Italy: Umbria, Spello, Montefalco & Assisi

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

Upon arrival at the Rome Fiumicino Airport, you are greeted by a VBT representative in the arrival terminal.  A complimentary car service will whisk you to Orvieto and your elegant and centrally located hotel. Today you’ll take it easy and have the rest of the day free to explore, using VBT’s city information as your guide.

Perched atop a 500-foot-high tufa cliff, Orvieto is easily explored on foot. Its most striking monument is the cathedral, with a distinctive striped façade of white and green stone and remarkable sculptures. Inside, don’t miss the Chapel of San Brizio, adorned with Luca Signorelli’s masterful Last Judgment fresco—an inspiration for Michelangelo’s later work. You may also wish to visit the ingenious Saint Patrick’s Well or join an optional guided tour of the city’s underground caves.

You’ll find many opportunities to shop for fine pottery and crafts, and to enjoy delicious local cuisine—especially dishes featuring regional truffles—at traditional trattorias.

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

After an included breakfast, meet your driver in the lobby and be ready to depart by private minivan at 10:00 a.m. You will arrive in Spello at approximately 12:00 p.m., where your VBT trip leaders will welcome you at your hotel.

Perched at the highest point in Spello, Hotel La Bastiglia offers panoramic views of the Umbrian countryside. After a brief introduction, follow your trip leaders’ recommendations for lunch on your own in town, or dine at the hotel’s restaurant. Hotel check-in begins at 2:00 p.m. Once settled in, change into your biking clothes and be ready at 3:00 p.m. for a safety briefing and a warm-up ride through the scenic countryside surrounding Spello.

As the sun sets, gather with your fellow travelers on the hotel terrace for a welcome reception. Dinner is served at the hotel this evening, featuring strangozzi spoletini—a traditional handmade pasta—and other Umbrian specialties.

Today's Ride Choices

Afternoon: Warm-Up Ride — 11 km (7 miles)

What to Expect:

Your warm-up ride is a scenic loop from your hotel, following quiet country roads south of Spello. The route begins with a steady downhill and finishes with a gradual climb back to the hotel.

Cumulative Distance Range: 11 km (7 miles)

Included Meals: Breakfast, Dinner

Today’s bike route, partly along bike paths, takes you into the heart of the Valle Umbra, a fertile valley cultivated with vineyards, cereals, and olive trees. First the Romans, and later Benedictine monks, drained the plain, which in antiquity was covered by shallow lakes. After crossing the city of Foligno, a picturesque, rolling country road leads you through the hamlets of Fabbri and San Luca before beginning a gradual climb that brings 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 character.

A highlight here is the former Church of San Francesco, now a museum, which you’ll encounter as you walk up to the Piazza del Comune—the town’s highest point and historic center. Along the way, you’ll find an abundance of wine bars, cafés, and restaurants. Choose one for lunch on your own—perhaps accompanied by a glass of the excellent Sagrantino di Montefalco DOCG, the area’s celebrated red wine.

A scenic country road takes you downhill to your next highlight: Bevagna, officially recognized as one of the most beautiful villages in Italy. Located along the ancient Via Flaminia, it was once a major Roman trading settlement. As you cross the elegant bridge into town, you’ll first spot the ancient city wash house and its scenic waterfall. Inside the city walls, you’re welcomed by Filippo Silvestri Square, the medieval heart of Bevagna. Admire the 1889 fountain, thoughtfully designed to complement the surrounding Romanesque architecture, including the Basilica of St. Sylvester, the Collegiate Church of St. Michael Archangel with its ornate portal and spired bell tower, and the Palazzo dei Consoli.

For dinner back in Spello this evening, your host Luca and his family draw on eight generations of culinary tradition to present a degustazione menu featuring truffles, bruschetta, and local specialties—expertly paired with rare and exquisite wines, carefully selected for the occasion.

Today's Ride Choices

Morning: Spello to Montefalco — 35 km (22 miles)

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

What to Expect:

Leaving Spello, you may encounter some traffic at first but soon veer onto easy and quiet country roads leading to Foligno. After briefly passing through the town, a bike path takes you back into the countryside. From here, prepare for a steady uphill climb into Montefalco. In the afternoon, enjoy a long downhill coast, followed by gently rolling country roads to Bevagna. As you leave this medieval town, follow a quiet bike path and continue on flat country roads, with traffic gradually increasing as you approach Spello.

Cumulative Distance Range: 33 – 68 km (21 – 43 miles)

Included Meals: Breakfast, Dinner

Enjoy a hearty breakfast this morning, then set out on a short ride flanked by olive groves to Assisi—arguably one of the most beautiful cities in Italy. The birthplace of Saint Francis, founder of the Franciscan Order and Italy’s patron saint, as well as Saint Clare (Santa Chiara), one of his earliest followers, Assisi is a designated UNESCO World Heritage Site.

Guided by our local expert Maura, you’ll stroll through cobbled alleyways and picturesque squares, learning about the life of Saint Francis and visiting some of the city’s most important landmarks. Among these is the Basilica of San Francesco, famed for its frescoes by Cimabue, Giotto, and other masters. You’ll also discover lesser-known highlights, such as the remains of an ancient Roman arena.

Afterward, return to Spello, where you might relax by the hotel pool or opt for a longer cycling route along the flanks of Monte Subasio to take in the stunning countryside.

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

Today's Ride Choices

Morning: Spello to Assisi — 11 km (7 miles)

Afternoon: Assisi to Spello — 11 km (7 miles) | Assisi Guided Walk — 3 km (2 miles)

What to Expect:

Leave Spello on a scenic country road popular with cyclists, known as the Olive Road for the olive trees that line its edges. This route is safe and free from traffic, though you should watch out for the occasional pothole. You’ll encounter very little car traffic all the way to the outskirts of Assisi. Once in town, a short climb leads you to the designated parking area. Most of the day is dedicated to exploring Assisi, including a guided walking tour along cobbled streets with some hills. We recommend packing comfortable walking shoes and wearing a mid-sleeve bike jersey for the day. In the afternoon, follow the same route back to the hotel in Spello. For those interested, an optional independent ride with a more challenging route is available later in the afternoon—ask your trip leaders for details.

Cumulative Distance Range: 11 – 22 km (7 – 14 miles)

Included Meals: Breakfast

After breakfast, you leave the hotel to cycle along easy country roads that quietly cross the Valle Umbra. Pedal through the small medieval village of San Giacomo, located along an ancient pilgrim route to Rome, before reaching a local agriturismo. Pause here for a tour of the historic olive mill, followed by a lunch of homemade bruschetta and frittata with fresh vegetables from the garden.

Just outside the town of Spoleto—easily recognized by the massive Albornoz Fortress rising high above it—you join an easy, scenic bike path leading into the Nera Valley. See for yourself why this region is renowned for its breathtaking gorges.

Leave the bike path at a mountain pass reaching 2,400 feet in elevation and enjoy an exhilarating descent into Sant’Anatolia di Narco, where another Umbrian treasure awaits: the Abbey of Saints Felice and Mauro. Tucked into a tranquil hamlet, this 12th-century former monastery is built on the legendary site where a Syrian monk is said to have slain a dragon. Admire its beautiful rose window, ancient frescoes, and dramatic views.

Back in the saddle, continue the final miles into Scheggino, a quiet and picturesque village perched above the Nera River. You’ll have time to stroll this picture-postcard town before visiting the Truffle Museum. Umbria—particularly the Nera Valley—is famous for its truffles, and here you can learn all about this prized delicacy.

Later, shuttle to your hotel, Relais Borgo Campello, nestled in the tiny hilltop village of Campello Alto and composed of a medieval castle and a convent. These two iconic buildings once served as beacons and places of rest for pilgrims walking the Via Francigena to Rome. Campello Alto, perched high on a hill, has retained its medieval charm. Our gracious hosts will guide you on a short walking tour of the convent, where you’ll see frescoes restored in part thanks to the VBT Travelers Fund. From the bar terrace, gaze out across thousands of olive trees and spot the trails once walked by ancient pilgrims. Later, enjoy your included dinner at the hotel’s restaurant.

Today's Ride Choices

Morning: Spello to Lunch Stop — 36 km (20 miles)

Afternoon: Borgo del Rio to Scheggino — 31 km (19 miles)

What to Expect:

Leaving Spello, you may encounter some traffic but soon transition to an easy and safe bike path. Continue on mostly flat or gently rolling country roads until your lunch stop. In the afternoon, the route follows a gradually climbing, well-worn unpaved bike path. If you prefer, you can bypass the path and ride the parallel paved road. Around the halfway point, the group shifts to a well-paved, traffic-free main road. From there, enjoy a descent nearly all the way to the hamlet of Sant’Anatolia di Narco. The final stretch follows the Nera River for a couple of miles along a state road with minimal traffic—especially at the time of our ride. A 20-minute shuttle completes the trip to your hotel.

Cumulative Distance Range: 31 – 67 km (19 – 39 miles)

Included Meals: Breakfast, Lunch, Dinner

A short shuttle takes you to the start of your route. From there, follow a shaded, rolling path into Rasiglia, a hamlet of medieval stone homes set in a lush, green valley. Sometimes called the “Little Venice of Umbria” for its waterways and bridges, Rasiglia was renowned for wool production during the 16th century, when heavy looms were powered by mills fed by the rushing waters. Delight in the town’s picturesque network of waterfalls, brooks, and ponds.

Continue to a higher plateau near the border of Le Marche. Here, at 2,600 feet, you’re rewarded with panoramic views of the Apennines, where the rolling hills and fertile soil are ideal for growing regional staples like barley, spelt, lentils, and chickpeas. Roll through this protected regional park to a local merenderia—a combination restaurant and grocery shop—where the owner, Gemma, serves a hearty soup and tagliere di salumi.

Afterward, your route follows the flat plateau before descending gently into Le Marche, an unspoiled rural region where you can cycle through rolling hills for miles without seeing a single car.

Continue on to your countryside retreat, where you can bask in the revitalizing energy of the resort’s award-winning spa, take a dip in the indoor or outdoor pool, or enjoy an evening passeggiata through the lush grounds. Dinner tonight is at the hotel restaurant, where your hosts have prepared a tasting of locally produced, zero-kilometer olive oils to accompany your meal.

Today's Ride Choices

Morning: Vene to Colfiortio — 30 km (19 miles)

Afternoon: Colfiorito to Borgo Lanciano — 36 km (20 miles)

What to Expect:

A short shuttle takes you to the start of the route in Vene. The morning ride features gently rolling terrain with minimal traffic, followed by a steady two-mile ascent to Colfiorito, reaching an altitude of 2,500 feet. After taking in the views across the wide-open plateau, descend a winding road into Serravalle di Chienti—a route favored by local cyclists. A short climb then leads through the charming hamlets of Gelagna and Raggiano before descending into Castelraimondo, where light traffic increases as you approach the hotel.

Cumulative Distance Range: 30 – 66 km (19 – 39 miles)

Included Meals: Breakfast, Lunch, Dinner

Wake up to a hearty breakfast before setting off on a stunning loop through the rolling hills of Le Marche. Often called the “New Tuscany,” this region remains blissfully undiscovered, with quiet roads where you’ll share the route with little more than a few local cyclists.

Your first stop is Pioraco, a small town nestled between dramatic limestone gorges. Though the 2016 earthquake left its mark on some historic buildings, the town retains its charm, with winding paths alongside a rushing river that has powered local paper mills for centuries.

Back on your bike, continue toward Il Casato Agriturismo, a family-run farmhouse where Andrea, the charismatic owner, will welcome you warmly. The scent of freshly baked bread and warm focaccia drifts from the kitchen, setting the stage for a leisurely, rustic lunch.

After your meal, the ride continues along a panoramic route with sweeping views of the Sibillini mountain peaks in the distance. Coast downhill to your countryside retreat, where you’ll have time to unwind.

This evening, trade your cycling gear for an apron during a hands-on cooking class, where you’ll learn to make handmade pasta and meatballs—a beloved regional specialty.

Today's Ride Choices

Morning: Borgo Lanciano to Il Casato — 34 km (21 miles)

Afternoon: Il Casato to Hotel — 7 km (4 miles)

What to Expect:

Start the day on smooth country roads with a gentle ascent into the historic village of Pioraco. From there, the route flattens briefly before leading to the day’s main challenge—a two-mile climb with a steady six percent gradient. After reaching the summit, enjoy a long, relaxing descent, followed by a final scenic climb to Il Casato, where stunning views of the Sibillini Mountains await. The afternoon ride is short and rewarding, following rolling, traffic-free country roads straight to the hotel.

Cumulative Distance Range: 7 – 41 km (4 – 25 miles)

Included Meals: Breakfast, Lunch, Dinner

After an included breakfast, complimentary transportation is provided to Bologna, where you will arrive at approximately 11:30 a.m. Your room may not be ready upon arrival, but you can store your luggage at the hotel reception. Located in the lively city center, your hotel offers easy access to a wide variety of lunch options on your own. Back at the hotel, meet your local guide at 3:00 p.m. to begin discovering this medieval town—its pedestrian alleyways and piazzas, mouthwatering food shops, and covered markets that have made Bologna famous around the world.

Included Meals: Breakfast

After an included breakfast* this morning, complimentary transportation to the Bologna Airport will be provided (approximately a 20-minute drive, depending on traffic) for your departing flight.

Included Meals: Breakfast

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

Start your first day off right as a VBT representative greets you at the airport. A complimentary car service will whisk you to your centrally located hotel.

Your accommodations for tonight are at the 25Hours Hotel Piazza San Paolino, a stylish and eclectic property located in Florence’s vibrant Santa Maria Novella district. This uniquely designed hotel blends Renaissance themes with whimsical, modern décor, and places you within walking distance of many of Florence’s cultural and culinary highlights.

You’ll have the rest of the day free to explore, using VBT’s city information as your guide.

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

Following brief introductions, travel approximately three hours by private motorcoach to Campello sul Clitunno in Umbria, with a short stop along the way to purchase lunch. Upon arrival, meet your VBT trip leaders, settle into your room, and change into your cycling gear. Later, take part in a safety session to prepare for your first ride.

Your accommodations for the next three nights are at the Relais Borgo Campello, nestled within the tiny hilltop village of Campello Alto. This remarkable property—comprising a restored medieval castle and former convent—once served as a resting place for pilgrims on the historic Via Francigena route to Rome. Today, it offers guests a peaceful retreat steeped in charm and history, with stone buildings, cobbled paths, and stunning views that preserve the spirit of centuries past.

Then it’s time for your first ride, an exhilarating spin through the verdant valley below, where hundreds of olive trees line the landscape. The nearby Clitunno River, immortalized by poet Giosuè Carducci, helped inspire the phrase “the Green Heart of Italy”, now synonymous with Umbria.

Back at the hotel, unwind on the shaded pometo, a peaceful terrace offering sweeping views of the valley. This evening, follow your gracious hosts on a short walking tour of the former convent, where the VBT Foundation sponsors the restoration of precious frescoes. Then enjoy a welcome cocktail on the panoramic restaurant terrace, followed by a dinner of local Umbrian specialties—including strangozzi spoletini—prepared with seasonal flair.

Today's Ride Choices

Afternoon: Warm-Up Ride — 13 km (8 miles)

What to Expect:

Your warm-up ride begins with a steady 0.62-mile (1-km) uphill climb that is very manageable—especially with an E–bike. From there, enjoy a long, scenic downhill glide on paved terrain, keeping an eye out for a few stretches with rough tar. The route then loops back along traffic-free country roads. You’ll finish with another gentle uphill climb—again, quite manageable—before coasting back to your hotel.

Cumulative Distance Range: 13 km (8 miles)

Included Meals: Breakfast, Dinner

After breakfast, depart the hotel for a ride along easy country roads that meander quietly past tiny fortified villages and open fields, backed by the gentle slopes of the Spoleto Mountains.

Just outside the town of Spoleto—easily recognized by the massive Albornoz Fortress perched high above—you’ll join a scenic bike path that winds into the Nera Valley, renowned for its breathtaking gorges and lush landscapes.

At the pass, reaching an elevation of 2,400 feet, you’ll leave the bike path and begin an exhilarating descent into Sant’Anatolia di Narco, where another Umbrian treasure awaits: the Abbey of Saints Felice and Mauro. Nestled in a tranquil hamlet, this 12th-century former monastery is built on the site where, according to legend, a Syrian monk slew a dragon. Admire its striking rose window, ancient frescoes, and stunning valley views.

Back in the saddle, continue to Scheggino, a peaceful and picturesque village perched on a hill above the Nera River. Enjoy lunch on your own and take time to stroll the charming streets before visiting the town’s Truffle Museum. Umbria—especially the Nera Valley—is famous for its truffles, and here you’ll learn all about this prized delicacy, including a tasting, of course!

Before dinner, regroup on the terrace, soak in the stunning sunset, and enjoy a tasting of Umbria’s celebrated olive oil. Dinner is served at the hotel this evening.

Today's Ride Choices

Morning: Hotel to Scheggino — 40 km (25 miles)

What to Expect:

The first part of today’s ride follows paved country roads. After about 10 miles, the route continues on a gradually climbing, well-traveled unpaved bike path. (An alternate route along a parallel paved road is available and more suitable for road bikes.) Midway through, all riders transition to a main road that is smoothly paved and largely traffic-free. Enjoy a scenic descent nearly all the way to the hamlet of Sant’Anatolia di Narco. From there, follow the Nera River for a few miles along a quiet state road, which typically has very little traffic—especially at the time of our ride. A 30-minute shuttle returns you to the hotel at the end of the day.

Cumulative Distance Range: 40 km (25 miles)

Included Meals: Breakfast, Dinner

Follow a shaded, rolling route into Rasiglia, a hamlet of medieval stone homes nestled in a green valley. Often called the “Little Venice of Umbria” for its charming network of waterways and bridges, Rasiglia rose to prominence in the 16th century for its wool production—powered by mills driven by the rushing waters. Discover more of this heritage at the Museo dell’Acqua, housed in a former mill, where you can view an impressive jacquard loom and learn about the town’s industrious past. Stroll through the village and enjoy its picturesque waterfalls, brooks, and ponds. You’ll visit on a Sunday, when the town comes alive with visitors, cafés, and street vendors offering local specialties such as lentils, chickpeas, and other regional products.

Continue your ride to a high plateau near the border of the Marche region. At 2,600 feet, surrounded by the gentle hills of the Apennines, the fertile soil here yields a vibrant mix of barley, spelt, lentils, chickpeas, red potatoes, and more. Cycle through this protected regional park, stopping at the marshland for photos of the wide, open landscapes. At lunchtime, meet Nonna Balè, a lively grandmother and avid motocross cyclist, who welcomes you with a hearty bowl of cereal soup and her homemade rocciata cookies.

Afterward, your route continues all the way to your hotel for the next three nights. Perched at the highest elevation in Spello, the Hotel La Bastiglia offers panoramic views across the Umbrian valley—an ideal setting to unwind and take in the scenery. Once a noble residence, the hotel has been artfully restored and features elegant rooms, an outdoor pool, and a renowned restaurant known for its regional cuisine. Gather on the terrace at sunset for a welcome reception with your travel companions.

This evening, join our local guide Maura for a walk through Spello’s cobbled streets, as she points out its well-preserved medieval architecture and shares stories of the historic towns you’ll explore in the days ahead.

Dinner tonight is on your own in Spello, where you’ll find several inviting restaurants tucked into this charming hillside town.

Today's Ride Choices

Morning: Vene to Colfiorito — 30 km (19 miles)

Afternoon: Colfiorito to Spello — 35 km (22 miles) | Spello Guided Walking Tour — 2 km (1.5 miles)

What to Expect:

Apart from a few stretches where the pavement is uneven or scarred—requiring extra caution from cyclists—the entire route is on paved terrain. The morning ride features some rolling miles and a 2-mile (3.2-km) gradual ascent with an average gradient of 4%. In the afternoon, you’ll follow a mostly descending route, with a mix of downhills and gentle rolling stretches. Your guided walking tour of Spello will lead you through the town’s cobbled alleyways, passing stone staircases, archways, and offering picturesque glimpses of the countryside. It’s a pleasant walk that rewards a bit of effort—just be sure to wear comfortable shoes.

Cumulative Distance Range: 30 km – 65 km (19 – 41 miles)

Included Meals: Breakfast, Lunch

Today’s bike route, partly along bike paths, takes you into the heart of the Valle Umbra, a fertile valley cultivated with vineyards, cereals, and olive trees. First the Romans, and later Benedictine monks, drained the plain, which in antiquity was covered by shallow lakes. After crossing the city of Foligno, a picturesque, rolling country road leads you through the hamlets of Fabbri and San Luca before beginning a gradual climb that brings 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 character.

A highlight here is the former Church of San Francesco, now a museum, which you’ll encounter as you walk up to the Piazza del Comune—the town’s highest point and historic center. Along the way, you’ll find an abundance of wine bars, cafés, and restaurants. Choose one for lunch on your own—perhaps accompanied by a glass of the excellent Sagrantino di Montefalco DOCG, the area’s celebrated red wine.

A scenic country road takes you downhill to your next highlight: Bevagna, officially recognized as one of the most beautiful villages in Italy. Located along the ancient Via Flaminia, it was once a major Roman trading settlement. As you cross the elegant bridge into town, you’ll first spot the ancient city wash house and its scenic waterfall. Inside the city walls, you’re welcomed by Filippo Silvestri Square, the medieval heart of Bevagna. Admire the 1889 fountain, thoughtfully designed to complement the surrounding Romanesque architecture, including the Basilica of St. Sylvester, the Collegiate Church of St. Michael Archangel with its ornate portal and spired bell tower, and the Palazzo dei Consoli.

For dinner back in Spello this evening, your host Luca and his family draw on eight generations of culinary tradition to present a degustazione menu featuring truffles, bruschetta, and local specialties—expertly paired with rare and exquisite wines, carefully selected for the occasion.

Today's Ride Choices

Morning: Spello to Montefalco — 35 km (22 miles)

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

What to Expect:

Leaving Spello, you may encounter some traffic at first but soon veer onto easy and quiet country roads leading to Foligno. After briefly passing through the town, a bike path takes you back into the countryside. From here, prepare for a steady uphill climb into Montefalco. In the afternoon, enjoy a long downhill coast, followed by gently rolling country roads to Bevagna. As you leave this medieval town, follow a quiet bike path and continue on flat country roads, with traffic gradually increasing as you approach Spello.

Cumulative Distance Range: 33 – 68 km (21 – 43 miles)

Included Meals: Breakfast, Dinner

Enjoy a hearty breakfast this morning, then set out on a short ride flanked by olive groves to Assisi—arguably one of the most beautiful cities in Italy. The birthplace of Saint Francis, founder of the Franciscan Order and Italy’s patron saint, as well as Saint Clare (Santa Chiara), one of his earliest followers, Assisi is a designated UNESCO World Heritage Site.

Guided by our local expert Maura, you’ll stroll through cobbled alleyways and picturesque squares, learning about the life of Saint Francis and visiting some of the city’s most important landmarks. Among these is the Basilica of San Francesco, famed for its frescoes by Cimabue, Giotto, and other masters. You’ll also discover lesser-known highlights, such as the remains of an ancient Roman arena.

Afterward, return to Spello, where you might relax by the hotel pool or opt for a longer cycling route along the flanks of Monte Subasio to take in the stunning countryside.

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

Today's Ride Choices

Morning: Spello to Assisi — 11 km (7 miles)

Afternoon: Assisi to Spello — 11 km (7 miles) | Assisi Guided Walking Tour — 3 km (2 miles)

What to Expect:

Leave Spello on a scenic country road popular with cyclists, known as the Olive Road for the olive trees that line its edges. This route is safe and free from traffic, though you should watch out for the occasional pothole. You’ll encounter very little car traffic all the way to the outskirts of Assisi. Once in town, a short climb leads you to the designated parking area. Most of the day is dedicated to exploring Assisi, including a guided walking tour along cobbled streets with some hills. We recommend packing comfortable walking shoes and wearing a mid-sleeve bike jersey for the day. In the afternoon, follow the same route back to the hotel in Spello. For those interested, an optional independent ride with a more challenging route is available later in the afternoon—ask your trip leaders for details.

Cumulative Distance Range: 11 – 22 km (7 – 14 miles)

Included Meals: Breakfast

Say goodbye to Spello this morning as your small group sets out for Perugia, the capital of Umbria. Retrace part of yesterday’s route to the outskirts of Assisi, then begin a steady uphill climb accompanied by beautiful views. Along the way, pause to visit San Gregorio, a small fortified hamlet that was once a source of contention between Perugia and Assisi.

Around noon, your scenic morning ride culminates at a picturesque agriturismo, where the warm-hearted owners—Elisa, Giusy, and Angela—welcome you with a delicious home-hosted lunch. Using a fireplace fueled exclusively with farm-sourced wood and a cast-iron pot, they prepare traditional regional specialties, including torta al testo and torta mischia. These unique types of focaccia are served with local cured meats and crispy vegetables from their garden. On cooler days, they may also offer imbrecciata di legumi, a rustic soup made from chickpeas, wild peas, and lentils, drizzled with fragrant, fresh olive oil.

In the early afternoon, hop back on your bike for a relaxing ride to your next hotel. You’ll follow a peaceful unpaved bike path along the Tiber River, passing fields of fava beans, tobacco, and towering trees that provide welcome shade along the way.

A final gradual hill leads you to your last hotel, the majestic Castello di Monterone. Located on the outskirts of Perugia, this true medieval castle has been meticulously converted into a hotel that retains its historic charm. A manicured rose garden and panoramic outdoor pool add to the ambiance, making your final day in Umbria truly memorable. This evening, gather with your fellow travelers for a welcome drink in the castle garden, followed by a farewell dinner at the hotel’s elegant restaurant.

Today's Ride Choices

Morning: Spello to Agriturismo Lunch — 33 km (21 miles)

Afternoon: Agriturismo Lunch to Hotel — 28 km (17 miles)

What to Expect:

Retrace part of yesterday’s route to Assisi, then continue on paved, rolling roads to your home-hosted lunch, enjoying spectacular vistas as you leave Assisi behind. In the afternoon, cycle a few more miles on paved roads before joining a relaxing, unpaved, and shaded bike path along the Tiber River, passing fields of tobacco and towering plane trees. The final stretch is a steady, gradual ascent on a wide city road—very manageable with an E–bike—leading to your castle hotel.

Cumulative Distance Range: 28 – 61 km (17 – 38 miles)

Included Meals: Breakfast, Lunch, Dinner

After breakfast, board the shuttle for a short ride into Perugia, where you’ll reunite with our guide Maura, who will reveal the many stories and hidden treasures of this fascinating city. A highlight of your visit is the Rocca Paolina, a Renaissance-era fortress originally built as a result of the salt trade. Destroyed, rebuilt, and then dismantled again in 1861, this mighty structure was carefully restored in the mid-20th century. Entering via a series of escalators, you’ll descend into its massive interior walls and explore ancient streets, courtyards, and towers now revealed to the public.

You’ll have free time for lunch at a restaurant of your choosing, with suggestions available from Maura or in your VBT city information. Perugia is the perfect place to satisfy a sweet tooth—it’s home to the Eurochocolate Festival, the largest chocolate festival in Europe, as well as Bacio Perugina, the famous chocolatier known for its iconic candies and creamy gelato.

Spend the afternoon at your own pace. Perhaps stroll through Piazza IV Novembre, the city’s historic heart, and admire the Fontana Maggiore, a magnificent medieval fountain. You may also visit the Gothic San Lorenzo Cathedral, with its Renaissance paintings and frescoes, or explore the Palazzo dei Priori, once Perugia’s seat of government and now a museum housing important works of art.

Alternatively, hop the shuttle back to your hotel, where you can relax by the pool and take in sweeping views of the countryside and the distant city. For dinner on your own, you may choose to dine at the hotel’s restaurant or take a taxi back into Perugia, just 10 minutes away.

Included Meals: Breakfast

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

Included Meals: Breakfast

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

Start your first day off right as a VBT representative greets you at the airport. A complimentary car service will whisk you to your centrally located hotel.

Your accommodations for tonight are at the 25Hours Hotel Piazza San Paolino, a stylish and eclectic property located in Florence’s vibrant Santa Maria Novella district. This uniquely designed hotel blends Renaissance themes with whimsical, modern décor, and places you within walking distance of many of Florence’s cultural and culinary highlights.

You’ll have the rest of the day free to explore, using VBT’s city information as your guide.

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

Following brief introductions, travel approximately three hours by private motorcoach to a small hamlet just outside Campello sul Clitunno in Umbria, with a short stop along the way to purchase lunch. Upon arrival, meet your VBT trip leaders, settle into your room, and change into your cycling gear. Later, take part in a safety session to prepare for your first ride.

Your accommodations for the next two nights are at Borgo della Marmotta, a tranquil country estate nestled amid olive groves and rolling farmland in the heart of Umbria. Once a working farm and rural hamlet, the property has been lovingly restored into a refined boutique hotel, blending rustic charm with modern comforts. Surrounded by greenery and shaded lanes, it offers a peaceful retreat with beautifully landscaped grounds, a swimming pool, and inviting common spaces perfect for relaxing after your ride.

Then it’s time for your first spin, an exhilarating ride through the verdant valley below, where hundreds of olive trees line the landscape. The nearby Clitunno River, immortalized by poet Giosuè Carducci, helped inspire the phrase “the Green Heart of Italy,” now synonymous with Umbria.

Back at the hotel, unwind in the shaded garden or by the pool. This evening, gather with your fellow travelers for a welcome cocktail in one of the estate’s elegant lounges, then move to the restaurant for a dinner of local Umbrian specialties—including strangozzi spoletini—prepared with seasonal flair.

Today's Ride Choices

Afternoon : Warm-Up Ride — 14 km (9 miles)

What to Expect:

Your warm-up ride begins with a steady 0.62-mile (1-km) uphill climb that is very manageable—especially with an E-bike. From there, enjoy a long, scenic downhill glide on paved terrain, keeping an eye out for a few stretches with rough tar. The route then loops back along traffic-free country roads. You’ll finish with another gentle uphill climb—again, quite manageable—before coasting back to your hotel.

Cumulative Distance Range: 14 km (9 miles)

Included Meals: Breakfast, Dinner

After breakfast, depart the hotel for a ride along easy country roads that meander quietly past tiny fortified villages and open fields, backed by the gentle slopes of the Spoleto Mountains.

Just outside the town of Spoleto—easily recognized by the massive Albornoz Fortress perched high above—you’ll join a scenic bike path that winds into the Nera Valley, renowned for its breathtaking gorges and lush landscapes.

At the pass, reaching an elevation of 2,400 feet, you’ll leave the bike path and begin an exhilarating descent into Sant’Anatolia di Narco, where another Umbrian treasure awaits: the Abbey of Saints Felice and Mauro. Nestled in a tranquil hamlet, this 12th-century former monastery is built on the site where, according to legend, a Syrian monk slew a dragon. Admire its striking rose window, ancient frescoes, and stunning valley views.

Back in the saddle, continue to Scheggino, a peaceful and picturesque village perched on a hill above the Nera River. Enjoy lunch on your own and take time to stroll the charming streets before visiting the town’s Truffle Museum. Umbria—especially the Nera Valley—is famous for its truffles, and here you’ll learn all about this prized delicacy, including a tasting, of course!

Back at the hotel, your gracious host Federico will lead you on an engaging walk through the village of Poreta and past hundreds of olive trees, ending at his family’s oil mill, where he’ll explain pruning techniques and the olive oil production process. The tour concludes at the restaurant, where you’ll enjoy a tasting of Umbria’s celebrated olive oil, followed by dinner.

Today's Ride Choices

Morning : Hotel to Scheggino — 36 km (22 miles)

What to Expect:

The first part of today’s ride follows paved country roads. After about 10 miles, the route continues on a gradually climbing, well-traveled unpaved bike path. (An alternate route along a parallel paved road is available and more suitable for road bikes.) Midway through, all riders transition to a main road that is smoothly paved and largely traffic-free. Enjoy a scenic descent nearly all the way to the hamlet of Sant’Anatolia di Narco. From there, follow the Nera River for a few miles along a quiet state road, which typically has very little traffic—especially at the time of our ride. A 30-minute shuttle returns you to the hotel at the end of the day. Later in the afternoon, join your host for a walk that includes a stretch of gravel and grass paths with a slight uphill incline. We recommend wearing comfortable walking shoes.

Cumulative Distance Range: 36 km (22 miles)

Included Meals: Breakfast, Dinner

Follow a shaded, rolling route into Rasiglia, a hamlet of medieval stone homes nestled in a green valley. Often called the “Little Venice of Umbria” for its charming network of waterways and bridges, Rasiglia rose to prominence in the 16th century for its wool production—powered by mills driven by the rushing waters. Discover more of this heritage at the Museo dell’Acqua, housed in a former mill, where you can view an impressive jacquard loom and learn about the town’s industrious past. Stroll through the village and enjoy its picturesque waterfalls, brooks, and ponds. You’ll visit on a Sunday, when the town comes alive with visitors, cafés, and street vendors offering local specialties such as lentils, chickpeas, and other regional products.

Continue your ride to a high plateau near the border of the Marche region. At 2,600 feet, surrounded by the gentle hills of the Apennines, the fertile soil here yields a vibrant mix of barley, spelt, lentils, chickpeas, red potatoes, and more. Cycle through this protected regional park, stopping at the marshland for photos of the wide, open landscapes. At lunchtime, meet Nonna Balè, a lively grandmother and avid motocross cyclist, who welcomes you with a hearty bowl of cereal soup and her homemade rocciata cookies.

Afterward, your route continues all the way to your hotel for the next three nights. Perched at the highest elevation in Spello, the Hotel La Bastiglia offers panoramic views across the Umbrian valley—an ideal setting to unwind and take in the scenery. Once a noble residence, the hotel has been artfully restored and features elegant rooms, an outdoor pool, and a renowned restaurant known for its regional cuisine. Gather on the terrace at sunset for a welcome reception with your travel companions.

This evening, join our local guide Maura for a walk through Spello’s cobbled streets, as she points out its well-preserved medieval architecture and shares stories of the historic towns you’ll explore in the days ahead.

Dinner tonight is on your own in Spello, where you’ll find several inviting restaurants tucked into this charming hillside town.

Today's Ride Choices

Morning: Vene to Colfiorito — 30 km (19 miles)

Afternoon: Colfiorito to Spello — 35 km (22 miles) | Spello Guided Walking Tour — 2 km (1.5 miles)

What to Expect:

Apart from a few stretches where the pavement is uneven or scarred—requiring extra caution from cyclists—the entire route is on paved terrain. The morning ride features some rolling miles and a 2-mile (3.2-km) gradual ascent with an average gradient of 4%. In the afternoon, you’ll follow a mostly descending route, with a mix of downhills and gentle rolling stretches. Your guided walking tour of Spello will lead you through the town’s cobbled alleyways, passing stone staircases, archways, and offering picturesque glimpses of the countryside. It’s a pleasant walk that rewards a bit of effort—just be sure to wear comfortable shoes.

Cumulative Distance Range: 30 km – 65 km (19 – 41 miles)

Included Meals: Breakfast, Lunch

Today’s bike route, partly along bike paths, takes you into the heart of the Valle Umbra, a fertile valley cultivated with vineyards, cereals, and olive trees. First the Romans, and later Benedictine monks, drained the plain, which in antiquity was covered by shallow lakes. After crossing the city of Foligno, a picturesque, rolling country road leads you through the hamlets of Fabbri and San Luca before beginning a gradual climb that brings 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 character.

A highlight here is the former Church of San Francesco, now a museum, which you’ll encounter as you walk up to the Piazza del Comune—the town’s highest point and historic center. Along the way, you’ll find an abundance of wine bars, cafés, and restaurants. Choose one for lunch on your own—perhaps accompanied by a glass of the excellent Sagrantino di Montefalco DOCG, the area’s celebrated red wine.

A scenic country road takes you downhill to your next highlight: Bevagna, officially recognized as one of the most beautiful villages in Italy. Located along the ancient Via Flaminia, it was once a major Roman trading settlement. As you cross the elegant bridge into town, you’ll first spot the ancient city wash house and its scenic waterfall. Inside the city walls, you’re welcomed by Filippo Silvestri Square, the medieval heart of Bevagna. Admire the 1889 fountain, thoughtfully designed to complement the surrounding Romanesque architecture, including the Basilica of St. Sylvester, the Collegiate Church of St. Michael Archangel with its ornate portal and spired bell tower, and the Palazzo dei Consoli.

For dinner back in Spello this evening, your host Luca and his family draw on eight generations of culinary tradition to present a degustazione menu featuring truffles, bruschetta, and local specialties—expertly paired with rare and exquisite wines, carefully selected for the occasion.

Today's Ride Choices

Morning: Spello to Montefalco — 35 km (22 miles)

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

What to Expect:

Leaving Spello, you may encounter some traffic at first but soon veer onto easy and quiet country roads leading to Foligno. After briefly passing through the town, a bike path takes you back into the countryside. From here, prepare for a steady uphill climb into Montefalco. In the afternoon, enjoy a long downhill coast, followed by gently rolling country roads to Bevagna. As you leave this medieval town, follow a quiet bike path and continue on flat country roads, with traffic gradually increasing as you approach Spello.

Cumulative Distance Range: 33 – 68 km (21 – 43 miles)

Included Meals: Breakfast, Dinner

Enjoy a hearty breakfast this morning, then set out on a short ride flanked by olive groves to Assisi—arguably one of the most beautiful cities in Italy. The birthplace of Saint Francis, founder of the Franciscan Order and Italy’s patron saint, as well as Saint Clare (Santa Chiara), one of his earliest followers, Assisi is a designated UNESCO World Heritage Site.

Guided by our local expert Maura, you’ll stroll through cobbled alleyways and picturesque squares, learning about the life of Saint Francis and visiting some of the city’s most important landmarks. Among these is the Basilica of San Francesco, famed for its frescoes by Cimabue, Giotto, and other masters. You’ll also discover lesser-known highlights, such as the remains of an ancient Roman arena.

Afterward, return to Spello, where you might relax by the hotel pool or opt for a longer cycling route along the flanks of Monte Subasio to take in the stunning countryside.

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

Today's Ride Choices

Morning: Spello to Assisi — 11 km (7 miles)

Afternoon: Assisi to Spello — 11 km (7 miles) | Assisi Guided Walking Tour — 3 km (2 miles)

What to Expect:

Leave Spello on a scenic country road popular with cyclists, known as the Olive Road for the olive trees that line its edges. This route is safe and free from traffic, though you should watch out for the occasional pothole. You’ll encounter very little car traffic all the way to the outskirts of Assisi. Once in town, a short climb leads you to the designated parking area. Most of the day is dedicated to exploring Assisi, including a guided walking tour along cobbled streets with some hills. We recommend packing comfortable walking shoes and wearing a mid-sleeve bike jersey for the day. In the afternoon, follow the same route back to the hotel in Spello. For those interested, an optional independent ride with a more challenging route is available later in the afternoon—ask your trip leaders for details.

Cumulative Distance Range: 11 – 22 km (7 – 14 miles)

Included Meals: Breakfast

Say goodbye to Spello this morning as your small group sets out for Perugia, the capital of Umbria. Retrace part of yesterday’s route to the outskirts of Assisi, then begin a steady uphill climb accompanied by beautiful views. Along the way, pause to visit San Gregorio, a small fortified hamlet that was once a source of contention between Perugia and Assisi.

Around noon, your scenic morning ride culminates at a picturesque agriturismo, where the warm-hearted owners—Elisa, Giusy, and Angela—welcome you with a delicious home-hosted lunch. Using a fireplace fueled exclusively with farm-sourced wood and a cast-iron pot, they prepare traditional regional specialties, including torta al testo and torta mischia. These unique types of focaccia are served with local cured meats and crispy vegetables from their garden. On cooler days, they may also offer imbrecciata di legumi, a rustic soup made from chickpeas, wild peas, and lentils, drizzled with fragrant, fresh olive oil.

In the early afternoon, hop back on your bike for a relaxing ride to your next hotel. You’ll follow a peaceful unpaved bike path along the Tiber River, passing fields of fava beans, tobacco, and towering trees that provide welcome shade along the way.

A final gradual hill leads you to your last hotel, the majestic Castello di Monterone. Located on the outskirts of Perugia, this true medieval castle has been meticulously converted into a hotel that retains its historic charm. A manicured rose garden and panoramic outdoor pool add to the ambiance, making your final day in Umbria truly memorable. This evening, gather with your fellow travelers for a welcome drink in the castle garden, followed by a farewell dinner at the hotel’s elegant restaurant.

Today's Ride Choices

Morning: Spello to Agriturismo Lunch — 33 km (21 miles)

Afternoon: Agriturismo Lunch to Hotel — 28 km (17 miles)

What to Expect:

Retrace part of yesterday’s route to Assisi, then continue on paved, rolling roads to your home-hosted lunch, enjoying spectacular vistas as you leave Assisi behind. In the afternoon, cycle a few more miles on paved roads before joining a relaxing, unpaved, and shaded bike path along the Tiber River, passing fields of tobacco and towering plane trees. The final stretch is a steady, gradual ascent on a wide city road—very manageable with an E–bike—leading to your castle hotel.

Cumulative Distance Range: 28 – 61 km (17 – 38 miles)

Included Meals: Breakfast, Lunch, Dinner

After breakfast, board the shuttle for a short ride into Perugia, where you’ll reunite with our guide Maura, who will reveal the many stories and hidden treasures of this fascinating city. A highlight of your visit is the Rocca Paolina, a Renaissance-era fortress originally built as a result of the salt trade. Destroyed, rebuilt, and then dismantled again in 1861, this mighty structure was carefully restored in the mid-20th century. Entering via a series of escalators, you’ll descend into its massive interior walls and explore ancient streets, courtyards, and towers now revealed to the public.

You’ll have free time for lunch at a restaurant of your choosing, with suggestions available from Maura or in your VBT city information. Perugia is the perfect place to satisfy a sweet tooth—it’s home to the Eurochocolate Festival, the largest chocolate festival in Europe, as well as Bacio Perugina, the famous chocolatier known for its iconic candies and creamy gelato.

Spend the afternoon at your own pace. Perhaps stroll through Piazza IV Novembre, the city’s historic heart, and admire the Fontana Maggiore, a magnificent medieval fountain. You may also visit the Gothic San Lorenzo Cathedral, with its Renaissance paintings and frescoes, or explore the Palazzo dei Priori, once Perugia’s seat of government and now a museum housing important works of art.

Alternatively, hop the shuttle back to your hotel, where you can relax by the pool and take in sweeping views of the countryside and the distant city. For dinner on your own, you may choose to dine at the hotel’s restaurant or take a taxi back into Perugia, just 10 minutes away.

Included Meals: Breakfast

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

Included Meals: Breakfast

At 12:00 p.m., meet your trip leaders at your first hotel in Spello.

Perched at the highest point in Spello, Hotel La Bastiglia offers panoramic views of the Umbrian countryside. After a brief introduction, follow your trip leaders’ recommendations for lunch on your own in town, or dine at the hotel’s restaurant. Hotel check-in begins at 2:00 p.m. Once settled in, change into your biking clothes and be ready at 3:00 p.m. for a safety briefing and a warm-up ride through the scenic countryside surrounding Spello.

As the sun sets, gather with your fellow travelers on the hotel terrace for a welcome reception. Dinner is served at the hotel this evening, featuring strangozzi spoletini—a traditional handmade pasta—and other Umbrian specialties.

Today's Ride Choices

Afternoon: Warm-Up Ride — 11 km (7 miles)

What to Expect:

Your warm-up ride is a scenic loop from your hotel, following quiet country roads south of Spello. The route begins with a steady downhill and finishes with a gradual climb back to the hotel.

Cumulative Distance Range: 11 km (7 miles)

Included Meals: Dinner

Today’s bike route, partly along bike paths, takes you into the heart of the Valle Umbra, a fertile valley cultivated with vineyards, cereals, and olive trees. First the Romans, and later Benedictine monks, drained the plain, which in antiquity was covered by shallow lakes. After crossing the city of Foligno, a picturesque, rolling country road leads you through the hamlets of Fabbri and San Luca before beginning a gradual climb that brings 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 character.

A highlight here is the former Church of San Francesco, now a museum, which you’ll encounter as you walk up to the Piazza del Comune—the town’s highest point and historic center. Along the way, you’ll find an abundance of wine bars, cafés, and restaurants. Choose one for lunch on your own—perhaps accompanied by a glass of the excellent Sagrantino di Montefalco DOCG, the area’s celebrated red wine.

A scenic country road takes you downhill to your next highlight: Bevagna, officially recognized as one of the most beautiful villages in Italy. Located along the ancient Via Flaminia, it was once a major Roman trading settlement. As you cross the elegant bridge into town, you’ll first spot the ancient city wash house and its scenic waterfall. Inside the city walls, you’re welcomed by Filippo Silvestri Square, the medieval heart of Bevagna. Admire the 1889 fountain, thoughtfully designed to complement the surrounding Romanesque architecture, including the Basilica of St. Sylvester, the Collegiate Church of St. Michael Archangel with its ornate portal and spired bell tower, and the Palazzo dei Consoli.

For dinner back in Spello this evening, your host Luca and his family draw on eight generations of culinary tradition to present a degustazione menu featuring truffles, bruschetta, and local specialties—expertly paired with rare and exquisite wines, carefully selected for the occasion.

Today's Ride Choices

Morning: Spello to Montefalco — 35 km (22 miles)

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

What to Expect:

Leaving Spello, you may encounter some traffic at first but soon veer onto easy and quiet country roads leading to Foligno. After briefly passing through the town, a bike path takes you back into the countryside. From here, prepare for a steady uphill climb into Montefalco. In the afternoon, enjoy a long downhill coast, followed by gently rolling country roads to Bevagna. As you leave this medieval town, follow a quiet bike path and continue on flat country roads, with traffic gradually increasing as you approach Spello.

Cumulative Distance Range: 33 – 68 km (21 – 43 miles)

Included Meals: Breakfast, Dinner

Enjoy a hearty breakfast this morning, then set out on a short ride flanked by olive groves to Assisi—arguably one of the most beautiful cities in Italy. The birthplace of Saint Francis, founder of the Franciscan Order and Italy’s patron saint, as well as Saint Clare (Santa Chiara), one of his earliest followers, Assisi is a designated UNESCO World Heritage Site.

Guided by our local expert Maura, you’ll stroll through cobbled alleyways and picturesque squares, learning about the life of Saint Francis and visiting some of the city’s most important landmarks. Among these is the Basilica of San Francesco, famed for its frescoes by Cimabue, Giotto, and other masters. You’ll also discover lesser-known highlights, such as the remains of an ancient Roman arena.

Afterward, return to Spello, where you might relax by the hotel pool or opt for a longer cycling route along the flanks of Monte Subasio to take in the stunning countryside.

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

Today's Ride Choices

Morning: Spello to Assisi — 11 km (7 miles)

Afternoon: Assisi to Spello — 11 km (7 miles) | Assisi Guided Walk — 3 km (2 miles)

What to Expect:

Leave Spello on a scenic country road popular with cyclists, known as the Olive Road for the olive trees that line its edges. This route is safe and free from traffic, though you should watch out for the occasional pothole. You’ll encounter very little car traffic all the way to the outskirts of Assisi. Once in town, a short climb leads you to the designated parking area. Most of the day is dedicated to exploring Assisi, including a guided walking tour along cobbled streets with some hills. We recommend packing comfortable walking shoes and wearing a mid-sleeve bike jersey for the day. In the afternoon, follow the same route back to the hotel in Spello. For those interested, an optional independent ride with a more challenging route is available later in the afternoon—ask your trip leaders for details.

Cumulative Distance Range: 11 – 22 km (7 – 14 miles)

Included Meals: Breakfast

After breakfast, you leave the hotel to cycle along easy country roads that quietly cross the Valle Umbra. Pedal through the small medieval village of San Giacomo, located along an ancient pilgrim route to Rome, before reaching a local agriturismo. Pause here for a tour of the historic olive mill, followed by a lunch of homemade bruschetta and frittata with fresh vegetables from the garden.

Just outside the town of Spoleto—easily recognized by the massive Albornoz Fortress rising high above it—you join an easy, scenic bike path leading into the Nera Valley. See for yourself why this region is renowned for its breathtaking gorges.

Leave the bike path at a mountain pass reaching 2,400 feet in elevation and enjoy an exhilarating descent into Sant’Anatolia di Narco, where another Umbrian treasure awaits: the Abbey of Saints Felice and Mauro. Tucked into a tranquil hamlet, this 12th-century former monastery is built on the legendary site where a Syrian monk is said to have slain a dragon. Admire its beautiful rose window, ancient frescoes, and dramatic views.

Back in the saddle, continue the final miles into Scheggino, a quiet and picturesque village perched above the Nera River. You’ll have time to stroll this picture-postcard town before visiting the Truffle Museum. Umbria—particularly the Nera Valley—is famous for its truffles, and here you can learn all about this prized delicacy.

Later, shuttle to your hotel, Relais Borgo Campello, nestled in the tiny hilltop village of Campello Alto and composed of a medieval castle and a convent. These two iconic buildings once served as beacons and places of rest for pilgrims walking the Via Francigena to Rome. Campello Alto, perched high on a hill, has retained its medieval charm. Our gracious hosts will guide you on a short walking tour of the convent, where you’ll see frescoes restored in part thanks to the VBT Travelers Fund. From the bar terrace, gaze out across thousands of olive trees and spot the trails once walked by ancient pilgrims. Later, enjoy your included dinner at the hotel’s restaurant.

Today's Ride Choices

Morning: Spello to Lunch Stop — 36 km (20 miles)

Afternoon: Borgo del Rio to Scheggino — 31 km (19 miles)

What to Expect:

Leaving Spello, you may encounter some traffic but soon transition to an easy and safe bike path. Continue on mostly flat or gently rolling country roads until your lunch stop. In the afternoon, the route follows a gradually climbing, well-worn unpaved bike path. If you prefer, you can bypass the path and ride the parallel paved road. Around the halfway point, the group shifts to a well-paved, traffic-free main road. From there, enjoy a descent nearly all the way to the hamlet of Sant’Anatolia di Narco. The final stretch follows the Nera River for a couple of miles along a state road with minimal traffic—especially at the time of our ride. A 20-minute shuttle completes the trip to your hotel.

Cumulative Distance Range: 31 – 67 km (19 – 39 miles)

Included Meals: Breakfast, Lunch, Dinner

A short shuttle takes you to the start of your route. From there, follow a shaded, rolling path into Rasiglia, a hamlet of medieval stone homes set in a lush, green valley. Sometimes called the “Little Venice of Umbria” for its waterways and bridges, Rasiglia was renowned for wool production during the 16th century, when heavy looms were powered by mills fed by the rushing waters. Delight in the town’s picturesque network of waterfalls, brooks, and ponds.

Continue to a higher plateau near the border of Le Marche. Here, at 2,600 feet, you’re rewarded with panoramic views of the Apennines, where the rolling hills and fertile soil are ideal for growing regional staples like barley, spelt, lentils, and chickpeas. Roll through this protected regional park to a local merenderia—a combination restaurant and grocery shop—where the owner, Gemma, serves a hearty soup and tagliere di salumi.

Afterward, your route follows the flat plateau before descending gently into Le Marche, an unspoiled rural region where you can cycle through rolling hills for miles without seeing a single car.

Continue on to your countryside retreat, where you can bask in the revitalizing energy of the resort’s award-winning spa, take a dip in the indoor or outdoor pool, or enjoy an evening passeggiata through the lush grounds. Dinner tonight is at the hotel restaurant, where your hosts have prepared a tasting of locally produced, zero-kilometer olive oils to accompany your meal.

Today's Ride Choices

Morning: Vene to Colfiortio — 30 km (19 miles)

Afternoon: Colfiorito to Borgo Lanciano — 36 km (20 miles)

What to Expect:

A short shuttle takes you to the start of the route in Vene. The morning ride features gently rolling terrain with minimal traffic, followed by a steady two-mile ascent to Colfiorito, reaching an altitude of 2,500 feet. After taking in the views across the wide-open plateau, descend a winding road into Serravalle di Chienti—a route favored by local cyclists. A short climb then leads through the charming hamlets of Gelagna and Raggiano before descending into Castelraimondo, where light traffic increases as you approach the hotel.

Cumulative Distance Range: 30 – 66 km (19 – 39 miles)

Included Meals: Breakfast, Lunch, Dinner

Wake up to a hearty breakfast before setting off on a stunning loop through the rolling hills of Le Marche. Often called the “New Tuscany,” this region remains blissfully undiscovered, with quiet roads where you’ll share the route with little more than a few local cyclists.

Your first stop is Pioraco, a small town nestled between dramatic limestone gorges. Though the 2016 earthquake left its mark on some historic buildings, the town retains its charm, with winding paths alongside a rushing river that has powered local paper mills for centuries.

Back on your bike, continue toward Il Casato Agriturismo, a family-run farmhouse where Andrea, the charismatic owner, will welcome you warmly. The scent of freshly baked bread and warm focaccia drifts from the kitchen, setting the stage for a leisurely, rustic lunch.

After your meal, the ride continues along a panoramic route with sweeping views of the Sibillini mountain peaks in the distance. Coast downhill to your countryside retreat, where you’ll have time to unwind.

This evening, trade your cycling gear for an apron during a hands-on cooking class, where you’ll learn to make handmade pasta and meatballs—a beloved regional specialty.

Today's Ride Choices

Morning: Borgo Lanciano to Il Casato — 34 km (21 miles)

Afternoon: Il Casato to Hotel — 7 km (4 miles)

What to Expect:

Start the day on smooth country roads with a gentle ascent into the historic village of Pioraco. From there, the route flattens briefly before leading to the day’s main challenge—a two-mile climb with a steady six percent gradient. After reaching the summit, enjoy a long, relaxing descent, followed by a final scenic climb to Il Casato, where stunning views of the Sibillini Mountains await. The afternoon ride is short and rewarding, following rolling, traffic-free country roads straight to the hotel.

Cumulative Distance Range: 7 – 41 km (4 – 25 miles)

Included Meals: Breakfast, Lunch, Dinner

After an included breakfast, complimentary transportation is provided either to the Foligno train station, where you will arrive by 10:00 a.m. (approximately a 50-minute ride), or to our post-tour hotel in Bologna, where the tour concludes upon arrival at approximately 11:30 a.m. From Bologna, you can catch a flight from the airport, take a train back to Rome, or continue on to other destinations.

Included Meals: Breakfast

At 10:00 a.m., meet your VBT representative in the lobby of our Florence hotel, 25hours Hotel Piazza San Paolino.

Following brief introductions, travel approximately three hours by private motorcoach to Campello sul Clitunno in Umbria, with a short stop along the way to purchase lunch. Upon arrival, meet your VBT trip leaders, settle into your room, and change into your cycling gear. Later, take part in a safety session to prepare for your first ride.

Your accommodations for the next two nights are at the Relais Borgo Campello, nestled within the tiny hilltop village of Campello Alto. This remarkable property—comprising a restored medieval castle and former convent—once served as a resting place for pilgrims on the historic Via Francigena route to Rome. Today, it offers guests a peaceful retreat steeped in charm and history, with stone buildings, cobbled paths, and stunning views that preserve the spirit of centuries past.

Then it’s time for your first ride, an exhilarating spin through the verdant valley below, where hundreds of olive trees line the landscape. The nearby Clitunno River, immortalized by poet Giosuè Carducci, helped inspire the phrase “the Green Heart of Italy”, now synonymous with Umbria.

Back at the hotel, unwind on the shaded pometo, a peaceful terrace offering sweeping views of the valley. This evening, follow your gracious hosts on a short walking tour of the former convent, where the VBT Foundation sponsors the restoration of precious frescoes. Then enjoy a welcome cocktail on the panoramic restaurant terrace, followed by a dinner of local Umbrian specialties—including strangozzi spoletini—prepared with seasonal flair.

Today's Ride Choices