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Destinations Europe Italy
Days: 8 | From: $7,010/per person
Get to know Umbria on this curated 8-day itinerary, ideal for those interested in Italian food, art, history, and getting off the beaten track. The journey begins in Assisi, where you'll learn about truffle-hunting traditions and sample Umbrian wine, before traveling to Orvieto, a striking hilltop Medieval town with roots dating back over 2,700 years. The trip ends in Rome, but not before diving further into Umbrian archelogy and picturesque Tuscan villages.
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Welcome to Italy! Upon arrival at the airport in Rome, you’ll be privately transferred to the historic town of Assisi. Located in the rolling hills of Umbria, Assisi offers medieval charm, basilicas, and the timeless serenity that once inspired St. Francis himself.
Upon arrival, check into your hotel and have the rest of the day to unwind or explore at your leisure.
Set just outside the historic town of Assisi, Borgo Antichi Orti is a charming retreat surrounded by nature and history. Once a Benedictine monastery, today it offers elegant suites inspired by the signs of the zodiac, blending rustic charm with modern comfort. Guests can enjoy a peaceful atmosphere, herbal gardens, and breathtaking views of the Umbrian countryside. Breakfast is a highlight, featuring fresh, seasonal ingredients — from homemade pastries to local cheeses and herbs picked straight from the garden.
Today, enjoy a private guided tour through Assisi, one of Umbria’s most treasured historic towns. Known as the birthplace of St. Francis, Assisi offers a range of medieval architecture and captivating views of the Umbrian countryside.
Visit the Basilica of St. Francis, famous for its striking Gothic design and the renowned frescoes by Giotto that depict the life of the saint. Continue to the Basilica of St. Clare and stroll through the Piazza del Comune, the city’s main square surrounded by Roman and medieval landmarks, including the Temple of Minerva and Cathedral of San Rufino.
The rest of the day is yours to explore on your own, or simply relax at the hotel.
*Includes: Breakfast
Today you’ll explore the stunning Umbrian countryside, beginning with an immersive truffle hunting excursion near the Tuscan border. This region is one of the few places in Italy where the prized white truffle can be found.
Your visit begins at a family-run truffle farm, where expert truffle hunters and their dogs will guide you through a hands-on demonstration of how truffles are found, processed, and used. You’ll learn to identify different truffle varieties, gain practical tips on cooking and preservation, and visit a small yet informative Truffle Museum. A highlight of the day is a cooking demonstration by a local chef, followed by a truffle-based lunch featuring traditional Umbrian dishes.
The day continues with a visit to the nearby village of Citerna, officially recognized as one of Italy’s most beautiful villages. You’ll also have free time to explore Montone, a picturesque medieval hilltop town known for its quiet charm, panoramic views, and inviting atmosphere.
*Includes: Breakfast, Lunch
Today, enjoy a private transfer to Orvieto with two stops along the way. First head to Spoleto, a city with deep historical roots and a remarkable artistic legacy. On a private walking tour, you’ll explore the city’s atmospheric streets, lined with Roman ruins, medieval landmarks, Renaissance treasures, and cathedrals and fortresses from the 14th-century.
Afterwards you’ll continue to Montefalco, a hilltop town known as the “Balcony of Umbria” for its sweeping views and its exceptional wines. Here, you’ll visit a winery and learn about the winemaking process from vineyard to bottle and sample the wines during an informative tasting.
Finally, continue to Orvieto and check into your hotel for the next three nights.
Set just before reaching the historic town of Orvieto, Palazzo Petrvs is a timeless residence steeped in elegance and tradition. Originally built in the 15th century as the home of a noble notary, it remains a remarkable example of Renaissance architecture and Umbrian craftsmanship. The palace features a graceful layout centered around a quiet inner courtyard, with high-ceilinged rooms, original wooden beams, and stone details carved from local tuff. Every corner reflects its aristocratic past, from the grand staircase to the centuries-old frescoes that still adorn some of the walls. Surrounded by rolling hills and vineyards, the property offers sweeping views and a deep sense of calm
Set out on a private guided tour of Orvieto, a striking hilltop town with roots dating back over 2,700 years, built atop a dramatic plateau of volcanic tufa stone. As you explore the town’s winding streets, you’ll encounter Gothic cathedrals, elegant palaces, centuries-old homes, and civic buildings, many carved from tufa stone.
The rest of the day is yours to continue to explore.
Discover the timeless charm of southern Tuscany with a visit to Pitigliano, known as “Little Jerusalem” for its well-preserved Jewish quarter and historic synagogue. Alongside a private guide, explore notable landmarks such as the Orsini Gate, the 16th-century aqueduct, Piazza della Repubblica, and the Cathedral of Saints Peter and Paul.
Pitigliano is also recognized for its wine production, particularly the Bianco di Pitigliano DOC, aged in ancient cellars carved into volcanic rock. The tour includes a walk through the medieval heart of town, passing the Church of Santa Maria and exploring the narrow streets of the Jewish quarter.
The day continues with a visit to Sorano, a cliffside village often compared to Matera for its cave dwellings and dramatic scenery. Stroll through its atmospheric alleys, browse local shops, and take in views from the Orsini Fortress.
Finally, enjoy free time in Sovana, a quiet and historically rich village. Explore its main square, visit artisan boutiques, and, if time permits, step into the Romanesque Cathedral of San Pietro.
On your way to Rome Fiumicino, enjoy a private guided tour of Tarquinia, one of the most important centers of ancient Etruscan civilization. Your guide will offer a glimpse into the past, with a visit to the Monterozzi Necropolis — a UNESCO World Heritage Site featuring over 6,000 tombs, some dating back to the 7th century BC. Around 200 of these tombs are decorated with remarkably well-preserved frescoes, making up the largest and most significant collection of Etruscan wall paintings in existence.
You’ll also have time to explore the charming medieval town of Tarquinia itself, where Renaissance palaces and cobblestone streets reflect centuries of layered history. This stop adds a fascinating cultural highlight to your journey before continuing on to Rome.
A contemporary and stylish hotel, Hilton Rome Airport offers comfort and luxury just outside of the Eternal City. Dine on modern Italian classics at Le Colonne Restaurant, offering roman specialties served on a marble buffet table or in the private dining area or Smoking Lounge. Opt for a more relaxed meal at Caffe Tevere Bistro and relax with live music at the Artist’s Bar. Enjoy a swim in the indoor pool with outdoor deck or have a relaxing soak in the whirlpool. The Hilton Rome Airport hotel is only a 5 minute walk from the Rome Fiumicino Airport and is easily reached via the moving walkway.
Say goodbye to Italy and transfer to the airport to catch your departing flight.
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