Bike tour Cortona Tuscany, food and wine
Starting from Cortona on the border Umbria/Tuscany You will discover Montepulciano, Pienza, Montalcino and val d’Orcia, Le crete area through a landscape of sculpted curves designed over the centuries by wind, rain, and man.
Wow Moments
- Learn the rich history of Cortona, Land of the Tuscan Sun
- Explore the medieval hilltop villages of Tuscany, each uniquely beautiful
- Scenic cycling through the stunning landscape of the Val d’Orcia
- The stark and alluring “lunar” terrain of the Crete Senesi region
The mystique of this land lies not only in its landscape, but also in its nature, its vineyards and its history: oak woods, olive groves and vineyards watch over enchanting hillsides, medieval villages and historical monuments. Glorious ending in Siena
DAY 1
We’ll meet you at charming Villa Marsili (you can arrive by the train to Cortona/Camucia station)
After bike fitting and orientation you’re free to explore this delightful hill town, made famous by Frances Mayes in her bestselling novel Under the Tuscan Sun, Stroll the winding narrow – and steep! – medieval streets, then enjoy a fabulous dinner at one of our recommended restaurants.
DAY 2
Ride to Valle di Pierle and his splendid castle “Rocca”.
The history of Val di Pierle is closely linked to the history of the splendid castle (la Rocca) that dominates the valley. The castle was built prior to the 10th century and belonged to the marquises of Monte Santa Maria Tiberina. Another climbs and reach the top of hill Cima di Tuoro from where you will be able to enjoy a stunning view of the Lake and its islands From the top enjoy the nice downhill to Tuoro sul Trasimeno Lake. You are in Umbria region now.
In Tuoro you can stop in the village at the beach. On the saddle again and back to Cortona on gentle terrain but remember last climb !!
Total distance: 50 km / 31 miles | +1042 m / -1038 m
difficult: challenge
DAY 3
Ride from Cortona to Pienza via Montepulciano, through vineyards.
This splendid little town – whose artistic and architectural heritage led it to be called the Pearl of the Cinquecento – has preserved its beauty intact.
Leave the hilltown taking soon a beautiful scenery back road leading you to Monticchiello: you are now at one door to Parco naturale e artistico della val d’Orcia.
It is an Unesco site with this main justification: “ The Val d’Orcia is an exceptional reflection of the way the landscape was re-written in Renaissance times to reflect the ideals of good governance and to create an aesthetically pleasing pictures.” Imagine cycling up and down in a scene from painting to get to the perfect Renaissance town Pienza, now famous also for the delicious sheep milk cheese: “pecorino”.
Total distance: 63,5 km / 39,5 miles | +1049 m / -1021 m
DAY 4
Circular bike ride into Orcia valley
is a completely country ride and for the first 15 km you will ride downhill and very easy gentle rolling hills. Then the gentle climb to reach Radicofani, a medieval and enchanting village with a 1200 dating Rocca. After a stroll around the stately old town, you’ll head back into the country, along some of those winding cypress-lined roads and stop in another medieval village Contignano. Have a light lunch to stoke your legs and back in the saddle take another scenery road back
Total distance 63,8 km / 39,8 miles | +1022 m / -1029 m
DAY 5
First pause in fairy-tale Bagno Vignoni, a miniature spa that is among the most unique towns in Europe, then push on to the monastery of Sant’Antimo, where you might catch one of several vesper services performed each day by the monks.
The famed wine town of Montalcino is your highlight: visit the fortress to see a breathtaking view of the entire valley you’ve just biked.
Total distance 44,4 km / 27,7 miles | +920 m / -876 m
DAY 6
Bike ride from Montalcino to Siena via Monte oliveto Maggiore and Asciano
On the way you’ll coast along the forested crest of a ridge, home to the famed Monte Oliveto Maggiore monastery. Stop here to visit the beautiful buildings and admire frescos. Afterwards, you’ll travel through the fascinating area called Le Crete, Tuscany’s answer to the Badlands. Often described as Italy’s best preserved medieval city, Siena rivaled Florence for dominance in Tuscany during the 1300s. You’ll have time to take a leisurely stroll about this medieval art city in the afternoon and to visit Piazza del Campo square, Torre del Mangia and the famous Duomo. The main square is famous because here it is held twice a year the disputed “Palio” horse race, which opposes the 17 “contrade” of this fascinating city.
Total distance 56.7 km / 35,5 miles | +1035 m / -1217 m
DAY 7
Enjoy farewell breakfast – end bike tour: Arrivederci
INFO TOUR
best period From March to end of October
DIFFICULTY medium
TOTAL DISTANCE 278 km / 174 miles in 5 stages
TOUR REVIEWS
Price & Inclusions
Price
Cost: Euro 1690 per person in double occupancy
Single room Supplement euro 690
Inclusions
Six nights in excellent four & three-star superior hotels
Six breakfasts
All Baggage transfers
RideWithGPS App: tracks, route notes, off-line navigation
Trip notes: Sightseeing & meals suggestions
Delivery bike at Cortona hotel & bike fitting
Pick-up of bikes and gear in Siena
Keepsake Cicloposse water bottle
Sales taxes
Not Included
Bike Rental per entire tour
Hybrid bike € 190 | Road bike, Gravel, E-Bike € 260 | E-Gravel € 350
City Tax each village charges a tax per day between euro 0,70 to euro 3,00
Villa Marsili is a charming and comfortable 4-star hotel set just inside the ancient walls of Cortona, making it an ideal base for enjoying one of Tuscany’s most fascinating hill towns.
We particularly like the location: once the bikes are put away, you can explore Cortona entirely on foot, wandering through its historic streets, shops, cafés and restaurants. The town, made famous to many international travelers by Under the Tuscan Sun, is a wonderful place to spend an evening and soak up the atmosphere. Villa Marsili combines the character of a historic residence with the comfort and warm hospitality that make for a very pleasant stay.
Cloister is one of those places where you really feel the history of Pienza. Set in a former 15th-century convent directly on Corso Rossellino, the town’s main street, it still retains the atmosphere and character of the original building, with its beautiful cloister at the heart of the property. What we particularly love is the garden at the back, with its swimming pool and wonderful views stretching across Val d’Orcia. You are right in the center of Pienza, with cafés, restaurants and little shops just outside the door, yet once inside, the hotel feels remarkably peaceful.
Vecchia Oliviera is one of our favorite choices for a self-guided stay in Montalcino. Located just inside the historic center, next to one of the ancient town gates, it is very convenient to reach by bike while restaurants, wine bars and the lively streets of Montalcino are all within easy walking distance. We particularly like its panoramic terrace, where breakfast is served overlooking the surrounding countryside, and the lovely small outdoor pool – a very welcome treat after a day on the bike. Comfortable, friendly and perfectly located for cyclists.
Villa STR is a great choice for a cycling stay in Siena. Set in a 19th-century villa just outside the busiest part of the historic center, it combines a quiet setting with the convenience of being only about a 10-minute walk from Piazza del Campo.
For us, its location works particularly well: once you arrive, the bikes can be safely stored in the hotel garage and you are free to explore Siena entirely on foot. After the lively streets and squares of the city, the peaceful garden is a lovely place to come back to and relax.
For those looking for a more refined and intimate stay in Pienza, La Bandita Townhouse is our luxury upgrade. This small boutique hotel occupies a beautifully restored historic building right in the heart of town, combining the character of old Pienza with contemporary Italian design and a wonderfully relaxed atmosphere. We like it for its stylish interiors, spacious and comfortable rooms, and the personal feel that comes with a small boutique property. Step outside and you are immediately in the historic center, with Pienza’s restaurants, cafés and charming streets all within a few minutes’ walk.
For those looking for a more luxurious and peaceful stay in Siena, Certosa di Maggiano is a very special upgrade. Set in a beautifully restored 14th-century monastery just outside the ancient city walls, it combines centuries of history with contemporary design, spacious surroundings and exceptional comfort.
What we particularly love is the sense of space and tranquility – you feel immersed in the Tuscan countryside while still being just minutes from the historic center of Siena. The beautiful grounds and swimming pool make it an especially welcome place to relax after a day on the bike.
Mastrojanni Wine Relais is a wonderful place to experience one of the things we love most about this part of Tuscany: the close connection between cycling, landscape and wine. Set within the renowned Mastrojanni Brunello estate, the relais sits in a spectacular panoramic position surrounded by vineyards and the rolling hills of the Val d’Orcia.
We particularly like the feeling of staying right where the wine is produced, while enjoying the comfort and relaxed elegance of a beautiful wine relais. Its location, not far from the Abbey of Sant’Antimo and some of our favorite cycling roads around Montalcino, makes it a very special stage!.
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Tour Reviews
Giuliana, We want to thank you for a wonderful vacation! Everything that you planned and advised was perfect. The routes were gorgeous and challenging. That meant some of us worked hard, but we did it and now feel we can tackle any bike route. And for the stronger bikers, they talk of coming back to Tuscany to live so they can have that kind of biking all the time. The hotels were charming, friendly and well located. The restaurants were all delicious. Thanks again for a truly memorable vacation.
Steve and I wanted to thank you for the wonderful bike tour through Tuscany. We had a great experience and want to come back many times! We loved the route you put together; it was such a great combination of fabulous riding, beautiful towns and so many fun experiences like wine tasting, gelato stops, etc. Thank you so much for your hospitality and caring about providing a quality experience. This was our first time to Italy and we know we will be returning!
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