✓ 2026: Free cancellation up to 7 days before (travel credits) · ✓ 2027: Book with just 10% deposit✓ 2026: Free cancellation up to 7 days before (travel credits) · ✓ 2027: Book with just 10% deposit
Madeira Cycling Holidays
Revel in Madeira’s picturesque pathways on pedals
Navigate Madeira's lush landscapes by bike
Pedal through the heart of Madeira's beauty
Uncover the island's charm on two wheels
Explore a cyclist's paradise on Madeira's roads
Cycle through Madeira's enchanting scenic routes
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Ultimate Madeira Cycling Holidays

7 days / 6 nights

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Uncover the mesmerizing allure of Madeira on two wheels, pedaling across stunning mountains and alongside the deep blue Atlantic, in a year-round cyclist's haven.

Starting Point

Santa Cruz

Finish Point

Funchal

Activity Level

4/5

Season

From April to October

Bike Type

Road Bike / Gravel Bike / E-Bike

Accommodation Level

Comfort

Daily Distance

12 – 30 mi

Daily Elevation

2789 – 6398 ft

Highlights

  • Traverse through Madeira's captivating towns like São Vicente, Funchal, Porto Moniz, and Calheta
  • Bask in the evergreen splendor of the 'flower island', enriched by a kaleidoscope of exotic flora
  • Dive into the natural volcanic swimming pools of Porto Moniz
  • Explore the iconic A-frame cottages in Santana and delve into the ancient caves in São Vicente
  • Indulge in the freedom of self-guided cycling, tailoring your expedition to your pace
  • Satiate your palate with authentic Madeiran cuisine, as you dine amidst quaint, picturesque settings

Our Bikes

To ensure the best possible experience on your cycling adventure, we offer top-quality bikes for rent. Our fleet features the latest models, meticulously maintained for both performance and comfort.

To match each rider with the right equipment, our team will also assist you in selecting the most suitable bike based on your physical profile, personal preferences, and the technical requirements of the tour.

What’s included in the price?

Self-guided

Those who like good adventure and limitless flexibility should go on a self-guided cycling holiday. It offers complete freedom, multiple detour opportunities, and exploration at your own pace without having to adapt to a group.

INCLUDED

6 nights in 3* hotels with breakfast
Digital guidebook with detailed itinerary and route instructions
GPS navigation with an easy-to-use app
Tour design and organization
Service and support during your tour
Luggage transfer

NOT INCLUDED

Tourist tax

OPTIONAL EXTRAS

Accomodation upgrade
Airport transfer
E-bike
E-road bike
Gravel bike
MTB
Regular bike
Road bike
Single supplement
Accommodation levelComfort

Carefully selected 3- and 4-star hotels, guesthouses, and B&Bs, all with private en-suite rooms and breakfast included. Expect comfortable, well-appointed rooms with attentive hospitality, typically in convenient and scenic locations — some properties also offer on-site dining.

Imagine pedaling through sun-dappled paths, with the Atlantic's cool breeze on your face and panoramic views that seem plucked from a dream.

That is what Madeira offers on a cycling holiday. Its  mild climate from February to December not only nourishes its nickname as the 'flower island' but also renders it an idyllic cycling retreat even in winter.

The route takes you from the tranquil beaches of Santa Cruz to the vibrant city of Funchal, revealing Madeira's hidden gems along the way. You'll traverse verdant hills, explore traditional villages like Santana with its iconic A-frame houses, and unwind in Porto Moniz's natural volcanic pools.

Each day presents a new challenge and reward, from ascending misty mountains to coasting through serene valleys, with every kilometer unveiling a new perspective on the island's natural splendor.

To ensure your holiday goes as smoothly as possible, we handle every detail. From comfortable accommodations to expert-crafted itineraries, GPS routes and round-the-clock support, your journey is in the best hands.

Whether you're an avid cyclist or a spirited explorer, this is a cycling opportunity you cannot let pass by!

Frequently Asked Questions

The best time for cycling in Europe depends on where you're headed. Here's a quick breakdown by season:

  • Spring (April–May) is ideal for Southern Europe — moderate temperatures, quiet roads, and the countryside in full bloom. Great for Portugal or Italy

  • Early summer (June) is the sweet spot across most of Central Europe — Austria and Slovenia are all at their best, with long daylight hours and alpine passes fully open.

  • Late summer to early autumn (August–September) suits places like Norway and Denmark — cooler temperatures, plenty of daylight, and far fewer tourists than peak season.

  • Winter is generally off-season for most European cycling destinations. The exception is warmer regions like the Canary Islands and southern Spain — all rideable year-round.

Still a hard choice? See our tour choosing guide that will answer any questions or doubts you still might have.

Our tours can be adapted to any bike type — whether road, gravel, or mountain bike. We are in constant communication with you to find the optimal conditions for your cycling holidays in Europe.

The most versatile option is a gravel bike, even if you are coming on a road cycling holiday. It does not really affect your road performance while allowing you to take some scenic backroads that can be in a slightly worse state than the main ones. A gravel bike is usually more comfortable as well.

Europe is a very diverse continent and there is something for every cyclist. Whichever bike you choose, we will find the perfect route for you.

We offer four types of cycling holidays, each suited to a different kind of rider — and it's worth noting that most of our tours are compatible with more than one bike type, so you're rarely locked into a single option.

  • Road cycling — best for avid cyclists with the endurance to handle multiple long days in a row. Expect high daily distances, paved roads, and a pace that rewards fitness.

  • Gravel cycling — suitable for anyone comfortable spending multiple days in the saddle with some moderate climbing. Terrain is mostly tarmac and gravel, stages are manageable, and the pace is flexible. Our most popular format.

  • E-bike holidays — ideal for those who want to cover the same scenic routes with less physical strain. Electric assistance makes longer distances and hillier terrain accessible to a much wider range of riders.

  • Mountain biking — suited to riders comfortable on technical terrain. Our MTB holidays tackle rougher trails, steeper descents, and more demanding surfaces. Adjustable to your skill level, but not recommended for complete beginners.

Absolutely — and in fact, most of our tours are designed with solo travellers in mind.

Our self-guided tours mean you cycle at your own pace, on your own schedule, without being tied to a group. You're independent on the road, but fully supported behind the scenes — we handle your accommodation, luggage transfers, and route planning, and our team is reachable throughout your trip.

If you're travelling alone, just let us know when booking. We'll advise you on the single supplement and flag which tours are most popular with solo travellers.

If you want to, sure! We are well aware that some people love to stay in groups while others prefer some more alone time on their trip. We wanted to give you the opportunity to do things your way — it is your holiday, after all!

As long as you respect the group timings and locations designated by your guide, please feel free to customise your itinerary by scheduling a free meeting with our specialists and we will see what we can do at the chosen destination!

On a self-guided cycling tour, you're in charge of your own pace and schedule — no group to keep up with, no fixed departure times, no guide leading the way.

Before your trip, we take care of everything behind the scenes. We plan your route, book all your accommodation, arrange daily luggage transfers, and load your GPS with turn-by-turn navigation. You receive a detailed digital guidebook covering each stage, what to expect on the road, and recommendations along the way.

On the day, you simply check out, drop your bags at reception, and ride. Your luggage arrives at the next hotel before you do.

Throughout the trip, our team is reachable if anything comes up — a question, a change of plan, or something unexpected. You're independent, but never on your own.

If you'd like to know more about how it all fits together, visit our self-guided tours manual.

On our guided tours, you will have professional local guides. Our guides will make sure that you will have expert guidance combined with great fun and a memorable experience.

Some of our Slovenian tours are also also available as group guided tours.

Every day starts with breakfast at your hotel. From there, the day is yours.

Your luggage is collected from reception and transported to your next hotel — so you set off with just a daypack. Your GPS route and daily notes are ready in the app.

Most stages take between 4–7 hours of cycling depending on the tour, with plenty of stops along the way.

You decide the pace, when to take breaks, and whether to linger somewhere that catches your eye.

By the time you arrive at your next hotel, your bags are already waiting. The evening is entirely free.

Hassle-Free

We take care of route planning, accommodations, luggage transfers, and all logistics, so you can focus purely on enjoying your ride.

Tried & Tested Adventures

Our cycling routes are hand-picked & tested, to ensure breathtaking landscapes, smooth roads, and maximum safety - giving you the perfect ride every day.

Unbeatable Support

Our 24/7 customer support is where we show our passion, ensuring your cycling holiday runs smoothly and your well-being is always our top priority.

Book with Confidence

We are a financially protected company, fully bonded and insured, keeping your money safe and allowing you to travel with confidence.

Local Experts

Our professional cycling guides in select locations know the local terrain and are trained to make this once-in-a-lifetime opportunity both safe and enjoyable.

from 1.649 € /person