10 days, 9 nights · Best for Art lovers seeking Italy's masterpieces across three iconic regions
Milan Rome and Perugia Cultural Travel Package
Discover vibrant Milan, the rolling hills of Umbria, and timeless Rome, where art, history, and culinary delights come together to create unforgettable memories for every traveler.
Your Adventure Starts Here
This is a starting point. Change the nights, choose the style of hotel, add the experiences you want. Your planner takes it from there.
Stop 1Milan, Lombardy
Milan
Fashion capital meets Renaissance masterpiece and Gothic cathedral
We base you in the historic center, steps from the Duomo's forest of marble spires and the vaulted arcade of Galleria Vittorio Emanuele II. Your private guide walks you through the Gothic cathedral and past Teatro alla Scala, then we hold tickets for Leonardo's Last Supper in the refectory of Santa Maria delle Grazie. The fresco fills the wall where Dominican friars once dined, Christ and the apostles rendered in perspective that changed painting forever.
Milan moves between couture and campanile, aperitivo bars and Pinacoteca galleries. We arrange the access and the expert, you take in the city that built fortunes on silk and finance.
Arranged for you: Private transfers from airport, two nights premium four-star accommodation in historic center, skip-the-line Last Supper tickets with guide, full-day private walking tour covering Duomo, Galleria Vittorio Emanuele II and Teatro alla Scala.
Your hotel
Styles, not names. We name the property once we know your dates and your party.
Interests in Milan
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Private rooftop tour of the Duomo Day Trips · Half day
Walk among the cathedral's pinnacles and statues high above Piazza del Duomo, where views stretch to the Alps on clear days.
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Pinacoteca di Brera guided visit Day Trips · Half day
Your art historian leads you through galleries holding Mantegna, Caravaggio and Raphael in the palace that houses Milan's finest collection.
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Shopping experience with personal stylist Day Trips · Half day
A fashion consultant escorts you through Montenapoleone showrooms and hidden ateliers, tailoring the route to your taste and size.
Day by day in Milan
Arrive in the vibrant city of Milan, Italy’s fashion and cultural capital. After a smooth landing, collect your luggage and enjoy a seamless private transfer to your centrally located hotel, nestled in Milan’s historic heart. Your accommodation places you steps away from world-class museums, chic boutiques, and the city’s finest restaurants.
After settling in, embark on an unforgettable experience with a visit to the Basilica of Santa Maria delle Grazie, home to Leonardo da Vinci’s legendary masterpiece, The Last Supper. Stand in awe of this iconic fresco, taking in the artistry and history that has captivated visitors for centuries. With your artistic appetite awakened, stroll through Milan’s elegant streets and enjoy a look into local life. Discover the imposing Castello Sforzesco which is a symbol of Milanese heritage. Here, you can explore fascinating exhibits or simply stroll through Pizza Gae Aulenti, marvelling at it's modern architecture.
As evening falls, treat yourself to an authentic Milanese dinner at a restaurant from our recommendation list. Indulge in regional specialties such as cotoletta alla milanese, savoring the flavors that define Lombardy’s cuisine. After a delightful meal, return to your hotel for a restful evening. Get ready for more adventures ahead!
Start your morning with a delicious Italian breakfast, fueling up for a day of discovery. Today, you will enjoy the luxury of a private walking tour guided by a local expert. Your journey will unveil Milan’s most celebrated landmarks. Marvel at the intricate spires and breathtaking stained glass of the Duomo di Milano, Italy’s largest and most magnificent cathedral. Wander beneath the soaring glass domes of the Galleria Vittorio Emanuele II, exploring luxury boutiques and historic cafés in this architectural masterpiece. Stand in awe of Teatro alla Scala, one of the world’s most renowned opera houses and a symbol of Milan’s rich musical legacy.
After your tour, savor a leisurely lunch at a local trattoria, soaking in the city’s vibrant atmosphere. The afternoon is now yours to explore Milan at your own pace. Delve into world-class museums such as Palazzo Reale, the Museo del Novecento, or the fascinating National Science and Technology Museum. For something truly unique, visit the Monumental Cemetery, where tombs and sculptures create an experience like no other. Art lovers will be drawn to the creative energy of the Brera district, a bohemian enclave filled with art studios, galleries, and stylish boutiques.
As evening arrives, return to your hotel to refresh before your final night in Milan. Treat yourself to a memorable dinner at a top-rated restaurant, reflecting on the city’s timeless elegance and vibrant culture before settling in for another restful evening.
Stop 2Perugia, Umbria
Perugia
Hilltop capital wrapped in Etruscan walls and chocolate
We drive you south from Milan through Modena, where your guide walks you past the Romanesque cathedral and Ghirlandina tower, both UNESCO-listed and built when the city grew rich on trade. Then the road climbs into Umbria's green hills and the medieval lanes of Perugia, your base for four nights. The city rises in tiers above the Tiber valley, its center ringed by gates the Etruscans cut into rock.
We arrange your visit to the Perugina chocolate museum, where you taste Baci and watch confections take shape. A private guide leads you through Assisi's basilica, Giotto's frescoes filling the upper church with scenes from Francis's life. In the countryside a winery opens its cellars for a tasting of Sagrantino and Grechetto, vines that thrive in Umbria's clay soils and summer heat.
Arranged for you: Private transfer from Milan with stop in Modena including walking tour, four nights premium four-star accommodation in Perugia, Perugina chocolate museum tickets and tasting, private full-day Assisi tour with guide, winery visit with cellar tour and tasting.
Your hotel
Styles, not names. We name the property once we know your dates and your party.
Interests in Perugia
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Truffle hunting in Umbrian woods Day Trips · Half day
Follow a trained dog and expert hunter through oak forests, then taste your finds shaved over tagliatelle in a farmhouse lunch.
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Ceramics workshop in Deruta Day Trips · Half day
Visit a master potter in the hill town famous for majolica, learning hand-painting techniques and creating a piece to take home.
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Private cooking class with Umbrian chef Day Trips · Half day
Prepare torta al testo, strangozzi and porchetta in a local kitchen, then sit down to the meal you made with regional wines.
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Lake Trasimeno boat excursion Day Trips · Full day
Cruise Umbria's largest lake with a private captain, visiting Isola Maggiore's fishing village and stopping for lunch by the water.
Day by day in Perugia
After a satisfying breakfast, bid farewell to Milan and embark on your scenic journey south towards the enchanting region of Umbria. En route, immerse yourself in the historic allure of Modena, a city renowned for its rich heritage and culinary excellence. Enjoy a private walking tour led by a knowledgeable local guide, who will bring to life the stories behind Modena’s most iconic monuments, including the majestic Cathedral, the lively Piazza Grande, and the striking Torre della Ghirlandina, all proudly recognized as UNESCO World Heritage Sites. Following your tour, indulge in an authentic Modenese lunch at a local restaurant. This is the perfect moment to savor the city’s world-famous Balsamic Vinegar of Modena.
In the afternoon, continue your adventure as you travel to Perugia, the vibrant capital of Umbria. Check into your charming hotel, ideally located in the heart of Perugia’s historic center. Once settled, enjoy the freedom to explore the city at your own pace. You might choose to visit the esteemed National Gallery of Umbria, home to a remarkable collection of regional masterpieces, or wander the medieval streets and soak up the city’s atmosphere.
As evening nears, treat yourself to your first taste of Umbria’s renowned cuisine at a local restaurant. After dinner, take a leisurely stroll through Perugia’s picturesque city center, perhaps indulging in a scoop of gelato before returning to your hotel for a restful night in this hilltop city.
Begin your day in Perugia with a delightful breakfast before setting out on a truly sweet adventure. Your morning is dedicated to the Perugina House of Chocolate, a captivating museum celebrating one of Italy’s most beloved chocolate brands. Dive into the fascinating history of Perugina, discover the secrets behind their iconic confections, and witness the artistry of chocolate-making firsthand. Don’t miss the chance to indulge in exclusive tastings! After your flavorful morning, return to the heart of Perugia for a relaxing lunch, where you can sample more Umbrian specialties and recharge for the afternoon ahead.
Next, join your expert guide for a private walking tour through Perugia’s enchanting city center. Wander cobblestone streets as you uncover the city’s most treasured landmarks, including the grand Duomo, the ornate Fontana Maggiore, and the historic Rocca Paolina fortress. Your guide will share stories that bring Perugia’s rich past to life, making every step a discovery.
As the afternoon transitions to evening, enjoy free time to explore more of Perugia at your own pace. Consider venturing into Perugia Underground, a labyrinth of ancient tunnels and Etruscan ruins hidden beneath the city. This is an unforgettable journey into the depths of history. Conclude your day with dinner at a charming trattoria, savoring another authentic Umbrian dish. Afterward, take a leisurely stroll through the softly lit streets before returning to your hotel for a restful night.
After breakfast, set out on a memorable journey to Assisi, the legendary birthplace of St. Francis and one of Italy’s most revered pilgrimage destinations. Relax during your comfortable private transfer as you travel through the serene Umbrian countryside to this charming hilltop town.
Upon arrival, meet your expert local guide for a walking tour of Assisi’s historic center. Marvel at the awe-inspiring Basilica of San Francesco, a UNESCO World Heritage Site distinguished by its Upper and Lower Churches, each adorned with priceless masterpieces. Stand before Giotto’s celebrated frescoes, which vividly narrate the life and legacy of St. Francis, and experience the spiritual aura that draws visitors from around the world. Continue your exploration with visits to the graceful Basilica of Santa Chiara, the imposing Rocca Maggiore fortress, and the Cathedral of San Rufino, each revealing a different facet of Assisi’s rich history. Don’t miss the Basilica of Santa Maria degli Angeli, uniquely built to shelter the Porziuncola, a tiny but sacred chapel at the heart of the Franciscan movement.
Pause for a relaxing lunch, then the afternoon is yours to enjoy at leisure. Stroll the streets of Assis, browse artisan boutiques for unique souvenirs, or simply soak up the tranquil atmosphere that makes this town so special. Later, return to Perugia via private transfer, where you can unwind and refresh at your hotel. Conclude your day with dinner, savoring the region’s culinary delights before settling in for a restful night.
Begin your day with breakfast at your hotel, then set out for an escape into the rolling hills of the Umbrian countryside. Often described as Italy’s hidden gem, Umbria’s landscapes rival those of Tuscany, offering breathtaking views of verdant vineyards, olive groves, and ancient hilltop villages.
Your journey brings you to a charming local winery, where you’ll be welcomed for an immersive tour of the vineyards and cellars. Discover the time-honored traditions and unique terroir that give Umbrian wines their distinctive character. As you explore, your host will share insights into the region’s winemaking heritage. Savor a guided tasting of the estate’s finest wines, enjoying the flavors and aromas that capture the essence of Umbria. Take time to relax and soak in the panoramic countryside vistas, perhaps pairing your wine with local delicacies for a truly authentic experience.
After your leisurely visit, return to Perugia, where you can refresh at your hotel and reflect on the day’s discoveries. In the evening, celebrate your final night in Umbria with a memorable dinner, toasting to the unforgettable moments and flavors you’ve enjoyed in this captivating region.
Stop 3Rome, Lazio
Rome
Colosseum to Sistine Chapel in the Eternal City
Your driver takes the Via Cassia south, stopping in Orvieto where your guide walks you to the cathedral's striped face and Signorelli frescoes inside the chapel. The town sits on a volcanic plug, tufa cliffs dropping to vineyards that produce Orvieto Classico. Then Rome spreads below as you descend from the hills, and we check you into a hotel near the historic center.
We hold skip-the-line access to the Colosseum, where your guide describes the velarium awning and trap doors that lifted animals into the arena. You walk the Sacred Way through the Forum, past the Senate house and Temple of Vesta. At the Vatican your guide leads you through the Raphael Rooms and into the Sistine Chapel, where Michelangelo's Last Judgment fills the altar wall and his Genesis scenes unfold overhead. St. Peter's Basilica follows, Bernini's colonnade embracing the piazza outside.
Arranged for you: Private transfer from Perugia with stop in Orvieto including walking tour, three nights premium four-star accommodation near Rome's historic center, skip-the-line Colosseum and Forum guided tour, Vatican Museums and Sistine Chapel guided tour with St. Peter's Basilica, private airport transfer.
Your hotel
Styles, not names. We name the property once we know your dates and your party.
Interests in Rome
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Borghese Gallery private tour Day Trips · Half day
Your art historian guides you through Bernini marbles and Caravaggio canvases in the cardinal's villa, then you stroll the surrounding park.
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After-hours Vatican experience Day Trips · Half day
Enter the Sistine Chapel before public opening or after closing, when the crowds thin and you stand beneath Michelangelo in near silence.
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Appian Way e-bike tour Day Trips · Full day
Ride the ancient paving stones past aqueducts, catacombs and umbrella pines, stopping at a family-run vineyard for lunch and wine.
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Private pasta-making class in Rome Day Trips · Half day
A local chef teaches you cacio e pepe, carbonara and amatriciana in a kitchen near Campo de' Fiori, followed by the meal with house wine.
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Ancient and Old Rome Walking Tour, Skipping the line at Colosseum Guided Tours and Sightseeing · Tour in a DayUnlock the secrets of the Eternal City, skip the lines and step into the world of emperors, gladiators, and gods on this lively, story-filled Roman adventure.
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Full Day Rome Tour Guided Tours and Sightseeing · Tour in a DaySee Rome your way in one unforgettable day. Vatican treasures, Imperial ruins, and iconic monuments with the ease of a dedicated tour escort.
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Papal Audience in Saint Peter’s, Vatican City Guided Tours and Sightseeing · Tour in a DayWitness a truly unforgettable moment in Rome, attend a Papal Audience and receive the Pope’s blessing.
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Rome by Bicycles Tour with English Speaking Guide Guided Tours and Sightseeing · Tour in a DaySee more of Rome with less effort, cruise past iconic landmarks on a fun, guided bike ride made for everyone.
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Rome by Night Guided Tour Guided Tours and Sightseeing · Tour in a Day
See Rome at its most magical, an evening stroll through illuminated fountains, grand piazzas, and ancient ruins.
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Rome by Night guided Tour with Dinner & Show Guided Tours and Sightseeing · Tour in a Day
Fall for Rome after dark. Glowing landmarks, a romantic evening stroll, and dinner with live music to seal the moment.
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Rome: The Eternal & Ancient Rome Tour Combo Guided Tours and Sightseeing · Tour in a DayExperience the magic of the Eternal City with a full-day tour showcasing Rome’s most iconic historical sites.
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Rome: The Eternal City Tour Guided Tours and Sightseeing · Tour in a Day
Discover Rome’s most iconic monuments in comfort on this tour.
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Skip the Line: Vatican Museums and Sistine Chapel Guided tours Guided Tours and Sightseeing · Tour in a Day
Skip the lines and step straight into the Vatican’s greatest masterpieces. Museums, Sistine Chapel, and St. Peter’s Basilica with an expert guide.
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The Ancient Rome Tour Guided Tours and Sightseeing · Tour in a Day
Walk in the footsteps of emperors and gladiators, discover the power, passion, and innovation that shaped the world in Ancient Rome.
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The Ancient Rome Walking Tour, Skipping the line at Colosseum Guided Tours and Sightseeing · Tour in a Day
Experience the ancient highlights of the Eternal City with a guided walking tour that takes you through Rome’s most iconic landmarks.
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The Christian Rome & Catacombs Tour with Hotel Pick Up Guided Tours and Sightseeing · Tour in a DayJourney through Rome’s spiritual heart, explore ancient basilicas, sacred relics, and the origins of Christianity in the Eternal City.
Day by day in Rome
Begin your day with a final breakfast in Perugia before checking out and setting off for the hilltop town of Orvieto, perched dramatically above the Umbrian plains. As your driver winds through the scenic countryside, soak in panoramic views that capture the region’s timeless beauty.
Upon arrival in Orvieto, meet your private guide for an immersive walking tour through the city’s medieval streets. Be astonished by the magnificent Orvieto Cathedral, renowned for its dazzling face of mosaics and sculptures. This is one of the most breathtaking sights in all of Italy. Continue your exploration with visits to the intriguing Pozzo della Cava, a network of ancient underground tunnels, and the legendary Well of St. Patrick, a display of Renaissance engineering that descends deep into the volcanic rock. After your tour, enjoy a leisurely lunch, perhaps pairing a traditional dish with a glass of the region’s crisp white wine. Re-energized and inspired, reunite with your driver and continue your journey south to Rome. The Eternal City awaits!
Arrive in Rome and check into your centrally located hotel. The rest of the day is yours to begin exploring the city’s vibrant streets, or simply relax and anticipate the adventures that await in Italy’s legendary capital.
After breakfast, set out for a day immersed in the wonders of Ancient Rome. Begin your adventure with a skip-the-line guided tour of the iconic Colosseum, where your expert guide will bring to life the epic tales of gladiators, emperors, and the dramatic spectacles that once captivated thousands. Explore the Colosseum’s different levels, gaining insight into its ingenious architecture and the pivotal role it played in Roman society.
Continue your journey as you stroll the ancient pathways of the Roman Forum, the bustling heart of political, religious, and commercial life in the Roman Republic and Empire. Marvel at the remnants of temples, basilicas, and triumphal arches that have stood the test of time. Ascend the Palatine Hill, one of the city’s legendary seven hills, and take in sweeping views over the ruins and the modern city beyond. Pause for lunch at a local trattoria or enjoy a quick bite of classic Roman street food, such as pizza al taglio, as you soak up the lively atmosphere.
The afternoon is yours to discover Rome at your own pace. Art and history lovers might explore the treasures of the Capitoline Museums or the National Etruscan Museum. Alternatively, wander to some of Rome’s most beloved open-air landmarks: toss a coin into the Trevi Fountain, climb the Spanish Steps, admire the artistry of Piazza Navona, or visit the archaeological site of Largo di Torre Argentina.
As evening falls, experience the authentic charm of Trastevere, a picturesque neighborhood known for its narrow cobblestone streets, vibrant nightlife, and traditional Roman trattorias. Savor a leisurely dinner where locals dine, then end your night with a stroll through the lively piazzas and perhaps a scoop (or two) of creamy Italian gelato before returning to your hotel for a restful night.
Start your final full day in Rome with a hearty breakfast, then prepare for an awe-inspiring journey through the Vatican, the heart of Catholicism and a wealth of world-renowned art and history. Meet your expert guide and step into the Vatican Museums, one of the largest and most celebrated museum complexes on the planet. Wander through lavish galleries, marveling at the intricate frescoes of the Raphael Rooms and standing in silent wonder beneath the breathtaking ceiling of the Sistine Chapel, painted by Michelangelo.
Your exploration continues in the majestic St. Peter’s Basilica, the largest church in the world and a masterpiece of Renaissance architecture. Absorb the spiritual atmosphere as your guide shares the stories behind iconic highlights, including Michelangelo’s poignant Pietà sculpture and the grandiose Baldachin by Bernini. With the guided tour concluding inside the basilica, you’ll have plenty of time to linger. Perhaps climbing to the top of the dome for panoramic views across Vatican City and Rome, or descending to the crypt to pay respects at the tombs of the Popes. Step out into the sunlit embrace of St. Peter’s Square before enjoying a leisurely lunch nearby, sampling Roman classics in the heart of the city.
In the afternoon, continue your sightseeing with a visit to Castel Sant’Angelo, a striking fortress with centuries of papal and imperial history. Cross the iconic Sant’Angelo Bridge, pausing to admire its marble angels, and make your way back into Rome’s historic center. Spend your last hours in the Eternal City shopping for unique souvenirs, revisiting favorite landmarks, or simply soaking in the vibrant Roman atmosphere.
As evening falls, gather for a memorable farewell dinner, raising a glass to the unforgettable experiences, art, and flavors that have defined your Italian adventure.
Day 10
Return Home
Check out and meet your driver for your private transfer to the airport, bidding farewell to Italy as you begin your journey home. Return with unforgettable memories and a heart full of Italian experiences.
Why plan with Trips 2 Italy?
Designed around you by Italian-born planners
Guides, drivers and boats for your party alone
Hand-selected hotels in every destination
Local English-speaking guides who know their city
Met at the airport, private transfers throughout
Testimonials
Hear from travelers who have planned Italy with us
They took the time to understand our preferences and designed an itinerary that was comfortable, personalized, and enjoyable. They offered thoughtful recommendations while never being pushy.
We missed our connecting flight in Munich. I had just got through customs and was looking up the number to call when Trips 2 Italy called me. They told me exactly what to do and they already knew what flight we had been rebooked on.
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Questions travelers ask
Where will we travel on this itinerary?
Over 11 days this journey brings you to Rome, Milan, Assisi, Orvieto, and Perugia. Each stop is woven into the itinerary with time for the landmarks, the views, and the local flavor that make it special.
How will we get around during the vacation?
Transportation is arranged as part of the itinerary, with comfortable train segments between the cities and vehicle transfers where they serve you best. Every connection is planned for you, so you can focus on the scenery instead of the logistics.
What kind of traveler is this package for?
It suits travelers who want Italy arranged by experts, with guided experiences balanced by free time to explore on your own.
Can we customize this itinerary?
Absolutely. Every Trips 2 Italy itinerary is designed to inspire and can be tailored end to end, from the number of nights and hotel categories to the experiences along the way. A minimum of 2 travelers applies.
What is the best season for this itinerary?
The package is available all year around on request. Spring and fall offer mild walking weather and lighter crowds at the major sights, summer brings long lively evenings, and winter rewards travelers with quieter museums and festive streets.