  Cycling: 39 miles; Terrain: Rolling hills, hilly; Elevation gain: ~1,650; Elevation loss: ~2,300'. Optional: 20 extra miles on hilly terrain.

• Day 5 Traverse the fascinating landscape of the Crete Senesi before entering Chianti and tasting its famed wine, Chianti Classico!

  Pedaling north, we pass two lovely southern Tuscan towns before making a stop at the impressive red brick Abbey of Monte Oliveto Maggiore, one of the most important Benedictine monasteries in Italy. Bernando Tolomei, a successful and pious Sienese merchant, founded the Benedictine order of Monte Oliveto Maggiore in 1313, and the monastery became a hermitage for the regional elite. The Great Cloister walls are decorated with marvelous frescoes depicting the life of St. Benedict. From the monastery we traverse the famous Crete Senesi region, a geologically fascinating area peppered with strange rock formations and lone farmhouses flanked by twin cypress trees.

  This afternoon we enter the Chianti Classico region passing through the picturesque towns of Castello di Bossi and San Felice, both of which have acclaimed wineries. 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 eat lunch in the town of Gaiole in Chianti, which has been ranked by Forbes magazine as "Europe's Most Idyllic Place to Live." A few more miles bring us to Radda in Chianti, our home for the night. Radda is a town with origins dating back to 2,000 B.C. Today its inhabitants are involved in the production of handicrafts as well as fine wines and olive oils. This afternoon we taste the region's famed wine and learn about its production at Castello di Albola winery. Breakfast and dinner included.

  Cycling: 37.5 miles; Terrain: Hilly; Elevation gain: ~3,300'; Elevation loss: 2,700'. Optional: 15 extra miles on hilly terrain.

• Day 6 Pedal hills blanketed with vineyards and forests and watch the towers of Siena, our final stop, materialize in the distance.

  The previous days have prepped our legs for the famed hills of Chianti which await us! 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 Castellina 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 enchanting city. We pedal to the front door of our hotel, perfectly situated on the edge of Siena's historic center. Late afternoon will afford the opportunity to shop, wander the medieval backstreets or relax in the famous square and watch local residents stroll by. A farewell dinner provides the opportunity to enjoy the region's renowned cuisine and toast to a great cycling adventure. Breakfast and dinner included.

  Cycling: 40 miles; Terrain: Hilly; Elevation gain: ~3,020'; Elevation loss: ~3,640'. Optional: 15 extra miles on hilly terrain.

• Day 7 Depart Siena any time or continuing exploring this enchanting city.

  Our adventure ends after breakfast at the hotel. Siena offers easy connections by train to Florence or Rome. Breakfast included.

Although we do our very best to adhere to the schedule above, this itinerary is subject to change for numerous reasons beyond our control including weather and terrain conditions.

Please check with us before purchasing your airline tickets to ensure your trip has the necessary minimum number of participants required to operate. 

We provide bikes that have been custom built by our guide for cycling conditions in Tuscany. Travelers have the choice of a hybrid bike (aluminum frame) with flat handlebars or a road bike (carbon frame) with drop handlebars. These bikes are Italian made with a carbon fiber fork, and Shimano Ultegra, Shimano 105 or Deore 27-speed components. They have a low gearing ratio to assist with hill climbing. Each bike is equipped with a map case and bicycle computer. Handlebar bags are also available for the hybrid bikes with flat handlebars.

If you are traveling alone and specifically request single accommodations, you will be asked to pay the full single supplement noted on the trip itinerary. If you wish to share accommodations, we will assign you a roommate if one is available. If a roommate cannot be found, you will be asked to pay a reduced single fee, which is half of the full single supplement. Please be advised that there are a limited number of single rooms available on most departures.

Six nights accommodation; meals as noted in the daily itinerary; 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; one cheese and olive oil tasting.

Airfare to Italy; train to Chiusi; transfer from Siena on Day 7; bicycle helmet (required, please bring your own); lunches and 2 dinners; beverages; optional guide gratuities; insurance of any kind; items of a personal nature.

This trip is rated Moderate Plus [3-4] and consists of a combination of moderate and more vigorous cycling days covering 35-40 miles over predominantly hilly terrain with some long, steep climbs. Daily rides have total elevation gains and losses ranging from ~1,600'-3,500' with hill grades averaging 4-8% with short pitches up to 15%. Vehicle support is available when needed. All participants should have cycling experience that includes maintaining control of the bike, shifting gears, braking, ascending hills, descending hills, cornering, riding in groups, riding with traffic, and knowledge of bicycle safety, in addition to being comfortable in the saddle for 4-6 hours per day. While the majority of the cycling route is on a paved surface, the pavement may be uneven, potholed, or topped with gravel or other debris. Additionally, the inclement weather may affect any riding surface causing additional debris or the surface to become slick. All participants should be comfortable riding on a variety of surfaces in addition to paved roads such as cobblestone streets, as well as city streets with vehicle traffic, and country back roads.

The countryside in Tuscany is very hilly with few flat sections, so a regular conditioning program beginning at least 3-6 months prior to departure is strongly recommended. Cycling hills, walking, running on similar terrain along with a daily stretching regimen are all great ways to prepare for this adventure.

Departures are scheduled to avoid mid-summer heat and crowds while still traveling during periods that typically offer ample amounts of sunshine. Daytime temperatures range from 70 - 80 F, dropping 10-15 degrees at night. Early May and October departures have slightly cooler temperatures. Rain is possible on any departure; while rain is not typical, participants must bring appropriate rain gear.

This trip is subject to the booking information set forth in the current REI Adventures Reservation Information. Please read this information carefully and call us if you have any questions. A full gear list and pre-departure information is sent upon sign-up. We highly recommend the purchase of travel insurance through REI Adventures. If coverage is purchased at the time of your initial reservation, the 'Pre-existing Conditions Exclusion' is waived (certain exclusions apply).

We look forward to having you join us for the trip of a lifetime! Why wait? Space is limited, reserve your adventure today.

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.

Gear Checklist

Things to Consider

• Always pack essential items such as your passport, REI Adventures final bulletin, money, set of cycling clothes and footwear, eyewear and medications in your carry-on baggage in case your luggage is delayed.
• Helmets are required, so please bring your own. We also recommend brightly-colored bicycle clothing for visibility and safety.
• Formal attire is not required at restaurants. Comfortable, casual clothes are appropriate for sit-down meals. We suggest bringing slacks, shorts that are mid-thigh or longer, skirts, or summer dresses in fabrics that are easy to wash and wear.
• Rain is possible on this trip. While it can be difficult to stay completely dry while cycling in the rain, full raingear—jacket, pants, shoe covers, helmet cover and gloves—can help make you more comfortable. The best raingear is waterproof, breathable and seals well against the rain.
• Cycling shoes designed for touring, sometimes called sport or touring shoes, are an ideal choice for this trip. They have recessed cleats and a more flexible rubber sole so that you can be as comfortable walking while off the bike as you are efficient when riding. There is a large selection of shoe options available to the touring cyclist all designed for style, comfort, and performance both on the bike and off. Be sure your cleat choice matches your pedal system (sold separately from shoes). Check your local REI store or REI.com for options.
• If you own road cycling shoes (stiff sole, protruding cleat, no traction), we suggest you bring cleat covers for short walks and/or be sure to keep a pair of walking shoes in the support van so you can change before walking around towns during lunch or other stops.
• If you are not bringing a shoe and pedal system, you will need a shoe designed for cycling or cross training to be used with the provided flat pedals (toe clips/baskets are optional). Consider these features if you are bringing a cross training shoe: lightweight, closed toe, designed with stiffer soles to provide more efficient energy transfer as you pedal. Stiff soles protect your feet while riding and support the full length of your foot to reduce cramping and fatigue.