The Tour

The Roadaway Experience

At Roadaway, we specialise in exploring Umbria the ‘Green Heart of Italy’ on two wheels, blending luxury accommodation with the rustic charm of Umbria’s finest cuisine, wines and hilltop villages.

During your stay, you’ll enjoy the comfort of our 5-star villa, Casa Della Speranza, perched atop a hill with panoramic views. Relax in the infinity pool or take advantage of the games room and gym, all while savoring exquisite Umbrian meals prepared by our in-house private chef.

Our dedicated Roadaway team will host, cook and guide you through every aspect of your tour. Whether you prefer long days cycling through the stunning countryside or shorter, more leisurely rides to local vineyards and charming tavernas, we tailor every itinerary to your preferences. From vineyard visits in Montefalco to a scenic ride around Lake Trasimeno or a journey through the fertile plains to Assisi, your options are endless.

The Roadaway team looks forward to welcoming you.

Three people cycling on a winding road next to a vineyard on sunny day.

What’s Included

We’ve taken care of every detail, so you can focus on enjoying the ride, the views, and the slower pace of life in Umbria.

Your tour includes everything you need for a relaxed, indulgent experience:

  • Private airport transfers to and from Rome or Perugia

  • 4 x meals cooked by our private chef including alcohol

  • Breakfast with fresh local produce to fuel your day

  • Tea, coffee, and snacks available throughout

  • Bike hire, including helmet and lock

  • A guided vineyard tour and wine tasting

  • Full access to all villa facilities, including:

    • Private gym

    • Swimming pool

    • Laundry facilities

    • Games room

All that’s left for you to do is unwind, explore, and enjoy every moment.

A lively outdoor dinner table set with wine glasses, bottles of wine, candles, bread, and dishes, overlooking a scenic green landscape with rolling hills.
Sample itinerary schedule with daily activities and scenic photos of countryside and vineyards.

Sample Itinerary

Tour Highlights

Terramante Wine Tasting

Terramante is a small, organic, family-run winery in the centre of Umbria. They focus on small-batch, high-quality production in limited quantities. A visit to the winery will introduce you to the techniques and special care with which they proudly produce their wines, all set in the magnificent surroundings of the Tiber River park.

Exploring Assisi

Perched on the slopes of Mount Subasio, Assisi is one of Umbria’s most treasured hill towns - renowned for its striking beauty as well as its deep spiritual and historical significance. Birthplace of St. Francis, the town features winding stone streets, rose-hued architecture, and panoramic views across the Umbrian valley. We’ll be riding to Assisi for lunch and back over the course of a day, allowing time to enjoy a relaxed meal and take in the views before returning to the villa.

An Afternoon in Montefalco

Often called the Balcony of Umbria for its scenic views across the valleys below, Montefalco is a hilltop gem surrounded by vineyards and olive groves. Rich in medieval charm and famous for its robust Sagrantino wine, the town offers a perfect blend of history, beauty, and indulgence. We will ride to Montefalco for lunch and a wine tasting before a late afternoon cruise back to the villa, giving you the chance to soak up the town’s warm atmosphere and wander its winding cobbled streets.

A collage of five photos showcasing Italian countryside scenes: a church at sunset, wine glasses at sunset, a castle on a hill, a narrow flower-lined street, and a cyclist riding through a vineyard.

Why Book with Us?

We don’t believe in rushing from place to place. At Roadaway, we’ve created something different - a cycling experience designed to slow you down, so you can truly savour the landscapes, flavours, and moments that make Umbria so special.

Relaxed, Luxury Travel

This isn’t a race, it’s a journey. Our tours are designed for comfort, leisure, and joy, with beautiful routes, boutique accommodation and all the details taken care of.

Thoughtfully Curated Experiences

From vineyard lunches to sunset swims, every part of your week is carefully considered. We handpick local partners, hidden-gem stops, and unforgettable touches that elevate your time in Italy.

Personal & Bespoke

We keep our groups small and our service personal. Each tour is tailored to the people on it, making sure your needs and pace are always at the heart of the experience.

Everything Included

No need to worry about logistics - transfers, meals, bike hire, and wine tastings are all covered. You can simply arrive and enjoy.

More Than Just Cycling

Yes, the rides are beautiful, but it’s also about the long lunches, the laughter in the villa, and the sense of slowing down and reconnecting. Let us take care of the details. You just enjoy the journey.

Two cyclists riding on a paved road through a green landscape with a hilltop town and a tower in the background, under a partly cloudy sky.

Enquiry Request

If you’re interested in booking a tour or would like to find out more, please complete the enquiry form.

We will be in touch as soon as possible.

What Our Clients Say

  • "Exceptional is the only word that comes to mind when friends have asked me how was my holiday with Roadaway Cycle Tours. The quality of the riding around Perugia, the level of hospitality offered by the team and the sheer magnificence of the views are as I said - exceptional. Throw in fantastic food, wine and accommodation and you have the perfect holiday for anyone wanting some time away with their bike."

  • "You won’t get a better experience of Umbria on 2 wheels. Fantastic hospitality, dining and riding. You’d be crazy not to go."

  • "A truly unforgettable trip! The team were excellent from the outset and catered to our every need. The villa was amazing with tons of space and facilities such as a gym, table tennis and infinity swimming pool. This made made down time and evenings all the more enjoyable. Not to mention quite probably some of the best cycling of my life! The routes were well planned across beautiful rolling hills and passing through idyllic local villages for the much needed coffee and pastry breaks. I’d book again in a heart beat- bring on next year!!"

  • "I’ve cycled in a lot of European countries on road, but gravel cycling in Italy just tops everything else. Italy being one of my favourite countries in the world, and seeing it via a gravel routes just made it better, Umbria is so unspoiled and less touristy, so lunch breaks, coffee stops and evening meals were faultless."

  • "Fantastic and professional hosts who took care of our every need who were very flexible and accommodating. The riding routes were varied and safe taking in the best of the Umbrian countryside and villages. The food and wine were traditional and first class as was the accommodation which was located in the perfect setting."

  • "Roadaway were superb, detailed knowledge of the area, felt very safe on the rides and the bikes were good quality. Highly recommended"

  • "We would highly recommend Roadaway. The team plan the scenic routes, and adapt the rides for all abilities. The stop offs for a coffee or beer in the gorgeous little towns en route were perfect."

  • "Roadaway were superb, detailed knowledge of the area, felt very safe on the rides and the bikes were good quality. Highly recommended."