Explore the wine country of Montalcino and hidden Tuscany on Foot! Immerse yourself in the rolling hills and rich history of Tuscany with our exclusive running adventure through the wine country of Montalcino and the hidden gems of Southern Tuscany! Lace up your shoes for daily village-to-village runs rolling through picturesque landscapes of vineyards, olive groves, and mountainous vistas.
Our route includes breathtaking destinations like the Val D’Orcia—a UNESCO World Heritage Site—along with lesser-known hill towns such as Seggiano, Arcidosso, and Vivo D'Orcia. Not only will you experience the thrill of running in one of the world’s most beautiful regions, but you’ll also indulge in local Tuscan delights. Enjoy hearty breakfasts, lunches, and delicious dinners, all featuring regional ingredients. And of course, no run in Italy would be complete without the occasional mid-run espresso break, where you can refuel while soaking in the views.
This once-in-a-lifetime experience is guided by a local expert who will unveil Tuscany’s hidden secrets, from ancient monasteries to the natural beauty of Monte Amiata. This running adventure offers the perfect balance of physical challenge and cultural immersion.
Join us for an unforgettable running holiday through the heart of Tuscany!
Set up a call to learn more from the trip leader
Running mileage will be between 8-14 miles per day and be supported with snacks. All you have to bring is a running pack with space for water, snacks, and whatever else you need for the day. Terrain is rolling occasionally punctuated by steeper climbs.
Total Cost $3725. Space for 6-10 runners. Non-refundable Deposit of $300 required to reserve spot.
October 5-11, 2025
Included:
What’s Included:
Daily Trail Runs: 8–14 miles per day on rolling hills with a few steeper climbs.
Lodging: shared accommodation. Single accommodation available upon request and for an additional fee.
Local Cuisine: hearty breakfasts, lunches, and dinners featuring regional specialties. And of course, no run in Italy would be complete without the occasional mid-run espresso break, where you can refuel while soaking in the views!
Transportation: transportation on the ground during the trip dates
Cultural Immersion: Visits to the Val D’Orcia UNESCO World Heritage site and historic towns like Seggiano, Arcidosso, and Vivo D'Orcia. Admission to any site visited included.
Coaching Support: In-person coaching with Coach Martin Benes.
Run Support: Mid-run snacks and hydration options, along with daily GPX files for route navigation. All you need to bring is a running vest or belt with space for water & snacks and whatever gear you want for the day.
Note: Actual routes may vary. Final itinerary and GPX files will be provided one month prior to departure
Not Included:
Airfare (Please wait for trip confirmation before booking)
Trip Insurance
Alcohol
Additional snacks
Personal purchases (souvenirs, equipment, etc.)
Any additional costs with having to change your trip, etc.
Explore the wine country of Montalcino and hidden Tuscany on Foot! Immerse yourself in the rolling hills and rich history of Tuscany with our exclusive running adventure through the wine country of Montalcino and the hidden gems of Southern Tuscany! Lace up your shoes for daily village-to-village runs rolling through picturesque landscapes of vineyards, olive groves, and mountainous vistas.
Our route includes breathtaking destinations like the Val D’Orcia—a UNESCO World Heritage Site—along with lesser-known hill towns such as Seggiano, Arcidosso, and Vivo D'Orcia. Not only will you experience the thrill of running in one of the world’s most beautiful regions, but you’ll also indulge in local Tuscan delights. Enjoy hearty breakfasts, lunches, and delicious dinners, all featuring regional ingredients. And of course, no run in Italy would be complete without the occasional mid-run espresso break, where you can refuel while soaking in the views.
This once-in-a-lifetime experience is guided by a local expert who will unveil Tuscany’s hidden secrets, from ancient monasteries to the natural beauty of Monte Amiata. This running adventure offers the perfect balance of physical challenge and cultural immersion.
Join us for an unforgettable running holiday through the heart of Tuscany!
Set up a call to learn more from the trip leader
Running mileage will be between 8-14 miles per day and be supported with snacks. All you have to bring is a running pack with space for water, snacks, and whatever else you need for the day. Terrain is rolling occasionally punctuated by steeper climbs.
Total Cost $3725. Space for 6-10 runners. Non-refundable Deposit of $300 required to reserve spot.
October 5-11, 2025
Included:
What’s Included:
Daily Trail Runs: 8–14 miles per day on rolling hills with a few steeper climbs.
Lodging: shared accommodation. Single accommodation available upon request and for an additional fee.
Local Cuisine: hearty breakfasts, lunches, and dinners featuring regional specialties. And of course, no run in Italy would be complete without the occasional mid-run espresso break, where you can refuel while soaking in the views!
Transportation: transportation on the ground during the trip dates
Cultural Immersion: Visits to the Val D’Orcia UNESCO World Heritage site and historic towns like Seggiano, Arcidosso, and Vivo D'Orcia. Admission to any site visited included.
Coaching Support: In-person coaching with Coach Martin Benes.
Run Support: Mid-run snacks and hydration options, along with daily GPX files for route navigation. All you need to bring is a running vest or belt with space for water & snacks and whatever gear you want for the day.
Note: Actual routes may vary. Final itinerary and GPX files will be provided one month prior to departure
Not Included:
Airfare (Please wait for trip confirmation before booking)
Trip Insurance
Alcohol
Additional snacks
Personal purchases (souvenirs, equipment, etc.)
Any additional costs with having to change your trip, etc.
