Italy 00:06 – 28 November 2021

Road Cycling Holidays in Italy

The beautiful Italian regions of Tuscany, Umbria & Emilia Romagna run border to border from the Mediterranean to the Adriatic coast forming Italy's Lycra waistband.

Road Cycling Experiences in Italy's heart lands

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 Leonard Lee 🚴‍♂️ Italy Week

Cycle with the Jolly Good VeloFULLY GUIDED
  • • Social Cycling & Fully Guided Rides
  • • Explore Italy's Best Cycling with Leonard
  • • 8 Days | 7 Nights | 6 Rides
  • • From $2,057 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

A Cycling Master Class with Alessandro Vanotti

Coaching for Cyclists Over 50FULLY GUIDED
  • • Spring Training Camp
  • • 🔴 BOOK NOW | 10 Places Available 🔴

This is the MAMIL belt and it is here that you find some of the most exciting cycling terrains anywhere on earth.

These famous regions offer the expert and leisure cyclist alike, harder climbs and challenges, classic locations and Giro d’Italia stages. 

Road Cycling Experiences
The Italian Cycling Federation has 5,310 registered amateur male cyclists aged between 50 and 54 years, the so-called Master Men 5

Why Should I Go to Italy for a Cycling Trip?

Cycling is one of the most popular sports in Italy.

The Italian Cycling Federation (FCI) membership has over 2,500 registered clubs.

The history and culture of the sport run very deep in the peninsular with its popularity reaching its peak in the 1940s and ’50s, following the remarkable achievements of Fausto Coppi and Gino Bartali.

And the country is home to the world’s oldest bicycle manufacturing company.  Bianchi is still very much in existence and producing world-class bikes. The company, founded in 1885, pioneered the use of equal-sized wheels with pneumatic rubber tyres. 

These Italian regions are accustomed to road cyclists and are ideal destination for six days in the saddle, under the beautiful Italian sunshine

What is the Cycling Like?

Your Destination Guide

From the coastline of Emilia Romagna with its expansive coastal flats, through the climbs of the Apennine Mountains in Umbria, and the endless rolling hills of Tuscany – these Italian regions are made for cyclists.

Choose a guided or the daily guided option and regardless of the cycling experience you are seeking Tuscany, Umbria, and Emilia Romagna offer everything that you look for from a top cycling week under the sun.

Tuscany suddenly looks a little more serious with each journey being 92% climbs and descents!

Tuscany

Without a doubt, the most famous Italian region and the dream destination for world travellers.

But what you may not be aware of is Tuscany’s cycling prowess. The Chianti hills are filled with enthusiastic cyclists from the holidaymaker to hardened professional, such as Mark Cavendish who has a training base and second home here.

Tuscany’s beautiful relief is dominated by hilly country and iconic hilltop towns. Hills make up nearly two-thirds (66.5%) of the region’s total area and mountains (the highest are the Apennines), a further 25%.

Your cycling holiday in Tuscany suddenly looks a little more serious with each journey being 92% climbs and descents! 46% of your saddle time is up!

Italy's 'Green Heart' is characterised by long wide valleys and even longer climbs!

Umbria

The quiet rural roads of Umbria pulsate with cyclists, particularly on a weekend.

Umbria is a region of central Italy, bordered by Tuscany, and is known as “the green heart of Italy”. The terrain is mainly hilly and mountainous, with a number of river basins including the Val Tiberina. It is home to Lake Trasimeno and Piediluco but its character is marked by green, low hills, with towns and villages of different sizes, having a long, rich history and a predominately Mediaeval look.

In 2021 the Giro d’Italia stage 11, known as the Wine Stage started in Umbria. Earlier in the year the Tirreno–Adriatico flew through the Niccone valley and across the north of the region.

Inland mountains and mile upon mile of flat and fast Coastal rides

Emilia Romagna

Cycling is in the blood in this wonderful part of the world. 

Not only is it the birthplace of one of the cycling greats, Marco ‘The Pirate’ Pantani, but it is also home to the very first Gran Fondo, the Nove Colli.

There is an astounding 8,000 kilometres of dedicated cycling routes on roads, cycle paths and off-road tracks in Emilia Romagna. They cover a wide variety of terrain from the hilly and mountainous landscapes of the Apennines to the salt lakes of the Po delta.

And the enthusiasm runs much deeper. 

In 2020 Emilia Romagna Cycling welcomed the national Grand Tour, the Giro d’Italia hosting 3 stages in Rimini, Cesenatico and Cervia. And between 24 and 27 September, 2020 in Imola the region played host to the 93rd edition of the UCI Road World Championships.

Bike trips in Italy
The extra ordinary swimming pool at Castello di Leonina near Siena

Your Accommodation

Personally Selected

Whether you’re based in the single-center bike hotel or on a grand tour of Tuscany, your accommodation is selected especially for its atmosphere, facilities and to give you the best possible experience.

All hotels have pools or spas or both and the location is a key consideration. 

In Emilia Romagna, you can watch the sunrise from the Adriatic. While in Tuscany, you can watch the sunset sitting atop a hill on the terrace of the Castello di Leonina with chianti Classico in hand, while that famous red sun slides behind the Siena skyline.

This is the very best end to a rider’s day. We choose very special places to stay, specifically with the cyclist in mind. We don’t always choose the obvious because we don’t always follow the rules.

You will stay in places that gently push the boundary, that you might not usually consider but that always provide memorable moments and valuable encounters.

We were hurtling along the road, the sun beating down, warm breeze penetrating the helmet vents when Tim at the head of the group raised his hand indicating a stop.

Why Should I Go On a Guided Road Cycling Holiday?

Whilst you will pay more for the experience, you get more experience in return.

Your guide knows every turn, twist, and how to ride the fast descents of this Tuscany route.

Along the way, you’ll hear facts, anecdotes, and detailed pre-ride briefings before each stage. Where and when necessary, your guide may elect to change the route to better suit the riders, weather, and conditions.

Go Guided: You get more from the experience.

“I will never forget it. We were hurtling along the road, the sun beating down, warm breeze penetrating the helmet vents when Tim at the head of the group raised his hand indicating a stop. We pulled into a small village cafe bar, typical welcoming rustic style. They made their own ice cream. We sat there on a bench in the sun for 5 or 10 mins in pure silence, scanning the Tuscany countryside before us, whilst savouring a piece of ice cream heaven. Having a local guide added so much to my cycling experience, it’s impossible to qualify but it is a far more than just a bike ride.” 

Calvin Booker. September 2020. Inspired ITALY GIROe Grand Tour of Tuscany

Pinarello Dogma F10 & Prince taking a little seaside sunshine in Emilia Romagna

Get the Full Italian Experience ...

How Good are Pinarello bikes?

Really, now that you’re here, you should go the whole distance and choose to hire one of the greatest Italian bikes – Pinarello. 

The Ineos Grenadiers cycling team needs no introduction and a significant part of that fame comes from six Tour de France wins in nine attempts – an achievement which has led Pinarello to the title of the most decorated bike manufacturer in Tour history, with an unprecedented 11 wins.

Most recently Tao Geoghegan Hart won the 2020 Giro d’Italia seated upon his Pinarello Dogma F12 and Ineos Grenadiers took the team prize. 

🟥 GCN and the Pinarello Dogma F12

About Pinarello

“In the 1980s Pinarello confirmed itself as one of the world’s leading bike manufacturers by winning some of the top races, including the 1981 Giro d’Italia and Vuelta a España; the 1984 Olympic road race in Los Angeles; and in 1988 the biggest of all bike races, the 1988 Tour de France, thanks to Pedro Delgado. Then, of course, came Indurain in the 1990s, who, as well as his five Tour victories, won the Giro on two occasions, the Olympic time trial, world time trial and claimed the hour record – all on Pinarello bikes.”

You can choose from a number of different Pinarello bikes. Ask for details.

How Do I Travel to Umbria, Tuscany or Emilia Romagna?

The regions are serviced by a number of regional, national and intercontinental airports. Wherever your journey starts there are a number of possibilities to consider as your destination.

✈️ Best Airport for Tuscany & Umbria

Pisa International Airport - Aeroporto Internazionale Galileo Galilei Pisa

Transfer time by private taxi to Cortona 200km and takes around 2h 20m.

Alternatively take the People Mover from the airport to Pisa Centrale train station, change at Florence to get the train to Cortona-Terontola which takes around 3h and costs around €25. Trains run regularly from Pisa airport to Cortona-Terontola where the hotel shuttle or a taxi can collect you.

✈️ Closest Regional AirportPerugia or consider Florence airport.

Rome airports are a good option too.

________________________________________________

🚄 TRAINS in ITALY

Train travel is simple and very inexpensive. We are always happy to help arrange transfers by train or private taxi where they are not included.

✈️ Best Airport for Emilia Romagna

Bologna Guglielmo Marconi Airport

Transfer time by private taxi to Cesenatico 130km c1h 20m

Alternatively, Bologna Centrale train station is a 15 min journey by taxi or bus. Trains run regularly from Bologna to Cesena where the hotel shuttle or a taxi can collect you.

✈️ Venice Marco Polo Airport – Good for Emilia Romagna. Around 2h 30m by taxi. Train transfer available.

✈️ Closest Regional Airport – Rimini or consider Ancona or Forli airports.

Alan couldn't keep away from the deserts! Its hardly surprising!

Pedals, Pasta & Prosecco

Italian Fuelling for Cyclists

If you could lend an ear to the chatter of the passing peloton made up of typical 50 to 60-year-old Italian cyclists, you can be assured that someone will be talking about food. They love it! 

Whether it’s the upcoming lunch stop or that post-ride dinner, Italian cyclists care passionately about what they eat, how they eat and the genuine quality of their food.

Italian cuisine needs little introduction to most.

Yes, pasta, pizza and Prosecco are readily available but it is the beautiful simplicity, flavours, and culinary variety that will take you by surprise. 

Freshly cooked food prepared from the best ingredients can be so simple, nutritious, and memorable. 

And of course, pasta dishes are great fuel for cyclists.

Whether you ride with us in Umbria, Tuscany, or Emilia Romagna we have some very memorable meals lined up for you. 

Picnic lunches in the piazza, wine tastings and food pairings or Dario’s mammoth steak night, you will enjoy the gastronomy of Italian cycling!

Italian Cycling: Factoids & Quotes

The 2020 Giro d’Italia

🚴‍♂️ Ineos Grenadiers won the highest prize money at the 2020 Giro d’Italia €430,693. 

🚴‍♂️ Team Sunweb recorded the second-highest winnings with a total of €278,093.

🚴‍♂️ Tao Geoghegan Hart, the individual winner of the 2020 Giro d’Italia took away €265,668. The second and third places’ prizes were worth €133,412 and €68,801 respectively.

🚴‍♂️ The 2020 Giro d’Italia route is estimated to be 3,496.8 kilometres. 

🚴‍♂️ Each ride covered an average distance of 166.5 kilometres per day. 

🚴‍♂️ In the 100th edition of the Giro d’Italia cycling race, held in 2017, the cyclists covered a total of 3,615.4 kilometres.

🚴‍♂️ The Giro-E 2020, the only road stage event in the world dedicated to electrically-assisted bikes. It is an e-bike experience that’s ridden on the same roads and on the same days as the Giro d’Italia.

🚴‍♂️ The main theme colour of the Giro d’Italia is pink because the La Gazzetta newspaper is pink.

Tim Hudson | Author | Founder, Director & Principal Ski & Bike Leader Inspired ITALY standing on the Giro d'Italia finish line in Cesenatico

Italian Cycling Quotes & Sayings

"... I have my bicycle.” Gino Bartali

🚴‍♂️ “Mangia e bevi” which translated means “eat and drink” is Italian cycling slang for ‘Up & Down,’ ‘Hill & Valley’ or ‘Climb & Descent’! It isn’t a lunch reference!

🚴‍♂️ “Everyone in their life has his own particular way of expressing life’s purpose – the lawyer his eloquence, the painter his palette, and the man of letters his pen from which the quick words of his story flow. I have my bicycle.” Gino Bartali

🚴‍♂️ “Good is something you do, not something you talk about. Some medals are pinned to your soul, not to your jacket.” Gino Bartali

🚴‍♂️ “Age and treachery will overcome youth and skill.” Fausto Coppi

🚴‍♂️ “Ride your bike, ride your bike, ride your bike.” Fausto Coppi

🚴‍♂️ “The mother of the imbecile is always pregnant.” Vincenzo Nibali

🚴‍♂️ “He is an intense man. And he’s an artist, and like all the real artists, he doesn’t always fit in with normal rules.” Mario Cipollini

Road Cycling Holidays in Italy

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 Leonard Lee 🚴‍♂️ Italy Week

Cycle with the Jolly Good VeloFULLY GUIDED
  • • Social Cycling & Fully Guided Rides
  • • Explore Italy's Best Cycling with Leonard
  • • 8 Days | 7 Nights | 6 Rides
  • • From $2,057 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

A Cycling Master Class with Alessandro Vanotti

Coaching for Cyclists Over 50FULLY GUIDED
  • • Spring Training Camp
  • • 🔴 BOOK NOW | 10 Places Available 🔴

“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

“..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

“... 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