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Discover what makes Medfeel the premier choice for cycling adventures in Mallorca
We leverage our local expertise to create bespoke journeys with handpicked stays, unforgettable routes, and authentic experiences.
Simplify your planning with everything you need (accomodation, transfers, rentals, routes, guides ...) in one seamless booking process.
Enjoy self-guided adventures with accurate and secure GPX files and on-route recommendations provided after booking.
Rely on expert assistance anytime, anywhere during your trip.
Book with confidence using secure and adaptable payment options.
For exclusive trips, local news and other curated active travel content.
Written by
Ata del Hoyo
Medfeel Experience Designer & Head of Growth
For many travellers, Venice is the destination. For us, it's where the journey truly begins.
Just beyond the canals lies a quieter, more authentic Italy—one of rolling vineyards, Renaissance villages, family-run wineries, and roads that seem designed to be explored at a slower pace. Here, every stop feels less like a tourist attraction and more like a personal discovery, where centuries of history, exceptional cuisine, and breathtaking landscapes come together to create one of Europe's finest cycling destinations.
Over the past several months, we've carefully explored this region to design one of the most distinctive Dolomites cycling holidays and bespoke cycling vacations in Italy available today. We've handpicked exceptional luxury hotels, partnered with passionate local producers, ridden hundreds of kilometres to identify the most rewarding roads, and curated experiences that showcase the very best of Veneto and the Dolomites.
The result is far more than a cycling tour. It's a thoughtfully crafted journey through Italy's cultural and natural heritage—from the elegant streets of Asolo and the UNESCO-listed Prosecco Hills to the dramatic alpine passes surrounding Cortina d'Ampezzo. Every day blends spectacular riding with remarkable hospitality, creating a truly premium experience for travellers seeking the finest cycling vacations in Italy.
When cyclists dream about Italy, Tuscany often steals the spotlight. Yet ask experienced riders where the country's most rewarding roads are found, and many will point north.
Veneto offers everything that makes Italy unforgettable without the crowds. Quiet country lanes weave through vineyards producing some of the world's finest Prosecco. Medieval villages sit untouched on hilltops. Renaissance architecture appears unexpectedly around every corner. Local cafés still serve the same families that have gathered there for generations, while mountain roads rise dramatically towards the UNESCO World Heritage landscapes of the Dolomites.
Within a single week, you'll experience two completely different worlds. The gentle elegance of Veneto gradually gives way to one of the most spectacular mountain ranges on Earth, where legendary Giro d'Italia climbs wind through towering limestone peaks that glow pink at sunset.
Your journey begins in Asolo, a picturesque hilltop town often referred to as The Pearl of Veneto. Elegant yet understated, Asolo has long attracted poets, artists and travellers searching for authentic Italian charm.
After settling into the beautiful Hotel Cipriani Asolo, you'll meet your guides and enjoy a relaxed introductory ride through quiet country roads that immediately reveal the rhythm of the region. The pace is gentle, allowing time to adjust to the surroundings before wandering through Asolo's cobbled streets, lively piazzas and artisan boutiques over an aperitivo.
It's an elegant beginning that perfectly introduces the philosophy behind our Italy bespoke cycling vacations: exceptional riding balanced with unforgettable cultural experiences.
The first full riding day showcases a side of Veneto that remains largely undiscovered by international visitors. Leaving Asolo behind, you'll pedal through vineyards, orchards and peaceful farmland while following the historic Piave River. Along the way, magnificent Palladian villas remind riders that this region was once one of Europe's cultural centres during the Renaissance.
One of the day's highlights is Borgoluce Estate, where cycling, gastronomy and sustainable agriculture come together beautifully. Family-owned wineries, historic castles such as Susegana and Collalto, and the peaceful Abbey of Saint Eustace transform the ride into a journey through centuries of Italian history.
Rather than chasing famous climbs, today celebrates the simple pleasure of cycling through landscapes where every village has a story and every café invites you to stop a little longer.
Today's ride introduces one of Italy's newest UNESCO World Heritage Sites. Leaving Asolo behind, the route winds through the spectacular Prosecco Hills towards CastelBrando. Endless vineyards blanket the rolling hills while small stone villages appear around every bend, creating scenery that feels almost cinematic.
Along the way you'll visit the extraordinary Tempio Canoviano in Possagno, the panoramic Osteria Senz'Oste, the beautifully preserved Abbey of Follina and the medieval village of Cison di Valmarino before arriving beneath the imposing CastelBrando.
This stage perfectly captures why cycling remains the finest way to discover Italy. Distances are long enough to explore, yet slow enough to notice the scent of vineyards, hear church bells echo through the valleys, and enjoy conversations with local producers who have shaped these landscapes for generations. Your evening inside CastelBrando feels like stepping into another era.
Few roads are as unique as Passo San Boldo. Often overlooked in favour of the Dolomites' more famous climbs, this engineering masterpiece is one of Italy's hidden cycling gems. Narrow tunnels carved directly into the mountainside connect a remarkable series of stacked hairpins unlike anywhere else in Europe.
The climb itself is never overwhelming, allowing riders to appreciate both the fascinating history of the road and the lush forests that surround it. It's a day that reminds us cycling isn't always about altitude or power numbers. Sometimes the most memorable roads are simply the ones that leave you smiling from the very first switchback to the last.
After breakfast, the scenery transforms dramatically. A transfer brings you into the heart of the Dolomites, where towering limestone peaks dominate the horizon and every road seems to have been designed for cyclists.
The afternoon ride tackles the legendary Passo Giau, one of the most iconic climbs in the Giro d'Italia. Endless switchbacks rise above alpine meadows before revealing panoramic views stretching across some of Europe's most spectacular mountains.
Descending via Rifugio Fedare, you'll quickly understand why riders from around the world consider this one of the greatest cycling destinations on Earth. For anyone searching for unforgettable Dolomites cycling holidays, this is the day you've been dreaming about.
Not every unforgettable ride requires smooth tarmac. Today's gravel adventure reveals a quieter side of the Dolomites, following forest tracks, alpine meadows and peaceful mountain valleys largely inaccessible by car. The destination is Lago di Landro, whose crystal-clear waters perfectly reflect the surrounding peaks on calm mornings. Along the route, the silence is broken only by birdsong, flowing streams and the crunch of gravel beneath your tyres.
It's a completely different rhythm from the previous day's alpine climbs—slower, more immersive and deeply connected to nature. For riders who appreciate adventure as much as performance, it's one of the highlights of our premium cycling vacations in Italy.
Every great cycling journey eventually reaches its final café stop. After breakfast in Cortina d'Ampezzo, you'll depart with unforgettable memories of elegant Venetian villages, UNESCO vineyards, hidden mountain roads, world-famous Dolomite passes and countless moments shared around exceptional Italian food and wine.
More importantly, you'll leave having experienced an Italy that many visitors never discover—one defined not by crowded landmarks, but by authentic encounters, remarkable hospitality and roads that continue calling you back long after you've returned home.
Our Veneto & Dolomites itinerary is much more than a cycling holiday—it's an invitation to experience northern Italy through its landscapes, traditions and people. From the timeless elegance of Asolo and the UNESCO-listed Prosecco Hills to the legendary climbs surrounding Cortina d'Ampezzo, every day has been designed to balance rewarding riding with authentic cultural experiences.
Throughout the journey, you'll stay in carefully selected luxury hotels, discover exceptional local gastronomy, visit family-run wineries, and ride some of Italy's most scenic roads, all while enjoying the peace of travelling with every logistical detail thoughtfully taken care of.
Whether you're climbing Passo Giau, sharing a glass of Prosecco overlooking the vineyards, or simply enjoying an espresso in a quiet village square, you'll discover that the most memorable moments often happen between the kilometres. It's this philosophy that defines our approach to premium cycling vacations in Italy.
If you're looking for bespoke cycling vacations in Italy, unforgettable Dolomites cycling holidays, or a luxury cycling experience tailored entirely around your riding style and travel preferences, we'd be delighted to help you create your perfect Italian adventure.
Because the finest journeys aren't measured by the distance you ride—they're measured by the stories you bring home.
