Self Guided Cycle Tours in Italy | How it Works

For Independently Minded Cyclists

Once Upon a Time

An Exceptional Place to StaySINGLE CENTRE | 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 ItalySINGLE CENTRE | SELF GUIDED
  • • 3, 5 or 7 Nights
  • • Umbria & Tuscany
  • • Set your Own Pace
  • • Prices from $467 per person

Fragrance & Flavours of Tuscany

The True Taste of TuscanySELF GUIDED
  • • 8 Day | 7 Night -OR- 6 Day | 5 Night
  • • EASY to MODERATE Cycling
  • • From $1,299 per person

The Da Vinci Road

Cortona | Montepulicano | Val d'Orica | Montalcino | ChiantiSINGLE CENTRE | SELF GUIDED
  • • 10 Nights
  • • EASY to MODERATE Cycling
  • • A SuperTuscan eBike Tour
  • • From $2,205 per person

If you’re an independently minded cyclist, Inspired ITALY self-guided cycle adventures in Tuscany and Umbria are perfect for you.

Take Me For a Self Guided Cycling Adventure in Italy
Freewheeling into the Val d'Orcia, Tuscany

📅 Choose Your Own Dates

You Can Select Any Start Date or Day

You do not have to arrive on a weekend. If the flights work for a Tuesday arrival, then that is fine by us and we work with you to coordinate flights and transfers.

💁🏼 You Are Fully Supported

We help you with your flight planning and transfers. Everyone at Inspired ITALY is a native English speaker. We are here, on the ground in Italy to meet you at your arrival hotel and to support you throughout your ride. We deliver your bikes and personally brief you about the bike and your week ahead. 

For guests who use WhatsApp, we create a Private WhatsApp Group about 10 days before your arrival. We call it your Virtual Guide and each day we send you updated weather, route highlights and general information.

Slow or Dead Slow! Its Difficult to find a Faster Pace in Rural Umbria

Freedom to Set Your Own Pace

Your Choice!

You have total freedom to start and finish your day whenever suits you. With no fixed commitments along the way, you can stop off where you want and when you chose. We will give you advice on what to see each and every day. In the end, it is entirely your choice as to what you choose to do!

🤸‍♀️ More Flexibility

We Provide You with a Detailed Itinerary. 

But you can use the Bosch Nyon GPS that we provide together with the good old-fashioned physical map and Google Maps to venture further afield should you so wish.

The Bosch Nyon is probably one of the world’s best eBike computers and onboard bike GPS systems. It is preloaded with your route. You can use its local knowledge and navigational power to visit off itinerary villages, vineyards, and castles! 

The Lunch & Dinner Options are Endless!

Cost Effective & Great Value

You Choose Your Own Wine!

You have total control over every element of your day and your budget. Accommodation is provided on a bed and breakfast basis (half-board available) so the choice for coffee, lunch, dinner, and which wine is all entirely your own. 

Of course, we can make recommendations.

🤙 We Are Local Hosts & Always On Call

We Are Here. We Live Here. 

We are always available to you 24/7 before, during, and even after your cycle trip. You can use your WhatsApp Virtual Guide to message or call at any time about anything. What is this on the menu? Can you recommend this restaurant? What time is best to set off in the morning? Can we book a cooking course?

Whatever your query our Virtual Guide has an answer!

The BOSCH Nyon Turn-by-Turn Navigation

On-Bike GPS to Show the Route Details

The BOSCH Nyon One of the Most Powerful Bike Computers Available!

It provides turn-by-turn navigation that is clear and easy to read. It even provides an estimated time of arrival and a terrain profile so you know exactly what is ahead. Many people also like a good old fashioned map which we happily supply! 

But Italian maps come with a warning! If you are used to detailed maps such as the Ordnance Survey maps that are readily available in the UK, you’ll be very disappointed with what you receive! On top of which, Italian road naming and numbering is very, erm, Mediterranean! All of which is why we give you a GPS and a pre-planned itinerary.

Annie in Tuscany riding the Raleigh Motus Grand Tour low-step, one of the most popular electric bikes sold in the United Kingdom and is ideal for touring in Italy. 

🚲 Electric Bikes are Standard

Cycling to be Enjoyed, Not Endured.

We have the largest fleet of electric bikes in Italy. Electric bikes mean that you can enjoy your trip cycling together.

Don’t be lulled or fooled into a false sense of security – electric bikes do not give you a free ride. Far from it! Our electric bikes are not motorbikes, scooters or mopeds. There is no twist grip. When you stop peddling you stop powering the bike! The bike only moves when you pedal. It is an ordinary bicycle with a pedal assist.

The Inspired ITALY e-Bike fleet uses a crank mounted pedal-assist system designed and built by world-leading Bosch e-Bike Systems. For those wanting to work out, you’ll get it while those preferring little assistance up the hills there is as much as you could possibly wish for. 

Make sure that you are fit and in good health. Our itineraries are designed for electric bikes which mean that you travel further and higher than you would on a ‘muscle bike’.

How Fit Do I Need To Be For a Cycling Holiday in Italy?

Easy Itineraries Require 1h to 2h Cycling per Day

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. Some itineraries require up to 3h to 4h cycling per day.

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 Self Guided Cycle Tours in Italy | How it Works

BE A TRAVELLER, not a tourist

A Full Bike & Itinerary Briefing including use of the GPS

Welcome!! Bike Drop Off, Fitting & Briefing

Comprehensive Briefings

Unless otherwise arranged, we meet you for breakfast on the first morning. We deliver your bikes to you at your hotel and ensure that the bike is properly adjusted to your style of riding and provide a detailed briefing on how to use the bike. 

Briefings are comprehensive and can take an hour depending upon your questions and queries.

 🧳 Luggage Transfers are Included

You Are Free to Focus On Your Cycling

While you are cycling, our network of local drivers transfer your luggage from hotel to hotel. Pack your bag and leave it in your room and when you arrive at your next hotel your bags are waiting for you. 

You are free to focus on your cycling and you only need to carry what you need for the day ahead. 

Annie in Tuscany, exploring the countryside

Our Knowledge, Your Choice

Where to Go & What to See

Each day via your Virtual Guide, we provide suggestions for stops along the way for cultural insights. Wineries, historical sights, castles, villages, restaurants, bars and cafes! We personally created each of these routes and we know them intimately. If you have a wish list, like a cooking lesson, a vineyard or wine tasting then just ask and we’ll do our level best to get you what you wish.

Should I Bring My Own Helmet?

Yes, Bring Your Own Helmet But…

If you prefer to travel light, we provide a good quality helmet for those who require them and it is included in the price.


The Pool at Villa di Piazzano, Cortona, Tuscany

Outstanding Hotels | Hand Picked Accommodation

We don’t just chose your hotel!

We have stayed in each of the hotels that you stay in to ensure that they provide you with the experience that you are looking for. 

All our tours are based upon ‘classic’ accommodation which you can upgrade to ‘indulgence’ on request and subject to availability.


We provide a good quality helmet for those who require them and it is included in the price

What Equipment is Included?

We provide …

– Helmet

– Water Bottle & Holder

– Rear View Mirror is fitted on the bike to help you keep the group together and improve safety

– A Pannier and/or Back-Pack (depending upon the bike & itinerary), sufficient room for a wallet, camera, sun cream etc. 

– Wet Weather Cape. Yes, it can rain occasionally. 

– Battery Charger and Power Adapter. 

– Spare Inner Tube because we don’t expect you to fix punctures. 

– Portable pump for roadside emergencies. 

– Hi-Visibility Jacket – in case of roadside maintenance. 

– Bike lock. 

The Lead Guest also carries BOSCH Nyon GPS, MultiTool Kit, Basic First Aid Kit and a local area map.

The Hutchinson family ready for their Self Guided Adventure with Inspired ITALY

What to Wear?

Don’t Get Caught Out

Even the hottest day of the year can start with a chill when you’re on a bicycle. Make sure that you have a windproof jacket and maybe even a pair of fingerless gloves if you choose to travel early or later in the season. Valley mists at the beginning and end of the season can hold early morning temperatures well below seasonal norms. We also think that padded shorts help the casual cyclist. You don’t have to buy the short, just the under short, then you won’t look like you have a Baboon bottom!

What Kind of Shoes Should I Wear for Cycling?

Sports Style Shoe with a Stiffer Sole

Shoes (and padded shorts) are the most important piece of clothing needed for your cycle adventure. Look for a comfortable sports-style shoe with a stiffer sole while ensuring that the sole isn’t too large and bulky. 

The stiff sole is important because it will help support your foot as you pedal. 

Annie & Bill from California | The Most Adventurous Self Guided Guests, Yet!

What is the Cycling Like? 😎

Your Destination Guide 🇮🇹

The expansive coastal flats of Emilia Romagna, the long deep valleys of Umbria are overshadowed by the Apennine Mountains and the endless rolling hills of Tuscany. 

These Italian regions are well accustomed to road cyclists and are ideal destinations for your self-guided cycling adventure.

🍷 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 a further 25% which is a good reason that we provide electric bikes as standard for our self-guided leisure cycling adventures.

🍝 Umbria

The rural byways of Umbria make for ideal cycling terrain. Long, wide valleys trimmed by the rising ground which make up the foothills of the Apennines and are no match for your electric-assist bicycle.

This is the ‘green heart of Umbria’ renowned for its traditional cuisine, food, and depth of history. First settled by Etruscans from around 750BC villages and hilltop towns are steeped in ancient history which is often still in daily use. At its heart is Assisi, home for St. Francis, the patron saint of animals. 

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

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

Bill & Annie, wine tasting at Avignonesi, possibly one of the best vineyards in Tuscany

When To Go on a Cycling Holiday in Tuscany or Umbria?

Spring, Summer or Autumn (Fall)

A significant factor in choosing the best destination for your cycling trip is the weather. 

April, May, and early June or late August, September and October offer the best weather months. Although, frankly, we cycle all year round.

Tuscany and Emilia Romagna have famous coastlines and mountain ranges that offer dependable weather patterns.

In the hottest summer months, heading to the hills will keep temperatures manageable and your natural pace keeps the temperatures surprisingly comfortable. 

Talk to us about your preferred cycling dates.


🚴‍♂️ 🚴🏻‍♀️ 🚴‍♂️ 🚴🏻‍♀️  🍇🍷☀️😎