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Justifiably famous for its fine food and wine, magnificent rolling landscapes and medieval walled hilltop towns, Tuscany is a classic destination for cyclists.
We have two tours available in this beautiful area, Tuscany Hills and the Best of Tuscany & Umbria. We outline our Tuscany Hills tour on the website but dossiers for both tours are available under our Dossier Tab.
Our "Tuscany Hills" tour is a trip through time, from Etruscans tombs to Romans ruins, from Medieval hilltop towns to Renaissance basilicas. It also offers an incredible diversity of landscapes, from the vineyard-covered hills of Chianti & Brunello, to the cypress-crested mounds of the “Crete.”
Your journey will begin in San Gimignano. This walled medieval town has been designated a UNESCO World Heritage Site for its 14 feudal towers still standing & early Renaissance frescoes. From San Gimignano you will bike through the vineyard hills of Tuscany to Siena, another UNESCO World Heritage Site & home to some of the most remarkable art & architecture from the 13–15th centuries.
In Siena you can enjoy a glass of wine in the piazza where the 400-year old tradition of the Palio horse race takes place, climb medieval towers, or indulge in the famous spiced cake, “panforte.” Then continue deep into the country to reach the peaceful abbey of Monte Oliveto Maggiore, founded in 1313, before continuing on to the charming hilltop town of Montepulciano, where you can enjoy breathtaking views of the rolling hillside, splendid medieval architecture, & the exquisite DOCG Nobile di Montepulciano.
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A downloadable version of the itinery is available from the Dossiers Tab
Itineraries
Day 1
Tuscany Hills 2025 tour - 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 Lecchi is a typical Italian villa perched on top of a hill with lovely panoramas of the surrounding Tuscan countryside.
Day 2
Villa S. Lucchese - Colle Val d'Elsa - San Gimignano 40 km
Departing from Villa San Lucchese first you encounter Colle Val d’ Elsa and its glass blowing artisans some of which you can visit. San Gimignano with its towers will request more time and a couple of hours of window shopping before starting back to San Lucchese
Day 3
Villa S. Lucchese - Abbadia Isola - Monteriggioni – Siena 42km
Your cycle winds its way through Chianti, in a landscape of vineyards and superb wineries. Castellina in Chianti is your first stop, well known for its links with the Chianti Classico wines bearing the famous black rooster symbol. The classical walled town of Monteriggioni which sits on top of a hill dominating the surrounding landscape awaits before arriving at the magnificent world heritage site of Siena with one of the most famous squares in Italy: Piazza del Campo.
Day 4
Siena, Buonconvento 40 km
A lovely day cycling through quiet Chianti roads watching the landscape change 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 beautiful 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 beautiful farm.
Day 5
Buonconvento/Montalcino 46 km
You cycle a 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 to reach our lovely hotel in Montalcino the Brunello home land, where you spend two nights.
Day 6
Sant’Antimo Abbey 33 km
A chance to relax and enjoy the beautiful town of Montalcino from the fortified walls and bastions with a 360° view. The castle 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
You cycle to Bagno Vignoni to Pienza, the renaissance jewel redesigned by the Pope Pio II to become a "liveable" town. Onwards to Montichiello, a lovely little village immersed in the "Crete". You can stop there for lunch or a cappuccino before continuing to Montepulciano one of the nicest Renaissance towns of Tuscany. A town famous not only for its wine but also well known for pecorino cheese and truffle production.
- 7 nights in village hotels
- All breakfasts
- GPS reader application*
- Luggage transfer
- 24-hour help line
- Transfers as per the itineraries
Not included:
- bike rental
*In an effort to reduce our carbon footprint and contribute to a more eco-friendly business model, we have decided to discontinue the printing of route notes on paper starting from this year. Instead, we will be transitioning to a digital platform that utilizes a GPS reader application. The new app offers several advantages, making it easier to access and navigate routes seamlessly. You will be able to download the GPX files directly on your mobile device, allowing for greater flexibility and convenience, making navigation more accurate and efficient.
All your accommodation is booked. Your luggage is transported from hotel to hotel. You are given a map with a fully researched route. You will also have a hotline number should you need any assistance in any way.
Bike hire is not included in the tour package. However it is of course possible to rent a touring bike.
Electric Bikes are also available to rent. Please email us for more details on this
The daily distance is approximately 45km
If you cant cycle for any reason you can get a lift with the person who will transport your luggage. There may be a small fee you can pay to the driver. you will need to let them know the day before if possible.
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 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 )
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)
TUSCANY HILLS SELF GUIDED 2025
€1270 per person sharing
€210 for single supplement (if travelling with others)
€330 for solo travellers supplement (if travelling alone)
THE BEST OF UMBRIA AND TUSCANY 2025
€1270 per person sharing
€210 for single supplement (if travelling with others)
€330 solo traveler supplement
Tour information:
The tours can run from April to the end of October.
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).