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Italy - Tuscany

Italy - Tuscany

Degree of difficulty - B

Justifiably famous for its fine food and wine, magnificent rolling landscapes and medieval walled hilltop towns, Tuscany is a classic destination for cyclists.

Our Safari begins in the heart of the Tuscan landscape where we are staying in a typical Italian villa for two nights. Our first day's cycle takes us amongst the vineyards of the chianti classico region to the magnificent San Gimignano where we can indulge in an ice cream in the cobbled town square. The next day we move on to the UNESCO world heritage city of Siena with its incredible piazza where we spend the night within this walled city.

A beautiful patchwork of neat vineyards, dark green olive groves, cypress trees unfold before us as we head towards the medieval towns of Montalcino and Montelpulciano, two of the best examples of walled towns in the region. We stay in them both to soak up their atmosphere whilst enjoying their excellent local food and wine, a wonderful end to a perfect week!


DAY 1 Arrival in Poggibonsi

You will be met by our representative at the train station in Poggibonsi and driven to your villa in Staggia near Castellina in Chianti (10 km – 20 min by car), where you will enjoy an excellent Italian supper. Villa Lechi is a typical Italian villa perched on top of a hill with lovely panoramas of the surrounding Tuscan countryside.

DAY 2 Colle Val de’Elsa, San Gimingnano, Lecchi 35 km
Departing from Villa Lecchi, first you will encounter the fortified town of Monteriggioni, its round distinctive shape dominating the surrounding plain; then on to Colle Val d'Elsa and its glass blowing artisans, some of which you can visit. The beautiful and famous walled town of San Gimignano with its lovely towers will require more time and a couple of hours of window shopping before heading back to Villa Lecchi.

DAY 3 Villa Lecchi, Castellina in Chianti, Siena 52 km
The day begins winding its way through Chianti roads, in a landscape of luscious, vineyards and superb wineries. Castellina in Chianti is our first stop for the day. The town has a number of buildings of historical and artistic interest and is well known for its links with the Chianti Classico wines bearing the famous black rooster symbol. Further along the route the classical walled town of Monteriggioni sits on top of a hill dominating the surrounding landscape. The final destination for the day is the magnificent world heritage site of Siena with one of the most famous squares in Italy: Piazza del Campo.

DAY 4 Siena, Buonconvento 32 km
A nice day through winding Chianti roads, while the landscape is changing from luscious, vineyards to the more linear cypress-crested hills of the "Crete" near Buonconvento. Murlo is a nice little village on your way to the nice farm where you are spending the night. You will be glad to get a refreshing dip in the swimming pool or a relaxing massage and a sauna at their beauty farm.

DAY 5 Buonconvento/Montalcino 46 km
The day starts with a few ups and downs before an engaging gentle 8km climb to reach the Monte Oliveto monastery, located in the heart of the “badlands” of the Crete Senesi. The monastery traces its foundation to 1313 and has three 15th century cloisters. The route then brings you through S. Giovanni d’Asso before you tackle the last climb of the day (4km) to reach our lovely hotel in Montalcino, the Brunello homeland, where we spend 2 nights.

DAY 6 Sant’Antimo Abbey
A chance for an easy day around this fortified town from the bastions of which you will enjoy a 360° view. The castle here is almost intact and is built into the walls of the town. A small and pleasant detour is to follow the descending trail that will lead you to the beautiful and peaceful church of Sant’Antimo where you may be able to listen to Gregorian chants.

DAY 7 Montalcino, Pienza/Montepulciano 45 km
From the thermal square of Bagno Vignoni to Pienza, the renaissance jewel redesigned by the Pope Pio II to become a "liveable" town; a dirt road will take you to Montichiello, a nice little village immersed in the "Crete". You can stop there for a nice lunch or just for a cappuccino before continuing to Montepulciano one of the nicest Renaissance towns of Tuscany. Visit the town that is also an agricultural centre well known for pecorino cheese and truffle production.

DAY 8 Homeward bound
Time to leave the bikes and the open roads and head home after breakfast. We will take you back to Chuisi Railway station where you can take a train back to Rome or Florence

Please note there is an "Easy" route option also, for more details please have a look at the tour dossiers.

€1090 per person sharing
€1270 for single occupancy (if travelling with others)
€1330 for solo traveller (if travelling alone)

€1020 per person sharing
€1200 for single occupancy (if travelling with others)
€1260 for solo traveller (if travelling alone)

€1090 per person sharing
€1270 for single occupancy (if travelling with others)
€1330 for solo traveller (if travelling alone)

Tour Includes

- 7 nights in village hotels
- All breakfasts and two dinners ( Tuscany Hills & Best of Tuscany & Umbria only )
- 27 speed hybrid bike / pannier bag
- Road books and maps
- Luggage transfer
- 24-hour help line
- Transfers as per the itineraries

E-Bike: €100
Road Bike: €40

Self Guided Tour Information

Start any day from 1 April to 31 Oct

Below is a list of places that we typically use, although of course this is depending on availability.

Best of Tuscany & Umbria


Day 12 Country House Treeesse Day 12 Country House Treeesse1 Day 12 Country House Treeesse2

Day 1 & 2: 3 S Country House


Day 3 La Corte del Poggio Day 3 La Corte del Poggio1 Day 3 La Corte del Poggio2

Day 3: La Corte del Poggio


Day 4 Hotel San Michele Day 4 Hotel San Michele1 Day 4 Hotel San Michele2

Day 4: Hotel San Michele


Day 5 Hotel Langolo Day 5 Hotel Langolo1 Day 5 Hotel Langolo2

Day 5: L’Agnolo


Day 6 Hotel FAttoria Pieve a Salti Day 6 Hotel FAttoria Pieve a Salti1 Day 6 Hotel FAttoria Pieve a Salti2

Day 6: Fattoria Pieve a Salti


Day 7 Hotel Dei Capitani Day 7 Hotel Dei Capitani1 Day 7 Hotel Dei Capitani2

Day 7: Hotel Dei Capitani

How to get to the start point in Siena: 

Closest airports to fly to: Pisa or Florence (both approx 1hr45mins), Rome(approx 4 hrs).

Trains to Siena TrenItalia 

As always please contact us in the office for more information (info@cyclingsafaris.com).

Tour map

We very much enjoyed this trip, though getting up some of those hills didn’t feel that ‘easy’! The bikes were brilliant - very light and well-geared, which helped a lot. Michele from Viadelsole was extremely helpful in explaining the routes; the directions were accurate and easy to follow. All the accommodation was of a high standard. We weren’t quite so keen on the agriturismo at Pieve a Salti but their swimming pool did make up for that.
We got a good feel for Tuscany - both the scenery and the lovely small towns we stayed at. The steep climbs to reach them were worth it!
All in all a really good experience, our first with Irish Cycling Safaris. So many thanks to you for organising it.

Barbara Lamplugh (Tuscany Easy June 2018)

We had a wonderful time on our Tuscany biking trip. The accommodations were perfect! Our favourite was the hotel in Montalcino with a view of the Tuscan Hills from our small terrace, but each had its own unique characteristics. Beppe and his staff there took great care of us. 
The maps and instructions for the self-guided biking were perfectly clear. The food was very good, local rep gave us good restaurant recommendations in Montalcino. 

Jennifer & Dwight (Tuscany Easy self guided June 2016)

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UCD, Dublin 4,

Telephone: +353 1 2600749
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