Begin your forever together in vibrant Milan, the hills of Umbria, and timeless Rome where art, chocolate, and romance create memories to last a lifetime.
Starting from $5844 per person
Milan Rome and Perugia Cultural Vacation Package | Vacation Package for 2025 – 2026
11 Days/10 Nights
Starting from
$5844.00
per person*
Milan Rome and Perugia Cultural Vacation Package | Vacation Package for 2025 – 2026
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A Travel Experience Like No Other
Curated by our Italy travel experts, this sample itinerary is a starting point for your dream Italy vacation. Tell us your interests and budget, and we’ll tailor it to your pace so you can enjoy Italy like a local.
Day 1
OUT-BOUND FLIGHT
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Board your overnight flight to Italy, filled with anticipation for the adventure ahead.
Day 2
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Private car transfer to your hotel in Milan’s historic center.
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Entrance to the Basilica of Santa Maria delle Grazie to view Da Vinci’s Last Supper.
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Stroll through Milan’s iconic streets and stroll through Piazza Gae Aulenti.
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Enjoy your first Italian dinner at a classic trattoria. Cotoletta alla milanese is a must-try!
Day 3
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Private walking tour: highlights include the Duomo, Galleria Vittorio Emanuele II, and La Scala Theater.
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Afternoon at leisure: visit Palazzo Reale, Museo del Novecento, or the Brera district.
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Evening dinner and overnight in Milan.
Day 4
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Depart Milan; stop in Modena for a private tour of the Cathedral, Piazza Grande, and Torre della Ghirlandina.
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Savor Modena’s balsamic vinegar during lunch.
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Continue to Perugia; check into your hotel in the historic center.
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Evening at leisure to explore Perugia and enjoy Umbrian cuisine.
Day 5
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Visit Perugina House of Chocolate for a guided tour and tastings.
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Afternoon private walking tour: Duomo, Fontana Maggiore, Rocca Paolina.
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Optional: Discover Perugia Underground and ancient Etruscan sites.
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Dinner featuring local specialties.
Day 6
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Guided tour of Assisi: Basilica di San Francesco, Santa Chiara, Rocca Maggiore, and Santa Maria degli Angeli.
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Afternoon at leisure for shopping or further exploration.
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Return to Perugia for dinner and rest.
Day 7
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Excursion to the Umbrian countryside; tour and tasting at a local winery.
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Leisure time to soak in panoramic views.
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Return to Perugia for a final dinner.
Day 8
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Morning visit to Orvieto: guided tour of the Cathedral, Pozzo della Cava, and Well of St. Patrick.
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Check-in at historical City Center Hotel
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Evening exploration of Rome’s city center.
Day 9
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Skip-the-line tour: Colosseum, Roman Forum, and Palatine Hill.
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Afternoon at leisure: museums, Trevi Fountain, Spanish Steps, Piazza Navona.
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Evening in Trastevere for dinner and gelato.
Day 10
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Tour of Vatican Museums, Raphael Rooms, Sistine Chapel, and St. Peter’s Basilica.
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Optional climb to the dome and visit to the crypts.
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Afternoon free for Castel Sant’Angelo, souvenir shopping, or final sightseeing.
Day 11
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Private transfer to the airport for your journey home, filled with unforgettable memories.
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Day 1
DEPART USA
Get ready for Italy! Go to the airport, check in for your overnight flight, and get comfortable. Think about the amazing art, food, and unforgettable experiences ahead. Have a great trip, your Italian adventure starts now!
Day 2
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!
Day 3
MILAN
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.
Day 4
MODENA AND 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.
Day 5
PERUGIA
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.
Day 6
ASSISI
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.
Day 7
UMBRIA COUNTRYSIDE
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.
Day 8
ORVIETO AND 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.
Day 9
ROME
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.
Day 10
VATICAN
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 11
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.
This Package Includes:
This is the Package Includes
• Roundtrip flights in economy class with in-flight meals, drinks, and entertainment. (*)
• 2 Nights accommodation in a premium 4 star HOTEL in Milan. (**)
• 4 Nights accommodation in a premium 4 star HOTEL in Perugia. (**)
• 3 Nights accommodation in a premium 4 star HOTEL in Rome. (**)
• 9 Daily Buffet Breakfast at your Hotel.
• 7 Private Tours and tasting as per Itinerary.
• Ground Transfer from/to Airport.
• Transportation as per itinerary with Private Driver .
• Vat Taxes and Service Charges (in Italy) included.
This Package Does Not Include:
This is the Package Doesn’t Include
• U.S. & Foreign Departure Taxes and Surcharges Fee(s) assessed by the Airlines.
• Hospitality city tax which varies by city and hotel category. Where applicable, it must be paid locally at the hotel.
• All which is not listed under “PACKAGE INCLUDES”
For additional information about Milan, Modena, Perugia, Assisi, Rome Other hotels, and destinations are available. Please don’t hesitate to ask our Trips 2 Italy travel assistants.
(*) Based on departure from Nyc Airport(s). Alternative U.S. based airport departure available upon request. Additional and different fares and fees may apply.
(**) Rate based on two adult persons sharing a double or twin bedded room with private bathroom. Single rooms are available at an additional supplement. Children’s, triple room rates and alternative accommodation arrangements are available upon request. (Additional and different charges may apply).
(***) Rate based on a Small group of minimum of 8 passenger traveling together (At least land portion). Party of less or more then 8 traveler(s) rate may change.
More Italy Cultural Travel Packages Choices
Terms and Conditions:
This is the Package Includes
• Roundtrip flights in economy class with in-flight meals, drinks, and entertainment. (*)
• 2 Nights accommodation in a premium 4 star HOTEL in Milan. (**)
• 4 Nights accommodation in a premium 4 star HOTEL in Perugia. (**)
• 3 Nights accommodation in a premium 4 star HOTEL in Rome. (**)
• 9 Daily Buffet Breakfast at your Hotel.
• 7 Private Tours and tasting as per Itinerary.
• Ground Transfer from/to Airport.
• Transportation as per itinerary with Private Driver .
• Vat Taxes and Service Charges (in Italy) included.
This is the Package Doesn’t Include
• U.S. & Foreign Departure Taxes and Surcharges Fee(s) assessed by the Airlines.
• Hospitality city tax which varies by city and hotel category. Where applicable, it must be paid locally at the hotel.
• All which is not listed under “PACKAGE INCLUDES”
For additional information about Milan, Modena, Perugia, Assisi, Rome Other hotels, and destinations are available. Please don’t hesitate to ask our Trips 2 Italy travel assistants.
(*) Based on departure from Nyc Airport(s). Alternative U.S. based airport departure available upon request. Additional and different fares and fees may apply.
(**) Rate based on two adult persons sharing a double or twin bedded room with private bathroom. Single rooms are available at an additional supplement. Children’s, triple room rates and alternative accommodation arrangements are available upon request. (Additional and different charges may apply).
(***) Rate based on a Small group of minimum of 8 passenger traveling together (At least land portion). Party of less or more then 8 traveler(s) rate may change.
More Italy Cultural Travel Packages Choices