Overview
A five day, self-guided holiday staying in a four-star hotel in Assisi throughout, which is perfect for cycling in Umbria, centre-based style. A sublime short break of winding trails and wine-filled wanderlust, this is a journey through some of Italy’s most handsome medieval cultural heritage, with ancient towns such as Montefalco, renowned for its wines, and Trevi, on the slopes of Mount Serano. Many of the trails on this tour take you through Mount Subasio Nature Park, and also on the Assisi-Spoleto Cycle Trail. Coming back every night to the ancient town of Assisi, famous for its outstanding churches, palaces and ancient architecture.
- Assisi
- Spello
- Montefalco
- Mount Subasio
- Bevagna
- Trevi
Itinerary
Day 1: Arrive at Assisi
Depending on the time of arrival, you have the opportunity to stroll the streets of Assisi with its many outstanding churches, palaces and ancient buildings, including the Basilica of St. Francis and its crypt, the Church of Santa Chiara, the Cathedral of San Rufino and the Minerva Temple dated to the Roman period.
On arrival at the hotel, you are given your bikes (if pre-booked) and maps and at 18h, there’s a welcome drink as the bike manager explains the routes.
- Accommodation: Valle di Assisi or similar in Assisi
Day 2: Spello and villages of Sagrantino | 62km
Start cycling for 15km along lush, green hills and villages as far as Spello, where we recommend taking a stop, to explore its cobblestone streets and many gates, including Porta Consolare and Porta di Venere. Or visit Palazzo Urbani-Acuti, the former residence of several important noble families over the years. Continue cycling through the village of Montefalco and ride across the Sagrantino vineyard-covered hills, where there is an abundance of wine-tasting opportunities, before heading back to the hotel.
- Cycling for the day: 62km, 5h, ↑510m ↓510m
Day 3: Spello and Mount Subasio | 55km
The first part of the ride brings you from the flatlands around Assisi back to Spello. Cycle uphill from Spello for around 7km through Monte Subasio Nature Park. Make your way through olive groves, followed by dense forest to the village of Collepino, located at an altitude of 600m on the sunny side of Mount Subasio. Descend for 8km along an undulating road which brings you to the villages of San Giovanni and Armenzano. Continue downhill to Assisi for a further 16km through more vineyard-covered hills all the way back to the hotel.
- Cycling for the day: 55km, 5h, ↑700m ↓700m
Day 4: Bevagna and Trevi | 65km
Cycle 2km along to Santa Maria degli Angeli. From here, it is an easy first climb of 5km to Stradone, followed by a gentle 8km ride to Budino via a quiet road surrounded by wheat and sunflower fields. Continue to Bevagna, a medieval village by the Topino River, where we recommend visiting Piazza Silvestri. The remaining 15km is more challenging as you cycle through typical rolling Umbrian landscapes to Trevi, an ancient town on the slopes of Mount Serano. The ride back is mostly flat and follows a different route, passing through Bevagna and Cannara. Today’s cycling comes to an end in the afternoon, with an optional tasting session of local wines and oil at the hotel (payable locally).
- Cycling for the day: 65km, 5h, ↑870m ↓870m
Day 5: Departure
Departure after breakfast.
What to expect
Accommodation
Standard accommodation for this trip is in a four-star hotel with a pool, gym and sauna. The hotel has been carefully selected based on a variety of criteria, including location, warm hospitality, fine local food, commitment to responsible tourism and suitability for cycling holidays. All rooms have en-suite or private bathrooms
Click to view default hotel
Valle di Assisi (Assisi)







This hotel is subject to availability. In the event of the particular hotel being fully booked for your chosen dates, we will replace it with a hotel of equal value and quality level. We will provide exact accommodation details to you upon booking confirmation.
Meals
Breakfast is included each morning. When no restaurant is available on the route, lunches and snacks can either be bought from local shops, or packed lunches can be pre-ordered from your hotel the night before. Dinner is available either from the restaurant at the hotel or in Assisi.
Difficulty and terrain
The trip is graded easy to moderate. The rides are on secondary roads with little traffic and gravel roads through olive fields, vineyards and medieval villages and tackling a few climbs. Near larger towns, the roads are well-travelled. Daily distances are about 60km. The trip is suitable for regular cyclists who have an active lifestyle (read more about difficulty grades). We are always happy to provide more recommendations for easier or more challenging routes when you are in situ. E-bikes are also available for rental on this tour
When to go
This trip is available from January till the end of December. You can start your holiday any day during this period, however a supplement applies if your tour has nights on Friday or Saturday. The flexibility of self-guided holidays means that there are no fixed dates and you can start your trip on any date during the season. Spring and autumn months are a preferred travel period if you want to avoid the summer heat of July and August. In September, you will enjoy pleasant temperatures and might also be able to catch the regional wine harvest.
For more information see our blog, Best time to go to Italy.
Getting there
Click to view travel options
By plane
Our recommended airports for this holiday are Umbria International Airport San Francisco D’Assisi (PEG), Firenze (FLR), Aeroporto di Roma Fiumicino (FCO) or Aeroporto di Ciampino (CIA).
By train or bus
If you are able to travel to Italy without flying, this holiday is reachable by rail, with a railway station in Assisi (3km from the hotel). For more details, see the national rail operator Trenitalia.
Arrival: If flying, Assisi is easily reachable by train from Rome (3h), Florence (3h) and Perugia (30mins). For more information and tickets, visit Trenitalia or use the Omio planner above. From Assisi train station, take a taxi (7mins, payable locally) or E067 bus line (20 mins, payable locally) to the hotel. For more information on buses, visit Bus Italia.
Departure: From Assisi, there are regular train services to Rome (3h), Florence (3h) and Perugia (30mins). For more information and tickets visit Trenitalia or use the Omio planner above.
Inclusions
Included
- 4 nights in private ensuite rooms
- 4 breakfasts
- Welcome drink
- Maps and GPS tracks
- Secure bike room
- Workshop for repairs/maintenance
- Laundry for cycling kit and shoe drying service
- Phone support by our local office/representative
Excluded
- Flights and connecting land transfers
- Lunches, dinners, drinks and snacks
- Bike rental
- Travel insurance (required – get a quote online)
- Personal expenses
- Local city tax and entry fees (payable locally)
- Any items not specifically mentioned as included in the programme
- eSIM data for international travel (get an eSIM)
Options, extras and supplements
- If you’re travelling in a group, a supplement applies to group members who would like to have a room of their own
- This holiday is available for solo travellers. However, a supplement will be charged as the cost of rooms and also luggage or private transfers (when applicable) is not shared. Please note that solo travellers are always accommodated in their own room. For logistical reasons, we don’t offer an option for solo travellers to share rooms with other solo travellers
- Bike rental
- Half-board upgrade including a two-course dinner and dessert (drinks not included)
- Extra nights
Bike rental
Rented bikes are picked up on arrival day. The rental bikes are the latest generation road bikes or e-bikes/gravel bikes by Bottecchia, Montana, Wilier, Cannondale and Sduro.
All bikes are equipped with a repair kit and pedals. Helmets can also be provided free of charge, but must be booked in advance.
You are expected to understand the basics of bike mechanics and how to mend a puncture or change a tyre. If something more serious happens to the bike that you cannot repair on the spot, call the bike manager and they will help you fix it or suggest the best and fastest solution.
Sample models: Bottecchia-315-316, E- BIKE Bottecchia BE 19/21, Montana VKT S6500, Wilier GTR team, Cannondale topstone-carbon-3 and Sduro Hardnine 3.0.





















































