Italy Itinerary blog Post

The Ultimate Italy Itinerary You Should Steal!

I have been to Italy 4 times and it never ceases to amaze me! Walking through ancient ruins and dining on delicious pasta and gelato – what’s not to love. My husband and I spent just over a month touring Italy finding the best locations to visit and we are sharing them all with you here. These are not only truly iconic Italian locations but also beautifully authentic ones that will leave a very special place in your heart.

So where to start – well I have the best locations in order from a clockwise route around the country. This was the route that we took in a camper van as we explored Italy in all its glory. When planning your Italy Itinerary – these are locations that you are not wanting to miss. Obviously you don’t need to visit them all at once but you will know how long you would need to spend in each location and can then plan your itinerary. Alternatively – do what we did and tour the entire country!


The first time I visited Assisi was on a school trip when I was about 14. We toured Italy in 7 days and I distinctly remember this jaw dropping world heritage town so vividly. It is so unique in its nature and truly breath taking, perched on a hill surrounded by lush Italian countryside.

Assisi, Italy

Italy is known for its rich history and Assisi was home to one of Italys most famous Saints – St Francis. Walk along the cobblestone streets of this medieval hillside town, past old houses and shops. Visit the Basilica of St Francis, one of the most spiritually powerful places in Assisi. You can easily walk around Assisi in a day – take in an audio tour to really understand the historical significance. We parked our camper van in an aire at the base of the town with breathtaking views of Assisi.

How long to spend in Assisi?

You could visit here for the day or spend a night and explore over two days. One full days sightseeing is enough to see what Assisi has to offer.


You cannot visit the Puglia region of Italy and not visit Alberobello. Home to the most stunning and unique Trulli Houses. These alone are sure to peak your interest and have been marked as a UNESCO World Heritage Site.

Alberobello, Italy Iitinerary

Trulli Houses are several thousand year old white washed stone huts with conical roofs. They were designed in such a way that they can be demolished quickly since they don’t have any mortar added to the brick. Why you may ask? Well it was all to do with avoiding property tax paid to the king in the 1500’s. When a royal inspection was to occur, the houses could be disassembled in order to pay less tax!

Alberobello is a very popular destination to visit as it has the highest concentration of Trulli houses in the region. It is 100% worth visiting and if you want to avoid the crowds we recommend visiting in off season or coming early in the morning.

We recommend staying in a Trulli house to get the most authentic experience. You can either do this in Alberobello or go a little further afield into the stunning countryside where you can find many more scattered around. We stayed in one in the countryside that had a swimming pool and served a delicious classic Italian breakfast. It was heaven.

How long to spend in Alberobello?

You ideally should spend at least one night here to soak in the Trulli experience. One days sightseeing is enough to take in the town and maybe more if you want to explore the countryside.


Nearby to Alberobello is the beautiful small town of Locorotondo. Known for its wine, circular structure and historical centre. It makes a great stop if you are in the area, especially since not many tourists visit.

As the town is designed in a circular fashion it makes a great maze of winding narrow streets and Catholic churches. Perfect if you want to wander and explore a quiet, authentic Italian town away from the hustle and bustle of Alberobello.

How long to spend in Locorotondo?

An afternoon or morning would be sufficient in order to see Locorotondo.


Located in Basilicata, a region of forests and mountains in Southern Italy, Matera awaits to amaze you.

Matera Italy Itinerary

The ancient city is famous for its Sassi district, a vast hillside complex of cave dwellings dating back thousands of years. The gorge surrounding Matera is home to over 150 rock cut churches.

Up until 1952 people still lived in the cave dwellings that make up the ancient city of Matera. Since then the original cave homes have been evicted due to safety and in their place are museums, cafes, hotels and restaurants.

Named as a European Capital of Culture for 2019, a World Heritage site and used as a movie set for Wonder Women and the new James Bond movie – No Time to Die.

This truly unique location is a must see when planning your Italy Itinerary.

How long to spend in Matera?

You could easily spend a night or two in Matera. There is a lot to explore in the town and in the surrounding countryside. It is a great place to cycle and you can join tours in the area.


This iconic seaside town is an absolute must see when visiting Italy and the Amalfi Coast. We have visited twice and loved it so much we still want to go back.

Known for its sweeping cliff side vistas, delicious locally grown lemons and close proximity to Capri – Positano is just an Italian dream.

the best Positano Viewpoint

There is so much to do when you visit Positano that you wouldn’t believe how small it actually is. You can hire boats for the day to explore the surrounding coves, take a private luxury boat trip to Capri for the day – home of the rich and famous. Spend the day on the stony beaches, drinking Aperol Spritz and eating delicious Italian pizza. Dine in dozens of restaurants overlooking the incredible views, whether that’s on the waterfront or up the steps to higher cliffside viewpoints.

Positano houses some incredibly luxurious hotels and also caters for those with a smaller budget. If you can’t stay in Positano there are plenty of ways that you can get here. Driving is quite difficult in a car as parking is limited but there are public buses that frequent the town from along the coast. You could also hire a traditional Italian Vespa scooter and zip along the winding roads that hug the cliffside. Living La Dolce Vita!

How long to spend in Positano?

Positano is one of those places where you could spend a day or even a week. We highly recommend that if you are wanting to spend more than a day in Positano then try and stay in the town, instead of nearby. This way you get to experience the true magic of Positano at night once the day tourists leave. The first time we visited we spent 3 nights in Positano and then the second we visited for a day.


If you want to learn some iconic Italian history then you must visit the ancient ruins of Pompeii.

This UNESCO World Heritage Site is overlooked by the Mount Vesuvias Volcano, which erupted in 79AD burying the town of Pompeii. What is most fascinating about Pompeii is that there are large sections of the town and its people that have been brilliantly preserved. This gives us an incredible insight in to the Roman cities civilisation providing information on the art, customs and trades.


The sites have been progressively excavated since the mid 18th Century and made accessible to the public. They continue to unearth new discoveries still to this day. Visiting Pompeii has been one of the most fascinating experiences we have ever seen.

There are several sites that you can visit including Pompeii, Herculaneum and Torre Annunziata. You can visit the site on the first Sunday of every month for free.

How long to spend in Pompeii?

You can easily see the main site of Pompeii in a day or two. There are several different routes that you can take viewing the site, some take a couple of hours if you are short on time and some take up to 8 hours. It really depends on how much you want to see. If you plan on visiting Herculaneum as well you will want to factor in another day. You can stay in Pompeii itself or travel from Naples or the Amalfi Coast.


As iconic as cities get in Italy – Rome is not to be missed. It feels silly even writing why you should visit Rome because it is just so fantastic and nearly everyone on the planet has heard of it. I have been three times and loved it every single time, and found I discovered new places on each visit.

But on the off chance that you haven’t visited Rome- here are my favourite places to visit and things to do when you do come.

My favourite sight seeing spots in Rome are:

  • The Colosseum, Roman Forum and Palatine Hill – all located in the same archeological area and most often get ticketed together. I 100% recommend getting a guided tour of these locations that include a guide or at least an audio tour and skip the line admission. There is too much to learn by yourself and it’s the best value for money.
  • The Pantheon – located around the corner from the Trevi Fountain, the Pantheon is an iconic site. It is the most preserved and influential building in Rome.
  • Vatican City and Sistine Chapel – this is the second place that I would recommend getting a tour guide and skip the line tickets.
  • Spanish Steps – an iconic location to take some time out from shopping along Via Condotti, Romes most luxurious street.
  • Trevi Fountain – the most famous fountain in the world. An iconic place to visit and I’d say the busiest attraction in all of Rome.
  • Borghese Gardens – the perfect place to go for a picnic away from the hustle and bustle of the city. Located in the city centre but feels worlds apart, this park is beautiful and a fantastic place to relax.
  • Walk around Monti and Trastavere – our favourite neighbourhoods. Home to incredible food and authentic Italian bars, dine on Aperitivo and drink red wine by the litre.
  • Enjoy a luxury Aperitivo in the 5* Hotel Hassler at the top of the Spanish Steps or on the rooftop of the 5* Hotel Raphael overlooking Rome at sunset, where Julia Roberts stayed whilst filming Eat, Pray, Love.

How long to spend in Rome?

3-4 nights would be the minimum amount of time that I recommend spending in Rome in order to give yourself enough time to see the main sights. If you have more time you could easily spend a week here.


The beautiful town of Siena sits in the wonderful region of Tuscany. The historical town centre has been classed as a UNESCO World Heritage site and is home to the famous Piazza del Campo. Home to the Palio di Siena – a horse race that takes place in the square twice a year where the riders race bare back wearing home colours of different districts. One of the most important events in Siena that draws thousands of spectators every year.

When we were there they had a Vespa parade, where hundreds and hundreds of Vespa owners were driving through the streets. I can’t think of anything more Italian than that.

Siena is also know for its art, medieval cityscape, museums and delicious cuisine. When in Tuscany it is a city that you do not want to pass by.

Siena italy

How long to spend in Siena?

I recommend spending at least one night in Siena before you head on to your next destination in Tuscany.


I would say Florence is the second city after Rome that you want to visit in terms of history, art and architecture. Florence is the capitol city of the Tuscany region and is home to many pieces of Renaissance art and architecture. If you have ever read any of Dan Browns books or seen the Da Vinci Code movie series, you will instantly be transported into the movie set, most noticeably if you visit the incredible Duomo. Florence is also home to the Galleria dell’Accademia which displays the very famous “David” sculpture by Michelangelo. You can visit the incredible Uffizi Gallery, walk across Ponte Vecchio and relax in the Boboli Gardens.

How long to spend in Florence?

I would recommend spending 1-2 nights in Florence. If you really want to soak in the art, at least 2 nights.


I cannot write a guide to Italy and not include one of the most famous locations. Venice is one of the most unique places that we have visited in the world. Narrow maze like lanes dotted with luxury shops, bakeries and tiny restaurants. Spend your days visiting the incredible churches, admiring the art work and spend the evenings drinking red wine and eating Cicchetti – a version of Aperitivo. Loosely translated to mean shady stroll – or in plain terms a pub crawl.

My favourite sight seeing spots in Venice are:

  • Rialto Bridge – an iconic location in the centre of Venice overlooking the Grand Canal.
  • St Marks Basilica – This free attraction is the perfect intro in to Venice.
  • St Marks Square – come to admire the architecture and check out the close by Basilica, Doges Palace and is right next to the water taxi terminals.
  • Bridge of Sighs – a historical site and famous photography opportunity.
  • Day trip to Burano – the most colourful fishing town you will ever see, this is not to be missed.
  • Visit Libreria Aqua Alta – a secret book store that once got flooded and now has ingenious ways to deal with it. They have a love for cats and have an instagram worthy rear garden with a staircase made from vintage books.
  • Doges Palace – Formerly the Doge’s residence and the seat of Venetian government, the Palace is the very symbol of Venice and a masterpiece of Gothic architecture.
  • Fondaco Dei Tedeschi – the best FREE rooftop view of Venice.

If you want a more detailed itinerary for Venice check out my Ultimate Budget Venice Guide blog post here. You can also check out my Top 10 Instagram Spots in Venice blog post here – this includes our favourite secret locations AND photography tips.

How long to spend in Venice?

Ideally you want to spend at least 3 nights in Venice to see everything – you could spend 2 nights if you have a jam packed itinerary.

The Dolomites

Once you reach Northern Italy this is where the scenery begins to change and the glorious mountain scapes of the Dolomites begin to take your breath away. North of Lake Garda you can venture in to the incredible landscapes, the area is vast so this could be a trip entirely in itself.

If you want a taste for the Dolomites to tack on to your Italian itinerary then we recommend visiting Molveno. Just north of Lake Garda, Molveno sits at the foot of the Brenta Dolomites. It is home to its own incredible lake and was a favourite on our trip. If you venture further north to Andalo you can do mountain biking here and its just beautiful.

How long to spend in the Dolomites?

If you are planning a trip to the Dolomites, these mountains on their own deserve at least 3-5 days. However if you are planning on visiting Lake Garda and want to experience the Dolomites for a short period of time we recommend visiting Molveno for 1-2 nights.

Lake Garda

Lake Garda is the largest lake in Italy and there are several locations that you will want to visit. They happen to be on the complete opposite side to each other, offering very different experiences.

On the southern end of the lake is the beautiful resort town of Sirmione. Known for its thermal baths and Rocca Scaligera, a medieval castle overlooking the lake. The town sits on a peninsula, beautiful holiday homes line each side and you cross a bridge into the centre. Here you will find restaurants, infamous ice cream shops serving the largest ice creams you have ever seen, incredible Lake Garda views and beaches.

In between the north and south end of the lake is the resort town of Toscolano-Maderno. Famous with Italian holiday makers, home to mansions and a beautiful marina. We adored this little town and it is a great place to stop overnight or even for a couple of nights.

On the northern end of Lake Garda you will find the town of Riva del Garda and Torbole. Known for kite and wind surfing since it generates so much wind. There are lots of walks that you can do here, along with water sports activities. It is a gateway to the mountains and worth stopping.

How long to spend in Lake Garda?

You could easily spend an entire week in Lake Garda just on its own vacation, however if you are short on time and want to include it in a multi city itinerary then 1-2 nights in each location would suit. To drive from Sirmione to Riva del Garda is just under 2 hours.

Lake Como

Famous for housing George Clooneys vacation home and offering absolutely stunning lake views, Lake Como is not to be missed on your Italian itinerary.


There are three main towns that you can visit, most notably being Bellagio where you can base yourself. Did you know you can visit all three of the famous towns in Lake Como all in just one day? From Bellagio you can catch a ferry to Menaggio and Varenna for only €4.60 each way. You can have breakfast in one, lunch at the next and dinner at the other. Make sure you stop at the most famous viewpoint in Bellagio and take a photo.

Lake Como has been a popular retreat for aristocrats and wealthy people since Roman times, and a very popular tourist attraction with many artistic and cultural gems. It has many villas and palaces such as Villa Olmo, Villa Serbelloni, and Villa Carlotta

How long to spend in Lake Como?

Lake Como, much like Lake Garda is a location that you could stay in for a week however you can get a taste for it in only a few days by using the ferry to travel.

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Hey there! I'm Rachel Hughes aka Ever The Wanderer. I am a Digital Media Creator and long term travel expert. I help people realise their worth and what they can achieve.

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