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Ultimate Madeira Cycling Holidays

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
8 Days / 7 Nights
Tour type
From: 1,649€/person
Suitable for most active people with good stamina and basic cycling experience

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

Revel in Madeira’s picturesque pathways on pedals

Revel in Madeira’s picturesque pathways on pedals

Navigate Madeira's lush landscapes by bike

Navigate Madeira's lush landscapes by bike

Pedal through the heart of Madeira's beauty

Pedal through the heart of Madeira's beauty

Uncover the island's charm on two wheels

Uncover the island's charm on two wheels

Explore a cyclist's paradise on Madeira's roads

Explore a cyclist's paradise on Madeira's roads

Cycle through Madeira's enchanting scenic routes

Cycle through Madeira's enchanting scenic routes

Want to make some changes?

Tailor made holidays - let us know what works for you and we will make it happen.
Customize your holiday

Included in price

Tour design and organization

Booklet with detailed itinerary and route instructions

Service and support during your tour

GPS navigation with an easy-to-use app

Accommodation as per itinerary

Luggage transfer

Optional Extras

Bike rental
Airport transfers
Extra days
Single supplement

Embark on a week-long cycling escapade around the enchanting island of Madeira, where lush meadows and the shimmering Atlantic invite experienced cyclists for an adventure of a lifetime. As you pedal almost the entire stretch of this Atlantic gem, explore both the pristine coastline and the heart of its countryside, unfolding a tapestry of vibrant hues from the rich flora that blankets the island all year round.

Madeira’s 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. As you cycle through, let the names of São Vicente, Funchal, Porto Moniz, and Calheta play a sweet tune to your wanderlust spirit, each town epitomizing a quaint, cozy aura intertwined with an exotic allure.

Each of the five daily stages encapsulates a unique experience, from immersing yourself in the vibrant bloom of Madeira’s floral world to catching breathtaking panoramic views atop steep cliffs. Venture into the quaint village of Porto Moniz to relish a refreshing dip in the natural lava stone swimming pools, a spectacular work of nature that promises to leave you spellbound.

From the heights of Cabo Girao to the depths of São Vicente’s ancient caves, every pedal stroke unveils a new narrative of Madeira’s rustic yet vibrant charm. Seize this self-guided cycling expedition that echoes the serene simplicity and bewitching beauty of Madeira, supported by a dedicated team ensuring a seamless, memorable journey from start to finish

Embark on a personalized adventure with our self-guided expedition, meticulously crafted by our specialists to align with your preferences, granting you the freedom to explore at your own rhythm.

Relish the liberty to pause and delve deeper whenever intrigued, choosing your destinations as your journey unfolds. Rest assured, with our dedicated 24/7 support at your disposal, assistance is always within reach at every turn.


Start planning today!

The sooner the better - guaranteed availability and best prices if you don't wait for too long.
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Things to know


Those who like a good adventure and limitless flexibility should go on a self-guided cycling holiday in Slovenia. We prepare the itinerary and book your accommodations; You enjoy the journey without our guide, being fully in charge of all the daily decisions. While you’ll have the full support of our team in case of any emergencies or concerns, a certain level of self-reliance is required.


We handle itineraries, accommodations, and anything else you prefer not to deal with, so you can enjoy a carefree holiday.

Completely Customizable

Flexibility is our middle name — whether you want more or less, or just beyond ordinary, we’ll make it happen.

Book with confidence

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

Unbeatable support

Our 24/7 customer support is where we show our passion, bringing you a better experience by making your well-being our number one priority.

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