Italy: Umbria, Spello, Montefalco & Assisi Guided Bicycling Vacation | VBT Bicycling Vacations Skip to Main Content
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Italy: Umbria, Spello, Montefalco & Assisi

With VBT’s deep Italian roots, we know where to find Umbria’s most scenic, low-traffic cycling routes for the best biking experience. Join us on an epic spin through the “green heart” of Italy—including the stunning hilltop city of Assisi—and many hidden gems with authentic local flavor. Cycle the delightful Umbrian countryside to the charming medieval village of Scheggino where you’ll enjoy a tasting of its famous black truffles and local olive oil. During a three-night stay in gothic Spello, you’ll explore this verdant city of hanging gardens—and pedal to the walled village of Montefalco, where you’ll discover its exquisite vintages. Spin along green valleys to the pristine medieval village of Sant’Anatolia di Narco above the River Nera—and cycle the unique landscape of the Colfiorito plateau with its peaceful lagoons and vibrant bird sanctuary. A final night’s stay in a Michelin-starred castle near Perugia brings together all the elements of history, fine dining, and opulence that make this Umbria vacation a delight for the senses.

Tour Highlights

  • Gain insights into local history on a guided walking tour of Spello.
  • Discover Assisi and learn about native son Saint Francis from our local expert.
  • Explore medieval Montefalco and Bevagna.
  • Taste torta al testo, a traditional dish, during a home-hosted lunch at a cozy agriturismo.
  • Experience the medieval ambiance and pampering service of a castle hotel.
  • Savor a delicious dinner with perfectly paired wines at a famous enoteca.

Positive Impact

VBT is proud to support Wine to Water with a donation on behalf of each guest on this tour. Wine to Water is an international organization providing access to clean drinking water and emergency supplies in water-challenged regions. We believe in giving back to the places that have enriched the lives of our guests. We’re committed to identifying and supporting sustainable initiatives in a variety of areas including education, world health, economic equality, safe drinking water, the environment, and the preservation of cultural traditions.

What to Expect

This tour offers a combination of easy terrain and moderate hills, ideal for beginners and experienced cyclists. Our VBT support vehicle is always available for those needing assistance with the hills. Two accommodations on this tour are on country estates in peaceful surroundings, and one is in a very small town. The roads are paved, with rough tar or potholes on some stretches. About 10% of the tour is on well-beaten unpaved bike paths.

  • Daily Mileage: 7-45 miles|
  • Biking: 1-5 hours|
  • Max Group Size: 22
Activity Easy/Moderate
Easy/Moderate
Bar Graph Beginner - Experienced
Cyclists
Vehicle Support Vehicle
Support

Average High /
Low Temperature (°F):

May72º/49º

Jun79º/54º

Sep80º/54º

Oct65º/44º

Average
Precipitation:

May2.9 in

Jun2.8 in

Sep2.7 in

Oct3.7 in

Air Package

Tour Only

Roundtrip international airfare

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Airport car service for arrival and departure

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One night in Florence and one night in Perugia in conveniently located hotels with daily breakfast

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6 nights, including 2 medieval castles and a hilltop hotel with beautiful views

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12 meals: 6 breakfasts, 2 lunches, 4 dinners

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2025

Step-Through Electric-Assisted Bicycle (E-bike)

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Road Bicycle (Carbon frame)

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Biking Packages Include:

Custom VBT Bike and Helmet

Two Local, Bilingual Trip Leaders

Support Vehicle

Luggage Transportation

Ride with GPS and Daily Route Notes

Welcome Reception

Facilitated Cultural Experiences

Your Choice of VBT Branded Gear for Your Adventure

Itinerary

Wed, May 7 to Fri, May 16, 2025

Show Itinerary:

Your vacation is about to begin! Spend your first night aloft and arrive ready for an unforgettable trip.

Your first day in Florence starts off right, as a VBT representative greets you at the airport. A complimentary car service will whisk you to your centrally located hotel. From here, you are perfectly positioned to explore this charming city at your leisure.

After an included breakfast, meet your VBT representative in the hotel lobby at 10:00 a.m.

After brief introductions, you travel approximately two hours by private motorcoach to Campello sul Clitunno, Umbria, with a short stop on the way to buy your lunch.

Your VBT trip leaders welcome you at your hotel and hold a safety session.  VBT’s main hotel for this tour is Relais Borgo Campello, spread within the tiny hilltop village of Campello Alto, and composed of a medieval castle and a convent. These two iconic sites were the poles of attraction for pilgrims walking the Via Francigena to Rome, and served as accommodation. The scenic site of Campello Alto, rising high on a hill, keeps intact the charm and millennial values of its history.

By the end of the safety talk, your room is ready, and you can settle in and change into your biking clothes. Get ready for your first thrilling spin down a green valley planted with hundreds of olive trees. Along the ride, you stop to visit a temple-shaped sachet. As small as it is, the Tempietto del Clitunno is considered one of the most interesting medieval monuments in Umbria — one of the very few and rare examples of Longobard architecture in Italy. The source of the Clitunno river is the subject of a poem by Giosuè Carducci, who described the place as “the Green Heart of Italy.” Today, the phrase represents Umbria.

Back at the hotel, take time to relax on the hotel’s shaded pometo, where you can enjoy wonderful views of the valley. Later, gather for a welcome cocktail on the panoramic restaurant terrace before moving to dinner, where delicious strangozzi spoletini and other Umbrian specialties are served.

Today's Ride Choices

Afternoon: Warm-up — 21 km (13 miles)

What to Expect:

Your warm-up starts with a .62-mile (1-km) steady uphill climb, very manageable — especially with an E-bike. The route continues on a long scenic downhill glide on paved terrain, where you need to watch for some stretches with rough tar. It then loops back on traffic-free country roads. Conclude your ride with another uphill climb — again very manageable — and then coast back your hotel.

Cumulative Distance Range: 21 km (13 miles)

Included Meals: Breakfast, Dinner

After breakfast, you leave the hotel to cycle on easy country roads that quietly meander by tiny fortified villages. One of them is the village of Eggi, rising on a low hill and inhabited since the Roman times.

Just outside the town of Spoleto, recognizable by the huge fortress of Albornoz rising high above it, you take an easy, scenic bike path leading into the Nera Valley. See for yourself why it is revered for its breathtakingly beautiful gorges.

Leave the bike path at the pass at 2,100 feet altitude, and embark on an exhilarating descent into Sant’Anatolia di Narco, where another small Umbrian jewel awaits: the Abbey of Saints Felice and Mauro. Tucked into a tranquil hamlet, this 12th-century former monastery is built on the site where a Syrian refugee slew a dragon, according to legend. Admire its beautiful rose window, ancient frescoes, and jaw-dropping views.

Back in the saddle, you ride the last miles into Scheggino, a quiet and picturesque village set on a hill above the river Nera. You have time to have lunch on your own and stroll this picture-postcard village before visiting the town’s Truffle Museum. Umbria, and the Nera Valley in particular, are famous for truffles, and here you can learn all about the precious mushroom — and enjoy a tasting, of course!

Back at the hotel, our gracious hosts take you on a short walking tour of your accommodation’s castle and convent. Your tour culminates on the terrace, where you enjoy a tasting of Umbria’s famous olive oil. Dinner is at the hotel tonight.

Today's Ride Choices

Morning: Hotel to Scheggino — 38 km (24 miles)

Afternoon: Walking tour — 1 km (0.8 miles)

What to Expect:

The first part of the ride is on paved country roads. After about 10 miles, the ride continues on a gradually climbing and well-beaten, unpaved bike path. Halfway, you shift to the main road, which is well paved and traffic-free. Descend almost all the way to the hamlet of Sant’Anatolia di Narco. From here, you ride a couple of miles along the river Nera, on a state road with little traffic — particularly at the time of our ride. A 30-minute shuttle completes the trip back to the hotel.

The walk led by your host in the late afternoon is partly on cobblestone and includes a short uphill and downhill from your convent-hotel to the castle of Campello Alto.

Cumulative Distance Range: 38 km (24 miles)

Included Meals: Breakfast, Dinner

Follow a shaded, rolling route into Rasiglia, a hamlet of medieval stone homes set in a green valley. Sometimes called the “Little Venice of Umbria” for its waterways and bridges, Rasiglia was famous for wool production during the 16th century, as the heavy looms could be powered by mills fed by the rushing waters. Discover more of this history and view a huge jacquard loom at the Museo dell’Acqua, housed in a former mill, and delight in the town’s picturesque network of waterfalls, brooks, and ponds. You visit on a Sunday, when the town comes alive with visitors, cafés, and street vendors selling local specialties such as lentils and chickpeas.

Continue to a higher plateau near the border of the Marche region. Here at 2,000 feet and surrounded by the sweet hills of the Appennines, the fertile soil is ideal for the production of a kaleidoscope of cereals and pulses: barley, spelt, lentils, chickpeas, red potatoes, and much more. Roll through this protected regional park all the way to the marshland as your tour leaders prepare a delicious picnic lunch.

Afterward, your route takes you all the way to your hotel for the next three nights. Located at the highest elevation in Spello, the Hotel La Bastiglia offers views that are unsurpassed. Admire the view at sunset, as you gather with your travel mates on the hotel terrace for a welcome reception. Our local guide Maura will join you and lead you on a walk along the cobbled streets of this pretty town, pointing out its medieval architecture and regaling you with fascinating stories of the  historic towns you will visit over the next few days.

Dinner tonight is on your own in Spello.

Today's Ride Choices

Morning: Vene to Colfiorito — 31 km (19 miles)

Afternoon: Colfiorito to Spello — 34 km (21 miles) | Spello walking tour — 2 km (1.5 miles)

What to Expect:

Apart from some stretches where the tar is uneven and scarred, and cyclists need to ride carefully, the entire route is on paved terrain. The morning route features some rolling miles and a 2-mile (3.2-km) ascent. In the afternoon, you follow a descending route, with downhills and rolling stretches.

Your guided walking tour of Spello will follow cobbled city alleyways. Stone stairs, archways, and picturesque glimpses of the countryside will make the walk pleasant and worth the little effort. Wear comfortable shoes.

Cumulative Distance Range: 31 km – 65 km (19 – 40 miles)

Included Meals: Breakfast, Lunch

On today’s longer and easier bike route, partly along bike paths, takes you right into the heart of the Valle Umbra, an ample valley cultivated with vineyards, cereals, and olive trees. First the Romans, and later Benedictine monks, drained the plain that in antiquity was covered by shallow lakes. From the bike path, you admire the hilltop towns of Trevi and Pissignano, before starting a gradual hill that takes you to the arched gate of the walled city of Montefalco. Completely surrounded by 13th- and 14th-century walls, the city retains much of its medieval past. Worthy of a visit is the Church of Sant’Agostino, which you encounter as you walk up to the Piazza del Comune, the highest point in town and once the center of the town life. If you continue on the main street to its end, you may discover why Montefalco is called the balcony of Umbria. Wine bars, cafés, and restaurants are abundant along the way. Take your pick for lunch on own — perhaps accompanied by the excellent Sagrantino di Montefalco DOCG red wine.

A scenic country road takes you downhill to the next highlight of the day: Bevagna, classified as one of the most beautiful villages in Italy. Located along the ancient Via Flaminia, it was once a very important Roman trading settlement. Crossing the spectacular bridge into town, you first see the ancient city wash house with its scenic waterfall. Entering the city walls, you are greeted by Filippo Silvestri Square, the medieval heart of the city. Admire the 1889 fountain designed to blend with the surrounding Romanesque architecture, including the Basilica of St. Sylvester, the collegiate church of St. Michael Archangel with its beautiful portal and spired bell tower, and the Palazzo dei Consoli.

For dinner in Spello tonight, your host Luca and his family rely on eight generations of family tradition to present a degustazione menu of truffles, bruschettas, and local specialties with wines that have been carefully curated for perfect pairings.

Today's Ride Choices

Morning: Spello to Montefalco — 39 km (24 miles)

Afternoon: Montefalco to Bevagna to Spello — 33 km (21 miles)

What to Expect:

Leaving Spello, you encounter some traffic but soon enter an easy and safe bike path. Continue on country roads, popular with cyclists, and prepare for an uphill climb into Montefalco. In the afternoon, coast down a long downhill and then ride slightly rolling country roads to Bevagna. Out of this medieval city, you follow a very quiet road and a bike path to Cannara. Travel country roads with increasing traffic as you approach Spello.

Cumulative Distance Range: 33 – 72 km (21 – 45 miles)

Included Meals: Breakfast, Dinner

Enjoy a hearty breakfast this morning, then spin along a short route flanked by olive groves to Assisi — one of, if not the, most beautiful city in Italy. The birthplace of Saint Francis, founder of the Franciscan Order and Italy’s saint patron, and of Santa Chiara, one of his early followers, it is a UNESCO World Heritage site. Guided by our local expert Maura, you will walk along cobbled alleyways and picturesque squares, learning about Francis’ life and viewing important city landmarks. Among these is the Basilica of San Francesco, renowned for its paintings by Cimabue and Giotto and other artwork, and lesser-known highlights, such as the ancient Roman arena.

Afterward, return to Spello, where you might relax by the hotel pool. Or take a longer bicycling option on the flanks of Monte Subasio to admire the beautiful countryside.

Lunch and dinner are on your own today. In Spello, you can find plenty of cozy restaurants featuring delightful Umbrian specialties.

Today's Ride Choices

Morning: Spello to Assisi — 13 km (8 miles)

Afternoon: Assisi to Spello — 12 km (7 miles) | Assisi walk — 3 km (2 miles)

What to Expect:

Leave Spello on a country road popular with cyclists. Flanked by olive trees, it is known as the oil road. It is safe and free from traffic, but be on the lookout for potholes. There is very little car traffic all the way to the outskirts of Assisi. In town, a short climb takes you to the parking area.

Most of the day is dedicated to the visit of Assisi and includes a walking tour on cobbled streets with some hills. We suggest that you pack comfortable shoes.

In the afternoon, you follow the same route back to the hotel. An optional moderate independent ride is offered later in the afternoon from Spello. Ask your trip leaders for details.

Cumulative Distance Range: 12 – 25 km (7 – 15 miles)

Included Meals: Breakfast

Say goodbye to Spello this morning as your small group sets out for Perugia, the capital of Umbria. Retrace yesterday’s ride to the outskirts of Assisi, then begin an uphill climb accompanied by beautiful views. En route, pause to visit San Gregorio and see why this small, fortified hamlet was a source of contention between Perugia and Assisi in the past.

Around noon, your scenic morning spin culminates at a picturesque agriturismo, whose owners — Elisa, Giusy, and Angela — welcome you and prepare a delicious home-hosted lunch. Using a fireplace fed exclusively with farm wood and a cast-iron pot, they cook the local specialty, torta al testo, using a traditional recipe. Savor this unique type of focaccia with local cold meats and crispy vegetables from their garden. On chilly days, they also offer imbrecciata di legumi, a soup that mixes check peas, wild peas, and lentils with fragrant, fresh olive oil.

Early this afternoon, re-mount your bike for the ride to your next hotel. Roll along a very relaxing, unpaved bike path that follows the Tiber River past fields of tobacco and big trees that shade your way.

A final, gradual hill takes you to your last hotel, the majestic Castello di Monterone. Located on the outskirts of Perugia, it is  a true castle, whose meticulous conversion into a hotel maintains its medieval ambiance. Its  manicured rose garden and panoramic outdoor pool also contribute to making your last day in Umbria a memorable one. Gather with your travel mates for a welcome drink in the castle garden and a farewell dinner in the hotel restaurant.

Today's Ride Choices

Morning: Spello to lunch stop — 33 km (21 miles)

Afternoon: Agriturismo to hotel — 27 km (17 miles)

What to Expect:

Retrace  yesterday’s route to Assisi, then continue on paved rolling roads to your home-hosted lunch, admiring spectacular vistas as you leave Assisi behind.

In the afternoon, spin a few more miles on paved roads, then enter a very relaxing, unpaved bike path along the Tiber River, past fields of tobacco and shaded by big trees. The last stretch is uphill almost all the way to your castle hotel — a steady and gradual ascent on a large city road, very manageable with an E-bike.

Cumulative Distance Range: 27 – 60 km (17 – 38 miles)

Included Meals: Breakfast, Lunch, Dinner

After breakfast, board the shuttle for a short ride into Perugia. Here, you are reunited with our guide Maura, who will reveal the many stories and treasures of the city. The highlight is the Rocca Paolina, originally a Renaissance defensive fortress built as a result of the salt trade. Destroyed, rebuilt, and destroyed again in 1861, this mighty edifice was carefully restored in the mid-1900s. Entering on a series of escalators, you see its massive walls from the inside, as you admire the ancient streets, courtyards and towers that are now on view.

You are free to find a restaurant for lunch, perhaps guided by Maura or by the city information provided by VBT. Perugia is the place to indulge your sweet tooth for dessert. The city is the home of the Eurochocolate Festival—the largest chocolate festival in Europe—and also of Bacio Perugina, the famed chocolatier renowned for its candies and gelato.

Explore at your own pace this afternoon. Perhaps you’ll stroll the Piazza IV Novembre, the city’s historic heart, and view the Fontana Maggiore, its magnificent medieval fountain. Here, you can also visit the Gothic San Lorenzo Cathedral, with its Renaissance paintings and frescoes, and the Palazzo dei Priori, once the seat of government and now an art museum.

Or hop the shuttle back to your hotel, where you can relax at the pool and enjoy wide-open views of the countryside and the distant city. For dinner on your own, you may dine at the hotel restaurant or take a taxi back to Perugia, only 10 minutes away.

Included Meals: Breakfast

After an included breakfast this morning, complimentary transportation to the Rome airport will be provided (an approximately two-hour drive, depending on traffic) for your departing flight.

Included Meals: Breakfast

Italy: Umbria, Spello, Montefalco & Assisi

Download Sample Itinerary:

Air Package (PDF) Tour Only (PDF)

Fri, May 9 to Thu, May 15, 2025

Show Itinerary:

Your tour starts at 10:00 a.m. at our Florence hotel. Your VBT representative will meet you in the lobby holding a VBT sign.

After brief introductions, you travel approximately two hours by private motorcoach to Campello sul Clitunno, Umbria, with a short stop on the way to buy your lunch.

Your VBT trip leaders welcome you to your hotel and hold a safety session. VBT’s main hotel for this tour is Relais Borgo Campello, spread within the tiny hilltop village of Campello Alto, and composed of a medieval castle and a convent. These two iconic sites were the poles of attraction for pilgrims walking the Via Francigena to Rome, and served as accommodation. The scenic site of Campello Alto, rising high on a hill, keeps intact the charm and millennial values of its history.

By the end of the safety talk, your room is ready, and you can settle in and change into your biking clothes. Get ready for your first thrilling spin down a green valley planted with hundreds of olive trees. Along the ride, you stop to visit a temple-shaped sachet. As small as it is, the Tempietto del Clitunno is considered one of the most interesting medieval monuments in Umbria — one of the very few and rare examples of Longobard architecture in Italy. The source of the Clitunno River is the subject of a poem by Giosuè Carducci, who described the place as “the Green Heart of Italy.” Today, the phrase represents Umbria.

Back at the hotel, take time to relax on the hotel shaded pometo, where you can enjoy wonderful views of the valley. Later, gather for a welcome cocktail on the panoramic restaurant terrace before moving to dinner, where delicious strangozzi spoletini and other Umbrian specialties are served.

Today's Ride Choices

Afternoon: Warm-up — 21 km (13 miles)

What to Expect:

Your warm-up starts with a .62-mile (1-km) steady uphill climb, very manageable — especially with an E-bike. The route continues on a long scenic downhill glide on paved terrain, where you need to watch for some stretches with rough tar. It then loops back on traffic-free country roads. Conclude your ride with another uphill climb — again very manageable — and then coast back your hotel.

Cumulative Distance Range: 21 km (13 miles)

Included Meals: Dinner

After breakfast, you leave the hotel to cycle on easy country roads that quietly meander by tiny fortified villages. One of them is the village of Eggi, rising on a low hill and inhabited since the Roman times.

Just outside the town of Spoleto, recognizable by the huge fortress of Albornoz rising high above it, you take an easy, scenic bike path leading into the Nera Valley. See for yourself why it is revered for its breathtakingly beautiful gorges.

Leave the bike path at the pass at 2,100 feet altitude, and embark on an exhilarating descent into Sant’Anatolia di Narco, where another small Umbrian jewel awaits: the Abbey of Saints Felice and Mauro. Tucked into a tranquil hamlet, this 12th-century former monastery is built on the site where a Syrian refugee slew a dragon, according to legend. Admire its beautiful rose window, ancient frescoes, and jaw-dropping views.

Back in the saddle, you ride the last miles into Scheggino, a quiet and picturesque village set on a hill above the river Nera. You have time to have lunch on your own and stroll this picture-postcard village before visiting the town’s Truffle Museum. Umbria, and the Nera Valley in particular, are famous for truffles, and here you can learn all about the precious mushroom — and enjoy a tasting, of course!

Back at the hotel, our gracious hosts take you on a short walking tour of your accommodation’s castle and convent. Your tour culminates on the terrace, where you enjoy a tasting of Umbria’s famous olive oil. Dinner is at the hotel tonight.

Today's Ride Choices

Morning: Hotel to Scheggino — 38 km (24 miles)

Afternoon: Walking tour — 1 km (0.8 miles)

What to Expect:

The first part of the ride is on paved country roads. After about 10 miles, the ride continues on a gradually climbing and well-beaten, unpaved bike path. Halfway, you shift to the main road, which is well paved and traffic-free. Descend almost all the way to the hamlet of Sant’Anatolia di Narco. From here, you ride a couple of miles along the river Nera, on a state road with little traffic — particularly at the time of our ride. A 30-minute shuttle completes the trip back to the hotel.

The walk led by your host in the late afternoon is partly on cobblestone and includes a short uphill and downhill from your convent-hotel to the castle of Campello Alto.

Cumulative Distance Range: 38 km (24 miles)

Included Meals: Breakfast, Dinner

Follow a shaded, rolling route into Rasiglia, a hamlet of medieval stone homes set in a green valley. Sometimes called the “Little Venice of Umbria” for its waterways and bridges, Rasiglia was famous for wool production during the 16th century, as the heavy looms could be powered by mills fed by the rushing waters. Discover more of this history and view a huge jacquard loom at the Museo dell’Acqua, housed in a former mill, and delight in the town’s picturesque network of waterfalls, brooks, and ponds. You visit on a Sunday, when the town comes alive with visitors, cafés, and street vendors selling local specialties such as lentils and chickpeas.

Continue to a higher plateau near the border of the Marche region. Here at 2,000 feet and surrounded by the sweet hills of the Appennines, the fertile soil is ideal for the production of a kaleidoscope of cereals and pulses: barley, spelt, lentils, chickpeas, red potatoes, and much more. Roll through this protected regional park all the way to the marshland as your tour leaders prepare a delicious picnic lunch.

Afterward, your route takes you all the way to your hotel for the next three nights. Located at the highest elevation in Spello, the Hotel La Bastiglia offers views that are unsurpassed. Admire the view at sunset, as you gather with your travel mates on the hotel terrace for a welcome reception. Our local guide Maura will join you and lead you on a walk along the cobbled streets of this pretty town, pointing out its medieval architecture and regaling you with fascinating stories of the  historic towns you will visit over the next few days.

Dinner tonight is on your own in Spello.

Today's Ride Choices

Morning: Vene to Colfiorito — 31 km (19 miles)

Afternoon: Colfiorito to Spello — 34 km (21 miles) | Spello walking tour — 2 km (1.5 miles)

What to Expect:

Apart from some stretches where the tar is uneven and scarred, and cyclists need to ride carefully, the entire route is on paved terrain. The morning route features some rolling miles and a 2-mile (3.2-km) ascent. In the afternoon, you follow a descending route, with downhills and rolling stretches.

Your guided walking tour of Spello will follow cobbled city alleyways. Stone stairs, archways, and picturesque glimpses of the countryside will make the walk pleasant and worth the little effort. Wear comfortable shoes.

Cumulative Distance Range: 31 km – 65 km (19 – 40 miles)

Included Meals: Breakfast, Lunch

On today’s longer and easier bike route, partly along bike paths, takes you right into the heart of the Valle Umbra, an ample valley cultivated with vineyards, cereals, and olive trees. First the Romans, and later Benedictine monks, drained the plain that in antiquity was covered by shallow lakes. From the bike path, you admire the hilltop towns of Trevi and Pissignano, before starting a gradual hill that takes you to the arched gate of the walled city of Montefalco. Completely surrounded by 13th- and 14th-century walls, the city retains much of its medieval past. Worthy of a visit is the Church of Sant’Agostino, which you encounter as you walk up to the Piazza del Comune, the highest point in town and once the center of the town life. If you continue on the main street to its end, you may discover why Montefalco is called the balcony of Umbria. Wine bars, cafés, and restaurants are abundant along the way. Take your pick for lunch on own — perhaps accompanied by the excellent Sagrantino di Montefalco DOCG red wine.

A scenic country road takes you downhill to the next highlight of the day: Bevagna, classified as one of the most beautiful villages in Italy. Located along the ancient Via Flaminia, it was once a very important Roman trading settlement. Crossing the spectacular bridge into town, you first see the ancient city wash house with its scenic waterfall. Entering the city walls, you are greeted by Filippo Silvestri Square, the medieval heart of the city. Admire the 1889 fountain designed to blend with the surrounding Romanesque architecture, including the Basilica of St. Sylvester, the collegiate church of St. Michael Archangel with its beautiful portal and spired bell tower, and the Palazzo dei Consoli.

For dinner in Spello tonight, your host Luca and his family rely on eight generations of family tradition to present a degustazione menu of truffles, bruschettas, and local specialties with wines that have been carefully curated for perfect pairings.

Today's Ride Choices

Morning: Spello to Montefalco — 39 km (24 miles)

Afternoon: Montefalco to Bevagna to Spello — 33 km (21 miles)

What to Expect:

Leaving Spello, you encounter some traffic but soon enter an easy and safe bike path. Continue on country roads, popular with cyclists, and prepare for an uphill climb into Montefalco. In the afternoon, coast down a long downhill and then ride slightly rolling country roads to Bevagna. Out of this medieval city, you follow a very quiet road and a bike path to Cannara. Travel country roads with increasing traffic as you approach Spello.

Cumulative Distance Range: 33 – 72 km (21 – 45 miles)

Included Meals: Breakfast, Dinner

Enjoy a hearty breakfast this morning, then spin along a short route flanked by olive groves to Assisi — one of, if not the, most beautiful city in Italy. The birthplace of Saint Francis, founder of the Franciscan Order and Italy’s saint patron, and of Santa Chiara, one of his early followers, it is a UNESCO World Heritage site. Guided by our local expert Maura, you will walk along cobbled alleyways and picturesque squares, learning about Francis’ life and viewing important city landmarks. Among these is the Basilica of San Francesco, renowned for its paintings by Cimabue and Giotto and other artwork, and lesser-known highlights, such as the ancient Roman arena.

Afterward, return to Spello, where you might relax by the hotel pool. Or take a longer bicycling option on the flanks of Monte Subasio to admire the beautiful countryside.

Lunch and dinner are on your own today. In Spello, you can find plenty of cozy restaurants featuring delightful Umbrian specialties.

Today's Ride Choices

Morning: Spello to Assisi — 13 km (8 miles)

Afternoon: Assisi to Spello — 12 km (7 miles) | Assisi walk — 3 km (2 miles)

What to Expect:

Leave Spello on a country road popular with cyclists. Flanked by olive trees, it is known as the oil road. It is safe and free from traffic, but be on the lookout for potholes. There is very little car traffic all the way to the outskirts of Assisi. In town, a short climb takes you to the parking area.

Most of the day is dedicated to the visit of Assisi and includes a walking tour on cobbled streets with some hills. We suggest that you pack comfortable shoes.

In the afternoon, you follow the same route back to the hotel. An optional moderate independent ride is offered later in the afternoon from Spello. Ask your trip leaders for details.

Cumulative Distance Range: 12 – 25 km (7 – 15 miles)

Included Meals: Breakfast

Say goodbye to Spello this morning as your small group sets out for Perugia, the capital of Umbria. Retrace yesterday’s ride to the outskirts of Assisi, then begin an uphill climb accompanied by beautiful views. En route, pause to visit San Gregorio and see why this small, fortified hamlet was a source of contention between Perugia and Assisi in the past.

Around noon, your scenic morning spin culminates at a picturesque agriturismo, whose owners — Elisa, Giusy, and Angela — welcome you and prepare a delicious home-hosted lunch. Using a fireplace fed exclusively with farm wood and a cast-iron pot, they cook the local specialty, torta al testo, using a traditional recipe. Savor this unique type of focaccia with local cold meats and crispy vegetables from their garden. On chilly days, they also offer imbrecciata di legumi, a soup that mixes check peas, wild peas, and lentils with fragrant, fresh olive oil.

Early this afternoon, re-mount your bike for the ride to your next hotel. Roll along a very relaxing, unpaved bike path that follows the Tiber River past fields of tobacco and big trees that shade your way.

A final, gradual hill takes you to your last hotel, the majestic Castello di Monterone. Located on the outskirts of Perugia, it is  a true castle, whose meticulous conversion into a hotel maintains its medieval ambiance. Its  manicured rose garden and panoramic outdoor pool also contribute to making your last day in Umbria a memorable one. Gather with your travel mates for a welcome drink in the castle garden and a farewell dinner in the hotel restaurant.

Today's Ride Choices

Morning: Spello to lunch stop — 33 km (21 miles)

Afternoon: Agriturismo to hotel — 27 km (17 miles)

What to Expect:

Retrace  yesterday’s route to Assisi, then continue on paved rolling roads to your home-hosted lunch, admiring spectacular vistas as you leave Assisi behind.

In the afternoon, spin a few more miles on paved roads, then enter a very relaxing, unpaved bike path along the Tiber River, past fields of tobacco and shaded by big trees. The last stretch is uphill almost all the way to your castle hotel — a steady and gradual ascent on a large city road, very manageable with an E-bike.

Cumulative Distance Range: 27 – 60 km (17 – 38 miles)

Included Meals: Breakfast, Lunch, Dinner

After an included breakfast, complimentary transportation is provided to the Perugia railway station, where you will arrive by 9:30 a.m. There you can take a train back to Florence or continue to other destinations.

Included Meals: Breakfast

Italy: Umbria, Spello, Montefalco & Assisi

Download Sample Itinerary:

Air Package (PDF) Tour Only (PDF)

Accommodations (Please Note: Days are based on the Air Package Itinerary. Accommodations may vary depending on departure date. )

Enjoy Your Vacation Longer With Low-Cost Trip Extensions

Airplane

Air Package Only

2025

2025 Pre-Trip Extension - Florence

2 Nights From $495 per person, double occupancy
Single Supplement: From $345

  • 2 nights at Hotel De La Ville
  • Airport car service for arrival
  • Hospitality desk
  • Daily breakfast
  • City information

Your vacation is about to begin! Spend your first night aloft and arrive ready for an unforgettable trip.

Your first day in Florence starts off right, as a VBT representative greets you at the airport. A complimentary car service will whisk you to your centrally located hotel. Here, a local VBT representative will be available at 5:00 p.m. to answer your questions, help you organize your time in Florence, and offer optional walking and biking tours to discover the secret corners of the city. From here, you are perfectly positioned to explore this charming city at your leisure.

After a delicious included breakfast at your hotel, you are free to explore on your own, using VBT’s included city information to guide your discoveries.

Included Meals: Breakfast

Hotel De La Ville

This hotel has been completely restored and sits in a convenient location in the heart of Florence, a few steps from the famous Duomo on the fashionable shopping street Via Tornabuoni, which is closed to car traffic and quiet. Enjoy spacious, comfortable, air-conditioned private rooms.

Wi-Fi In Room
FREE WiFi Included
Air Conditioning
Air Conditioning
Airplane

Air Package Only

2025

2025 Post-Trip Extension - Orvieto

2 Nights From $345 per person, double occupancy
Single Supplement: From $145

  • 2 nights at Hotel Palazzo Piccolomini
  • Private transportation to Orvieto
  • Airport car service for departure
  • Daily breakfast
  • City information
1 Begin your Post-Trip Extension

After a delicious included breakfast at your hotel, private transportation is provided to Orvieto, where you will spend the next two nights.

Orvieto rises on a natural tableland on top of a 500 feet-high tufa cliff emerging from the surrounding plains. The city can be easily explored on foot. The most remarkable monument is the cathedral with its striped façade of white and green stones and remarkable sculptures.  Inside, don’t miss the Chapel of San Brizio, adorned by Luca Signorelli’s masterful fresco, Last Judgment, the inspiration for the more famous work by Michelangelo.  Later maybe visit the ingenious Saint Patrick’ Well and perhaps join an optional guided visit to the city’s underground caves.

You will find ample opportunities to shop for fine pottery and crafts and enjoy delicious dishes at simple trattorias that feature local truffles.

Use VBT’s included city information to guide your discoveries.

Included Meals: Breakfast

2 Continue your Post-Trip Extension

After a delicious included breakfast at your hotel, you are free to continue exploring on your own, using VBT’s included city information to guide your discoveries.

Included Meals: Breakfast

Departure Airplane

After an included breakfast this morning, complimentary transportation to the Rome airport will be provided (an approximately one-and-a-half hour drive, depending on traffic) for your departing flight.

Included Meals: Breakfast

Hotel Palazzo Piccolomini

Two palaces—one with a medieval tower—have been lovingly restored and converted into a welcoming hotel that respects this history while offering contemporary comforts. This respect for history and architecture is married to art appreciation, with beautiful Renaissance, medieval, and Etruscan appointments inside and out. In your room, enjoy a flatscreen TV, minibar, air conditioning, and free WiFi. Or relax in the reading lounges or lounge bar. You’ll also appreciate the prime location of the Hotel Palazzo Piccolomini, which is set in the heart of Orvieto and offers easy access to local attractions.

Wi-Fi In Room
FREE WiFi Included
Air Conditioning
Air Conditioning
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For more information, call: 800-245-3868

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