The Tour

The Roadaway Experience

We specialise in exploring Umbria the ‘Green Heart of Italy’ on two wheels, where spectacular rides meet five-star comfort.

Our team will host, cook, and guide every part of your stay, so all you need to do is ride and relax.

Choose full-day rides through rolling hills or gentle cycles to vineyards and tavernas, every itinerary is tailored to your group preference. From Montefalco’s vineyards to Lake Trasimeno and the winding roads to Assisi, each route reveals a new side of Umbria.

Your home base is our 5-bedrom luxury villa, Casa Della Speranza, perched on a hill with panoramic views. After a day on the bike, unwind in the infinity pool, enjoy the games room or gym, and savour gourmet meals prepared by our private chef.

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.

Tour Highlights

Terramante Wine Tasting

Terramante is a small, family-run organic winery in central Umbria, focused on carefully crafted small-batch wines. During your visit, you’ll learn about their winemaking techniques, enjoy tastings of their signature wines, and take in the scenic surroundings of the Tiber River park.

Exploring Assisi

Perched on Mount Subasio, Assisi is renowned as the birthplace of St. Francis and for its striking historic and spiritual charm. We’ll cycle there for lunch, giving you time to wander the winding streets and enjoy panoramic views over the Umbrian valley before returning to the villa.

An Afternoon in Montefalco

Known as the Balcony of Umbria, Montefalco sits atop rolling hills surrounded by vineyards and olive groves. Famous for its robust Sagrantino wine and medieval character, the town is perfect for a relaxed lunch, a wine tasting, and a stroll through its cobbled streets and charming squares before heading back to the villa.

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

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.

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 within 24 hours.

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."