Cycling and Walking Holidays

Tuscany offers a wonderful venue for walking and cycling holidays – thousands of acres of wooded valleys, rolling open countryside and farm tracks to explore.

We are in the process of developing walks and cycle tours to suit all ages and abilities, supervised by our British staff based in Tuscany. By making use of our own minibuses and cars we are able to offer the chance to enjoy parts of Tuscany without the requirement to find circular routes or to have to double-back to return to a starting point.

We can drop you off at a starting point for a particularly interesting walk for instance and collect you later that day. In this way you can really enjoy the parts of the countryside that you want to see without enduring parts you might not to see.

We are happy to discuss your specific requirements and tailor-make an itinerary especially for you and your group. As an example we arranged a 5 day tour of southern Tuscany for a group of 6 keen cyclists from Ireland. Based at the Hotel Bosco della Spina, near Murlo, we planned different routes each day radiating from the hotel in different directions. They cycled up to 120 kms per day, dining each evening at local traditional restaurants that we were able to recommend to them. Our service included airport transfers, to alleviate the requirement for car hire, daily transfers from the end of their cycle route and then transfers to and from restaurants each evening (allowing the group to enjoy the local Tuscan wine to the full!).

Sample Itinerary

Day 1

Depart from home city for your flight to Italy (Rome, Pisa or Florence).

Day 2

Arrive in Italy, and transfer to Poggibonsi and our hotel. Poggibonsi, situated between Siena and Florence, is served by frequent bus and train service from both cities. Off the tourist path, the town has retained its regional authenticity and is a conveniently located starting point for our adventure.

Day 3

After breakfast, our staff will give a orientation briefing before we begin our ride through the countryside past the hilltop town of Castellina in Chianti and the walled 13th-century village of Monteriggioni. This afternoon, we cycle over rolling terrain dotted with farms, small villages and fields of sunflowers, to our charming hotel for the next three nights. The Villa Cennina is a converted country house that overlooks the distant towers of Siena and is a perfect base of exploration for our itinerary. Tonight's dinner is in the hotel garden. Cycling: 35 miles.

Day 4

Today's ride takes us through the beautiful wooded hills west of Siena known as La Montagnola. We follow an old pilgrimage route past ancient churches and stone farmhouses, and enjoy a picnic amidst the olive groves and medieval towers of the tiny hamlet of Torri. A treat awaits upon our return to our guesthouse this afternoon as a wine-tasting precedes tonight's dinner allowing us to sample some of the region's delicious vintages. Cycling: 37 miles.

Day 5

Historic Siena, originally established as a Roman military colony in the first century BC, is home to an incredible number of artistic and architectural treasures. This morning, a short but hilly ride takes us into this enchanting city where we'll have time to shop, wander the medieval backstreets, visit the museums or just relax in the famous square (Il Campo) and watch local residents stroll by. Cycling: 25 miles or optional 40 miles.

Day 6

Those who have seen Bertulucci's Stealing Beauty or The English Patient will immediately recognize the Crete Senese, with its vast and undulating wheat fields punctuated by majestic cypress trees and the occasional farmhouse. We'll spend much of the day on our bikes exploring this haunting region located in the central Tuscan countryside. Late this afternoon, we transfer to our next hotel in Asciano. This small town has a history of some 2,500 years and a fascinating new museum that recounts the history of the Etruscan people Cycling: 38 miles.

Day 7

We begin the day with a challenging but rewarding ride to the fabulous monastery of Monte Oliveto Maggiore. Giovanni Tolomei of Siena founded the Benedictine order of Monte Oliveto Maggiore in 1313 and upon arrival at the monastery, we'll seek out the Great Cloister where famous frescoes are found depicting the life of St. Benedict. A gorgeous afternoon ride to the striking hilltop town of Montepulciano takes us along small roads that wind their way up, over, around and between tiny villages surrounded by olive groves and vineyards. Our hotel for the next two nights is located inside the walls of Montepulciano and affords spectacular views to the south over the Valley of the Orcia and on to Lago di Trasimeno. There is time to explore the town's labyrinth of narrow streets and enjoy a cool glass of Prosecco in the main piazza before dinner. Cycling: 30 miles.

Day 8

Our final day of cycling incorporates a fantastic ride into the Orcia Valley and through Pienza. All of Pienza's major buildings were constructed between 1459 and 1462 as Pope Pius II, a local boy, issued a Papal Bulletin decreeing that Pienza was to be a regional center of art. The Duomo was one of the first Renaissance cathedrals in Tuscany and was consecrated in 1462. This afternoon, one final rolling ride brings us back to Montepulciano where we have our farewell dinner and toast one another with the town's famous Vino Nobile di Montepulciano. Cycling: 30 miles.

Day 9

After breakfast transfer back to Rome, Pisa or Florence.

Cycling Day with Picnic Lunch

The Tuscan countryside around our featured hotels offers some great cycling, best enjoyed with the help of some local knowledge.

We have planned a number of different routes - some starting at your accommodation and others requiring a transfer to and from the beginning and end of the route. You will be provided with bicycles (including children's bikes, child seats and 'tag-a-longs' for children if required) and a detailed map of the route, showing points of interest and places to visit. A picnic lunch will be provided at a pre-determined point. Lunch will be typical Tuscan fare. On some routes we will offer a meal at a restaurant instead of a picnic. Although most of our planned routes avoid the most undulating countryside, it should be noted that much of the Tuscan terrain is hilly and all routes include short climbs. All avoid the major roads however. Some routes are paved and some are on dirt track ('strada bianca').

What's Included?

All minibus transfers.

Comprehensive route map/planner.

Bicycle hire including children's bikes, child seats and tag-a-longs.

Picnic or restaurant lunch.

Emergency minibus rescue service!!!

Sample Routes

Route 1

The Lands of the Berardenga Running through the Chianti hillside, east of Castelnuovo Berardenga, this route is on mostly unpaved roads and is a chance to really appreciate the Chianti countryside. Lunch is taken beside a pretty mountain stream and the views from the area near Montebenichi are spectacular.

Start and return point: Hotel Borgo Monestero, Bucine

Distance: 30 kms

Road Type: Mostly unpaved

Transfer times to start / finish of route: From the Borgo Monastero - 0 minutes. Casabianca - 25 minutes. Le Piazze - 50 minutes.

Route 2

A lovely route starting at Pienza, the home of Pecorino cheese, taking in the wine cellars of the fine Nobile di Montepulciano wines. The city is definitely worth a visit and wine tasting is available. After a picnic (or light lunch at the Trattoria di Gagnano) the route then winds its way south and then east to one of the prettiest stone villages in the Vald'Orcia - Monticchiello and then back to Pienza.

Start and return point: Pienza

Distance: 25 kms

Road Type: Mostly paved

Transfer times to start / finish of route: From the Borgo Monastero - 1 hour. Casabianca - 40 minutes. Le Piazze - 75 minutes.

Route 3

Lago Trasimeno. Starting at the town of Passignano on the north side of Lago Trasimeno, our route goes east and then south following the lake shore. You will pass plenty of quiet beaches, before the route passes through Monte del Lago and San Feliciano. After a picnic on the banks of the lake, the route now continues west and finishes at Castiglione del Lago.

Start point: Passignano

Return point: Castiglione del Lago

Distance: 37 kms

Road Type: Paved

Transfer times to start / finish of route: From the Borgo Monastero - 35 minutes. Casabianca - 30 minutes. Le Piazze - 1 hour.

Route 4

Chianti Classico. Our route starts at the Hotel Le Piazze and continues down through the vineyards of Fizzano onto Lilliano and then climbs up to Castellina in Chianti. After a brief visit to this typical Chianti town, the route continues on to Rada in Chianti and then on to Gaiole in Chianti, finishing up with a wine tasting at the attractive Castello di Meleto.

Start point: Hotel Le Piazze

Return point: Castello Meleto

Distance: 32 kms

Road Type: Paved and unpaved

Transfer times to start / finish of route: From the Borgo Monastero - 50 minutes. Casabianca - 1 hour. Le Piazze - 0 minutes.

To discuss your walking or cycling holiday requirements, click on the 'Contact Us at the top right-hand side of the page.