14 Day Italy Itinerary: See the Best of Italy in 14 Days

by | Jun 19, 2022 | Europe live work and play, Live Work Play Travel | 15 comments

I was told if you throw a coin from your right hand over your left shoulder into the Trevi Fountain in Rome, it will ensure your return to Rome one day. Well it worked! I have returned to Rome on a number of occasions and each visit I throw another coin in. This 2 week Italy Itinerary will take you to Rome to throw a coin in the fountain as well as many other ‘must see’ places in Italy. We start in the north in Milan and head south ending on the Amalfi Coast. 2 weeks in Italy is nowhere near enough to appreciate everything Italy has to offer, but it is a start. Without further ado, here is how to spend 2 weeks in Italy – let’s get travelling Italy.

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How to Get to Italy


Italy is found in Central Europe. It has borders with France, Switzerland, Austria and Yugoslavia. To get to Italy you can easily drive from one of these countries. You could also fly from anywhere and land at a major Italian airport such as in Rome or Milan or you could sail from another European country or country on the Mediterranean.


How to Get Around Italy


Italy is very easy to get around. It has an extensive network of rail and bus routes. It also has a number of airports. Most who visit Italy will travel by bus, train or car. There are bus passes and train passes making it easy to get around Italy. If you hire a car you will have the flexibility to go where you want, when you want.


Best Time to Visit Italy


Italy can be visited any time throughout the year but most people are influenced by the weather and events they want to attend. During the summer months it can get very hot in Italy, plus this is the time many tourists visit so accommodation and entrance fees to many things are more expensive. If you don’t mind the cold weather, even snow, you could visit during the winter months. Many choose to visit Italy in the Spring or Autumn when the weather is nice and costs are so expensive. Crowds are also less. But really, anytime is a good time to visit Italy.


Where to Stay in Italy


Italy has lots of accommodation available. It ranges from hostels to hotels you may splurge on once in a while. I have included suggested accommodation options after each place visited.


Italy Itinerary at a Glance


Italy 14 Day Itinerary Map.


1 – Arrive Milan
2 – Milan
3 – Milan to Venice via Verona
4 – Venice
5 – travel Venice to Florence – heart of Tuscany
6 – Florence
7 – Cinque Terre
8 – Cinque Terre to Rome via Pisa
9 – Rome
10 – Rome
11 – travel Naples
12 – Naples
13 – travel to Amalfi Coast via Pompeii
14 – Amalfi Coast – leave for home


14 Day Italy Itinerary


This 14 day tour of Italy starts from the city of Milan and ends on the Amalfi Coast. Why? Well, why not! This itinerary starts in Northern Italy and works its way down to Southern Italy. You will be travelling one way and not backtracking.


Days 1-2 Milan


Arrive in Milan and head to your hotel to drop off your luggage before you begin exploring the fashion and design capital of Italy. Milan is the largest industrial city in Italy with many different industrial sectors. It is an attractive city for designers, artists, photographers and models. You will also be delighted by its many luxury boutiques in the historic centre. But not only that, you will be pleasantly surprised by the diversity of the neighbourhoods and the multitude of museums and sites to visit. These include the grandiose cathedral, the Sforza Castle and the Teatro alla Scala. Make time to appreciate the splendour and religious significance of the Last Supper mural. Painted by Leonard da Vinci, it is on display at the Santa Maria Delle Grazie. It depicts Christ and the apostles at the last supper before Christ’s crucifixion. Don’t forget to shop till you drop, you could pick up a bargain in one of the markets.

Once you have visited Milan, and if you have enough time, you could make a detour to visit the nearby Lake Como. Lake Como is just one of the lakes in an area known as the Italian Lake District. An area very dear to Stendhal and the musician Franz Liszt, you can take a boat trip on the lake or stroll among the olive groves.

Where to stay in Milan (book for 2 nights)

Milan has a variety of accommoodation. I recommend Ostello Bello if looking for a hostel as it is only .6km from the centre of the city. If you are after a hotel room for your stay in Milan, check out pricing and availability of Art Hotel Navigilli or if wanting a splurge, check out the Hilton Milano. For more hotel options check out Booking.com.

For tickets to sites and to jump the queues check out the following:

Days 3-4 Venice (via Verona)


Leaving Milan, head east towards Venice stopping in Verona. Verona is a medieval old town and is famous for the tiny ‘Romeo and Juliet’ balcony made famous in William Shakespeare’s play of the same name. You can find the balcony at 23 Cappello Street. Verona is more than just this balcony, it is on the Adige River and is home to ancient Roman landmarks. Some of them are well preserved such as the Ampitheatre.

Continue on to Venice, known as the ‘City of Canals’. Venice is probably one of the most picturesque cities in Italy. With its canals, striking architecture and beautiful bridges, Venice is one of the most popular destinations in Italy. San Marco Square and the Rialto Bridge are just some of the many wonders to explore in the city. The best known means of transport on the waterways of Venice is the gondola. It is also advisable to get on a ferry and visit the small island of Murano with its historic glass factories and the colorful Burano. Every February, Venice organizes a fantastic carnival in which people dress up in magnificent costumes. Even though on the exxy side, be that tourist who takes a ride in one of the iconic gondolas along the Grand Canal, one of the most famous waterways in the world. Take a ride during the day and then at night and get different perspectives of the city.

Where to stay in Venice (book for 2 nights)

Many stay in the central district of Venice where you will be able to commute on foot around Venice very easily. However, if you are driving, there are no cars in Venice and you will need to leave your vehicle on the outskirts. Maybe you would prefer to stay with your car and commute into the city, which isn’t very far. Just 400m from the centre of Venice is Ostello S. Fosca – CPU Venice Hostel while the Ai Mori is not too far away. For more accommodation options in Venice check out Booking.com.

For tickets to sites and to jump the queues of sites in Venice check out the following:

Days 5-6 Florence and Tuscany

Leave Venice and continue south to encounter hills that frame small towns, estates and vineyards, olive groves that overlook and complete a panorama that is already unique and fascinating, loved by both Italians and foreigners. You’re in Tuscany and soon to arrive in Florence, a real open-air museum and the heart of Tuscany. Florence, the cradle of the Renaissance, is the city of artists such as Leonardo da Vinci, Michelangelo and Botticelli. 


Statue of David in Florence. A Must See On Any Trip to Italy.

Statue of David – a must see when in Italy


Florence is home to many monuments and museums. Starting with the Duomo of Florence, perhaps the most famous cathedral in the world and the jewel of the city. If the Duomo is the most important religious building in the city, Palazzo Vecchio is the most important administrative building. Pass through the Ponte Vecchio, an extremely famous and ancient bridge; it is the only bridge in Florence that survived the Second World War. Also not to be missed is a visit to the Uffizi Gallery, a renowned art museum considered one of the most important Italian museums in the world. Inside the museum there is an immense collection of Renaissance art by artists such as Botticelli, Da Vinci, Titian and Raphael. If wanting to see Michelangelo’s David, he is currently in the Accademia Gallery of Florence (Galleria dell’Accademia di Firenze) in Florence and was once of my goals not to miss when I was in Florence.

Where to stay in Florence (book for 2 nights)

Florence has a variety of accommodation available for your 2 nights stay. If seeking a bed in a hostel check out Ostello Bello Firenze or for a hotel room check out Hotel Kraft in the centre of Florence. For more accommodation options visit Booking.com.

For tickets to sites and to jump the queues check out the following:

Day 7 – Cinque Terre


Up early for the 2.5 hour train trip to Cinque Terre for the day. Trains leave from Florence’s train station about twice an hour and reach La Spezia train station about 2 hours after that. At La Spezia switch to the 5 Terre Express train, a fast regional train that runs every 15 minutes and connects all five villages of Cinque Terre.

Cinque Terre is made up of five beautiful hillside or some say seaside villages: Monterosso, Vernazza, Corniglia, Manarola and Riomaggioreon. They make up a 2 mile / 3 km stretch of Italy’s northwest coast which is actually a national park. Referred to as the Italian Riviera due to its dramatic setting of Italian houses on the coast. As long as you don’t want to spend time lazy on the beaches you can visit Cinque Terre in one day. You can either walk between the villages or catch the train as no cars are allowed. The five villages are connected by hiking trails if you want to explore this way, but it can take around 6 hours, depending on how fast you walk. Spend the night at Cinque Terre and enjoy a meal in a restaurant with view over the ocean.

For tickets to sites and to jump the queues check out the following:


Days 8 – Cinque Terre to Rome via Pisa


Sharyn Holding Up Leaning Tower of Pisa Italy

Don’t forget to get a photo holding up the Leaning Tower of Pisa!


Head to Pisa for the morning. Most go to Pisa to see the Leaning Tower so you can see this plus a few other things in 2-3 hours. After the Leaning Tower of Pisa was constructed it immediately started to sink into the marshy ground on one side. Most of the time it is open to be climbed. And it is well worth the climb to to the top where you can see across all of Pisa. 

Now, we head to Rome. If driving, take the Chianti Road which unites Florence and Siena. This ‘wine trail’ winds through, among others, Castellina in Chianti, Radda in Chianti, Gaiole in Chianti, Greve in Chianti, up to Siena among wine cellars, pecorino cheese producers and places where time seems to have stopped. A journey along the Chianti Road means not only enjoying the beauty of the landscape, it is a unique food and wine experience. If you are a lover of good wine and good living, this is one of the obligatory trips to do in Italy. Continuing further you arrive in Siena and from this magnificent medieval city you can reach Val d’Orcia, between the wine towns of Montalcino and Montepulciano, and go as far as Bagno Vignoni and its thermal baths.

If travelling by train or bus, don’t worry, you will pass through this fabulous countryside on your way to Rome.

Where to Stay in Rome (book for 3 nights)

Rome has plenty of accommodation for your 3 nights. If seeking a bed in a hostel check out the RomeHello Hostel which is only 1km from the centre of Rome. For a hotel room, you are spoilt for choice but check out pricing and availability for the Termini Terrace. For more options visit Booking.com


Days 9-10 Rome

After leaving Tuscany, here we are in Rome, the “Eternal City”. It is impossible to overlook the wonders of Rome. The capital is certainly one of the places to visit in Italy. Rome will offer you an unforgettable walk to the Colosseum, among the ruins of the Roman Forum, or among the Renaissance monuments of Piazza del Campidoglio. Rome is in fact full of ancient monuments, splendid squares and museums. To visit there are certainly the Colosseum, the Roman Forum, the Pantheon, the Spanish Steps, Piazza Navona and the equally famous Piazza di Spagna. And don’t forget to throw a coin into the Trevi Fountain.

Venture into the Vatican City, the city within a city and visit the Vatican and its wonders. Stand in awe in the Sistine Chapel and St. Peter’s Basilica. Near the Vatican City you also find Castel Sant’Angelo. Finally you can proceed towards Trastevere, a district south of the Tiber river, very characteristic and traditional. I highly recommend that you stop and eat in one of the Roman trattorias in this area, but you don’t have to.

Love Rome: extend your stay to 3 days – here’s what to see and do

For tickets to sites and to jump the queues check out the following:


Days 11-12 Naples


Naples is famous for its rich history, architecture, way of life and its gastronomy, such as the famous pizza. The city tour can start in Via Toledo, the longest shopping street in Naples. Here you can find numerous elegant boutiques. The Royal Palace, Castel Nuovo, the cathedral, the catacombs, Castel Dell’Ovo, the Maschio Angioino, the underground excavations, Piazza del Plebiscito, Posillipo, Vomero and Mergellina: these are just some of the things to see in Naples, without forgetting the suggestive “Spaccanapoli”, the central street of the city and a tour of the Naples metro stations, among the most beautiful in Europe. One of the must-see works of art, among the most evocative in the world, is the Veiled Christ, a life-size sculpted marble statue that represents the dead Jesus Christ covered by a transparent funeral sheet made from the same block as the statue. It is a 5-minute walk from Piazza del Gesù Nuovo. 

For dinner, enjoy one of the most famous foodstuffs to come from Naples – the pizza! You will find many pizza parlours and restaurants all over the city. Choose one and enjoy. Or why not participate in a pizza making cooking class.

Where to stay in Naples (book for 2 nights)

There are a number of hostels in Naples offering cheap and comfortable accommodation. Check out the Naples Experience or if after a hotel room check out rates and availability of Bellini House B&B.


Day 13 – Naples to Amalfi Coast via Pompeii


Pompeii Italy Is Full of Artifacts After Mount Vesuvius Blew Up And Covered The City In Ash and Lava.

Discover the artifacts at Pompeii


Leave Naples for the short trip to Pompeii. Pompeii is an archaeological site that shouldn’t be missed. It was a thriving city in 79AD and then there was a catastrophic eruption of Mount Vesuvius and the city was buried under metres of ash and pumice. Walk around the preserved area to see the excavated ruins of streets and houses. Nowadays Mount Vesuvius is mostly considered safe to climb and you can trek to the crater of the mountain if you are feeling energetic and have time. You will be treated to breathtaking views over the area if you do the climb.

After Pompeii, head to the Amalfi Coast, a gorgeous stretch of coastal land. Spend the night at the Amalfi Coast. There is plenty of accommodation available here on the Amalfi Coast for your last night in Italy.

Where to stay on the Amalfi Coast (1 night)

The Amalfi Coast has a variety of accommodation available, I stayed at Amalfi Centro. You can check out pricing and availability here. 


Day 14 – Full day Amalfi Coast and leave Italy


It is your last day in Italy, and depending on what time you are leaving Italy maybe rent a car, if you don’t have one and drive the Coast Road through charming cities with stunning views of the Amalfi Coast. Some places to visit while here are Valle delle Ferriere, the Amalfi Cathedral and Villa Cimbrone Gardens. Or perhaps go on a boat trip and sail around this magnificent area. 

From the Amalfi Coast there are a number of options to leave Italy. Return to Rome to fly out or catch a boat from Naples, Palermo or Brindisi to other parts of Europe.


Are you Ready for Your 2 Weeks Holiday in Italy?


This itinerary takes you from the top to the bottom of Italy. It takes in the ‘must see’ places in Italy, plus loads more. If you have been to Italy or planning your trip to Italy, I would love to hear in the comments following.



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Trevi Fountain On 14 Day Italy Itinerary PIN

Thanks for sharing!

Useful Travel Resources for Your Next Adventure!


Accommodation: Where Will You Sleep Tonight? If you want a bed in a hostel dorm find a great deal with HostelWorld. I mostly stay in hotels now, Booking.com is my favourite site for booking hotels from budget to ‘I feel like splurging’. For something completely different I house and pet sitting through Trusted Housesitters – this has saved me thousands on accommodation, no joke!

Flights: I always head to Skyscanner first to find a cheap and flexible flight.

Car Rental: When I need to rent a car I turn to RentalCars.

Train Travel: I love riding the train rails and get the best value from raileurope. And Japan has a great one too – JapanRail Pass.

Bus Travel: Check out Busbud for bus tickets.

Pre-organised Tours: I’ve been on a few in my time with Contiki being my first and favourite. if you are 18-35 years of age you should check them out.

Jump-the-queue entrance tickets: I don’t enjoy standing in long queues which is why I book my entrance tickets and day trips in advance. My favourite website to book them in advance is GetYourGuide.

Travel Insurance. There are a number of reasons why travel insurance is important and I never travel without having bought a policy as you never know when something might happen. SafetyWing is great digital nomads and long-term travellers and World Normads has policies for general and adventure travel.


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Hi. Sharyn here. Savvy Australian female with a passion for travel and working abroad. I’m on a mission to provide you with my best tips, tricks and hacks to work abroad and travel the world. If I can do it, so can you!  Read more.


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  1. Linda Jane

    Two weeks in Italy would be a dream holiday and your itinerary looks amazing! Thanks so much for the travel inspiration!

  2. simplyjolayne

    My husband and I are just now in the process of planning an anniversary trip to Italy later this summer. I am excited to return to Italy!

  3. Travel Heal Love

    What a great guide, you definitely put all the hotspots for a great trip in Italy. I am Italian and I have been to all the places listed here and I can confirm you cannot miss any of them! Also, I like how many things you included in 14 days! Thanks for sharing!

    • Sharyn McCullum

      Glad you liked the guide – sometimes you only have 14 days holiday so I have tried to cram in as much as possible.

  4. Petra

    This sound so amazing! I have been long time planning a trip to Italy with my husband. Its also option for us to have wedding there. What would be best place for that in your opinion? You shared some great tips here, thank you!

    • Sharyn McCullum

      I think Italy has some special places to get married. You could consider by the ocean on say the Amalfi Coast or you could consider a winery in Tuscany. What are your thoughts?

  5. Josy A

    That is one jam-packed itinerary! It sounds like you have covered lots of the most famous spots – it might just be a bit too speedy for me. I’d like to go to fewer places, but spend a bit longer in each.

    p.s. driving along the Chianti Road between Florence and Siena sounds sooo fun! I’d want to stop and try the wines!!

  6. Amy

    I read this post thinking two weeks was a great amount of time to explore Italy, but after reading about all these spots I’m going to need a month!

  7. Venaugh

    Thanks for planning out such a great trip! I love that you planned out time to explore every area and not just Rome and even included places to stay. Makes planning so much easier!

    • Sharyn McCullum

      Italy is more than ‘just Rome’ which is why the itinerary only spends a few days there. Like any country, there is plenty to see and do in other parts so I have included some suggestions – glad you like them!

  8. Angie Kunze

    I haven’t been to Italy yet, in fact, it isn’t even on my radar yet! This is a great itinerary and I’ll be saving for later. I’d love to see the artifacts in Pompeii and medieval old town Verona sounds right up my alley.

  9. Lisa Manderino

    I did a similar trip but only 8 days. I had to leave out Milian and Cinque Terre….I have to go back and do more of northern Italy! Such a fun itinerary!

    • Sharyn McCullum

      You have to adjust what you see and do to the time you have available. At least you had 8 days in Italy!

  10. Ashlee Fechino

    The ultimate guide! This is exactly what I would love to have to plan our next 2 week trip to Italy. Thank you for sharing.

  11. Chelsea

    Now that the world is open again I have seen so many people exploring Italy!! This looks amazing and definitely on my bucket list.


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