How to plan a perfect 2-week Italy itinerary – 14 unforgettable days in Italy

You’ve been planning a 2 week Italy itinerary for a while and still feel in a stalemate? Don’t worry, you’re not alone. The country is so packed with things to do, wonderful places to visit, and great food to try that anyone traveling to Italy for the first time is bound to feel overwhelmed. Fret not, we’re here to help.

This guide of ours, even though extensive and detailed, will touch the most popular cities you can’t miss in 2 weeks in Italy. Those places you really can’t afford to miss if it’s your first time in this beautiful country. We will squeeze as much as we can into a two-week Italy tour itinerary. It’s not strictly a Rome Florence Venice itinerary, it includes also other places, but it’s pretty classic.

If, on the other hand, you prefer to enjoy the country without the hassle of organizing and planning everything on your own, your best bet is to book a great escorted tour to Italy and relax while the tour leader does everything for you.

A Perfect 2-Week Italy Itinerary

  1. Milan, explore northern Italy
  2. Places to visit in Venice
  3. Hiking Cinque Terre
  4. Things to do in Florence
  5. Things to see in Rome
  6. What to do in Naples
  7. Hidden gems and alternative itineraries
  8. Tips for planning a trip to Italy your own
Two-week Italy itinerary
Rome’s Trevi Fountain, a must in your Italy trip itinerary

Planning the best 2 weeks in Italy

Granted, with so much to see, planning your best 2 week Italy itinerary is not easy. Our extensive guide will provide you with the essentials to organize a perfect vacation on your own. If you are visiting for the first time, 2 weeks in Italy are enough to see the main attractions in the main cities.

Planning 14 days in Italy, you will have the time to explore the classics such as Rome, Florence, and Venice. If you want to enjoy a place longer, visit more attractions or take some day trips, you can easily spend 3 weeks in Italy. If you have less time, you can avoid some attractions and spend 10 days in Italy. For sure, we give you the essential tips on how to plan a trip to Italy on your own.

If it’s not your first time or you have more than two weeks in Italy, check out our other guides on specific areas like Sardinia, Sicily in the cities of Catania and Agrigento, and Trentino Alto Adige, both its cities and the Dolomites mountain range.

We will see when is the best time to visit Italy depending on what type of holiday you want, we will suggest the best car rentals in case you want to embark on an Italy road trip, we will tell you what to pack and obviously what to visit to make your holiday smooth and unforgettable.

This guide will empower you to plan a trip to Italy on your own. For each city, we will provide you with the best day tours if you wish to optimize the time of your 2 weeks Italy itinerary and have more in-depth information. At the end of this guide, you will also find a selection of the best tours to Italy in case you want a hassle-free holiday where expert organizers take care of the details and the logistics for you.

Where to go: your itinerary for two weeks in Italy

1. Landing in Milan and exploring northern Italy, first step of your Italy trip itinerary – 2 Days

Milan is Italy’s “Wall Street”, a bustling financial hub that attracts businessmen for work or business-oriented travelers. However, with a long history and a good deal of historical landmarks and artistic attractions, Milan has been imposing itself also as an exciting tourist destination for travelers from all over the world. On your 2-week Italy itinerary, we suggest spending 2 days in Milan.

Some of the most important places to visit in Milan are:

  • The Duomo. The most popular among Milan’s landmarks, the city’s cathedral is a must. Its Gothic facade never fails to bedazzle visitors and passers-by, the inside is a fascinating journey into Milan’s history and culture, and its rooftop gives you a great view of the city and its architecture. Click here for Walks of Italy’s Best of Milan Tour that includes a visit to The Last Supper and the Duomo’s rooftop.
  • Sforza Castle. Residence of one of Milan’s most prominent families, the Sforza Castle today hosts several exhibitions, both temporary and permanent, as well as being a cultural centre.
  • Galleria Vittorio Emanuele II. Known as Milan’s parlour, this long covered gallery is lined with cafes and shops of the most exclusive brands. It’s close to the Duomo’s square, so you can’t miss it!
  • Da Vinci’s The Last Supper. Don’t miss the famous mural painting by Leonardo Da Vinci in UNESCO-listed Santa Maria delle Grazie church, beautiful Renaissance building by architect Donato Bramante.
  • La Scala Opera House. Milan’s opera house, this is a beautiful Neoclassic building worth a visit even if you are not going to see the performances. You can visit both La Scala and the museum but call first because if there are rehearsals you can’t visit the theatre hall.
  • Navigli. Milan’s canals are a great place for a walk both day and night. This is one of the favourite hangouts for aperitivo, dinner or a night out.

READ MORE: Check out our extensive guide to Milan to find out what to do if you have more time.

The next stop in your two-week trip to Italy is La Serenissima, so book your Milan to Venice train and get to one of the world’s most romantic cities. Click here to check timetables and prices with Omio.

2. Venice, the most Serene, the romantic stop in your 2 week Italy itinerary – 2 to 3 Days

Two-week Italy itinerary

One of the most popular destinations in Italy, Venice is as gorgeous as it gets. Unprecedented views, a unique urban landscape, and a long history are the perfect combination for an unforgettable trip. And if you go for the Carnival, the colorful and fascinating masks will add to the charm of the city.

How many days in Venice? We suggest 2 to 3 but it really depends on how much time you have, how much you want to enjoy and explore the city and, last but not least, by your budget.

Some of the things to do in Venice in your two weeks in Italy are:

  • Piazza San Marco. One of the key landmarks in Venice that make the city famous is its central Piazza San Marco, the very first place tourists visit. Surrounded by San Marco Basilica and the Doge’s Palace, this piazza is really gorgeous.
  • St. Mark’s Basilica. One of the most symbolic buildings in Venice, San Marco Basilica is a gorgeous piece of Oriental-style architecture dating back to the 11th century. Click here to book the exclusive tour of St. Mark’s Basilica after closing time.
  • Doge Palace. Standing exactly where it stood throughout the centuries, the majestic Palazzo Ducale is an important piece of the city’s republican past. Get a VIP entrance to the Doge Palace with Walk of Italy’s Secret Passages tour.
  • Jewish Ghetto. Europe’s oldest Jewish ghetto, Venice one was created in 1516 and is now a lovely neighbourhood to stroll around the city’s traditional architecture and eat delicious local treats.
  • Canals and Bridges. The beauty of Venice is in its architecture and this is directly related to its unusual layout. Instead of streets, in Venice you have canals and bridges, instead of buses, you will take the boat or if you don’t mind forking out good cash, a gondola. One of the most scenic things to do in Venice is certainly strolling around its bridges, Rialto and the Bridge of Sighs being the most famous. Click here to book Venice Boat Tour to visit the city and its bridges from the water and cruise the Grand Canal.
  • Gallerie dell’Accademia. This art gallery hosts the larger collection of Venetian paintings from the Byzantine and Gothic 14th century to the Renaissance.
  • Basilica dei Frari. Often neglected by the hasty traveller, this monumental Basilica is 102-meter long and boasts an impressive collection of artwork and 17 altars. It’s also the resting place of several notables, from Antonio Canova to Titian to several Doges.

Unless you are part of an organized tour, from Venice to the Cinque Terre, I definitely suggest you take the train as it’s cheap, comfortable and you can find different times of departure. Click here to book and see the prices on Omio

Before leaving northern Italy, take a day trip to Bologna and try some of its famous dishes!

3. Cinque Terre, hardly missing in all Italy itineraries – 2 Days

The quaint villages of the Italian Riviera never fail to bedazzle travelers from all over the world. If you want to spend three weeks in Italy, you can stay a bit longer in the Liguria region and explore also cities like Genoa and La Spezia.

Close to La Spezia, the capital of the province, are also beautiful places like Lerici and Tellaro, a sea resort cherished by writers and artists. Being on the coast, you will find great fish restaurants. Alongside the five scenic villages part of the Cinque Terre, La Spezia’s coastline boasts also other towns worth a stop, such as Portovenere, Le Grazie, and Levanto.

The five villages known as Cinque Terre are:

  • Monterosso al Mare. It’s the largest of the five towns and boasts also the largest beach of the coastline. Which is why it’s the most popular both day and night for evening parties and entertainment.
  • Manarola. Famous for its Nativity Scene set for Christmas, here you can also visit 14th-century San Lorenzo Church and the remains of the local stronghold.
  • Vernazza. This is a very scenic village, some consider the most beautiful. It has two beaches and several nice restaurants. You will spend your time wandering up and down its cobbled alleys.
  • Corniglia. The smallest and tallest village of the Cinque Terre, here you can visit its famous churches and sanctuaries as well as the remains of old Genoese strongholds.
  • Riomaggiore. The closest village to La Spezia city, from its train station you can start the famous Via dell’Amore hiking route and the dock from where to take the ferries for the local tours and cruises.

READ MORE: Check out our complete guide for more info on a Cinque Terre holiday.

From Cinque Terre to Florence, too, you can take the train. First, a regional to get to La Spezia and Genoa, then a high-speed train to Florence. Click here to check timetables and prices with Omio.

4. Florence, a must in your 2 weeks in Italy itinerary – 3 to 4 Days

Two-week Italy itinerary
Santa Maria Novella in Florence, a must in your two-week Italy itinerary

The birthplace of the Renaissance, Florence is included in most tours, so very likely your Italy travel itinerary will have it, too. Its history was heavily influenced by the rule of the Medici family, and today we can still see much of their legacy. Walking around Florence will fill you with beauty and culture. Enjoy its ancient art and architecture all around the city centre, walk along the Arno river and linger in the Ponte Vecchio bridge for some shopping and photo snapping.

We wrote a full guide to Florence, but here are some of the best things to do:

  • Duomo and Giotto’s Bell Tower. Santa Maria del Fiore Cathedral and the adjoining bell tower and gorgeous Baptistery are possibly the most photographed and visited landmarks in Florence and for sure one of the first places travellers head to as soon as they arrive. Click here for a full experience of Florence Duomo and Michelangelo’s David.
  • Uffizi Gallery. A huge art collection, at the Uffizi you will find the paintings and statues of some of the world’s most famous artists such as Leonardo Da Vinci, Botticelli, Caravaggio, Raphael, Cimabue and many others. Here the line is very long, so if you want to skip it and optimize your time inside the museum with a guide, check out Walks of Italy’s 3-hour Uffizi Tour comprehensive also of Palazzo Vecchio.
  • Santa Maria Novella Basilica. Located near Florence main train station, this beautiful Dominican basilica built with a mix of Gothic and Romanesque styles includes great artwork, paintings, chapels, a big garden and a cloister.
  • Pitti Palace. Residence of many of Florence ruling families, Palazzo Pitti today is a large complex of art galleries and royal apartments.
  • Boboli’s Gardens. Adjoining to the Pitti Palace, the elegant Giardini di Boboli were built in 1418 when Luca Pitti bought this vast land with the aim to build a mansion (Pitti Palace will be built 40 years later). One of Florence largest parks, Boboli Gardens are one of the most important examples of Italian gardens of the 16th century.
  • San Lorenzo Cathedral. The personal cathedral of the powerful Medici family, San Lorenzo huge church also hosts a museum showing the donations received in the centuries, most of them by the same Medicis. Close is also the burial place of the Medicis, known as Cappelle Medicee.

The whole region of Tuscany is amazing, so if you can stretch your holiday a couple more days, you might like to explore also other cities such as Siena and Pisa and the countryside with a day trip from Florence to the Chianti region and San Gimignano town. Click here to check availability and price.

Florence is not too far from Rome, with Trenitalia’s Frecciarossa or Frecciargento high-speed trains, it takes an hour and a half. Click here to book and see the prices on Omio.

5. Rome, unmissable even if you are on a 1-week Italy itinerary only – 4 to 6 Days

The capital of the ancient Roman empire boasting some 3000 years of history and rich civilization, the places to visit in Rome are endless. From the archaeological sites of the Roman Forum to the quaint neighborhood of Trastevere to the Vatican City, the more you manage to devote to Rome, the better you will experience the city. It goes without saying that Rome is a must-see, especially if it’s your first 2-week or even a 10-day trip to Italy.

Some of the things to do in Rome in your 2 weeks in Italy include:

  • Colosseum. Possibly the most famous and photographed landmark in Rome, the Coliseum was built in 70 AD to host fights among gladiators, public shows, animal hunts and even naval battles.
  • Roman Forum. Located in the valley between the Palatine and the Capitoline Hills, the Roman Forum was the heart of ancient Rome, where senators and public figures held their speeches, where they organized the city’s markets, court trials and pretty much everything concerning the public life. Click here for the VIP Colosseum and Roman Forum Tour.
  • Baths of Caracalla. Gorgeous ancient public baths, these included also a gym, a library, and different rooms for the baths experience and a wellness centre. They are often skipped for lack of time, but if you can make it, they are really beautiful.
  • Vatican City. The seat of the Christendom and papal residence for centuries, the Vatican City is packed with sites to visit such as the Sistine Chapel, the Vatican Museums and obviously St. Peter’s Basilica. If you want to fully enjoy the Vatican, the best thing you can do is to skip the lines, especially to the museums and the basilica. In this case, the convenience of booking a tour, apart from VIP access, is that your guide will take you directly to the places you shouldn’t miss. The Vatican is really big! Click here to see Take Walks’ Private Vatican Tour.
  • Trastevere. A gentrified former working-class neighbourhood, Trastevere is the place to go for a good night out. During the day, however, you can also visit the museum of Roman popular traditions that sometimes hosts also temporary exhibitions and Villa Farnesina where are Raphael’s frescoes.
  • Hadrian Mausoleum. Built by Emperor Hadrian as his own funerary mausoleum in the 2nd century, this is also known as Castel Sant’Angelo and is located along the Tiber River, giving beautiful views both day and night.
  • Pantheon. A very old building, it was a temple devoted to all gods built with an “oculus”, a hole in the big dome to symbolize the direct contact with the divine. Now it’s a Catholic church that hosts several tombs of members of the former royal family and of the famous painter Raphael.
  • Piazza Navona. Huge elliptical piazza in the city centre not far from the Pantheon, Piazza Navona has three fountains, the largest being Bernini’s Four Rivers Fountain standing in front of Borromini’s Sant’Agnese church.
  • Spanish Steps. Rome’s most famous staircase, the Spanish Steps lead to St. Trinità dei Monti church, ordered by French king Louis XII, while at the bottom you can view Bernini’s sculpture known as La Barcaccia.
  • Trevi Fountain. An absolute must, especially if you are visiting Rome for the first time, is Trevi Fountain, the gorgeous baroque fountain built between 1732 and 1762.

READ MORE: Check out our guide to what to do in 4 days in Rome.

Rome is divided into “Rioni”, neighborhoods, and each of them has its own landmarks and personality. From Prati to Trastevere to Testaccio and Ostiense, countless are the things to see in Rome, the restaurants where you can try the traditional food, the park where to run, jog or chill out for an afternoon, the museums, the palaces and more. To get around and see how to best enjoy Rome, check out my full guide of the city, or click here to see what are the best Rome tours if you wish to save some time but still visit the most important sites.

My eBook “Tasting Rome by Neighbourhood” suggests five daily Rome itineraries in as many districts, giving you the chance to explore the popular and lesser-known areas of the city stopping to eat in the best restaurants along the way. All the meals of the day are covered, from breakfast to dinner, with some suggestions also for aperitif and gelato.

Your next stop when planning a 2 week trip to Italy for the first time is Naples, the gorgeous capital city of the Campania region not too far from Rome. With Trenitalia high-speed trains you will reach it in a little more than an hour. Click here to book and see the prices on Omio.

READ MORE: Find Rome’s best restaurants with our comprehensive guide to the top places to eat in Rome.

6. Naples to give a delicious touch to your 2-week Italy vacations – 3 Days

Famous for having invented the pizza, alongside delicious cuisine, Naples has a lot to offer to the curious traveler who wants to dig deep into the local history and culture. Walk around its city center, enjoy the view of the Vesuvio volcano and the beach, explore its wonderful coastline and soak in its rich tradition.

Some of the best things to do in Naples in your 2 weeks in Italy include:

  • Royal Palace. Naples’ Palazzo Reale is located in Piazza del Plebiscito, an old square that in the Middle Ages was used for public tournaments and shows in the age of the Bourbons. It has been made pedestrian so now it’s the place where locals and tourists like to relax in a historical promenade.
  • Archaeological Museum. Launched in 1816, Naples’ Museo Archeologico displays a huge collection of ancient relics, among which you will find relics from Pompeii and others from the Greek-Roman age, Etrurian and Egyptian, and ancient coins from a private collection.
  • Duomo. Naples’ Santa Maria Assunta Cathedral shows the paintings of Luca Giordano and is the place where locals worship San Gennaro, patron of the city. Here you can also see the Treasure of San Gennaro, all the precious donations given by kings, presidents, and leaders of the world for centuries.
  • Spaccanapoli. This is the long road built by the Romans to better organize the city, and it runs from the Quartiere degli Spagnoli to Forcella district. Wandering this road you will also wander the city’s history and multifaceted society. Here, in fact, you are going to see old buildings, churches, shops, abusive street vendors and local restaurants that release the unique scent of Napoli’s cuisine.
  • Sansevero Chapel and the Veiled Christ. A hidden gem near Spaccanapoli is Cappella Sansevero where you can admire the incredible sculpture of the Veiled Christ (Cristo Velato), a masterpiece by Giuseppe Sanmartino where you will totally mistake the marble veil that covers the body of the Christ for a fine fabric!
  • Underground Naples. Beneath the surface, you can visit another Naples, the hidden spots, and nooks that citizens have used for different purposes such as shelter during the bombings, the hideout for the runaway criminals and water spring. Today, you can visit also museums, the relics found after ongoing archaeological diggings, and the Bourbons Gallery.
  • Pompeii and Ercolano. I know time is short, but once you are in Naples, we recommend you devote a day to visit the ruins of the ancient cities of Pompei and Ercolano, destroyed by the Vesuvio eruption in 70 AD. They are very easy to reach via a short ride on the Circumvesuviana train and you can spend there the whole day. Book a great Pompeii tour with an archaeologist.

Hidden gems + alternative Italy itineraries

If you like to discover also more offbeat destinations or you can afford a longer holiday, say 3 weeks in Italy, you can really add some interesting places to your Italy itinerary.

For example, you are back in Rome after this two-week Italy trip and you have one extra week? Catch a plane to Sardinia and enjoy a fantastic offbeat destination! To be able to stray off the bigger cities and explore their traditional soul, make sure you rent a car.

If you enjoyed the northern cities and want to explore more of them, a nice alternative is to explore the Trentino Alto Adige region or the beautiful city of Turin.

Alternatively, you can spend more days in some of the cities of our 2 weeks in Italy itinerary and take some day trips. From Florence, you can enjoy a great day trip to Pisa or Siena. From Rome, you can visit Viterbo, Bracciano, Cerveteri or several other towns. From Venice, you can head to Verona and come back in the evening. From Naples, alongside Pompeii, you can take a day trip to Sorrento and the Amalfi Coast.

The possibilities are endless, and soon we’ll be publishing a full northern Italy itinerary and an exciting offbeat Italy itinerary!

Essential tips for two weeks in Italy

1. Best time to travel to Italy

Boasting a mild climate and the advantages of four seasons, depending on what your ideal holiday is, any time is good to visit Italy.

Do you like skiing? Explore the beautiful Dolomites in Trentino Alto Adige. Do you prefer chilling out in the sun? Discover the gorgeous beaches in Sardinia in summer.

As far as the main cities go, any month is good to visit. In Rome, Florence and Venice there are so many things to see and do that really any season is good. If you are quite free to choose your holiday time, I would probably avoid July and August as they are very crowded and can be very hot. So not so pleasant to walk around the city center.

Spring and Fall are both great seasons to visit the big cities both to avoid the crowds and to have a more pleasant climate.

2. How to get around Italy

Italy has a great and very widespread railway system, so if you are traveling independently, you can totally rely on Trenitalia or Italo Treno. After each major city, I mentioned the transport you can book to get to your next stop but Italy railway is great to reach also smaller towns and even tiny villages. The perfect way of traveling around Italy for two weeks.

If you are visiting the cities and towns within the railway network, you are covered. But if you are planning on getting off the train route, relying solely on the buses might not be as straightforward. So for example, if you want to visit the Tuscany countryside or some parks outside Rome, I suggest you rent a car. Definitely, the best option when planning a 2-week Italy road trip.
Click here for more info and to book a car in Italy.

READ MORE: For more tips, check out our extensive guide to planning a trip to Italy.

3. What to pack for Italy

As Italy has four seasons, you can decide what to pack once you know when you are traveling. Spring is a very popular season thanks to its mild weather, but it can sometimes be tricky as temperatures change all of a sudden.

Avoid annoying online surcharges and nasty surprises by weighing your suitcase with one of the best digital luggage scales.

My advice would be to wear different layers so that you can cover them in the evening when it’s usually colder. If you are planning a 2-week trip to Italy in Spring, make sure you pack some pretty flexible clothes.

The beginning of the Fall in Italy is pretty nice as the summer heat is mostly gone and the winter cold has not arrived yet. Mostly, you can wear light clothes and carry a jacket, a light jumper, and a light scarf for the evening. Make sure you pack an umbrella.

If you are wondering what to pack for Italy for the winter, it’s pretty straightforward: warm clothes, a jacket, a coat, warm trousers, and sweaters. Quite straightforward is also packing for a summer Italy trip: shorts, t-shirts, sandals or summer runners, and obviously a bikini if you are going to the beach!

For some peace of mind, especially on public transport, you might want to wear a security belt. Or the anti-theft clothes of Clever Travel Companion. They have a pretty wide choice of models, colors, and clothes such as scarves, boxers, leggings, tops, t-shirts, women’s underpants, and more.
Click here to check models and prices.

READ MORE: Italy packing list: What to pack for Italy season by season


A perfect two-week Italy itinerary
about me: Angela Corrias
About the author

I'm Angela Corrias, an Italian journalist, photographer, and travel writer located in the heart of Italy's capital. Welcome to my website, your comprehensive source for your travels and expert guidance for crafting your dream travel experience.

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