2 Weeks in Italy: The Ultimate Backpacking Itinerary

Taking you to the country that introduced the world to the phrase, ‘dolce far niente’ or the art of doing nothing, mouth-watering cuisine such as pizza and pasta, is known for its art throughout the country and is home to the most celebrated couple of all time, Romeo and Juliet. 

Yes, I am talking about Italy, the country that gave us so much history and culture that a week or two here seems like not enough at all. 

Innumerable movies have been made romanticising the beauty of Italy, but having had a chance to explore this country in person, I can say that no amount of photographs or motion pictures can do justice to the country’s art and architecture, or its way of living or the people. 

I travelled across Italy for fifteen days, immersing myself in the grandeur of the country, Italian cuisine and trying to take in as much as possible of this country. Here, in this article, I have compiled the best places to visit in Italy for you, both within a week and two. Depending on the amount of time you have, you can follow my guide to the Italian tourist spots. 

However, if you want to travel slowly in Italy (which I highly recommend) or would rather not go to some of the tourist spots, you may skip them. This ultimate itinerary for Italy will help you plan your accommodations, where and how to go from one place to the other, transportation and commute in Italy and some important tips and tricks. 

One Week in Italy: Visit the Best Italian Cities

In my honest opinion, a week in Italy is too little, but to make the most of it, here is a guide that you can follow.

If you are curious about how to reach Italy and other details of Italy, read our guide here – Italy Travel Guide

Best Time to Travel in Italy

The best time to travel to Italy is during the spring (April to early June). The weather is mild and backpacking is easier during this season. Alternatively, you can also visit Italy during the fall (September to October), when the crowds are less. 

Winter is usually harsh, but if you are looking to try out winter adventure sports, the months of December to February are ideal. Also, you would be witnessing Christmas in Italy, which is an experience in itself. 

Summers in Italy are mild, compared to the tropics. But since the summers are also vacation days for the locals, most of the places would be crowded at this time. 

The Map I Followed

This is the map I followed for my first week in Italy, which will guide you from Milan to Rome and back. 

Commute in Italy

The best way to travel through Italy is to rent a car. This gives you the freedom to move at your own pace and wherever you want without much hassle. We used the service of Rentalcars by Booking.com. All you need is a credit or a debit card to book it and show the voucher while picking it up.

You can also rent bikes, but for a safe trip, it is essential to have motorbike insurance to travel around without any worries.

Day 1: Reach and Explore Milan

Milan is hands down one of the most beautiful cities in the world and the largest city in Italy. I started my backpacking journey in the northern city of Milan.

Things to remember:

• Arrange a SIM card for yourself from one of the local stores and soak in the streets to get comfortable with your new surroundings. You can get a local SIM card from the airport (although the price might be higher over there) or from the official mobile network stores. Alternatively, small tobacco shops known as Tabaccheria sell SIM cards too. 

Food

• Do not miss out on pizza, wine, and gelato. Italian cuisine has absolutely no competition. So, whether you are a vegetarian or a non-vegetarian, I recommend trying out Italian cuisine as much as you can while you are in Italy. 

Places to Visit

• Explore places like Piazza del Duomo, where history, art, and fashion radiate. The piazza is the city square and is dominated by the Milan Cathedral or Duomo. Being the centre of the city, the piazza is a significant landmark from an artistic and cultural perspective. 
• Visit the Piazza del Duomo both during the day and at night to admire the Last Supper here. It is one of the famous paintings by Leonardo da Vinci. 
• Make sure that you buy your tickets to see the Last Supper well in advance it is quite difficult to get a reservation. 
• If you are not planning to visit Venice, then you can get the canal experience right here in Milan. One of the most scenic routes for this is along the Naviglio Della Martesana.
• Other than these, you can also visit the Church of Santa Maria delle Grazie, Grand Galleria Vittorio Emanuele II, Milan Archaeology Museum, Piazza dei Mercanti, etc.

Transport

Right outside the Milan Malpensa Airport, there are several airport shuttles that take 50-60 minutes to reach the main station, Milan Centrale. From here, you can take the metro lines that connect to various other parts of Milan.

• Tickets can be bought either onboard or online.
• The bus departure point is outside the airport building.
• The buses operate from 06:00 hours to 00:30 hours, and transfers and taxis run 24/7.
• After reaching Milan, you can hop on a metro to reach your hotel.

Etiquettes

It is always good to know a few local words to converse with people. Italians know English but feel great when someone says a few Italian words. Some of them to remember are – “Grazie” and “Piacere” (a pleasure), and “Ciao” (bye)

SIM

My recommendation for any tourist in Italy would be to get a prepaid SIM card from TIM or Iliad. TIM also has a great 4G/5G network and includes free EU data roaming. 

To buy a SIM, you must have your passport. The SIM can be purchased in any supermarket, or even in the airport or other phone stores.  Further, Lycamobile is widely used in Italy and has top-up options.

Accommodation in Milan

Milan has a wide range of hotels and hostels. You can also couch surf here, where you stay with the locals and pay nothing for it. But below are a few of my recommendations:

Backpacker’s Hostel: Most backpackers’ hostels in Milan have free wifi, a clean space for you and more importantly, they will be safe. Whether you choose a dorm or a private room, it can be easy on your pockets, and you may end up finding people to spend your days with. 

Mid-range Hotel: Hotel Midtown Milano is a good option if you want to stay in a private room. This hotel has Air conditioning, free WiFi, Heating, a Dressing Room and a 4-hour front desk.

Luxury: If you are game for spending money and getting a luxury stay here in Italy, definitely stay in either of these – Meliá Milano, Hotel Pierre, or Château Monfort

Day 2 and Day 3 – Exploring Cinque Terre

Cinque Terre, also known as Italy’s Fabulous Five, is one of the most colourful towns I have been to. It is a destination with timeless appeal, and even two days are not enough to explore this place. However, if you have just one day to spend in Cinque Terre, then here is what you need to know.

Cinque Terre has five villages, namely:

• Manarola
• Riomaggiore
• Corniglia
• Vernazza
• Monterosso al Mare

You can hike here, watch the sunset and sunrise along the beach, sit in a café or watch the fishing boats along the coast. It will give you the real Italian vibe with timeless appeal, and one day will not be enough to appreciate the beauty of this place.

How to Reach Cinque Terre from Milan

Cinque Terre is just 3 hours away from Milan. Given the transportation system in Europe, I would say that the train is the best way to reach Cinque Terre. There are both direct and indirect trains to Cinque Terre from Milan.

• Direct: Intercity trains leave Milan throughout the day and will drop you off at Monterosso, the first village of Cinque Terre.
• Indirect: You would have to change the train once or twice, depending on the route you have chosen. Mostly, you would need to change at Genoa or Pavia. 

Before you start your journey, make sure to check your route and train timing on Google Maps for real-time updates. 

Regional trains are the most cost-effective option, but if you want to travel faster, then I recommend you to book a Milan-Monterosso train. It is costlier when compared with a regional train, but you can avail of a 60% discount if you book it in advance.

Transportation in Cinque Terre

In Cinque Terre, there are local trains or Cinque Terre express trains which run along the coast between the stations of La Spezia Centrale and Levanto. It stops at all the villages. To avail of this train, you can buy a Cinque Terre Train Card, or every trip would cost you a hefty amount. 

Accommodation in Cinque Terre

Accommodation in the Cinque Terre is expensive. So, it is better if you book well in advance.

Backpacker Hostel – Perla del Levante Hostel is a very good budget hostel in Cinque Terre and offers free Wifi with breakfast.

Mid-range Hotel – Albergo La Lampara is a good option if you want to stay in a private room. It has air-conditioned rooms and a traditional Ligurian restaurant. Besides, the best part is, it has a beachfront.

Luxury – If you want to enjoy luxury, then stay at the Park Hotel Argento. It has a swimming pool, bar, restaurant, and breakfast.

Day 4: Florence

Before you have second thoughts about going to Florence, let me tell you two fun facts about this city:

Fun Fact 1 – The entire city is a UNESCO World Heritage site.

Fun Fact 2 – It is said that the richest family in Florence in 1427 are still the richest

Florence is the capital of Tuscany in Italy. If you are looking for streets full of art and romance, this is the place you should visit. You can see world-class art, sculptures, and museums of Botticelli and Michelangelo in Florence. It is the home to works of art by Leonardo da Vinci, too and the birthplace of the Renaissance. A few of the attractions that you should not miss are the Duomo and Battistero, Ponte Vecchio, and Galleria Degli Uffizi.

Further, if you have enough time, try to spend 3 days in Florence to learn more about this culturally rich city, wine and dine and enjoy the slow pace of Italian life.

How to Reach Florence from Cinque Terre

There are 15 regular trains from Cinque Terre to Florence, which include direct trains from Cinque Terre’s La Spezia to Florence.

The first train leaves at 4:30 AM in the morning, while the last train leaves at 11:34 PM and takes about 2 hours to reach.

Accommodation in Florence

Backpacker Hostel – Hostel 7 Santi is the place I stayed in Florence. The best part of this hostel is that it is just 300 m from Firenze Campo di Marte Train Station.

Mid-range Hotel – Chianti House is such a beautiful property despite being in the mid-range. It has Air conditioning, free WiFi, mountain view, city view, river view, you name it!

Luxury – Haggi’s Residence is a beautiful property that will make you not want to leave it at all. However, there are many other options to choose from if you want to get the feel of an Italian luxury accommodation. 

Days 5 and 6: Rome and Vatican City

Stepping into the past is how best I can describe Rome. It is the capital city of Italy. The coolest fact about Rome is that there lies an independent country inside the city itself – the Vatican City.

However, being a major tourist destination, Rome is quite crowded, and you would have to stand in long queues to buy a ticket to any place. Hence, I recommend buying tickets online well in advance to avoid wasting your time. 

Places to See: In a day you can easily visit Palatine Hill, Colosseum, Pantheon, Roman Forum, Trevi Fountain (A Must), and Imperial Fora.

The next day, head to the Vatican City on a train and explore St. Peter’s Basilica along with the museums there. They are so marvellously designed, from masterpieces of painting to sculptures, the most breathtaking one being the Sistine Chapel.

How to Reach Rome from Florence?

There are several trains from Florence to Rome every day. The fastest trains can take as little as 1.5 hours to reach Rome; on the other hand, the slowest can take up to four hours. Depending on your budget and time, book the tickets accordingly and plan well. 

I must warn you that if you decide to book the slower train and if it is crowded, you will have to stand on the train for four hours. 

Read our guide here to know more about travel in Italy – Italy Backpacking Guide

Accommodation in Rome

It is better to stay in the City Centre as you will have easy access to both transportation and restaurants. 

Rome has a lot of options for staying, being a major tourist spot, but here are some of my recommendations. 

Backpacker Hostel – Sunshine Hostel, Hostel Roma, Evening Star Termini, Two Ducks Hostel

Mid-range Hotel – Lungotevere Suite, Sistina Spanish Steps, BDC – King Termini Apartment

Luxury – Grand Hotel Palace Rome, Baglioni Hotel Regina, Palazzo Montemartini Rome, Roma Luxus Hotel

Two Weeks in Italy – A Perfect Backpacking Itinerary

If you ask me, I would say that even two weeks in Italy are not enough to appreciate the history, culture and beauty this country holds. However, I had only two weeks in Italy and here is what you can do too if you are travelling on a tight schedule. 

The Map I Followed

This is the map I followed throughout the second week. You can club the first week’s and second week’s itinerary and cover all four corners of Italy. Below you will find all the details of what I did after my Rome visit.

Day 7: Explore Orvieto and Civita

Orvieto was my favourite place in Italy, for I thoroughly enjoy landscapes and silence. I wanted to add an offbeat destination in my itinerary to my trip and explore the countryside. 

From Orvieto, I visited the little village of Civita. And I am glad I did because moving away from the crowded streets to a few offbeat, sleepy towns was a welcome change. 

Orvieto is located in the Umbria region of Italy and is situated on the summit of a large, flat hill made of volcanic ash rock. While Orvieto is so unique, seeing Civita felt like seeing a castle floating mid-air, and if you are in Orvieto, you must not miss on Civita. Civita can be accessed via a pedestrian bridge from the nearby ticket office in Bagnoregio village. 

How to Reach Orvieto and Civita from Rome?

Orvieto: There are both regional as well as Intercity trains from Rome with a difference of just 10 minutes. Therefore, I wouldn’t say that intercity trains make much sense, knowing that it is priced slightly higher.

The first train starts at 6 AM and the last one is at 11:55 PM from Roma Termini. Further, it takes about an hour to reach Orvieto from Rome.

Civita: Reaching Civita is easy. There are regular buses from Piazza della Pace (at the lower level of the Orvieto train station) every two hours. It will drop you at Bagnoregio, from where you can walk through the romantic lanes to reach Civita.

For more information on train and bus timetables, you can check out the guide here. 

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Accommodation in Orvieto

Finding a hotel for yourself in Orvieto is not difficult. The number of hostels is next to none here. So, you would have to book a hotel or B&Bs as per your price range.

Mid-range Hotel – Hotel Posta, Casa Piagge, Charming Apartment, La Collina

Luxury – Podere Pescara, Appartamento LaRosa, Orvieto Aroma

Now, if you are looking to add a few offbeat locations in your Italy Itinerary, read about these 5 lesser explored gems of Italy.

Day 8: Skydiving in Nettuno

I went to Nettuno near Rome for skydiving. To say that it was amazing would be an understatement. From witnessing an amazing landscape to meeting exceptionally friendly divers, the entire experience was surreal.

Details for the Skydiving experience:

Address: Strada Ponte Materiale, All’interno del Club Le Grugnole, 00048 Nettuno RM, Italy

Phone number: +39 06 9885 0024

Website: Crazy Fly

Email: info@paracadutismonettuno.it

Opening Days: Every Saturday, Sunday and holidays from 9:00 AM onwards

How to Reach Nettuno From Rome?

There are direct trains between Rome and Nettuno that take about an hour to reach. Once in Nettuno, you can either take a taxi or arrange a pickup for yourself by contacting Crazy Fly.

But do remember that this pickup service needs to be booked in advance. So, let them know a couple of days before.

Days 9, 10 and 11: Sicily

If you have watched The Godfather or read the book by Mario Puzo, you would know about the city I am about to write about. The largest island of the Mediterranean Sea, with a unique culture of its own, Sicily is an autonomous region of Italy. It is separated by the Strait of Messina, which is roughly 3 KMs long.

Places to Visit

There’s so much to see in Sicily that a trip won’t be enough to cover it all. One can spend months over here. Below are a few of the must-see places in Sicily if you are here for a shorter duration. This is also what I managed to see in 3 days comfortably.

Mount Etna – Explore Italy’s tallest and active volcanic mountain, which is a UNESCO World Heritage site. There is a bus that drops you off at the foot of the mountain, from where you can either hike or take a cable car.

Isola Bella – Explore a small island in Taormina, Isola Bella, which is also known as The Pearl of the Ionian Sea. It was private property until 1990 and is now a nature reserve.

Taormina – This town is one of the prominent attractions of Italy and is perched on a hill 250 m above the sea. It has several monuments and historical beauties as the Greek Theatre, concerts and cultural activities.

How to Reach Sicily From Rome?

Flights

There are frequent flights from Rome to Palermo in Sicily. If you book your tickets well in advance, then flights could be the best possible commute between the two. Do ensure to check the luggage limits well in advance, as European flights are very strict with this system.

However, I would prefer a train and below is the reason why –

Train

I will recommend this even though it is time-consuming. The train is transported on a ferry across the Straits of Messina, and later it continues on the rail tracks in Sicily.

There are direct air-conditioned Intercity trains and takes about 11.5 hours of the journey. Further, while the train is on the ferry, you can get down and head up on deck to enjoy the views of Sicily.

Further, it also saves on a night’s accommodation. It is a win-win to cover the distance while sleeping, which will save both time and money, along with being a unique journey in itself.

Accommodation in Sicily

I would suggest you stay in the Taormina area of Sicily as it will give you access to Catania as well as Messina, because Taormina lies in the centre of it.

Backpacker Hostel – Le Coccole, SIC rooms and beds

Mid-range Hotel – Mara’s Home, Calumidda, Dimora Umberto Apartment

Luxury – Romano Palace Luxury Hotel, Le Suites del Duca di Sarro, Hotel VdB NEXT, Teatro Massimo

Day 12: Venice

Venice lies in the northeastern region of Italy and is home to 450 bridges and 120 islands. While planning a trip to Venice, you should not miss out on the gondola ride, the Basilica San Marco, and the Doge’s Palace. There’s something extremely romantic about Venice, plus there is so much history and culture here.

How to Reach Venice from Sicily?

Flight is the only option for this one and the most recommended one as well. Marco Polo Airport is the nearest and the only airport in Venice. You can also check flights to Valerio Catullo Airport, an airport in Verona, which is an hour away from Venice. From here you can take a train for your onward journey.

Accommodation in Venice

B&B or Guest House – Venice Luxury, Ca’ Spezier, Ca’ Crea 1 

Luxury – Sina Centurion Palace overlooks the Grand Canal and offers 5-star luxury in Venice.

Days 13 and 14: Dolomiti

The Dolomites are just gorgeous!! I had the pleasure of visiting Santa Maddalena Val di Funes and the 3 Zinnen. The Dolomites are huge, and there is a lot to see. And if you are a hiking enthusiast, then you are in luck because there are several day hikes to do in the Dolomites.

Below, I am listing down the places I visited, which you should too, along with the transportation facilities here in the Dolomiti.

How to Reach the Dolomiti from Venice?

Most tourists explore the Dolomiti in their private vehicles. Since I was backpacking as a solo traveller, the only option I had was to figure out the local commute. Here is how you can reach the Dolomites. 

Venice to Bolzano: Take a train from Venice. You will have to change to Verona and catch another one to Trento. Trento is the start of the Alps region. However, if you want to visit Santa Maddalena Val di Funes, a beautiful mountainous village, take a train to Bolzano instead.

Bolzano to Santa Maddalena Val di Funes: From Bolzano, board a bus to Brixen, from where you will find a bus with line 330 to Val di Funes. 

Santa Maddalena Val di Funes to Toblach: Next, you need to reach Toblach if you want to explore Tre Cime. To reach here, again take line 304, which will drop you off directly in Toblach.

Toblach to Tre Cime di Lavaredo: There are many buses from Toblach to Tre Cime. The bus will take you to the foot of the hike, from where you would have to trek for an hour to reach this beautiful place.

Accommodation in the Dolomiti

I suggested places like Bolzano and Toblach because you will also find Youth Hostels over here. They have the best services despite being hostels. I will strongly recommend you to try these hostels because they are not only a cheaper available option but also provide a comfortable stay.

Bolzano: Rittnerstr. 23 Via Renon, I-39100 Bolzano, Phone: +39 0471 300 865

Toblach: Dolomitenstr. 29 Via Dolomiten, I-39034, Toblach, Phone: +39 0474 976 216

The Map I Followed

I was so excited to write this blog. Italy is my favorite country, and I am sure it will be yours too. Let me know if this blog helped you in the comments below, and ask any queries. I love answering questions 🙂