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5-Day Italy Itinerary: Rome, Milan & the Riviera
5-Day Italy Itinerary: Rome, Milan & the Riviera
5-Day Italy Itinerary: Rome, Milan & the Riviera
5-Day Italy Itinerary: Rome, Milan & the Riviera
5-Day Italy Itinerary: Rome, Milan & the Riviera
5-Day Italy Itinerary: Rome, Milan & the Riviera
5-Day Italy Itinerary: Rome, Milan & the Riviera

5-Day Italy Itinerary: Rome, Milan & the Riviera

5 Days

2 Stops

Private transfer

From$2,000
per person
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  4. 5-Day Italy Itinerary: Rome, Milan & the Riviera
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Itinerary inspiration

Explore the best of Italy in just five days with this carefully designed itinerary that blends ancient history, vibrant cities, and coastal charm. Begin your journey in Rome, where timeless ruins, Renaissance piazzas, and the treasures of the Vatican offer a deep dive into the cultural heart of Italy. With a private guide, marvel at the Colosseum, stroll through the Roman Forum, and uncover hidden corners of the Eternal City. Next, travel north to Milan, Italy’s capital of fashion and design. Admire its sleek elegance, visit the iconic Duomo, and discover the city’s artistic heritage with the help of a curated city experience that balances leisure and exploration.More...

Cap off your adventure in the stunning Cinque Terre, where colorful cliffside villages cascade toward the sea. Wander scenic coastal paths, taste Ligurian specialties, and enjoy breathtaking views that define the Italian Riviera. With private transfers, seamless train connections, and thoughtfully planned experiences, this five-day Italy itinerary is perfect for first-time visitors or those short on time. Whether you're drawn to ancient wonders, modern culture, or scenic coastlines, this trip delivers Italy’s most iconic highlights in one unforgettable journey.Less

Rome

Day 1 - 2

Experience Rome, the bustling capital of Italy. This city, rich with exciting history and culture, offers an unparalled mix of ancient explorations and modern living. Immerse yourself in the past and explore the Colosseum, the Roman Forum, and the Vatican. Wander through other must-see destinations like The Spanish Steps, Trevi Fountain, and Pantheon. Experiencing the culinary scene is a delight, from traditional pasta to world-renowned Italian gelati. You can explore daily markets such as Campo de' Fiori for local ingredients and fresh food. A stay in Rome promises great experiences all year round, but it is advisable to take seasonality into account. While spring (April–May) and fall (September–October) offer pleasant weather and less crowds, summer (June–August) has a lively, spirited atmosphere — but can also be hot. No matter when you go, visiting Rome promises an unforgettable journey through the centuries. The unique combination of a rich historical past mixed into a thriving and vibrant modern community makes Italy's Eternal City one of the world's most intriguing and inspiring tourist destinations.

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Your accommodation

Hotel Trevi
Hotel Trevi
Hotel Trevi

Hotel Trevi

The Hotel Trevi is a luxury hotel in Rome, Italy. Being in the city center, the hotel is ideally located not far from the Spanish Steps and the Pincio Terrace, which offers breathtaking views of Piazza del Popolo and the city skyline. The hotel's rooms are modern and elegantly furnished and all equipped with amenities such as air conditioning, bathroom with toiletries, minibar, TV and free Wi-Fi. Other services offered to you include a fresh breakfast with homemade cakes and sweets every day.

Your activity

Vatican & Castel Sant’Angelo Tour

Vatican & Castel Sant’Angelo Tour

Take the tour of the Vatican Museums and Sistine Chapel with no queue at all! No stress to access the Vatican: your professional guide will take you inside and accompany you in a memorable visit to one of the most important art collections worldwide. Admire the numerous halls of the museum, including the spiral staircase, the beautiful Raphael’s rooms and their famous paintings, before entering the Sistine Chapel, Michelangelo’s masterpiece. On your way out from the Sistine Chapel, you will go inside St. Peter’s Basilica through an exclusive access skipping long lines. The tour wouldn’t be complete without a walk in St. Peter’s Square, the open space before the basilica, redesigned by G. L. Bernini, an architectural masterpiece of the Baroque age. Your day continues with a visit of Castel Sant’Angelo, originally built as the tomb of Roman Emperor Hadrian, was later converted into a military fortress, the Pope’s residence, a Renaissance-era prison, and then finally into a museum to preserve the history of Rome. Built in 135 AD, the castle now houses Hadrian’s tomb, Papal apartments, and several magnificent works of art including paintings, sculptures, pottery, frescoes, murals, and more. Choose this tour if you would like to enjoy a professional guided tour to the Vatican Museums, the Sistine Chapel and Castel Sant’Angelo with skip the line access thanks to a special agreement we have. Tour ends at Castel Sant’Angelo area. 

Milan

Day 3 - 5

The vibrant metropolis of Milan is the capital of Italy’s Lombardy region in northern Italy. Always at the forefront of international fashion, Milan’s sleek, glamorous facade has earned it a reputation for superficiality and excessive consumerism. However, beneath the surface lies a treasure trove of historical and architectural wonders—from its magnificent Gothic churches, Baroque mansions, and Art Nouveau palazzos to the striking modern skyscrapers of the Porta Nuova financial district. Must-see landmarks include the spectacular Milan Cathedral (Duomo), the glass-vaulted Galleria Vittorio Emanuele II, and of course, La Scala—one of the world’s most renowned opera houses. Milan offers something for everyone: those in search of high-end designer shopping will be more than satisfied, as will visitors interested in fascinating historical sites and extraordinary architectural achievements.

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Your accommodation

Hotel nhow Milano
Hotel nhow Milano
Hotel nhow Milano

Hotel nhow Milano

Hotel nhow Milano is located right in the heart of Milan’s fashionable Via Tortona, with easy access to the Navigli, with its lively bars and restaurants, the MUDEC museum, and the Armani Silos. Accommodation consists of guest rooms and suites, each equipped with air conditioning, an en-suite bathroom, a minibar, a coffee machine, a digital safe, and a flat-screen TV with cable channels. A delicious breakfast is served daily for your enjoyment. Other amenities offered are internet access, a fitness centre, an on-site restaurant, a bar, and a terrace.

Your activity

Guided Walking Tour in Milan

Guided Walking Tour in Milan

Enjoy a private guided tour of Milan, led by your expert guide, and explore the city’s most iconic landmarks. Your experience begins with hotel pickup if your accommodation is located in the central area; otherwise, a convenient meeting point will be communicated. Start your adventure with a visit to the magnificent Duomo di Milano, where you will not only admire the stunning interior of this Gothic masterpiece but also have the chance to ascend to the terraces. With a ride in the elevator, you will reach the top for panoramic views of Milan, offering an unforgettable perspective of the city and the cathedral itself. The tour continues with external visits to the Sforza Castle, Colonne di San Lorenzo, and the famous Scala Opera House, among other important landmarks. Explore Milan’s rich history and culture as your guide shares fascinating insights along the way.

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Tips for your Italy itinerary 5 days

Late spring (April–June) and early fall (September–October) are the best seasons to explore Rome, Milan, and the Cinque Terre. The weather is warm but not too hot, and the coastal trails of the Cinque Terre are especially pleasant in these months.

➔ Best time to travel Italy

Tailor-made Italy trips start at around $2,000 per person. Rome and Milan offer a wide range of accommodations, while the Cinque Terre can be more expensive due to limited availability in the coastal villages.

➔ Travel cost Italy

In Rome, the Colosseum and Vatican are must-sees, while Milan offers the Duomo and world-class shopping. The Cinque Terre adds colorful seaside villages and hiking paths along the Italian Riviera, making the journey diverse and memorable.

➔ Things to see Italy

A guided city tour in Rome, visiting museums in Milan, and hiking or boat rides in the Cinque Terre are ideal choices. These activities balance cultural depth with time outdoors on the coast.

➔ Activities Italy

Book tickets early for major sites like the Vatican Museums and Milan’s Last Supper. Trains are the fastest way to travel between Rome, Milan, and the Cinque Terre, while traveling light makes navigating the coastal villages easier.

➔ Insider tips Italy

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Blick auf den Big Ben in London
Portugal, England & Italy Itinerary: 2 Weeks of Culture and Charm
Portugal, England & Italy Itinerary: 2 Weeks of Culture and Charm
Portugal, England & Italy Itinerary: 2 Weeks of Culture and Charm
Portugal, England & Italy Itinerary: 2 Weeks of Culture and Charm

Portugal, England & Italy Itinerary: 2 Weeks of Culture and Charm

15 days

5 stops

From $5,500 p.p.

Ein verziertes Gebäude mit farbenfrohen Mosaiken, geschwungenen Balkonen und einzigartigen Fensterformen, das neben traditionelleren Strukturen steht. Grüne Zweige recken sich über die Stadt, und der Himmel ist hell und teilweise bewölkt.
Eine britische königliche Wache in roter Uniform und Bärenfellmütze steht stramm vor einem Wachhäuschen in der Nähe eines Fensters und einer schwarzen Lampe im Buckingham Palace.
Europe Multi-City Itinerary: From Lisbon to London
Europe Multi-City Itinerary: From Lisbon to London
Europe Multi-City Itinerary: From Lisbon to London
Europe Multi-City Itinerary: From Lisbon to London

Europe Multi-City Itinerary: From Lisbon to London

15 days

6 stops

From $5,700 p.p.

Alley im Stadtteil Albaicin in der Altstadt von Granada Andalusien
Seville, Rome, Athens & London: 21-Day Itinerary
Seville, Rome, Athens & London: 21-Day Itinerary
Seville, Rome, Athens & London: 21-Day Itinerary
Seville, Rome, Athens & London: 21-Day Itinerary
Seville, Rome, Athens & London: 21-Day Itinerary

Seville, Rome, Athens & London: 21-Day Itinerary

21 days

6 stops

From $7,100 p.p.

Die Bronzestatue eines Mannes in dramatischer Pose steht inmitten antiker Steinsäulen und Ruinen in Pompeji, Italien, mit einem klaren blauen Himmel und dem Vesuv im Hintergrund.
Madrid, Naples, Crete & London: 21-Day Itinerary
Madrid, Naples, Crete & London: 21-Day Itinerary
Madrid, Naples, Crete & London: 21-Day Itinerary
Madrid, Naples, Crete & London: 21-Day Itinerary
Madrid, Naples, Crete & London: 21-Day Itinerary

Madrid, Naples, Crete & London: 21-Day Itinerary

21 days

6 stops

From $7,600 p.p.

Tourlane trip reviews

Excellent

4.5 of 5

4,542Reviews

We would like to thank Alexandra Egertz...

We would like to thank Alexandra Egertz...

R

rosi eckstein

Friendly and competent advice that fulfilled all our wishes. We are looking forward to our upcoming trip to Italy and will get in touch again afterwards to let you know if everything went well.

08/27/2025
As always 😀👍🏻 very satisfied …

As always 😀👍🏻 very satisfied …

C

Carsten

Italy trip …

Italy trip …

M
Manuela Schumacher

Manuela Schumacher

Simply perfect

Simply perfect

E

Eyvette Thompson

Italy trip

Italy trip

C

Caroline Bohrmann

Start planning your next trip
  • We are once again very satisfied with Tourlane and the collaboration with Ms. Calabrese. She provided me with detailed information and prepared and organized the Italy trip excellently. Happy to book again 😊

    07/11/2025
  • It was a very nice trip and overall we are very satisfied. The Tourlane navigation could be a bit more precise. All the hotels were very good 👍 It was a wonderful time that we would happily repeat again and again.

    06/23/2025
  • We were interested in a round trip through Italy and shortly after our inquiry we already received an appointment for a consultation. The conversation with our Italy expert, Lara Schmidt, was simply great. She not only took all our wishes into account, but also rightly advised against one or two locations because of the weather/season. Shortly afterwards we received our offer (route, hotels, rental car), and what can we say — we got a perfectly arranged trip that really included and even exceeded all our wishes. That’s why we confirmed the trip with Lara directly in the next call and are super excited. @Lara: A BIG THANK YOU for the great exchange — you do this with so much heart and en...

    03/18/2025
  • Lara has organized my IT Trip for summer with my family. She had some many great ideas and provided so much information about the different regions. I´m really looking forward! Thank you Lara :-)

    02/11/2025