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Road Cycling Holiday in Italy

Unforgettable rides through the woods and along the lakes, chasing mountains and rolling hills, toward medieval historical centers and archeological sites. A castle will be your home and your base throughout your stay, allowing you to explore Alta Tuscia, a strip between Tuscany, Umbria, and Lazio. Expert guides will lead you along unbeaten paths and ancient trails

Key information

  • Trip type: Guided
  • Lodging: Center-based
  • Terrain: hilly
  • Starts in: Grotte di Castro
  • Ends in: Grotte di Castro
  • Difficulty level: Challenging (Cyclist needs to have high level of fitness, must be an active rider, the terrain includes really challenging climbs/or 46-80 or more miles per day)
  • Total Distance: 275 Miles / 443 Kilometers
  • Type of bike: Road bike

Meet the instructors



  • Exhilarating cycling across Lazio, Tuscany, and Umbria regions
  • 5 cycling guided excursions with professional guides
  • Get a glimpse at traditional Tuscan life: the food, the wine, the culture
  • Wine tasting at Fattoria Aldobrandesca Antinori vineyard for 2 people
  • 7 nights accommodation in the old granary of the Castle
  • Full board meals, delicious traditional Italian cuisine

Skill level

  • Intermediate
  • Advanced

5 days with instruction in English
The organizer also speaks: Italian
Airport transfer available:
Ciampino–G. B. Pastine International Airport (US$ 174 per person)
Airport transfer available:
Leonardo da Vinci–Fiumicino Airport (US$ 174 per person)
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Check-in Time:
Check-out Time:

A few meters from the castle is the ancient restored farm houses, which in the past represented the heart of all the company’s production activities. The farm has been transformed into a welcoming and comfortable structure, where comfortable apartments furnished with antiques, mostly coming from the Castle, have been created.


Day 1

After check-in and welcome drink, you'll meet the guides and brief about the program. A guided tour of the Castle and the welcome dinner in the taverna will finish the day.

Day 2: Lake Bolsena and ancient hilltop towns tour

This ride follows the natural contour of enchanting Lake Bolsena, so after leaving the castle in the morning, you descend along the crater of this ex-volcano, crossing the village of Gradoli with its beautiful Renaissance palace built by Pope Paulus 3rd Farnese around 1500. After a few km, you reach the water following a beautiful road running parallel to the shore among olive trees and cultivated fields.

The road bordering the beach reaches the enchanting little harbor of Capodimonte dominated by a medieval fortress.

After Marta the fishermen's village, the road climbs from the shore to the top of the crater along a steady uphill road, for about 3 / 4 km. At the top, a fantastic view of the lake and surroundings in any direction is the special prize for the effort.

The old Roman road ”Via cassia” will lead you down along the hills to the town that gives the name to lake Bolsena.

An ancient Etruscan and then Roman center, Bolsena is also famous for the miracle of Corpus Christi providing one of the first Christian holidays.

Following the same road after about 10 km of flat terrain, you arrive below the town of Grotte di Castro where again your legs and lungs will have to make an effort to reach the top of the crater, from there following constant up and down after about 5 km you will reach again the castle.

Total: 80 kilometers

Day 3, Umbria: Orvieto town tour

Passing through the hills between Castel Giorgio and Castel Viscardo, you descend into the valley where the beautiful city of Orvieto stands over a big volcanic rock. A steep hill road leads us inside the massive medieval walls. At the top, you follow narrow streets until the magnificent Duomo appears dominating the scene over the square with its incredible façade. The Tower of Mauritius, the Moro Tower, and St. Patrick's Well, are just some of the other wonders you can enjoy in this beautiful town.

Besides this is wine heaven, and the hills around are covered with vineyards and olive trees. In the many wine bars around here, you can taste the famous Orvieto Classico wine, and olive oil accompanied by local hams, cheeses, and salami. But you must be careful and avoid eating or drinking too much because on the way back you must be ready for the hills. A steady uphill road climbs twisting along the side of the volcanic plateau.

Once at the top, you will follow the road along the plateau direction east watching the mountains, time for speed if you still have energy in your legs. After crossing Grotte di Castro with an enchanting view of Lake Bolsena in the background, you finally enter the last ups and downs before your home: S. Cristina castle.

Total: 95 kilometers

Day 4, Tuscany: Pitigliano, Sovana, Sorano: fortresses in the rock

Northwest of the castle going through the ups and downs of the southern hills of Grosseto province, in Tuscany you reach the "tufo rock fortress towns". Pitigliano is the first one you reach. It is also known as the Little Jerusalem because it used to have a tiny juice ghetto now abandoned, but still an enchanting fortified village dominated by the Orsini castle. What a place to explore, following the narrow streets inside.

Then you will reach Sovana, considered one of the most beautiful villages in the area, and finally Sorano, defined as the fortified rock of Tuscany built on the side of a gorge, along a path in the archaeological Park of Tufo, an area characterized by the Vie Cave. It is a network of narrow routes carved in the rock by the Etruscans who lived here many centuries before Christ. These are incredible pieces of engineering trapped between suggestive and steep walls of rock. The road you follow is quite challenging and undulating, with frequent changes in gradient.

After a few kilometers of relief where you are allowed on a slightly flat stretch, the road climbs again with a few ramps to negotiate in order to reach the top at S. Valentino. From here the continuous undulation gets more regular and less challenging. Onano and its medieval castle is the last village before the castle.

Total: 71 kilometers

Day 5: Day off to explore the surroundings

Today you have a day off to rest or explore the surroundings.

Day 6: Tour of the Farnese Duchy of Castro

From the castle to the west, you head towards the sea, the land slopes down and we enter what around the year ad 1500 / 1600 was the Duchy of Castro. The first part of the tour is easy and the road follows a long valley in between hills inside what once was a big “caldera” a volcano now extinguished.

Suddenly the road turns right and you find the towns of Ischia di Castro and Farnese, where the domain of the powerful Farnese family is still evident after many centuries in the impressive buildings, streets, and squares. The view of the area is incredible and the road starts a challenge up and down through woods, gorges, and hills climbing slowly but constantly on the way home.

The sceneries around you are so beautiful but the road is unforgiving slowly but steadily going up, then the climb increases along the border of the crater of Lake Mezzano at 650 meters. From the top, you can stop for a well-deserved panoramic view of the region. The final descent along the opposite side of the crater brings our wheels towards home, but not after having coped with those last hills before the castle.

Total: around 90 kilometers

Day 7, Mount Amiata: the big mountain

For every cyclist around here, this is the challenge: Mount Amiata (1734 meters). It can be climbed from different sides, and it can really offer hard bread to chew even for the best athletes. It is definitely the highest point of this tour.

From the castle, the beginning is ideal because after a few easy ups and downs, the road keeps going down until it reaches the bottom at Paglia river valley. Along the Via Cassia, the old Roman road, you reach the foothills of Mount Amiata. You have enough flat roads to warm up your legs. Then the climb to the summit begins.

Ride on 28 kilometers of road that climbs constantly on the mountain, between the sulfur springs, the gradient for a while increases before crossing Piancastagnaio and Abbadia San Salvatore. Then you pass in front of the old mines, and along hairpin bends in the shade of chestnut and beech woods, the road keeps going up and up and up. It seems never to finish with the big mountain towering above you. When you think it will never happen you get to a clearing, where just above it you can see the cross on the summit.

It's done, you have made it. A quick stop to eat and drink something and it is time to start going back because it isn’t finished at all.

Most of the first part of the return is downhill and with time enjoy the fantastic landscape but on the last part, the hills take over again.

Concentration has to come back, just to negotiate the last ups and downs that here arrive after 100 km of effort.

Finally, you arrive at the castle, and you can relax and enjoy your achievement of the day, she is there watching you from the DISTANCE like a big sleeping giant: Mount Amiata.

Total: around 107 kilometers

Day 8

Departure after breakfast.


This holiday is located in Southern Tuscany, one and a half hours from Rome, halfway between Orvieto and Siena, closely bordering the regions of Umbria and Tuscany. The breathtakingly splendid 17th-century castle, Castello di Santa Cristina, has been the property of the noble Caterini family for generations and has its own fairy tale turret!

Over the past ten years, the castle’s nearby 18th Century ivy-covered farmhouse and out-buildings have been carefully restored to retain their authenticity and separated into 8 self-catering cottages and 14 bedrooms with Bed & Breakfast for guests, furnished with original pieces it can offer you unique country holidays.

A perfect location for family holidays where you can explore the various neighboring historic towns including Orvieto, Sorano, Acquapendente, Grotte Di Castro, and many more. The castle offers sensational Tuscan cuisine, fantastic cooking courses, and unique weddings on the castle grounds.

The Castello di Santa Cristina is also an ideal place for a horse riding holiday. On the exciting trail excursions, you travel as far as Proceno, Lake Bolsena, Lake Mezzano, and the beautiful nature reserve Selva Del Lamone.


The meals include all buffet breakfasts

The following meals are included:

  • Breakfast

The following dietary requirement(s) are served and/or catered for:

  • Vegetarian
  • Vegan
  • Regular (typically includes meat and fish)
If you have special dietary requirements it's a good idea to communicate it to the organiser when making a reservation

Spa treatments

  • 50-minute massage: 85 EUR per person

What's included

  • 7 nights accommodation in the old granary of the Castle
  • Delicious traditional Italian cuisine
  • Breakfast included
  • Exhilarating cycling across Lazio, Tuscany, and Umbria Regions
  • 5 cycling guided excursions with professional guides
  • Fabulous insight into traditional Tuscan life: the food, the wine, the culture

What's not included

  • Transfer services
  • Airfare
  • Bike rental (30 EUR per day)

How to get there

Recommended Airports

Airport: Ciampino–G. B. Pastine International Airport Airport transfer available: Ciampino–G. B. Pastine International Airport (US$ 174 per person) Additional charges may apply. You can request this in the next step.
Airport: Leonardo da Vinci–Fiumicino Airport Airport transfer available: Leonardo da Vinci–Fiumicino Airport (US$ 174 per person) Additional charges may apply. You can request this in the next step.

Cancellation Policy

  • A reservation requires a deposit of 36.3% of the total price.
  • The deposit is non-refundable, if the booking is cancelled.
  • The rest of the payment should be paid on arrival.

Value for money
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8 days / 7 nights
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