Skip to main content

FREE SHIPPING on orders over $150 | Shipped Orders May Take 2 Weeks To Arrive


In consideration of the current international health environment, particularly that being experienced by our friends in Italy, we have chosen to postpone our May trip to Umbria.

We look forward to the possibility of rescheduling our trip to the third or fourth quarter of 2020 and hope you will join us for an unforgettable cycling vacation!


On this trip, we’ll ride through Umbria, the green heart of Italy. Climb breathtaking roads through the countryside, explore historic sites, and relax at Italian 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 places in Italy. The routes are challenging. The destinations are world class. A week with us will build your fitness and your confidence, and will reward 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 Casale i Perugini. A renovated farmhouse approximately 4 miles to the north of Perugia in the small village of Colle Umberto, i Perugini is equally ideal as a launching-pad for cycling adventures to points north, south, east, and west! Its pool and sunny courtyard provide an ideal place to meet before our rides, regroup after, and relax in-between. All riders have their own bedroom in shared or single apartments equipped with full kitchens, linens, and towels. Prior to your arrival, we will have stocked your kitchens with breakfast foods, coffee and tea, and snacks for the road. Our goal in selecting i Perugini as our home away from home is to allow you to focus on what you came to Italy to do: ride! Knowing where you’ll lay your head at the end of a long day on the bike and exploring cities like Assisi, Siena, Gubbio, and Orvieto makes your life simple. Relax. Enjoy. Leave the rest to us.

SAMPLE ITINERARY (subject to change)

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 on a rental bike
  • If you arrive with the shuttle, enjoy a short and easy spin to Tuoro Sul Trasimeno.
  • Dinner tonight at Il Convento Ristorante in Corciano.

Day 2

  • 7-8am. Group breakfast and coffee at winery
  • 8:30am 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
    • 57 miles with 2000’ of climbing
  • Lunch in Castiglione del Lago
  • Post ride. Relax and enjoy Castiglione del Lago, a beautiful lakeside town close to Montemelino. 
  • 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. 
    • 67 miles with 7200’ of climbing
  • Lunch: Siena
  • Post Ride: Exploration of Siena. Optional wine tasting and museum visits. Shuttle back to Montemelino at 9pm.
  • Dinner on your own in Siena.

Day 4

  • 7-9am. Group breakfast and coffee at winery
  • 9:30am Optional Ride: Perugia: Perugia is a beautiful and ancient city. First occupied by the Etruscans and then the Romans before serving as a Papal capita, 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.
    • 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
  • Dinner at Montemelino

Day 5

  • 7-8am. Group breakfast and coffee at winery
  • 8:30am Ride: Orvieto: We’re heading south to explore the heart of Umbria, winding our way through Perugia 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
  • Group lunch at restaurant in Orvieto
  • Post Ride: Explore Orvieto. Shuttle back to the winery at 8:00 pm.
  • Dinner on your own in Orvieto

Day 6

  • 7-7:45am: Group breakfast and coffee at winery
  • 8:30am 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 4pm.
  • 7pm shuttle to farewell dinner at Osteria a Priori in Perugia.

Day 7

  • Group breakfast and coffee at winery
  • 7 am: Shuttle departs for Rome


Riding attendee: $3,000 ($1,500 deposit required)

Non-riding partner: $1,500 ($750 deposit required)

Bike rental: $500 - BMC RoadMachine01 Four - includes fitting upon arrival