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Panoramic view of the historic town of Assisi

Rome, Assisi & Magical Umbria Premium Adventure

Small Group Departure in Italy - Example 8 Day Tour
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Embark on this premium adventure through the heart of Italy and explore the timeless beauty of Rome, Assisi, and Umbria. This 8-day tour will take you through some of Italy's most beautiful and historic regions, where you'll experience unforgettable moments and create lasting memories. Your journey begins in the eternal city of Rome, where you will stay in a hotel near the historic center. Explore the city's iconic landmarks, such as the Colosseum, Vatican City, and Trevi Fountain, with a private guide who will give fascinating insights and stories. The magical region of Umbria, renowned for its rolling hills, vineyards, and olive groves, will be explored over the following days. Discover picturesque towns such as Spello, Bevagna, and Montefalco, where you will enjoy wine tastings and local cuisine.
Woman in a Sagrantino vineyardDelicious cheeses and wines enjoyed at a vineyardVisit Rome's famed ColosseumExplore the ancient Roman ForumThe medieval village skyline of Spelloancient bridge, canal of the old mills and waterfalls in the medieval town of BevagnaRocca Maggiore, a medieval fortress that dominates the city of UmbriaItalian medieval basilica dedicated to St. Francis of AssisiThe Basilica of Superiore di San Francesco in AssisiPanoramic view of the historic town of Assisi
  • Join a guided tour in Rome that takes in the Colosseum and Trevi Fountain.
  • Discover the stunning countryside of Umbria and it's beautiful vineyards
  • Explore the Unesco-listed hill town of Assisi, birthplace of Saint Francis
  • Take a wine tasting tour in Montefalco's local wineries
  • Learn how to make delicious Umbrian cuisine with a cooking class
Places Visited
  • Europe
  • Italy
  • Rome
  • Province of Perugia
  • Assisi
  • Bevagna
  • Collazzone
  • Collepepe
  • Collepino
  • European Union
  • Montefalco
  • Perugia
  • Spello
  • Todi
Activity Level: Easy Active
Moderately active but not overly strenuous. This level includes activities like casual cycling, yoga, or excursions/activities that typically last 3-5 hours total each day.

Full Itinerary

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Day 1: Arrive in Rome

The adventure begins in the endlessly fascinating city of Rome. Meet your group and gather for the first time at your four-star accommodations near Rome Termini train station, then head to a nearby trattoria for a welcome dinner of traditional Roman dishes. 

Day 2: Rome on Foot | Collepepe

  • Hotel
  • 1 Breakfast, 1 Dinner
After breakfast, meet your certified tour guide and explore the iconic marvels of the Eternal City on foot. Along your walking tour, visit the Colosseum, the Roman Forum, and the Pantheon, three landmarks that showcase the grandeur of ancient Rome. Your expert guide will share the history and stories behind these incredible structures, making your visit a truly immersive experience.

After your walking tour there is free time for lunch before a private transfer away from the bustle of the city to the tranquil Abbazia Collemedio resort in the Umbrian countryside. The staff will be waiting with sparkling wine and appetizers for an extra-warm welcome.

Day 3: Bevagna to Montefalco | Wine and Olives

  • Hotel
  • 1 Breakfast, 1 Lunch, 1 Dinner
Enjoy your first guided walk in Umbria this morning after breakfast. The circular route begins and ends in the medieval town of Bevagna. From here, travel to Montefalco, a hilltop town overlooking vineyards that produce the much-revered Rosso di Montefalco and Sagrantino wines, the latter of which can be aged up to 30 years.

The villages of Bevagna and Montefalco are considered among the most beautiful villages in the country and make a perfect introduction to the splendor of the region. Along the route, make a stop for a picnic lunch. Later in the afternoon, visit Cantina Baldassarri, a celebrated vineyard, and olive oil mill, to sample their fine wines and virgin olive oil, accompanied by charcuterie, bruschetta, and cheeses.

Distance covered: 13.0 km / 8.1 Miles
Total Ascent: 370 Meters
Duration of Activity: 5 - 6 Hours

Day 4: Walk to Collazzone | Todi

  • Hotel
  • 1 Breakfast, 1 Lunch
Explore the resort's surroundings this morning after breakfast by starting at the front entrance and traveling to the hilltop village of Collazzone. Upon your return, head to the hotel kitchen and join a local chef for a hands-on cooking class, learning how to prepare perfect fresh pasta, tiramisu, and flan.

Afternoon free time allows you to relax by the pool before visiting Todi, another magnificent medieval village where you can enjoy the hilltop location and watch the sunset. Your leader will be happy to suggest some of the many fantastic restaurants in the area where you can have dinner.

Distance covered: 7.0 km / 4.4 Miles
Duration of Activity: 3 Hours

Day 5: Assisi Exploration

  • Hotel
  • 1 Breakfast, 1 Dinner
Take a transfer to Assisi this morning, a Unesco-listed hilltop town and, as the birthplace of Saint Francis, one of the most important pilgrimage destinations in Italy. You’re free to explore it solo, but don’t miss the 13th-century Basilica di San Francesco, an astounding early Gothic complex home to the tomb of Saint Francis and celebrated frescoes by Giotto. You may also want to visit the pink-and-white-striped Basilica of Santa Chiara, admire the towering columns at the Temple of Minerva, and explore the spectacular 12th-century stone fortress of Rocca Maggiore that protected the town for centuries.

Day 6: Perugia | Chocolate Experience

  • Hotel
  • 1 Breakfast, 1 Dinner
Today you will travel to Perugia, a buzzing university town and capital of the Umbria region. The first stop is Casa Museo Del Cioccolato, where you will dive deep into the world’s favorite treat and taste a few samples. You will also learn about Baci Perugina, a world-renowned local chocolate with a hidden love message inside.

After that, head to Perugia's city center. There is free time to explore before a guided tour taking in many of the city's landmarks, including Piazza IV Novembre and Rocca Paolina, a medieval fortress built for Pope Paul III with a network of underground tunnels and chambers to explore.

Day 7: Spello to Collepino | Walk the Path of Olives

  • Hotel
  • 1 Breakfast, 1 Lunch, 1 Dinner
Today you will take a circular walk from Spello, a medieval town where cobbled streets are brought to life with marvelous flower displays. Your guide will help you  navigate the crisscross of ancient streets and alleys, giving you time to appreciate the Town of Flowers.

Walk a section of the Path of Olives, admire the Roman aqueduct and ancient abbeys, and reach the village of Collepino, which occupies the sun-soaked face of Mount Subasio.

Though the region has a long association with producing wine, craft beer has become increasingly popular here. So to end this walking adventure, visit a craft beer factory and sample a selection of their expertly created drinks—an ideal way to toast the last night of the trip.

Distance covered: 11.0 km / 6.8 miles
Duration of Activity: 5 - 6 Hours

Day 8: Rome | Return Home

  • 1 Breakfast
Enjoy your last breakfast together this morning and bid a fond farewell to Abbazia Collemedio. Then catch a transfer back to Rome Airport, where the tour comes to an end.


Abbazia Collemedio Resort & Spa

Abbazia Collemedio Resort & Spa
Hotel Outdoor Pool
Outdoor Living Area

Rome - Hotels

Dates & Prices

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Per person starting at
$2,879 2-3 travelers


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  • 7 Breakfasts, 2 Lunches, 6 Dinners, 1 Box Lunch
  • 7 Nights Accommodations
  • 7 Days Locally Hosted Guide Service
  • Accommodations as listed
  • Ground transportation as listed
  • Activities as listed
  • Meals as listed
  • Access to a 24-7 Emergency line while traveling
  • All private airport transfer and ground transportation as per the program
  • Welcome aperitivo and complimentary spa access
  • Wine, beer and olive oil tastings with nibbles
  • Chocolate experience in Perugia
  • Gratuities
  • Travel Insurance
  • Personal Expenses
  • Flight costs (please request a quote)
  • Additional excursions during free time
  • Fuel and transportation surcharges (when applicable)
  • Medical services and visas
  • Local taxes (approximately €6 per person)


When to Go

Good to ideal period to travel, and many people choose to visit at this time.


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The trip was terrific with great planning on your part. Most of the adventures were not mainstream and somewhat off the beaten path which made it especially enjoyable!! We felt taken care of and you all were readily available to respond to questions and issues. I would highly recommend your company and friends have already expressed interest based on our pictures and excitement.
Gale Cantor
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