Aspects of Assisi Cycling Tour, Italy

Few places can stir emotions quite as intensely as Umbria and, to visit here is to embark on a journey into a timeless world of sun-drenched landscapes, ancient hill villages and some of the finest art collections in Italy.

This 8-night independent cycling holiday combines gentle pedalling through olive groves, sunflowers fields, vineyards and apricot orchards with the chance to explore some of the most fascinating towns and historic villages in the country. You’ll freewheel along the stately Roman Via degli Ulivi and follow in the footsteps of emperors at the sacred springs of Campello sul Clitunno.

Highlights include the lovely hilltop wine village of Montefalco, ‘the balcony of Umbria’, and the fascinating historic city of Spoleto crammed with exciting Roman remains including Emperor Vespasian’s mother’s house, and fascinating original atrium, baths and mosaics. And, of course, no trip here would be complete without spending time in magical Assisi - be sure to visit St Francis’ Basilica with its beautifully ornate frescoes and his peaceful forest retreat on Monte Subasio where he used to stroll and preach to the birds.

The hotels we’ve selected for this holiday are pretty special too, ranging from an elegantly restored, antique-filled farmhouse in the heart of the Umbrian countryside, to a panoramic 4* hotel in Spello with a first class restaurant and one of the most prestigious wine cellars we’ve ever stumbled upon!

Detailed Itinerary:

Day 1 - Arrive at Ripa
You arrive at our beautifully restored hotel overlooking Assisi in time for a dip in the pool before dinner.

Day 2 - Ripa/Spello 26km/16mi
Your first day's cycling takes you through the Chiasco Valley, on country lanes passing sunflower fields, ochre-coloured farmhouses and meadows redolent with wild apricots and figs. Enjoy spectacular views of Saint Francis' Basilica as you approach Assisi, your lunch spot for today, before cycling on along the lovely traffic-free Via degli Ulivi and through olive groves to Spello.

Day 3 - At Spello
Perched on a hilltop and surrounded by well-preserved mediaeval walls, picturesque Spello provides the perfect retreat for spending today at leisure. If you didn't get time to fully explore Assisi yesterday, it's a short cycle back to explore its magnificent historic centre including the beautiful Piazza del Comune, the 13C Giotto frescoes and well-preserved temple of Minerva. There's also a trail to the hermitage where St Francis used to preach to the birds. The great art city of Perugia is just a 20min train ride away, or of course you could just relax by the hotel's panoramic pool and terrace overlooking the stunning Chiona Valley.

Day 4 - Spello to Spoleto 36km/22mi
Today is level cycling most of the way along the Teverone Valley with some of the best views of the week. We strongly recommend the short uphill detour to Trevi, a beautiful hilltop village dating back to Roman times and capital of the Umbrian olive oil industry. Finally through ancient San Giacomo and on to one of the friendliest hotels we've ever stayed in just outside of Spoleto.

Day 5 - At Spoleto
Our hotel here is just 3km from the fascinating historic city of Spoleto. Apart from being a great art city, Spoleto has buildings seemingly reflecting every major architectural style in history, including a Roman arch, a C10 church, C12 Duomo and a 80m high C14 aqueduct. The castle here was a former prison and now houses an impressive art museum. Lots of lovely cobbled squares crammed with traditional trattorias for lunch.

Day 6 - Spoleto to Bevagna 32km/20mi or 34km/21mi
The wines of Montefalco are known throughout the world, in particular the fine red Sagrantino. There is a climb up to the old village itself, 'the Balcony of Umbria', but you are well rewarded with winetasting, magnificent views and beautiful mediaeval streets. Then it’s all downhill from here past lush green fields, poppies and buttercups with splendid views over Bevagna, Monte Cucco and the Marche Apennines beyond. Fabulous panoramic terrace for pre-dinner drinks - views across the entire valley.

Day 7 - At Bevagna
This morning maybe wander into the mediaeval walled town of Bevagna, our absolute favourite in Umbria. Visit the C13 Gothic Palazzo dei Consoli, the golden mediaeval theatre, or the C2 Roman temple and baths that include a spectacular lobster mosaic. And then enjoy a relaxing afternoon by the pool with sleepy views over the 'green heart of Italy', the dreamy Umbrian countryside.

Day 8 - Bevagna/Ripa 33km/21mi or 49km/31mi
Not long after leaving Bevagna this morning you find yourself freewheeling down into the tiny, circular walled village of Torre del Colle with its photogenic little streets. Then flat cycling across the plain into the old wine town of Torgiano with its famous Lungarotti cellars, where it’s time for a visit and some tasting before cycling on the 'Wine and Art Road' to Brufa, perhaps stopping to try some of the local olive oil.

Day 9 - Leave Ripa
If you want to visit Perugia (local bus or taxi approx 25 mins) we recommend staying on for extra nights here, otherwise we take you to the station to catch the train to Rome and your flight home.

Is this trip for you?
This is no minimum number 2 Cycle level (See Headwater’s Cycle Rating System) with lots of hills! This holiday would appeal to couples, older children and groups. This holiday is the ideal way combine cycling through Italy’s ‘green heart’ with the opportunity to visit some of the country’s best known and most fascinating historical and art cities.