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Umbria and Southern Tuscany

Our next trip to Umbria is scheduled for September 4th to September 10th, 2022 and will feature a visit by and rides with Tour de France and World Champion Cadel Evans!


On this trip, we’ll ride through Umbria, the Green Heart of Italy and one of the most underrated destinations in Italy, on roads that will take you into Southern Tuscany. Climb breathtaking passes through the Apennines, explore historic sites, and relax at local cafes and wineries. With support from Italian speaking guides, you'll make memories to last a lifetime in a place as timeless as it is beautiful.

Our routes will take you to some of the most beautiful destinations in Italy, including Assisi, Cortona, Orvieto, and Siena. The routes are challenging. The accommodations are world class. A week with us will build your fitness and your confidence, all while rewarding you with a once in a lifetime opportunity to experience the less traveled roads of Umbria and Southern Tuscany.


Our home in Italy is the delightful Montemelino Winery. Surrounded by vineyards and olive trees, Montemelino is a small organic farm of just over 60 hectares, located on the northern hills of Lake Trasimeno, between Umbria and Tuscany. With a breathtaking view of the lake and comfortable accommodations in restored farm houses, this Italian setting can't be beat.

Have a non-riding companion? Bring them along! All our rides are van supported and end in one of our destination cities, all a mornings ride from Montemolino. Your non-riding companion will have the option of riding a van direct to the destination city for sight seeing or, of course, they can opt to relax by the pool at Montemolino!


Our Umbria package includes all of the following:

  • Two-day visit by and rides with Tour de France Champion, Cadel Evans 
  • 6 night accommodation at Montemelino Winery in either a private apartment with terrace or private room in a shared apartment.
  • Shuttle to / from Rome Fiumicino Airport 
  • All Breakfasts and 3 course dinners with wine pairing 
  • 1x Lunch at Montemelino 
  • 1x Wine and Olive oil tasting at Montemelino 
  • Van Support during the rides
  • Professional bike mechanic and bike fitter on staff
  • Expert, Bi-lingual guides
  • Optional walking tours of daily ride destinations
  • Optional cooking class
  • Ride nutrition 
  • Suggested, preparatory training plan leading up to the trip


Pricing for 5 days of riding, 6 nights of accommodation at Montemelino Winery:

  • Private Apartment: $3200 (Booked for September 2022)
  • Private Room and Bath in Shared Apartment: $2949
  • Private Room w/ Shared Bath in Shared Apartment: $2549
  • Additional Rider in a Shared Room: $1500
  • Non-riding partner, friend, family member in shared room: $1000

A Note on Daily Structure

When designing this trip, we wanted to build into it a hominess that we have found lacking in many other destination focused cycling vacations. Riding through Italy is rewarding, but also relatively demanding. For many riders, traveling to a new destination nightly is great. For others, however, it adds an unnecessary low level of stress to what should be a relaxing, once in a lifetime bike adventure.  So, instead asking riders to repack their bags every morning only to unpack them in a new hotel the same night, we decided to find a central location, in a beautiful setting, from which we could lead daily, point to point rides to some of the most breathtaking cities and towns in Umbria and Tuscany. From Montemolino the cities of Siena, Arezzo, Assisi, Gubbio, Orvieto, Perugia, and Cortona are a ride away. Upon arriving in each day's destination city, our support vans, a change of clothes, and your non-riding partner will be waiting. You'll have the afternoon to explore a new place, eat and drink your fill, and pick up some souvenirs before taking the vans home to Montemolino for dinner and a great night sleep in a familiar bed with all your gear ready for the next day. Each apartment is set-up with a small kitchen and refrigerator, providing our riders with the option of making their own meals or storing some post ride treats. 

Umbria is our home away from home. We want to make it feel like your home, too.  

Sample Itinerary

There are more rides in Umbria and Southern Tuscany than we could do in a year, let alone one week. We shape our itineraries based on the size and composition of each group. Below you'll find a sample itinerary to some of our favorite destinations.  

Day 1

Welcome to Italy!

  • Shuttle service from Rome Fiumicino Airport to Montemelino Winery departs at 12 pm
  • Upon arrival, settle into your room and enjoy  a complimentary aperitivo.
  • Conte’s mechanics build your bike and/or get you dialed in for the week with a complimentary fitting.
  • If you arrive with the shuttle, enjoy a short and easy spin to Tuoro Sul Trasimeno.
  • Dinner tonight at the Winery

Day 2

Castiglione del Lago

  • 7-8am. Group breakfast and coffee at winery
  • 8:15am Ride: Giro Del Lago: We’re circumnavigating Lake Trasimeno and getting the lay of the countryside we’ll explore for the rest of the week.
    (37 miles with 1000’ of climbing)
  • 1pm Post Ride Lunch and Wine Tasting at Montemolino
  • 7pm Dinner served at the winery.

Day 3


  • 7-7:45am. Group breakfast and coffee at winery
  • 8 am Ride: Siena: This one’s for all the Chianti! We will take a van shuttle to the border of Umbria and Tuscany before climbing up into Tuscany. We will ride through the quintessentially Italian Chianti wine region and towns of Greve, Radda, and Gaiole before dropping into Siena for lunch and wine tasting.
    (60 miles with 5000’ of climbing)
  • Lunch: On your Own in Siena
  • Post Ride: Exploration of Siena. Optional wine tasting and museum visits. Shuttle back to Montemelino at 9pm.
  • 7pm Group Dinner in Siena

Day 4


  • 7-9am. Group breakfast and coffee at winery
  • 9:30am Optional Ride: Perugia: Today we'll do a shorter ride to Perugia, the beautiful and ancient capital of Umbria. First occupied by the Etruscans and then the Romans before serving as a Papal capital, the city was also central to the Allied advance against embedded German armies during WWII. Today we’ll take a short ride around and up into town to explore some of that history. Today you also have the option of skipping the ride and taking the shuttle directly to town or relaxing at the winery.
    (35 miles with 3000’ of climbing)
  • Group lunch in Perugia
  • Post ride, spend some time exploring the town. Shuttle back to the winery at 3pm
  • 7pm Dinner at the Winery

Day 5


  • 7-8am. Group breakfast and coffee at winery
  • 8:15am Ride: Orvieto: We’re heading south to explore the heart of Umbria, winding our way around Lago Trasimeno before tackling the big mountains. After a well earned descent, we’ll ride up into the ancient Etruscan city of Orvieto where you can explore ancient Etruscan art, architecture, and tombs while eating gelato in the shadow of a medieval duomo.
    (61 miles with 5200’ of climbing)
  • Lunch: On your own in Orvieto
  • Post Ride: Explore Orvieto. Shuttle back to the winery at 4:00 pm.
  • 8pm Dinner at the Winery

Day 6


  • 7-8 am: Group breakfast and coffee at winery
  • 8:30 am Ride: Cortona: We’ll spend the day under the Tuscan sun, riding our way across the mountain ridges divide Umbria and Tuscany before dropping down to Cortona to take in our final views of Lake Trasimeno.
    (52 miles with 5200’ of climbing)
  • Group lunch in Cortona.
  • Explore the small and beautiful town of Cortona. Optional wine tasting. Shuttle back to Montemelino at 5pm.
  • 7pm Dinner at the Winery

Day 7

  • Early Breakfast and Coffee Available Prior to Departure
  • 7 am: Shuttle departs for Rome

Reserve Your Spot

Ready to learn more and secure your place on this incredible cycling adventure?