Italy 21:13 – 17 October 2021

Cycling Holidays in Italy

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Better by Bicycle

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Europe Active Holidays
The experience is deeper and better paced than any alternative method of touring.

Italy Looks Better From a Bicycle 🚴‍♂️

Italian’s ❤️ Cyclists

Italy look’s even better from a bicycle!

And the smells are more fragrant, the colours more vibrant and reality is even more real!

From your bicycle saddle, the experience is deeper and better-paced than any other way that you could possibly consider to tour Italy.

And I can tell you that you’ll receive a better welcome because Italian’s really do love cyclists. Arriving at the hotel, restaurant, or cafe bar on your bike makes you different.

You are far more a traveller than a tourist. 

How Safe is it to Ride a Bike in Italy?

Italy loves a person on a bike. Here’s why …

The country hosts some of the world’s greatest and best-known cycling events. The world famous Giro d’Italia, the Strade Bianche and the famous vintage bike rally, L’Eroica.

Over the last 100+ years, Italian history is scattered with notable cyclists. WWII resistance hero Gino Bartali through to the Marco Pantani and Vincenzo Nibali.

Italy is a very safe place to ride a bike.

Steve, cycling through the village of Montefollonico, Tuscany

How Do I Do a Cycling Holiday in Italy?

First Decide Where You Want To Go.

The type of cycling varies from region to region. Here is a short summary of what to expect:

☀️ Tuscany is great for both road bikes and leisure cycling. Tuscany is hilly, so for leisure cyclists, it is much better to take an electric bike. Road cycling is pretty damn epic, particularly in the Chianti region. Cycling in Tuscany is hugely popular and welcomed.

  BEST FOR: WEEK-LONG, SMALL GROUP GUIDED ADVENTURES

☀️ Umbria, whilst a neighbour to Tuscany, the cycling is very different. The valleys are longer and wider which means that cycling is generally easier but there are still some hills! Umbria is ideal for leisure cycling. The food and wine here are remarkable and well worth a visit with highlights such as Assisi, Montefalco and Lake Trasimeno.

  BEST FOR: WEEK-LONG, SMALL GROUP GUIDED & SELF GUIDED TOURS

Emilia Romagna is Italy’s home for road cycling.

☀️ Emilia Romagna is Italy’s home for road cycling. Offering the mountains of the Apennines to the west, the vast expanse of flats of the Po valley to the north and the Adriatic coast to the east. You can have a coastal cycling break with everything! 

  BEST FOR: WEEK-LONG DAILY GUIDED SINGLE CENTRE ROAD CYCLING

Other popular cycling regions include the Italian Dolomites, for serious road and off-road cycling, and Puglia has some delightful seaside leisure cycling. 

What style of holiday you would prefer?

Cycling Tours are particularly popular in Tuscany and Umbria.

What Type of Cycling Holiday Should I Do?

There are two types of cycling holiday, single centre and tours.

Cycling Tours are particularly popular in Tuscany and Umbria. You get to explore the area and see far more of the region than you would from a single centre cycling holiday. Tours can be short or long and taken over 4, 5, 7 or 10 nights. Your luggage is transported from hotel to hotel by your tour operator. 

A cycling tour can be self-guided or guided. With the self-guided option, you navigate a pre-planned route using a GPS system on the bike, supported by a good old fashioned map. At Inspired ITALY we also provide a 24/7 ‘virtual guide’ using WhatsApp. 

If navigation is a concern to you, then you should opt for a guided cycling holiday. You’ll get far more from the experience, particularly if this is your first time on a cycling holiday or cycling in Italy. Your guide will not just show you the way, you’ll learn a lot more about the area, its history, local stories, the flora and fauna and, most importantly, where the best coffee, ice cream and lunch stops are!

Single centre holidays are very popular particularly in Emilia Romagna, although the Salt Path ride from Rimini to Venice is an exceptional highlight. Single centre holidays are best suited for short breaks of 3, 4 or 5 nights. We offer single-centre holidays in Emilia Romagna, Umbria and Tuscany.

Leisure cycling holidays are about cycling together. If you haven’t experienced riding an e-Bike, read on!

How Fit Do I Need to be for a Cycling Holiday in Italy?

This is Cycling to be Enjoyed, not endured! 

For the easiest rides, you need to be able to cycle for 60 to 120 minutes per day. Typically, rides are broken into shorter sections. On an easy itinerary, you cycle for 20 to 30 minutes in any one stretch between stops. On average 60% of the ride is done before lunch and the rest after. 

Unless you specifically book a road cycling holiday, all Inspired ITALY holidays are on electric bikes. So, if you get tired you can select extra assist and the cycling becomes easier. For those wanting more of a workout, they select less power or turn the power off.

Inspired ITALY leisure cycling holidays are about cycling together. This is Cycling to be Enjoyed, not endured! 

If you haven’t experienced riding an e-Bike, read on!

The Raleigh Motus Grand Tour Low-Step Trekking Bike

What Bicycle is Right for my Cycling Tour in Italy?

an enjoyable experience for all and not just the fittest. 

Our fleet of electric bikes include a low-step frame bike from Raleigh with a sit-up riding position that is ideal for leisure cycle touring; Haibike gravel-style bikes both powered by BOSCH and we have a select fleet of carbon fibre road race bike powered by Fazua.

These bikes enable guests to cycle together and overcome the issue of varying fitness levels. After all, you’re on holiday, so we want to make it an enjoyable experience for all and not just the fittest. 

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If Lycra is your chosen uniform, then we have some exceptional models and rides for you to experience!

While your luggage is transferred for you, you carry just what is needed for your day

What Should I Pack for a Cycling Holiday in Italy?

Your luggage is transported for you from hotel to hotel

For leisure cycling, we recommend a good pair of sport style shoes with a good firm sole. This will help support your foot while cycling and of course while exploring the medieval hilltop towns of Italy. 

Otherwise, invest in a pair of padded shorts. Whether you choose to use the liners or an actual pair of shorts, your bum will thank you in the long run!

Whatever time of year you choose to visit, always make sure that you have a lightweight windproof jacket. You’ve heard of wind chill? Well, when riding, you’re creating your own wind chill and a beautiful early morning breakfast taken on the hotel terrace can turn chilly when in the saddle!

You will need to take care not to get too much sun exposure. A combination of sun cream, maybe a neckerchief and something to wear under your helmet to stop the top of your head from getting burnt through the helmet vents.  

Much better than riding around in a rental car and you get to see so much more. 

Is a Cycling Holiday Good for the Environment?

You become part of the environment rather than whizzing through it. 

Yes, it is much better than riding around in a rental car. You get to see so much more.

Electric bikes allow people to enjoy cycling together, putting fewer cars on the road and improving the environment for everyone. 

On a bicycle, you can access the town centres rather than parking on the outskirts. 

How Should I Prepare for my Cycle Holiday?

Whether you’re an accomplished cyclist or a first-timer, do take as many preparation rides before your holiday as you can. Your bum and your legs will thank you and your cycling holiday will be so much more enjoyable.

Easier cycle tours mean 1 to 2 hours riding per day

How Long Will I Cycle Each Day?

There are various itineraries available. The easier cycle tours mean 1 to 2 hours riding per day where other trips you can ride for 4 to 5 hours for the keen road cyclist. 

People often ask ‘how far do I have to cycle?’ It is the wrong question. You should always ask ‘how long will it take and then how far is it. This way you can get a better feel for the difficulty of the ride(s).

active holidays europe families

What Should I Expect from an Italian Cycling Holiday?

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Lots of sunshine, an outstanding selection of wines, memorable meals and wonderful foods. Culinary delights, Olive oil, pasta and spaghetti, cultural arts, remnants of the renaissance, UNESCO world heritage sites, rural landscapes, vineyards and wineries, and scenes plucked straight from the middle ages. Local traditions and the tranquillity of the side road.

Oh and ice cream – always worth a special mention! 

It is nearly impossible to put into words what you’ll experience from the saddle of your bicycle. We haven’t even mentioned the people! Without a doubt, you’ll get far more from this than from any other Italian holiday.

Umbria for Wine Lovers🍷🍇

Explore & Delight in Umbria's Rural WineriesFULLY GUIDED
  • • ☀️ 6 Days | 7 Nights or 4 Days | 5 Nights
  • • 🍇 Umbria's Best Wine Tours & Tastings by Bike
  • • Easy Cycling
  • • From $3,296 per person

Tuscany for Wine Lovers: Terroir of Tuscany🍷🍇

Chianti | Brunello | Vino Nobile & more...FULLY GUIDED
  • • ⭐️ Sunday Times Best Cycling Breaks
  • • MODERATE to EASY
  • • 7 Nights
  • • From $3,596 per person

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

Villages of the Upper Tiber Valley

Sansepolcro | Montone | Assisi | MontefalcoFULLY GUIDED
  • • ⭐️ NEW
  • • EASY CYCLING
  • • 7 NIGHT Itinerary
  • • From $2,387 per person

The Leonard Lee 🚴‍♂️ Italy Week

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

Umbria for Food & Wine Lovers: Our Umbria 🍷🍝

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

The Day I Saw Siena

Chianti | Siena | San Gimignano | VolterraFULLY GUIDED
  • • EASY CYCLING with some short moderate sections
  • • 7 Nights
  • • From $3,296 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
  • • 🔴 REGISTER NOW 🔴

Once Upon a Time

An Exceptional Place to StayPRIVATE | SELF GUIDED
  • • 3, 4 or 5 Nights
  • • Umbria & Tuscany
  • • Short Stay | Tuscany Bike Trips
  • • Average hours of activity: 2h to 3h
  • • Prices from $1,187 per person

Walk Ride Swim

An Active Holiday in Rural ItalyPRIVATE | SELF GUIDED
  • • 3, 5 or 7 Nights
  • • Umbria & Tuscany
  • • Set your Own Pace
  • • Prices from $467 per person

“..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 in Cesenatico 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, Cycling & Giro d’Italia Experience in Emilia Romagna

“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

“Thank you for the most fabaroonie Ski Safari ever! I’ve enjoyed them all, but this one was the best in my opinion.”

DOLCE TEMPO Ski Safari by Manda Bennett

“We are enjoying every moment! Last night treated with a live Italian music show in the piazza - what a wonderful and beautiful day it was!!! The routes are so beautifully thought out!”

Rochelle Joubert, South Africa

“This trip is crazy beautiful, we enjoy every moment thx 👏”

Rochelle Joubert, South Africa

“I would ride this day everyday of the year and never get bored, thank you 😊”

FJ Joubert, South Africa

“Although we researched the tour, we underestimated how hilly the terrain was in Tuscany. However, this trip will remain in our memory for a long time to come. We will definitely be back! Thank you Inspired Italy, you made our holiday so much fun...”

Colin & Heather, Canada

“Got to our destination early to find our luggage already in our room. That set the tone of the adventure. Seamless logistics happening in the background.”

John H, Zimbabwe

“Had a fantastic 4 day adventure cycling around lake Trasimeno. We departed after a late breakfast the next morning with a lot of excitement and a little trepidation. We soon relaxed and enjoyed the beautiful countryside.”

John H, Zimbabwe

“We are a family of four from the USA; 2 young adults and 2 older adults in our 60's. Inspired Italy exceeded our expectations providing us with a lifetime of memories of beautiful cycling scenery, fairytale medieval towns, fabulous meals, fantastic wine tours and beautiful, intimate boutique hotels.”

Montanino Family, USA

“The route had been thoughtfully put together, it was incredibly varied. It did put us through our paces, both physically and mentally (one of us is in our late seventies)”

Alistair M, Canada

“Inspired Italy - it is their first-hand personal experience and knowledge which allows you to eat and stay at the most amazing places ..”

David C, UK

“The cycling was fun and I felt calm and exhilarated at the same time with a chance to feel the breeze, take in the views of the beautiful countryside”

Mary Thomas, UK

“Stunning Hotels, amazing dining, breathtaking scenery and all enabled by the fantastic team at Inspired Italy and their outstanding e-bikes!”

Andrew M

“We had a terrific week in Umbria and Tuscany. The 'e' was certainly popular on the steeper hills. Nothing was too strenuous.”

Jonny Woods & Family

“What surprised me was how relaxing it was and how you just switch off and enjoy the beauty of it all.”

Hazel Dumore

“I started e-biking after a hip operation. I had an initial idea that biking would involve staying in youth hostels. Far from it! This was really up market - great hotels, fantastic food and serious wine.”

Paul Gregory

“My wife and I wanted a holiday with a difference and a bit of an adventure - and that's what we got. From start to finish the management, arrangements and attention to detail for this e-cycling holiday were excellent.”

Ashely Blackett

“eBikes were amazing and enabled the whole family with different levels of cycling experience and fitness to enjoy a really memorable holiday. Thanks Tim and the team at Inspired Italy!”

Phil Dunmore

“What an amazing time! From the bike rides, to the hotels and the food, everything was perfect. E bikes are my new favourite thing!”

Georgia Dunmore

“What an amazing holiday! From someone who hadn’t been on a bike for years and was a bit nervous about the week it way surpassed my expectations! E bikes are the way to go!”

Hazel Dunmore

“I have just finished a 6 day bespoke ski safari with the wonderful Tim. I thoroughly enjoyed our adventures on the slope and meeting new people within the group. Everywhere we looked we were provided with another jaw dropping view, and the conditions were perfect for me all week. Our refugio’s were so homely and the hosts made us feel welcomed and special. The food provided was excellent and varied. Tim was an amazing leader and has so much knowledge of all the areas we covered. His commentary was a great addition to our coffee stops! I’m looking forward to another ski week and hopefully a walking/ E bike adventure in the near future! Lark”

Lark Ash-Wheeler

“The Umbrian route was stunning - the land that time forgot, the Italian drivers courteous, the roads in the main very quiet. The food and hotels were great and we felt, even self guided, fine.  The SAT navs really were very good - I always get lost!

Inspired Italy made it fun, hassle free and personalised. So, in a nutshell, I couldn't recommend it more.”

Nicola Odey on a Private, GPS Self Guided Umbria Electric Bike Adventure

“Fantastic experience! Sleeping at the top of the mountain and early morning untracked corduroy or powder.”

Grant Milne

“The memory of that day will stay with me forever……it started with 2 fresh runs down Marmolada and ended with a blissful stay at Averau! Unreal!”

Karen White on a Family Dolomites Ski Safari

“it was without a doubt the best week of our lives so far (except perhaps our wedding week!)”

Bethany & Dan O’Mullane

“… we had all had an ABSOLUTE BALL ...”

Felicity ‘Billy’ Clark on a Private Dolomites Ski Safari

“10 out of 10 - a wonderful unique experience. Skiing perfectly groomed pistes at 8:30 in a foot of fresh powder before anyone else”

Lizzie Norton, former owner of Ski Solutions Ltd.

“Ian and I loved your guided e bike holiday around Tuscany. It was beautifully organised with every little detail thought of, including the most perfect lunch stops and, of course amazing hotels!”

Sir Ian & Lady Collett

“We were very uncertain whether to opt for the guided or the self-guided, but having opted for the guided tour we now realise that there are some significant advantages.”

Nigel & Alwyn Vaughan on a Guided Umbria Electric Bike Adventure

“Writing [the Google review] pulled on my heartstrings and made me want to do it all over again.”

Marion Clare Williams, USA on a Guided Umbria Electric Bike Safari

“Bikes always enable their riders to be ‘at one’ with the environment and these electric bikes, by removing the really hard effort normally required, allow one to progress through difficult terrain while still enjoying the trip.”

Christian Wolmar. Award Winning Writer & Broadcaster Specialising in Transport

“.. we were always a little hesitant because of the hills, but Ebike rentals from Inspired Italy solved that problem and then some! We felt like we were in Tour d'Italia without the effort. The bikes are fantastic, and all the equipment is first-class.”

John Sweazey, USA

“.. with the eBikes, we powered effortlessly up hills that would have been otherwise painful in the hot sun. Less time sweating meant more time to enjoy the stunning scenery. I've spent countless days on the lake but cycling around it was a totally different experience and I'd do it again in a heart beat. Highly, highly recommended!”

Anna T-B, London, UK. Lake Trasimeno eBike Tour

“I rushed home to tell my cousin, all about our bike holiday. They booked immediately! It was one of the best holidays that I have ever had..”

Suzanne Dale, UK. Umbria and Tuscany eBike Safari

“Out of interest, Christian and I rode our ordinary bikes up to Castel Rigone a few days later. The difference was astonishing: I felt the hill would never end”

Deborah Maby, UK. Umbria eBike Tour

“Don’t imagine an e-bike will do all the work for you ..”

The Oldie Magazine

“Fantastic way to bike-ride in Italy without worrying about the hills

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Mark Dale, UK. Guided Umbria & Tuscany eBike Tour

“Puts the joy back into cycling”

Graham Adamson, Canada – Guided Tuscany eBike Tour

“...so great to have a leader. No stopping at the top to look where to go. No worrying about when or where to eat. Just great skiing and great new friends...”

Missey Zlotcha, USA. Dolomites Ski Safari

“... all we had to do was enjoy some of the best skiing we've ever had ...”

Jo Metcalfe, Tailor-Made Dolomites Ski Safari

“We had the most marvellous Dolomites Ski Safari, it was beyond anything I had ever expected. Such an adventure in such an awe inspiring landscape, all so well planned and executed. Our guide wasn't half bad either, in fact he was terrific.”

Belinda Callaway on a Dolomites Ski Safari

“A huge thank you for a really fabulous week. Once my first day nerves had calmed down I really enjoyed the skiing!!”

Katie, a solo skier from the UK

“Thanks everyone for putting up with the lone Yank. Y'all were way too much fun to travel with.”

Paul Dowler, a solo skier from Utah, USA

“A great “thank you” to Tim and Louise, for the inspiration to do this, in this way.”

Tim Ferrari, a solo skier from Scotland

“It made such a lovely change to be skiing on such empty slopes and in such good snow conditions, and the views were, of course, superb. A lovely holiday, and great company. Thank you.”

Patricia, a solo skier

“This is a fantastic opportunity to never ski the same run twice, to be guided by an expert not only on the slopes but on the ‘watering holes’ too! To be the only people at the top in the morning is a real treat. Skiing with a small pack seemed to make no difference, much to my surprise! All I would say is it is worth getting fit before you go. I thoroughly recommend this wonderful original ski holiday.”

Lavinia Shaw-Brown on a Dolomites Ski Safari

“I did endless research beforehand wondering whether it would work out as a holiday, was Italy the right spot and Inspired Italy the right company? All I can say all 8 of us loved it. There was a pretty wide range of fitness levels, but with the 4 speeds on the eBike it was not a problem.”

Nicola Odey on an Umbria eBike Safari

“The Inspired ITALY Dolomites Ski Safari was not only the best ski holiday but the best holiday we have ever had. Tim’s local knowledge and rapport with the locals added an extra dimension to the trip. We really felt that we got to know this beautiful part of Italy as well as enjoying some incredible skiing on uncrowded slopes.”

Jo & Adam Metcalf on a CLASSIC Dolomites Ski Safari

“The Umbria eBike tour was fantastic, the bike technology, sat nav and organisation brilliant. Dee said she would book it again next year, which is the best endorsement”

Robin Welch, Umbria eBike Tour

“What a great feeling it is when you stood there on the top of the mountain and pointed to the piste saying: "Guys, the piste is yours!" And we skied down, on, a totally fresh and empty slope, in the morning sun. THAT is something no other operator can provide!”

Karl Lintner on the CLASSIC Dolomites Ski Safari

“An enormous 'thank you' for all that you did to ensure that we had one of the best, if not the best, skiing holidays ever.”

Ally Gregory on a Dolomites Ski Safari

“Once again, many thanks to you and your team for an excellent week.”

John Daines on a Dolomites Ski Safari

“… it is seriously the best ski trip we have done for a long time … possibly ever.”

Diane Farmer on a Dolomites Ski Safari

“Fantastic experience! Sleeping at the top of the mountain and early morning untracked corduroy or powder”

Grant Milne on a Dolomites Ski Safari

“Huts don't have to be hardcore, especially when your staying in the jewel of the Dolomites darling!”

Fall Line Magazine

“I cannot now imagine a skiing holiday that does not involve those early morning runs and watching the sunset at 2,800 metres.”

The Times: Christian Wolmar

“A scene that is quiet the most idyllic I've seen in any winter landscape”

SNOW Magazine

“These are not the kind of places you stumble upon by chance and perfectly illustrate the wisdom of tapping into local knowledge.”

SNOW Magazine

“Just a short note to say thank you for everything last week. All 6 of us had a fantastic time. Everything worked like clockwork from arrival to departure. Our three days guiding were terrific. The Paul Simon duo (call me Betty and you can call me Al) are amazing as of course is Tim!! Willies for steak and vino will be a long term memory. Hotel Grones is brilliant and staff are the best around. Thanks again. Hope to see you all again next year ...”

Eamonn B; Dublin on a Tailor-Made Dolomites Ski Safari

“We were always a little hesitant because of the hills, but eBike from Inspired Italy solved that problem and then some! We felt like we were in Tour d'Italia without the effort. The bikes are fantastic, and all the equipment is first-class.”

John Sweazey on an Umbria eBike tour

“An utterly, utterly fab ski holiday and thank you SO much for organising it all. We could/would NEVER have experienced such a thing had it not been for you. I honestly NEVER want to ski anywhere else again and we would LOVE to do it again next year.”

Deborah Maby, Jan ’14

“My wife and I wanted a holiday with a difference and a bit of an adventure - and that's what we got. From start to finish the management, arrangements and attention to detail for this e-cycling holiday were excellent.”

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Inspired Italy

Office Hours 8:00 to 17:00 Popeshead Court Offices, Peter Lane, York. YO1 8SU, United Kingdom.