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Wondering when is the best time to visit Umbria?

With warm temperatures, blue skies, and fewer crowds, the shoulder season of April to June and September to November is an ideal time to explore the beautiful Italy destinations. Let our expert travel advisors help you plan your perfect adventure the next time you visit Umbria.

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Experience the hilltop towns, local traditions, unforgettable food, and slower pace that make Umbria one of Italy’s most memorable regions. With raro, you’ll go beyond the highlights to experience the authentic heart of Italy.

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Umbria, Italy

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Umbria, Italy · Multiple Departures

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Explore Umbria

looking for the ultimate Italian vacation experience?

Explore the hidden gems of Umbria and immerse in these medieval cities in Italy.

Experience the best of Umbria with a journey curated by our travel experts. From historic hilltop towns to rolling vineyards and charming countryside, Umbria offers the perfect balance of culture, adventure, and relaxation. Whether you’re savoring local wines, exploring medieval villages, or immersing yourself in the region’s rich history, this is Italy at its most authentic. Learn more about this unforgettable experience.

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Discover Italy

Experience Rome and Umbria hidden corners, unforgettable meals, rich history, and authentic local culture. From the Eternal City to the heart of Italy’s countryside, immerse yourself in the atmosphere, flavors, and moments that make this journey unforgettable.

Indulge in Wine Tasting

Wine aficionados will truly enjoy a journey through the vineyards of Paolo and Noemia d’Amico winery. Sip on exquisite wines crafted with passion and expertise while learning about the entre winemaking process.

Picturesque Landscape

Prepare to be awe-struck by the captivating charm of Civita di Bagnoregio, an ancient hilltop village suspended in time. Let the serene ambiance of the valleys transport you to a bygone era.

Enchanting villages and sceneries straight from storybooks

Ready to uncover Umbria? Don’t miss out on this opportunity to experience the region like a local. With travel raro as your guide, your Umbrian adventure will be nothing short of extraordinary.

Start your journey today and let’s create memories in Italy that will last a lifetime.

The Journey

Day 1 - Arrive in Rome
Welcome to Rome! Upon arrival you will be greeted at the airport by your Host(s) and private driver and then transported to your hotel. Following time for unpacking and refreshing you have the entire afternoon to explore the beautiful streets of the capital city. One of Italy’s crowning jewels, this metropolitan city offers up glimpses of history and culture around every turn. Your host can give you recommendations for places to explore and shop during your free time today. Later that evening, you and your fellow travelers will meet with your Host(s) for a welcome dinner to get the trip kicked off right. Cheers to the adventures that will follow!
All Meals
All Activities
Transportation
Dedicated Host
Worry Free
Airfare not included
Day 2 - Adventure Rome
You will start your day with a delicious Italian breakfast and of course robust Italian coffee. After breakfast, you will depart to tour Domus Aurea, an ancient historical site that was once the most lavish palace in Rome. Take in the architectural beauty of this iconic monument before you head to lunch at one of our favorite local eateries. Here you may encounter handpicked baskets of fresh mushrooms that make their way into your pasta, and plates of aged to perfection prosciutto with all the homemade bread your heart desires. Be sure to grab a glass of Italian wine or beer and cheers with your fellow guests to your first full day in Roma!
Following lunch, you can explore all that the Eternal City has to offer. Perhaps venture to the Coliseum and find your inner gladiator or enter Vatican City and marvel at St Peter’s Basilica. Whether a pasta making class is more your speed, or some shopping at the Spanish Steps is calling your name, you will surely enjoy your time in the city.
After all your explorations you will have worked up an appetite just in time to meet your fellow travelers for a drool worthy dinner. Following dinner, you can turn in early or explore a bit of the Roman nightlife. Your host can recommend good places to rub elbows with the locals should you desire. Just remember we are off to Umbria tomorrow!
All Meals
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Dedicated Host
Worry Free
Day 3 - Travel To Orvieto
Today your journey to Italy’s green heart begins! You will travel to Orvieto on our private bus with a special stop on the way, the magical city of Civita di Bagnoregio. Rising from the valley floor, Civita stands as a monolithic relic to times past. This medieval village is only reachable by pedestrian bridge, but trust us, what awaits you at the top is worth the walk. The sweeping, panoramic views are things that travel dreams are made of. The small cobblestone alley ways lead to one picturesque view after another. You will have lunch here in one of the adorable cafes and soak up all the village has to offer. Quaint, quiet, and filled with history this idyllic Italian storybook village will burn itself into your heart and memories.
After lunch you will continue your journey through some of Italy’s hidden gems and arrive in Orvieto. A hilltop town anchored at its center by a gothic cathedral that is a gleaming mass of mosaics, stained glass, and sculpture. You will get two nights to explore this city of cultural significance and fascinating configuration with its secret underground world.
All Meals
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Dedicated Host
Worry Free
Day 4 - Explore Orvieto
Buongiorno from Orvieto. Fill up on breakfast at your hotel before venturing off to see all that this city has to offer. Orvieto sits in splendor atop a plateau that overlooks a valley and winding river so there are plenty of sights to take in. Its magnificent cathedral duomo, is one of Europe’s greatest examples of Gothic architecture and warrants time for exploration. The duomo is located at the center of town, so after your tour it’s easy to venture through the grid of narrow streets that make up the old city. You will find cafes, wine bars, and shops tucked away down every lane.
Next, have some lunch with your travel mates and then be prepared for something unique and uncommon. Beneath Orvieto lies a hidden secret, a dark labyrinth and underground world built during the Etruscan times. You will tour this once forgotten honeycomb of caverns that were originally used as hideouts and escape hatches when the city was under siege. After being awestruck by this find, you can grab an espresso or a cocktail at one of the many quaint cafes before meeting your companions for some fine Umbrian cuisine.
All Meals
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Dedicated Host
Worry Free
Day 5 - Todi & Spello
We will travel by bus to Todi. Once we arrive, we will meet our guide at Tempio di Santa Maria della Consolazione, a Renaissance-style church, followed by lunch at La Cantina Del Mercataccio. Afterwards, we will leave for Spella, known as one of “The Most Beautiful Villages of Italy” for its gorgeous cultural and historic components as well as its awe-inspiring views. We will check into our hotel, where we will also share dinner later in the evening.
All Meals
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Dedicated Host
Worry Free
Day 6 - Spello & Rasiglia
This morning finds you in Spello ready for another day of exploring the small villages that make Umbria so special and unique. After a fine Italian breakfast at your hotel, you will board our private minibus and take a short drive to Rasiglia, a quaint little village forgotten by time. Here you will find storybook scenery interspersed with small wooden bridges, under which run lively streams from which you can admire the clear, clean water which makes its way down several small falls . The hill on which the village sits is completely wooded and all of the small houses here are built entirely out of stone. You will have a lunch consisting of the lentils and legumes the region is well known for producing. After lunch, spend some time in the few local shops and perhaps pick up some handmade leather goods or textiles made on the onsite loom.
After your explorations in Rasiglia you will return to Spello and have some time to yourself to relax, freshen up, or explore the town before yet another amazing Italian dinner in the town.
All Meals
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Dedicated Host
Worry Free
Day 7 - Assisi
Today’s journey will take you to the birthplace of one of Italy’s patron saints, St Francis. Here you will see the impressive Basilica di Francesco d’Assisi that was built in his honor; boasting a collection of frescoes and paintings that rivals many museums. Don’t be surprised to see monks in long robes roaming the streets or pilgrims making their way to pay their respects. Before lunch, spend time strolling the narrow cobblestone streets and wide piazzas, or visiting one of the many churches or basilicas. After a lunch of locally sourced delicacies and regional wine, you will head back to Spello for the evening. Gather with your fellow travelers for dinner to delight in more local fare. We promise you won’t be tired of it.
After your explorations in Rasiglia you will return to Spello and have some time to yourself to relax, freshen up, or explore the town before yet another amazing Italian dinner in the town.
All Meals
All Activities
Transportation
Dedicated Host
Worry Free
Day 8 - Montefalco
This morning after breakfast we take a short bus ride to the small medieval town of Montefalco. It’s famous for its perch high on a hilltop that offers breathtaking views of endless green valleys and sprawling vineyards. Here you will take note of the earthy cuisine and crisp wine the village is known for. You will enjoy a private wine tour, tasting, and lunch with a bit of time to explore the fresco filled churches that give this town its charm.
You will return to Spello in the evening where you can relax or explore before meeting for another amazing Italian feast of the senses.
All Meals
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Dedicated Host
Worry Free
Day 9 - Gubbio
Today you will be captivated by the hidden gem of Gubbio. Its stony façade emerges from the mountain side, a relic of times past. This gorgeous medieval town is famous for its ruins, mix of roman and gothic architecture, and suspended Piazza Grande. Be sure to explore the Roman theater and take the funicular, a tiny ski lift like cage, to the top of Mount Ingino for endless views of the green valleys below.
Before you depart, be sure to get baptized as “mad” at the Fontana dei Matti as folk lore from the town states that three laps around it will make you officially a lunatic. Pop into a nearby shop to make it official with your own license to be crazy. There are also lots of small shops for you to peruse before departing back to Spello for the evening.
All Meals
All Activities
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Dedicated Host
Worry Free
Day 10 - Castiglione in Teverina / Rome
You will spend your final day in Italy making our way back to the Eternal City. After departing for Rome in the morning, we will make a memorable stop in Castiglione in Teverina, for a wine tasting at a vineyard like nothing you have ever seen. Not a detail has been missed in this impeccable estate where all of your senses will be captivated at once. Indulge in velvety wines while looking out at the sprawling vineyards, manicured gardens and breathtaking vistas that surround the estate. After what can only be described as a momentous experience at the winery you will surely need a bite. Good thing our next stop is lunch at a favorite local eatery. Have your fill before we finish the final leg of our journey back to Roma. Once arriving in Rome, you will check into your accommodations and have a farewell dinner with your fellow travelers and now friends, as you reflect on all of the unique experiences you shared along the way.
All Meals
All Activities
Transportation
Dedicated Host
Worry Free
Day 1 - Arrive in Rome
Welcome to Rome! Your journey begins with a warm welcome at the Roma Fiumicino International Airport (FCO) from your Host(s) and a private driver. After settling in, the afternoon is yours to uncover the city’s treasures. Rome, a cultural masterpiece, invites you to wander through its historic streets. Your Host(s) can suggest spots to explore and shop. Come evening, join your Host(s) and fellow travelers for a delightful welcome dinner, marking the start of unforgettable adventures ahead.
All Meals
All Activities
Transportation
Dedicated Host
Worry Free
Airfare not included
Day 2 - Depart for Spello
Embrace your day with an authentic Italian breakfast accompanied by robust coffee. After, venture to the historic Domus Aurea, a once extravagant palace, now a historical marvel. Feast your eyes on its architectural splendor before indulging in lunch at a cherished local eatery. Here, relish dishes infused with freshly picked mushrooms and perfectly aged prosciutto, complemented by homemade bread and Italian wine or beer.
Afternoon invites you to explore Rome’s grandeur. Visit the Coliseum for a taste of ancient glory or lose yourself in the magnificence of St. Peter’s Basilica within Vatican City. Whether it’s a pasta-making class, shopping at the Spanish Steps, or other Roman pursuits, cherish your moments.
As twilight arrives, join fellow travelers for a delectable dinner. Post-dinner, choose to retire early or delve into Rome’s nightlife, with your host suggesting local hotspots for an authentic experience. Tomorrow, Umbria awaits!
All Meals
All Activities
Transportation
Dedicated Host
Worry Free
Day 3 - Rasiglia
Welcome to Spello, your gateway to another enchanting day of discovering the unique charm of Umbria’s villages. Fuel up with a delightful Italian breakfast at your hotel before stepping onto our private minibus for a brief journey to Rasiglia – a time-forgotten village.
In Rasiglia, a fairy tale unfolds with wooden bridges over lively streams and cascades, showcasing the pristine water that meanders through the village. Nestled on a wooded hill, its stone houses stand as a testament to its history. Savor a lunch featuring the region’s renowned lentils and legumes. Afterward, peruse local shops for handcrafted leather goods and textiles, showcasing the village’s artisanal heritage.
Returning to Spello, unwind, freshen up, or explore the town at your leisure before an exquisite Italian dinner awaits. A perfect day to remember!
All Meals
All Activities
Transportation
Dedicated Host
Worry Free
Day 4 - Assisi
Today’s journey will lead you to the hometown of Italy’s patron saint, St. Francis. Marvel at the grandeur of the Basilica di Francesco d’Assisi, a tribute adorned with frescoes and paintings akin to esteemed museums. Monks and pilgrims grace the streets, adding to the spiritual aura.
Before lunch, wander through cobblestone streets, immerse in the tranquil atmosphere of piazzas, and explore churches and basilicas. Indulge in a lunch of locally sourced delicacies and regional wine. Upon returning to Spello, reconvene with fellow travelers for another delectable dinner, celebrating the region’s flavors. A day imbued with culture, spirituality, and culinary delights.
All Meals
All Activities
Transportation
Dedicated Host
Worry Free
Day 5 - Montefalco
After breakfast, a brief bus ride transports us to Montefalco, a charming medieval town nestled high atop a hill. Behold panoramic vistas of lush valleys and expansive vineyards. Discover the village’s rustic cuisine and exquisite wines. Delight in a private wine tour, tasting, and lunch, followed by a chance to explore its fresco-adorned churches.
Back in Spello, the evening welcomes relaxation or further exploration before reuniting for another tantalizing Italian culinary experience.
All Meals
All Activities
Transportation
Dedicated Host
Worry Free
Day 6 - Gubbio
Today, the enchanting secret of Gubbio unfolds. Its rocky visage emerges from the mountainside, a relic of ages past. This medieval wonderland boasts ruins, a fusion of Roman and Gothic architecture, and the suspended Piazza Grande. Delve into the Roman theater and ascend Mount Ingino via the funicular for panoramic vistas over the verdant valleys below.
Before you bid farewell, take part in the whimsical tradition at Fontana dei Matti – legend says circling it three times grants you the title of “mad.” Visit a local shop for your official “crazy” license. Explore the quaint shops before returning to Spello for the evening.
All Meals
All Activities
Transportation
Dedicated Host
Worry Free
Day 7 - Castiglione in Teverina / Rome
On your closing day in Italy, we journey back to the Eternal City. Morning brings departure for Rome, with a remarkable pause in Castiglione in Teverina. Here, an extraordinary vineyard awaits, an experience beyond compare. Immerse your senses in this flawless estate, savoring velvety wines amidst sprawling vineyards, manicured gardens, and breathtaking vistas.
After this unforgettable encounter, relish a satisfying lunch at a cherished local eatery. Then, as we complete the final stretch to Rome, check into your lodgings. The day culminates in a farewell dinner with newfound friends, reminiscing on the unique escapades shared throughout this journey.
All Meals
All Activities
Transportation
Dedicated Host
Worry Free
Day 8 - Departure
Bid Italy adieu, carrying cherished memories of its rich culture, picturesque landscapes, and newfound friendships.
All Meals
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Transportation
Dedicated Host
Worry Free

group travel that doesn't feel like group travel

Villages and scenery you’ve only seen in books.

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Ready to uncover Umbria with Tony’s? Don’t miss out on this opportunity to experience the region like a local. With raro as your guide, your Umbrian adventure will be nothing short of extraordinary.

Start your journey today and let’s create memories in Italy that will last a lifetime.

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Leon's Place Hotel, Rome

Set within the beautifully restored Palazzo Fabi Altini, Leon’s Place is where Roman grandeur meets refined modern design. Just steps from Via Veneto and the leafy paths of Villa Borghese, this boutique hotel sits in one of the city’s most elegant neighborhoods, a place where every street corner leads to another story waiting to be discovered.

Each of the 56 rooms blends period architecture with contemporary comfort, from marble bathrooms to sleek furnishings that feel both timeless and fresh. Start your morning with a cappuccino in the garden courtyard, unwind with a steam session in the spa after a day of exploring, and end the evening with aperitivo at the Visionnaire Cafe as the warm Roman light fades into gold.

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