The Leonard Lee 🚴‍♂️ Italy Week

Join Leonard Lee YouTube Cyclist in Italy

Cycling in Tuscany & Umbria with the Jolly Good Velo

Regardless of Shape, Size & Age | Fun Cycling for All

Join Leonard as one of just ten cycling guests for a week of fully guided rides.  The quiet rural roads of Tuscany and Umbria play host to six days of wonderful social cycling and the perfect blend of Italian culture, food, wine, and good friends with Leonardo served up as the main course!

🚴🏻‍♀️ 🇮🇹 Ride, Eat & Drink with Leonard Lee in Classic Italian Style 🇮🇹 🚴‍♂️


🚴‍♂️ Maximum 10 Cycling Guests 🚴‍♂️

Prices from $2,287 per person View Prices


  • 🚴‍♂️ 10 Cycling Guests Max + non cycling partners
  • ☀️ 8 DAYS | 7 NIGHTS & 6 RIDES with Leonard Lee including ...
  • Private Taxi Transfer From & To Perugia Airport or Terontola-Cortona Rail Station
  • EXCLUSIVE use of a Quiet Country Hotel with Spa, Pool, Gardens & Gym
  • Super Half Board: Breakfast; Post-Ride Lunch & Dinner with Water & House Wine
  • Local Excursions including Wine Tasting & Dinner, Pizza Night & Visit to Preggio
  • Emergency Back-Up & Support Vehicle
  • Daily Guided Rides With Leonard, Roberto & Tim
  • BICYCLE & EQUIPMENT: Rent a top Carbon Bike or bring your own
  • RENT A BIKE: Carbon Muscle Bike or Electric Bike
  • PEOPLE ALSO ASK FOR … Non Cycling Partner Package £976 GBP


  • DAILY RIDE DISTANCE: From 30km to 110km
  • Easy, Moderate & Difficult Rides Available
  • DAILY SADDLE TIME: 3h to 5h
  • *FREE* FTP Test [Optional] & Cycle Coaching
  • We have 105 5⭐️ guest reviews on Google & Tripadvisor

    Tripadvisor: READ OUR REVIEWS



The extensive ride catalogue includes gentle routes along the valleys of Tuscany and Umbria, 75Km around Lake Trasimeno, and long steady climbs in Apennine foothills. There are a lot of different itineraries to choose from with full details available online.

The evening ride briefing details the plan and activities for the following day. Full stats and information are also available on the noticeboard. You can choose to ride with the group, take a rest day by the pool, or even take a self-guided ride should you prefer.


✈️ SATURDAY 🚌 GROUP TRANSFER TO THE HOTEL | Departure time is to be confirmed in advance. Transfer time from Perugia airport is 45m and from Terontola-Cortona station 35mins. 🍻 At the hotel there is a welcome drink & briefing with your host, guides and Leonard Lee.


🚴🏻 SUNDAY: Ready to Pedal! Your cycling adventure starts. An easy ride today. c75km mainly flat. Lunch in Citta di Castello with partners.

🏋️‍♂️ Activity: Optional FTP test


🚴🏻 MONDAY: An easy ride to the hilltop town of Montone. 

🍷🍇 Activity: Wine tasting & dinner at the vineyard of Il Girasole di San Andrea.


🚴🏻 TUESDAY: Lake Ride - two climbs and largely flat around Italy's largest peninsular lake. 

🍪 Activity: How to make your own Energy Balls & natural protein drinks


🚴🏻 WEDNESDAY: Under the Tuscan Sun - a ride to Tuscany and along the lakeshore and return to base for lunch and a relaxing afternoon.

🍕Activity: Pizza evening at Le Fornaci.


🚴🏻 THURSDAY: Big Climb Day - this is the day you’ve been waiting for! A great day to test those new legs!

🏰 Activity: Visit the ancient village of Preggio & dinner at La Castagna.


🚴🏻 FRIDAY: Recovery Day Ride: Some may choose the pool, others the ride. 


✈️ SATURDAY: Departure Day


🚴🏻 🚴🏻 🚴🏻 🚴🏻  | 🚴🏻 🚴🏻 🚴🏻 🚴🏻


☀️ 07.30: The perfect start with a healthy cyclist's breakfast: Breakfast is not only fuel for your ride, but it is also a culinary moment! Choose from a banquet of fresh, healthy, local food including pastries, fruit, and eggs, coffee, juice, yoghurt and more.

🍌 08.30: Bike Check & Prep: Remember to collect your mineral salts and banana while en route to set up your bike.

🚴🏻 09:00-09.30: Grand Depart: Your group gathers at the hotel entrance, led by the guide and Leonard. We confirm the route details, count that we have everybody and off we go. Get the adrenaline up and the legs pumping.

🍝 c13.00/14:00: Lunch Out or Return to Hotel: After a 3-5 hours ride your return to the hotel to have a shower and the post-ride lunch buffet. 

🏊‍♂️ Up to 19.00: Relax by the swimming pool or unwind in the whirlpool. 

🍽 20.00 Dinner: In Italy, the food is so important! You will taste the delicious recipes, made with local and fresh products and enjoy your meal with a glass of Italian wine.

🍻 21:00-23:00 Relax & Talk Cycling: Fueled by the local wine, discuss the day's events and what's coming up tomorrow! That’s what a cycling holiday is all about!

🛌 Sleep Well! It’s time to go to bed for a well-earned rest. A new exciting cycling adventure is waiting for you tomorrow!


🚴🏻 🚴🏻 🚴🏻 🚴🏻 🚴🏻  | 🚴🏻 🚴🏻 🚴🏻 🚴🏻 🚴🏻



Long and flat, short and hilly and every possible combination in between, there is a plethora of options to suit all riders. Fun is the underlying theme and the aim for each and every ride. 

EASY: Città di Castello

Ride through the Umbrian valleys of Niccone and Upper Tiber stopping for a light lunch in the heart of Citta di Castello.


🟥 Check the Route HERE


Valley Ride & Sunday Lunch in Citta di Castello


72.7Km; Ascent 692m with no CATEGORISED climbs; Lowest point 247m highest 318m

It's not all about cycling! Italy is renowned for its wine and cuisine. There are plenty of opportunities for you to try the wine, grappa and local delicacies such as porcini, wild boar and truffle. Leonard is seen here trying some local grappa!

MODERATE: The Lake Loop

This is an extraordinary ride taking in the views, history and microclimate of Lake Trasimeno, Italys' fourth-largest lake


🟥 Check the Route HERE


Lake views.


84.5Km; Ascent 1,198m with one CAT 2 and one CAT 3 climb of 4.3% and 4.9% average.

Leonard stopping for a roadside water top-up in Tuscany


This single climb ride takes you to the hilltop medical town of Montone. Lunch or coffee in the piazza is a setting straight from a film.


🟥 Check the Route HERE


The Village of Montone


86Km; Ascent 1,046m with one CAT 3 climb.

Hilltop villages are a great feature of our tours. Ideal for coffee stops, a little local culture and history

HARD: Fiorentino

This ride is tough but perfectly formed. A long warm-up before you hit the first long steady climb which to all intents and purposes is 13Km long, ramping up along the way. 


🟥 Check the Route HERE


The long, steady climb into Tuscany


93.5Km; Ascent 1,528m with two CAT 4 climbs and one CAT 2.

The views of the Upper Tiber Valley are spectacular. Throughout the day I have been seeing hundreds of other cyclists out on the road. It’s absolutely incredible. It just makes you feel like part of the Italian cycling culture. Ciao, Ciao, Ciao! (a beautiful moment)”

Area Map

AN INVITATION from Leonard Lee

“I have been seeing hundreds of other cyclists out on the road. It’s absolutely incredible. It just makes you feel like part of the Italian cycling culture. Ciao, Ciao, Ciao! (a beautiful moment)”

Hello there!

  My first time cycling in Italy turned out to be very special. I cycled in Tuscany, Umbria and Emilia Romagna. It really is a great place to ride a bike. 

  Inspired ITALY and I have worked to create an Italian Cycling Experience to share with you, the Leonard Lee YouTube Channel viewers.

  We will run two back-to-back cycling weeks for 12 guests to join me each week. We can ride together and experience this great cycling area.

  The full details of the trip are available on this page but to get a real flavour of what you can expect, watch my videos.

  If you have any questions, do get in touch with Inspired ITALY.

  Hope to see you in Italy and thanks for watching!

    Ciao, Leonardo

    The Jolly Good Velo

VIDEO: Cycling in Italy - What the Guests Say

Cycling in Italy is one of my greatest lifetime cycling memories.

From the renaciance scenerary of Tuscany to the Giro d'Italia in Emilia Romagna and being part of the amazing Italian cycling culture.

We tasted the local wines and sampled the food and enjoyed wonderful cycle routes.  I made four videos of my visit to Emilia Romagna and five in Tuscany.

Take time to watch them to get an idea of my Italian Cycling Week.

Ciao, Leonardo


🟥 Watch Leonard in Umbria


Cycling is great in Tuscany & Umbria

Get More from Your Ride: IN A SMALL GUIDED GROUP

Words by Tim Hudson | Founder, Director & Principal Ski & Bike Leader


The idea for the Leonard Lee Italian Cycling Week was born in Emilia Romagna. Leonard and I cycled together and most of the time we rode in a group of 10 or so including Leonard and me. The pace was always good and on occasion, I took the lead.

This was a great new experience and feeling for me.

It was as near to a real a paceline as I have ever experinced and the drafting and leading were exciting parts of the ride and first time experiences for me. We visited historic towns, ate endless amounts of really wonderful food and sipped on local wines.

One of my best ever cycling experiences!

Now, we want to share these experiences with you, the Leonard Lee subscribers and viewers.  We hope that you will join us.


On the finish line of the 2020 Giro d'Italia

A Home for Italian Cycling

Unquestionable Cycling Pedigree

From the legend of Gino Bartoli to modern-day cycle hero Mark Cavendish, the Strada Bianche, l’Eriocia and the Giro’s Wine Sages all have their hearts here in Tuscany.

There are few places on earth that offer such a great blend of near-perfect cycling terrain – oodles of flat, fast and low-traffic roads around the valleys of Umbria and the shores of Lake Trasimeno or head to the hills and some epic routes taking in the climbs of the iconic Apennine mountains and foothills.

This is why cycling is so popular here. 

In 2021 the famous wine stage of the Giro d’Italia started in Umbria and finished in Montalcino. Did you see it on TV? If not, watch the video below…

🟥 VIDEO: Watch Giro d’Italia 2021 | Stage 11 | Highlights from Perugia, Umbria to Montalcino, Tuscany

“I thoroughly enjoyed my week and can highly recommend experiencing Italy to anyone looking for a cycling holiday, and I'm hoping to book another holiday with them next year.”

There’s a beautiful pool, with awesome deck chairs and grass to chill on.

This is where you stay ... Le Fornaci

Clean, cool, country stylish, and great views

Le Fornaci is beautifully managed and the pool and amenities are top-notch including a lovely gym with floor to ceiling windows and a small spa.

You can walk along the valley and cycle the local hills of this stunning area. It is truly spectacular.

The host Simone greets you in excellent English and offers such wonderful hospitality with genuine kindness.

Le Fornaci is close to Cortona, Assisi, Arezzo, Perugia and lots of other Italian gems. The local village is a 5-minute walk away – perfect for a morning coffee/gelato and a game of Briscola.

Wood Fired Pizza Oven | Inside & Outside Dining | Large Pool | Gym | Spa | Large Lawns 

The Leonard Lee 🚴‍♂️ Week



No. We help you to find the best flights and give you guidance on airports but please book your own flight. The destination airports are Pisa or Florence. We can advise on alternative airports if you so wish.



Yes. There is a group transfer included in the price from Pisa and Florence airports.



All rooms are single occupancy. Most rooms are double rooms used for single occupancy.



There are various transport options from the airport to the destination hotel, including private taxis, trains and buses. We will help you with the details.



The Leonard Lee 🚴‍♂️ Italy Week suits riders of all abilities. It is recommended that put in some preparation work in advance so that you get the most from the week. Remember, there are six rides over six days. Of course, you can choose to take a rest day at any time.



Yes, definitely! Contact us with the details and we will happily make the necessary arrangements.



You may cancel your reservation at any time. Whilst our terms and conditions apply, we always take a pragmatic view and always endeavour to find the best solution for both parties.



Yes. If you cannot attend and you transfer the booking to someone else that’s fine! We will charge an administration fee. So long as we are fully informed.



Yes, in fact, it is better to do this rather than bringing your own bike.



It is a condition of booking that you have in place comprehensive travel insurance to cover cycling insurance to cover your bike (even though it is rented), luggage, plus personal accident and injury.



It is highly recommended that you wear a helmet.



A full kit list is sent to you well in advance of the event.



Yes, in fact, we encourage it! There is a full program of activities for partners which is designed so that you share as much of this experience as possible.

Read More

Other Inspired ITALY Guided Cycling Adventures

... definitely go for a guided option. Tim’s knowledge of the area is sublime and he always has a random fact or story about wherever you are. He just makes the whole trip even better Can’t wait to come back again.

Calvin Booker, Raleigh Bicycles, UK

GIROe: Grand Tour of Tuscany

Chianti | Val d'Orcia | MontepulcianoFULLY GUIDED
  • • ☀️ 8 Days | 6 Stages | 7 Nights 🆕
  • • Tuscany's Best Cycling Terroir on a Carbon Road Bike
  • • See it on YouTube
  • • From $2,957 per person

The Italian Road Bike Experience

Home of the GranfondoDAILY GUIDED
  • • Birth Place of Marco Pantani
  • • Easy to Expert Cycling
  • • 5 or 7 Nights
  • • From $2,500 per person

Umbria for Food & Wine Lovers: Our Umbria 🍷🍝

Niccone Valley | Montone | Gubbio | AssisiFULLY GUIDED
  • • 7 or 5 Nights
  • • EASY CYLING with a few short moderate sections
  • • 🍷Tastings & 🍝 Cooking Lesson
  • • From $3,347 per person

“We are reasonably keen, but ‘mature’ leisure cyclists and at first we were a little apprehensive about our abilities. Tim and Roberto gave us advice and encouragement so that we were able to pace ourselves and complete each of the daily rides with confidence.”

Graham Stanley

“This was my first cycle holiday and can’t be more positive about the equipment, route planning and guiding. Thank you Tim and Roberto for being wonderful hosts.”

Andrew Le Poidevin

“ confidence grew; and, though I had been a bit worried about the longest ride, by the end of that day, I didn’t want the 100km ride to end.”

Barbara Stanley

“..definitely go for a guided option. Tim’s knowledge of the area is sublime and he always has a random fact or story about wherever you are. He just makes the whole trip even better. Can’t wait to come back again.”

Calvin Booker | Raleigh Bicycles, UK

“Tim [the guide] actually rode with us, pointing out lots of very interesting fact and figures along the way. All our luggage was transported between hotels so all we had to carry were the things we needed for the ride”

Leonard Lee | Club Cyclist & Youtuber

“... a wonderful experience and I would have no hesitation recommending Inspired Italy to anyone thinking of a cycling holiday in Italy.”

Leonard Lee | Club Cyclist & YouTuber

“I thoroughly enjoyed my week and can highly recommend experiencing Italy to anyone looking for a cycling holiday, and I'm hoping to book another holiday with them next year.”

Alan Parkinson, Road Cycling in Italy

“I am a fairly experienced cyclist but I've never ridden an e-bike so had no idea what to expect. My inner roadie wanted to do the climbs without assistance. But it was just easier to use the motor to push you up the many Tuscan hills and enjoy the views and the ride rather than push yourself to exhaustion. The routes varied from a relatively easy 45 km/700 metres vertical to a challenging 100km/1300 metres.”

My First Ever Ride on an Electric Bike by Leonard Lee


$2,287 per person

Your adventure includes:

Your adventure includes:

  • ☀️8 Days, 7 Nights & 6 Rides with Leonard Lee
  • Private Taxi Transfer From & To Perugia Airport or Terontola-Cortona Rail Station
  • ⛱ Private Bike Hotel with Exclusive use including Private Pool & Spa
  • Super Half Board: including Breakfast & Post-Ride Lunch; Dinner including Water & House Wine
  • 🍕🍷 Pizza Evening
  • 🍇🍷 EXCURSION: Local Food & Wine Tasting at I Girasoli di Sant'Andrea
  • 🍷🍝 EXCURSION: An evening in Preggio with dinner
  • 🚴‍♂️ Guided Daily Group Rides
  • 🚴‍♂️ Inspired ITALY Cycling Jersey
  • 🚴‍♂️ Laundry for Technical Clothing (deliver the dirt, collect the clean)
  • 🚴‍♂️ Water, Mineral Salts & Banana for Your Rides
  • 🚴‍♂️ GPX Files of your Rides
  • 🚴‍♂️ Bike Room
  • Entrance to the HOTEL SPA for 3 hours per day
  • Free Wifi
  • Fitness Room
  • Technical Assistance in case of accidents or faults
  • Daytime & Evening Entertainment