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Cycle Milan to Venice 2024

Challenge level: 3 out of 5

When can I go?

12 September - 16 September 2024 On Sale
Duration 5 days

What does it cost?

Registration fee (payable today) Info $300
Remaining amount
Total commitment Info

Cycle Milan to Venice 2024

After conquering this sublime, mostly flat challenge three times, we are delighted to experience "La Dolce Vita" again in 2024! 

Join us in Italy's fashion capital for a three-day cycle from Milan to the maze of canals that makes up Venice. We'll cycle over 350km in three phenomenal days with postcard-perfect scenery every pedal of the way.

Our idyllic route will take us along the southern edge of the Dolomites, past vineyards, the stunning lakes of Iseo and Garda and into Fair Verona, the setting of Shakespeare's Romeo and Juliet.

We'll experience Italy in the best way, taking in not just the tourist hot spots, but also the tranquil towns, small roads and rolling hills of the countryside. 

Our last day on the bikes sees us cycling right to the edge of Venice for a fantastic celebration. Then, you'll have a free day to explore the canals and islands of Venice, filled with the triumph of conquering an epic bike ride for the charity of your choice.

Challenge Grading Explained

Despite the backdrop of the Dolomites on parts of your ride, this challenge is loved for its relatively flat cycle throughout. The distances each day are challenging but you will enjoy well maintained tarmac roads through this beautiful region of Northern Italy.

Your itinerary

Day 1
UK - Milan

Our Italian adventure begins in the evening, when we meet at our hotel in Milan.

To give you more flexibility, you arrange your own flights to and from Italy. This means you can book them from your local airport and easily extend your stay in Bella Italia before/after the challenge. 

Our hotel will be very easy to get to from the airport and we'll send you clear directions closer to the time.

We recommend you book your flight to come into the Linate Airport, as this is closest to the city centre, where our hotel will be. If your flying to one of the other airports in Milan, there will be good city links, so you'll still find us easily. 

Our friendly Dream Team will already be at the hotel when you check in and so we'll be able to answer any questions and help you out if you need. Then you're free to relax or explore the amazing city of Milan.

As your evening (and indeed, your day if you choose to fly in the morning) you'll need to arrange your own meal(s) - a perfect opportunity to take your pick of Milan's exquisite restaurants.

Day 2
Milan – Brescia | approx. 120km

Meeting as a group for the first time this morning, we have breakfast at the hotel and a challenge briefing, before we transfer away from the city traffic to the outskirts of Milan, where we have our bike fitting and start our challenge.

Leaving Milan, we head East, towards the hills of Northern Italy, which make mesmerising views as we draw closer. Our pretty route takes us through tranquil towns and suburbs and we stop for lunch en route to the gorgeous Lake Iseo.

This is the first of several stunning lakes we’ll see on our challenge and signals that we’ve almost finished our day’s cycle. Eventually, we reach the nearby city of Brescia, where we stay for the night.

You can always count on Italy for magnificent architecture and Brescia does not disappoint. Originally founded 3,200 years ago, Brescia has a beautiful historic centre and is home to the San Salvator Basilica, a former monastery.

Day 3
Brescia – Verona | approx. 105km

Today’s a true highlight of our idyllic cycle and we enjoy ridiculously beautiful scenery as we pedal towards the home of Romeo and Juliet.

Although we cycle through the hills today, you’ll be pleased to know that our route is still flat as we continue east through the hills on the southern edge of the Dolomites.

This brings us to the gorgeous Lake Garda, Italy’s largest lake, where we stop for lunch and admire our surroundings. We then hop back on our bikes to ride along the southern shore of the lake to our hotel in Fair Verona.

Simply put, this city is heaven for romantics. Home to Shakespeare’s star-crossed lovers, Romeo and Juliet, every street is like something out of a movie set, full of balconies, flower beds and of course, exquisite architecture.

If you have energy left in the evening, why not visit Juliet's balcony and leave a message for her on the courtyard wall? It's also rumoured to be good luck if you touch the breast of her statue.

Day 4
Verona - Mestre | approx. 125km

Our last day of cycling takes us through wonderful rolling hills, though again, we manage to avoid a tough terrain and our route remains fairly flat, stopping for lunch along the way.

Drawing closer to our finish line, we approach the metropolis of Venice and complete our ride when we reach Mestre, part of mainland Venice on the North Western shore of the Adriatic Sea.

We dismount our bikes here as it isn’t possible to cycle right into the tourist centre without a dip in the sea!

Tonight, we gather for a group dinner to bid ourselves a big Bravo for our fantastic achievement, before settling down for a well-earned rest.

Day 5
Mestre – UK

Today, we part ways and after breakfast at the hotel, you're free to make your own way back home to the UK or spend longer in this stunning city, exploring the unique islands of Venice as you wish.

A city like no other, Venice has a whopping 118 little islands separated by canals and linked by around 400 bridges.

A famous romantic landmark, Venice is renowned for its historic architecture and its gondolas, but those aren’t the only features of this special city.

Venice is also an important location in European historic and artistic history, home and influence to many a work of Renaissance Art and the birth place of the composer, Antonio Vivaldi.

Needless to say, there’s lots for you to see and plenty of great places to eat and relax.

Book my place

Funding options

Self Funded

Pay the registration fee (£249) and challenge costs (£1,295).


Pay the balance

  • Pay a non-refundable registration fee of £249 when you book, which is used to administer the challenge in Italy.
  • Pay the challenge cost of £1,295 yourself 12 weeks before the challenge starts.
  • The challenge costs cover your food, accommodation, luggage transportation, outdoor remote first aid trained challenge guides, bike hire and mechanics, and medical support, including a UK doctor with expedition medicine training.
  • Choose to fundraise as much as you can for the charity, hospice or animal sanctuary of your choice with no minimum target, or make a personal donation.
  • Please remember, your flights are not included. You arrange your own flights to and from Italy.
Book my place


Pay the registration fee (£249) and fundraise £2,590 or more for your chosen charity.


Minimum sponsorship target

  • Pay a non-refundable registration fee of £249 when you book, which is used to administer the challenge in Italy.
  • Fundraise the minimum sponsorship target of £2,590 for a charity, hospice or animal sanctuary of your choice at least 12 weeks before the challenge.
  • Providing you have raised the funds, the charity you are supporting will pay the challenge costs (£1,295) on your behalf.
  • The challenge costs cover your food, bike hire and mechanics, accommodation, luggage transportation, outdoor remote first aid trained challenge guides, and medical support, including a UK doctor with expedition medicine training.
  • Please remember, your flights are not included. You arrange your own flights to and from Italy.
Book my place

Cycle Milan to Venice 2024

This charity bike ride is not designed for Olympic athletes – it is designed for people looking for an amazing overseas challenge to train and get fit for. A number of the people who will take part in this challenge will have a low level of fitness when they sign up.

It's a relatively flat route, but we'll cycle long distances, so we strongly recommend you train. Once you sign up for Cycle Milan to Venice 2024, we'll send you a training plan, which builds up over time and will set you up for success. Remember, the more you train, the more you'll enjoy the real deal! We also recommend you check out our expert cycling tips here and our indoor training ideas here for the days when you don't want to face the weather.

You'll probably also be pleased to hear that the route isn't very hilly. As you can see from this route map (subject to change), it is mostly flat, despite riding up to the lakes with views of the mountains.

You'll probably be pleased to hear that the route isn't very hilly. As you can see from this route map (subject to change), it is mostly flat, despite riding up to the lakes with views of the mountains.

Please don't be! The majority of people will sign up on their own and our Dream Challenges are renowned for the incomparable camaraderie and lifelong friendships made as our groups take on these incredible feats together.

Once you've signed up for the challenge, we'll send you a link to a private Facebook group for everyone registered for Cycle Milan to Venice 2024.

Please feel free to use this space to swap questions, advice and updates with your fellow cyclists on your training and fundraising.

You may also want to reach out to the fellow participants in this group to see if there's anyone in your local area you can meet up to train and fundraise with.

One of the amazing things about our charity cycling challenge from Milan to Venice is that people of all ages will come together to do something very special. Everyone who is 18 years old or over by the challenge is more than welcome to join the ride.

16 and 17-year-olds may participate if given permission by Dream Challenges. Please get in touch with us to discuss this. Simply email bookings@dream-challenges.com or call us on 01590 646410 (Monday-Friday, 9am-5pm) and we'll be happy to help.

No, your main luggage will be transported each day by our support team. Each participant, however, will be organising their own flight to and from Italy, so you'll be responsible for your luggage on the plane and your journey to the hotel.

We advise you to pack light and you'll also need a small bag to go on your bike or a waist bag for things like your camera, sun cream, tissues etc.

Any extra items you may need during the day can be carried on the support vehicle, which you will have access to at the snack stops and lunch.

A cycle helmet is essential and must be worn at all times. Cycling shorts are also recommended and everyone will need their own water bottles or a camel back-type hydration system. Apart from that, no specialist equipment is required.

We will supply you with a list of everything you will need to take before you go. Cyclists will have the use of 18 or 21-gear bikes and we suggest you bring the saddle or gel cover you are used to riding on.

We provide you with very good 18 or 21-gear bikes for this challenge and we suggest you bring the saddle or gel cover you are used to riding on. 

Yes, of course! As you are responsible for organising your own flights to and from Italy, it is completely up to you which dates you book them for (as long as they give enough time for you to take part in the full cycling challenge).

You need to arrive at our first hotel on Day 1 to say hello to our Dream Challenges team and get a good rest. We meet as a group for the first time the next morning for breakfast and our challenge briefing. We’ll send you details and directions closer to the time.

Your registration fee of £249 per person is used to administer the challenge and secure your seats with the airline.

Your challenge costs of £1,295 (ie. 50% of the fundraising target if you choose sponsorship) cover:

  • Meals food throughout your challenge, except for dinner on Day 1 and your lunch and dinner on Day 5.
  • Accommodation.
  • Bike hire and mechanical support.
  • All transfers and luggage transportation throughout the challenge in Italy.
  • A team of awesome, outdoor remote first aid trained local guides and Dream Challenges staff.
  • Full support from the Dream Challenges office in the lead-up to and during your challenge.
  • Medical support, including a UK doctor with expedition medicine training, who will accompany us throughout our cycling challenge.
  • Your Cycle Milan to Venice 2024 medal.

In addition to paying your registration fee (£249) and either self-funding the challenge costs (£1,295) or fundraising the minimum sponsorship target (£2,590), you will need to budget for your:

  • Flights and transport to and from our hotel in Italy at the start and end of our charity challenge — these will not be included, so you need to arrange and pay for these yourself.
  • Personal travel insurance to cover your charity bike ride in Italy.
  • Dinner on Day 1.
  • Lunch and dinner on Day 5. 
  • Gratuities.
  • Personal expenses.

Travel Insurance
You will need to take out your own personal travel insurance covering health, accident, loss and repatriation. We advise you to arrange your insurance as soon as you can after you register to ensure you have coverage for your booking as well as the challenge in Italy itself.

In your Welcome Pack, you will receive information about an insurance provider that specialises in our type of overseas challenges and also covers you for cancellation due to medically-diagnosed COVID-19. You can, however, take arrange insurance with another provider, as long as it covers you for a charity bike ride in Italy.

Please ask the insurer about the nature of the cover. It is your responsibility to ensure you have adequate coverage for your challenge.

Currently, UK citizens do not require a visa for Italy, but we'll let you know if this changes before the challenge in 2024.

The Dream Challenges team are here to help you achieve your charity cycling challenge in Italy, and we will support you all the way. We're always on hand to answer any questions that you may have about your training or the challenge itself.

Once you've signed up, we will send you a Cycle Milan to Venice 2024 Welcome Pack with everything you need to know about your overseas challenge, including the itinerary, an example insurance policy, details about our challenge destination and the weather we can expect while we're cycling in Italy, the structure of an average cycling day, a full kit list and a realistic training plan to help you get fit for the bike ride. The training programme builds up gradually as the challenge gets closer.

We'll also send you regular email updates in the lead-up to the adventure with more important details, motivational resources, and seasonal fundraising ideas.

During the cycle, we'll have a UK doctor with expedition medicine training accompanying the group at all times, along with a team of outdoor remote first-aid trained challenge guides.

As we're not medically trained, we're afraid we can't offer you advice on this. We recommend you contact your GP or your local travel clinic, who will have the latest travel health advice.

We also recommend you visit the NHS Fit for Travel website here, to keep up to date with current travel health news and advice on staying healthy abroad.

NHS Fit for Travel website: https://www.fitfortravel.nhs.uk/home

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