Ride Overview
The paths once traveled by the “Briganti” to escape the law 200 years ago now offer an extraordinary experience to explore this beautiful region on horseback, just as these outlaws did! The magnificent horses and expert guides will show you a week steeped in history. Every day you’ll explore one of the most pristine territories in Italy. This is a week full of breathtaking nature and a journey into history among castles and archaeological sites that frame this historic landscape.
Your incredible accommodations for the week are an amazing 17th century castle – the family of whom still own it today. It’s location is ideal – at the crossroads of Lazio, Tuscany and Umbria – a perfect blend of nature, wellness and culture – all within 1.5 hours of Rome!
The castles ivy shrouded farmhouse and out-buildings – your home for the week – have been restored to not only offer incredible comfort but true authenticity. In all, they offer 8 cottages and 14 private bedrooms. All rooms are furnished with original pieces, many of which came from the castle itself.
The grounds offer lovely walking or relaxing as well as a welcome swimming pool (open on June 1 annually).
On the main floor of the Farmhouse is the large “taverna” with brick vaulted ceilings. The space contains the dining room, billiard room, ping-pong room, plus a large kitchen equipped for cooking courses but also open to guests during the stay.
2026 Dates: Weekly from Sunday-Sunday, March-October
Rates: $3,060.00 USD (or 2550,00€) per person in a single/double room.
Please Note: This ride is for intermediate level riders and folks must be comfortable to W/T/C on a trail.
***If you do not wish to join the afternoon activities, the team on site must be alerted the day prior as transfers are arranged ahead of time (and paid by the guests) so a driver is contracted, and the charge will apply if the driver comes. When you visit the villages, you may find yourself with extra time and not much to do—the host recommends a hired local guide, but this will also need to be arranged ahead of time.
Included
- 7 nights accommodation
- 5 days of guided riding (half days, 1 full day)
- All meals
- Welcome drink upon arrival
- Horse and all tack
- Guiding services on the trail rides
- 1 cooking class
- 1 - 30 minute massage
- Full use of the swimming pool, tennis court and onsite amenities
Not Included
- Airfare
- Travel Insurance (highly recommended)
- Airport transfers to/from Rome (about 200€ each way for 2-3 people)
- Train station transfers from Orvieto (about 75€ each way for 2-3 people)
- Private transfers, €30–35 per person, cash only
- Alcoholic beverages
- Wine tasting at Fattoria Aldobrandesca Antinori, Pitigliano → card accepted on site
- Afternoon transfers and entrance fee for tours (based on group size, paid onsite - approx. 200€)
- Any activities not listed in the itinerary
- Gratuities for the team at the end of your stay
Day 1: Arrival
After check-in and a welcome drink, you will meet your guides for an introduction to the program and a guided tour of the castle.
Dinner in the old taverna.
Day 2:
After breakfast (served in the old stables of the Castle from 8AM-10AM), you will meet your horse to begin your ride towards the hills that frame the western plateau on which the castle stands. A spectacular panoramic point with a breathtaking view, from the crater of Lake Bolsena to the hills surrounding Lake Mezzano.
With the hilly terrain, this is the perfect way to not only get to know your horse for the week, but to get a feel for this area - not just under saddle, but to experience the panoramic views and to see why this location was so strategic.
You'll have lunch back at the castle before being taken by vehicle to a wine tasting at Fattoria Aldobrandesca Antinori in the afternoon. While savoring the vintage, you'll learn about Tuscany's rich winemaking traditions.
Afterward, you'll have the chance to visit the enchanting town and medieval fortress of Pitigliano before coming back to the Castle for dinner.
Day 3:
Another lovely breakfast in the stables before you head out on today's ride. You'll have the chance to take a different route which will show you more of the lush landscape of this area, again with incredible views in all directions.
Enjoy lunch back at the Castle before you head out to visit the town of Bolsena and a guided tour of the Palazzo Cozza Caposavi and the Basilica of Santa Cristina.
Dinner back at the castle.
Day 4:
Today is a mostly full day ride - so be sure to enjoy a nice breakfast!
You'll will mount up and ride through ancient paths - entering the wooded hills surrounding Onano, passing by maritime pines that tower over an Etruscan site. You will reach the Mezzano crater plain and have lunch at the Fra Viaco farm restaurant, where you can also cool off with a swim in the crystal-clear waters of the lake. Lake Mezzano is the second smallest volcanic lake in all of Europe.
After lunch, you will climb back up through centuries-old chestnut woods to return to the castle. About 5 hours/32 km).
NOTE: some weeks today's ride may be offered in two sections, one in the AM and one in the PM.
Day 5:
Mounting up a bit earlier today closer to 9AM, you will ride in the surrounding area for a couple of hours before you leave for lunch and a visit to the city of Sorano "the city of rocks", carved from volcanic rock.
Visiting it is like taking a journey through time: a typical and charming village with the little houses all leaning against each other and picturesque alleys - it's thought that it was initially inhabited by the first known civilization of the Iron Age followed by the Etruscans.
After lunch, to complete your visit, you will stop at Necropoli Estrucan archeological park of Sovana and the Sorano Thermal Bath before returning back to the Castle.
Day 6:
After breakfast, you have a chance to relax before you begin your hands on cooking class - learn how to make authentic dishes from this area, including the famous pasta, and about the local ingredients, all of which are farm to table.
Enjoy the feast that you've created for lunch with a nice glass of wine.
Afternoon ride around 3PM before coming back to the Castle for dinner.
Day 7:
The morning is free for you to enjoy as you wish - you can relax at the castle and use the swimming pool, tennis court, game rooms or treat yourself to a massage or go for a walk in the surrounding countryside.
But after lunch, around 3PM, you have a visit to the town of Orvieto, one of the most striking, memorable, and enjoyable hill towns in central Italy. You'll marvel at its magnificent cathedral and fascinating history. If you like, the tourism office offers guided visits (not included). Here is a good resource for more information on the town: https://www.cntraveller.com/gallery/orvieto
Day 8:
After one last breakfast, it's time to say Ciao and arrivederci.
***This program may be changed due to weather, unforeseen issues or to better suit guest needs during any week. Please note that all afternoon tours and transfers (excluding the wine tasting) are paid in cash on arrival.
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Sydney A.
Three friends and I just got back from an unforgettable week in Italy on the Tuscany Outlaw Trail trip, and we’re already dreaming about going back! We chose this adventure because it welcomed riders of varying skill levels and mixed in plenty of other activities, but staying at the beautiful Castello di Santa Cristina turned out to be the cherry on top.
The owners of the castle, Antonello and Cristina, and their team (especially the wonderful Giulia) were incredibly warm and made us feel welcome and right at home. We stayed in the cozy “Marta” and “Capodimonte” cottages, which sit back-to-back. Each has two bedrooms with ensuite bathrooms, a small living area, and a kitchenette. The best part? They’re connected by two kitchen doors that can be opened to create a perfect shared space for a group of four (or more) — or locked for more privacy. They were super comfortable, private, and homey.
The food was great. Breakfast was a solid European buffet, but lunch on the patio and dinner in the Taverna were the highlights. Endless carafes of their dangerously addictive local white wine (“vino bianco”) were offered at every meal. (That wine should come with a warning label because it’s impossible to stop at just one glass!) The meals included a variety of pastas and meats, but the fresh caprese salad and the incredible barbecue chicken and ribs (as good as any Southern BBQ back home) were the standouts for me. The only real bummer? No authentic Italian pizza all week. I’m still a little salty about that (jk).
We also enjoyed the day trips to nearby towns, wine tasting, and especially the memorable castle tour with Antonello and Cristina.
And now for the important part: The riding was fun! On the second afternoon we did a quick assessment in the arena with Susan (one of the guides and trainers). She had each of us walk, trot, and canter so she could gauge our skills. The whole group rode at the pace of the least experienced rider, so we mostly walked and trotted at the start but worked up to some nice canters by the end of the week. (Our group was the exception; most of the other guests were advanced and did a lot of cantering.)
The horses were well-trained and responsive. I got to ride three different horses during the week and really liked all of them, but my favorite was Tina, a beautiful black Friesian-cross with a sweet personality. I seriously wanted to bring her home with me! The trails through the Tuscan countryside were lush with some stunning views. They’re often narrow so you ride nose-to-tail, but there’s still plenty of trotting (and cantering when possible), so it never felt boring. The horses handled everything beautifully — even when several herding dogs at a sheep farm ran up and barked at us, they didn’t bat an eye. The guides were experienced and worked very hard, though they didn’t talk much during the rides (understandable while riding single file).
A few more notes: The itinerary was in a completely different order than what we expected. Most of our rides were in the late afternoon, which meant rushing through the morning excursions and skipping the vino bianco at lunch (tragic, I know ��). We opted out of the full-day ride on our last day and did a regular two-hour hack instead — our group decided we weren’t quite up for that much saddle time. I recommend hiring a guide/translator for the day trip to Sorano.
TLDR: Five stars all the way! Wonderful hosts and staff, amazing castle setting, good food and wine, and enjoyable riding on lovely horses. If you’re considering this trip, just book it — you won’t regret it.