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Venice at twilight canal and architecture

Cycle Milan to Venice 2021

Challenge level: 3 out of 5

When can I go?

30 September - 4 October 2021 On Sale
Duration 5 days

What does it cost?

Registration fee (payable today) Info $223



Remaining amount
Total commitment Info

Cycle Milan to Venice 2021

The Challenge

Join us in Bella Italia on an exquisite three-day cycle from the amazing architecture of Milan to the maze of canals that makes up Venice.

Following an idyllic flat route, we ride through enchanting scenery, while we get fit, make a bunch of new friends and raise vital funds for your chosen charities.

Our 355km cycle takes us along the southern edge of the Dolomites, Lake Iseo and the heavenly Lake Garda, passing through Fair Verona, the setting of Shakespeare's Romeo and Juliet, to a finale at the edge of Venice.

We end with a free day to explore the canals and islands of Venice, while telling yourself a big “Bravo” for conquering an incredible challenge for the cause that means the most to you.

COVID-19 - keeping you safe
As we hope you know, the health and safety of our participants is always - and has always been - our highest priority.

Our team of experts here at DC has created a brilliant 14-step initiative, to minimise the risk of coronavirus and maximise your safety. Please click here to see our ground-breaking plan and rest assured that you're safe booking with us.

free transfers for all 2021 challenges!

If you feel worried about travelling as your 2021 challenge draws closer, you can transfer your booking and registration fee balance to another 2021 or 2022 challenge free of charge, up until 12 weeks before your departure date.

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 your registration fee and your challenge costs yourself.


Pay the balance

  • Pay the non-refundable registration fee of £149 which is used to administer the challenge.
  • Pay the challenge cost yourself 12 weeks before the challenge starts.
  • The challenge costs cover your food, accommodation, bike hire, guides, medical and technical support.
  • 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 your registration fee and raise the minimum target for your chosen charity.


Minimum sponsorship target

  • Pay the non-refundable registration fee of £149 which is used to administer the challenge.
  • Fundraise the minimum sponsorship target for a charity, hospice or animal sanctuary of your choice.
  • Your charitable funds must be paid in 12 weeks before your challenge starts.
  • Providing you have raised the funds, the charity you are supporting will pay the challenge costs on your behalf.
  • The challenge costs cover your food, accommodation, bike hire, guides, medical and technical support.
  • Please remember, your flights are not included. You arrange your own flights to and from Italy.
Book my place

Cycle Milan to Venice 2021

Many people who take part in this type of challenge are not regular cyclists, so it's imperative that everyone follows a reasonably serious course of training before the challenge. We'll send you a comprehensive guide to training when you register, which builds up gradually as the start date gets closer. Cycle Milan to Venice 2021 is a perfect motivation to get fit, make amazing new friends and have an experience of a lifetime.

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 life long 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 2021. 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.

Absolutely not! One of the amazing things about the challenge is that people of all ages will come together to do something very special. As long as you're 18 years or over by the time we depart for the challenge, you are more than welcome to join the ride!

Yes, of course! Cycle Milan to Venice 2021 is an Open Challenge, which means you choose how you fund your adventure.

You can self-fund and pay the challenge costs yourself without the pressure of a minimum sponsorship target; or you can choose sponsorship and commit to raising a minimum amount for a charity of your choice.

It's your chance to do something amazing for the cause closest to your heart; whether you choose to support your local hospice, an animal sanctuary or a national charity. It's completely up to you.

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 own 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 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 non-refundable registration fee of £149 per person is used to administer the challenge.

Your challenge costs of £1,100 (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
  • All transfers in Italy
  • A team of awesome, 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 two doctors for groups of over ten participants, who will accompany us throughout the challenge
  • Mechanical support
  • Your Cycle Milan to Venice 2021 medal

In addition to paying your registration fee, you will need to budget for your:

  • Flights to and from Italy - these will not be included, so you need to arrange and pay for these yourself
  • Personal travel insurance to cover your challenge.
  • Dinner on Day 1
  • Lunch and dinner on Day 5 
  • Gratuities
  • Personal expenses


You will need to take out your own personal travel insurance covering health, accident, loss and repatriation.

We have found an insurance policy provider that covers you for this and we will send you the details once you register for the challenge.

Currently, UK citizens do not require a visa for Italy, but we'll let you know if this changes before the challenge in 2021.

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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