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How To Spend 2 Weeks in Italy: Itinerary Advice From An Italian

Italy is located in the middle of the Mediterranean Sea and is home to some of the most beautiful views and experiences (and no, I’m not just saying it just because I’m Italian).

Being Italian I get asked a million times for Italy travel advice, so I decided to put together this ultimate Italy 2-week itinerary that covers all the major sights and cities. 

This Italy two week itinerary starts with the history and beauty of the Eternal City, Rome, to then head over to Tuscany for a bit of exploration in Florence and Pisa, before heading to Cinque Terre for an amazing hiking experience.

After that this Italy travel itinerary continues on to the city of fashion, which also happens to be my hometown, Milan, and then ends in Venice, the city of lovers.

What to do in Milan in one day

Exploring Piazza del Duomo in Milan, Italy

Two weeks in Italy aren’t enough to see the whole country, I’ve lived here for 18 years and there are regions I still haven’t been to either!

But it’s a great start and a good enough amount of time to travel comfortably around Italy and see all the main tourist hotspots.

I’ll also go over useful travel information like how to get around Italy, where to stay, what to pack and more. Ready to discover how to spend 2 weeks in Italy?

Admiring the colourful houses of Manarola, one of the five towns along the Sentiero Azzurro in Cinque Terre, Italy

Admiring the colourful houses of Manarola, one of the five towns along the Sentiero Azzurro in Cinque Terre, Italy

Do you need travel insurance for 2 weeks in Italy?

After my personal experience spending two nights in a private hospital in Tenerife, and having to pay for it out of pocket (it wasn’t cheap), I always recommend getting travel insurance.

You might not end up needing it, but for a small fee you can travel without worries. Personally, I suggest getting your travel insurance with  Heymondo.

Heymondo offers tailor made travel insurance, providing the best value for money for your specific trip. You can also buy it once you’re already abroad and have forgotten about it before flying (which, if you’re anything like me, is quite likely).

Besides the usual cancellation, medical expenses, luggage coverage and general travel insurance services, Heymondo also has a 24/7 doctor chat and instant assistance through their app.

As a Greta’s Travels reader, you get 5% off your Heymondo travel insurance!

Click here to get your 5% off Heymondo travel insurance!

Exploring the Golfo di Orosei and Cala Luna by kayak in Sardinia, Italy

Exploring the Golfo di Orosei and Cala Luna by kayak in Sardinia, Italy

Italy Itinerary: 14 days of exploring

Let’s dive right in to our 2-week Italy itinerary!

Day 1: Arrive in Rome – Colosseum & Trevi Fountain

You should start your 2 week trip to Italy in Rome. After all it’s the capital of Italy, the Eternal City and it’s home to some of the worlds most ancient and beautiful history and art.

You’re only going to spend two days in Rome, so you’ll need to hit all the major attractions on your first day.

Plan your flight strategically, so that you land in Rome in the early morning. This gives you the ability to see a decent amount of the gorgeous ancient city right on day one. The first stop on your Italy route will be the ancient Colosseum!

There are many guided tours of the Colosseum, which will provide you with the knowledge about the brave gladiators, and the bloodthirsty entertainment that took place in Rome’s most famous monument.

The queue to go inside the Colosseum can get pretty huge so make sure to book online beforehand, or check out this guide to skipping the line at the Colosseum on a budget

Click here to book your Colosseum skip the line tour!

Enjoying the beauty of the Colosseum in Rome, Italy

Enjoying the beauty of the Colosseum in Rome, Italy

Next, you’ll want to visit Trevi Fountain. It’s a beautiful monument decorated with sculptures and is a must-see when in Rome. I recommend walking there from the Colosseum, as this will take you past the famous Fori Romani.

These are a series of public areas that are centred around a monument. These were an integral part of Roman culture, and each served a different purpose in ancient times.

With its beautiful statues and white marble, the Trevi Fountain is without a doubt one of the most Instagrammable places in Rome.

They say if you throw a coin in the Trevi Fountain, you’ll get the chance to visit Rome again. I do it every time I go to Rome, just to be sure (and so far I’ve always gone back so I think it’s working)!

From the Trevi Fountain you can walk onwards to Piazza del Popolo and Piazza di Spagna, to see the famous Spanish steps and enjoy the view from Villa Borghese over the rooftops of Rome.

The Trevi Fountain in Rome, Italy

The Trevi Fountain in Rome, Italy

You can end your first day in Rome with a dinner out in Trastevere. Trastevere is one of my favourite areas in Rome, with lots of osterie and trattorie to choose from for your aperitivo or dinner options.

I’ve eaten before at Osteria Cacio & Pepe and loved it, but most restaurants there will be good. It’s also a fun area to go bar hopping after dinner.

Eating spaghetti carbonara in Rome

Eating spaghetti carbonara in Rome

Where to stay in Rome

My ex-boyfriend is from Rome so we tried our fair number of bnb and apartment rentals in Rome. Here are some great accommodation options for every budget.

Budget: Palladini Hostel:Budget option for the backpackers or hostel lovers; this hostel is super central, close to the train station and all the action of Rome, with spacious dorms and a lively atmosphere

Mid-range: Tridente Rooms: Mid-range option, the rooms are simple but spacious and it’s right next to Villa Borghese, in the heart of all the Rome attractions

Luxury: Hotel Eden – Dorchester Collection: Luxury option, it’s beautifully decorated and very conveniently located in the centre of Rome

Click here to book your accommodation in Rome!

Castel Sant'Angelo in Rome, Italy

Castel Sant’Angelo & Ponte Sant’Angelo in Rome, Italy

Day 2: Rome – Visit the Vatican

On the second day of your Italy travels, I recommend paying a visit to the famed Vatican museum. It’s one of the most popular tourist attractions in Rome, and it’s not hard to see why.

The best Italian trips include something ancient and something beautiful. This attraction just happens to include both! 

You can take a guided tour of the Vatican Museum and the Sistine Chapel, where you can ogle at masterpieces done by the great Michael Angelo, admire the incredible architecture, as well as learn about the cities fascinating past.

Visiting the Vatican Museum will easily take up a whole half-day, if not more depending on how long you want to spend in the museum. You can also go to the top of the dome and see an epic view over Rome.

I recommend buying your tickets online beforehand or you might end up queueing for hours just to get in.

Click here to book your Vatican Museum & Sistine Chapel skip the line tickets!

Approaching St. Peter's Basilica in the Vatican

Approaching St. Peter’s Basilica in the Vatican

In the late afternoon and early evening you can grab dinner and drinks around Campo Dei Fiori, where all the students and young people in Rome go out in evenings.

Once it’s properly dark you can also wander around the Fori Romani, where they play projections and light shows that aim to teach the public about these areas that played such an important part in Roman history.

You’ll see what the Fori Romanis looked like when they were built, which is an interesting insight into the past of this wonderful city.

Lost somewhere in the wobbly side streets of Rome

Lost somewhere in the side streets of Rome

Day 3: Rome – Pantheon & Fori Romani

Start your third day in Italy off the right way by visiting the Pantheon! It’s an ancient Roman temple that was later converted into a church, and holds great cultural significance within the Italian community. 

The architecture is absolutely stunning! This circular building is beautiful both inside and out, and it is also free to visit.

However, with free attractions comes queues, so I recommend you head to the Pantheon as soon as it opens to make sure you miss the crowds.

Alternatively, you can take a guided tour of the Pantheon, which allows you to skip the line, and learn the history of the Pantheon from a knowledgeable guide.

Close to the Pantheon is Gelateria 100 Palme, an ice cream shop that sells over 100 different flavours. Needless to say every time I go to Rome I try a different flavour.

Click here to book your Pantheon skip the line tour!

The Pantheon in Rome, Italy

The Pantheon in Rome, Italy

Best tours in Rome

These highly rated tours are a must during your time in Rome!

Vatican Museums & Sistine Chapel Skip-the-Ticket-Line Entry – Like I already said, if you only have two days in Rome you don’t want to waste part of that time queuing up for things! 

Rome: Colosseum, Roman Forum, Palatine Hill Priority Tickets – Same goes for the Colosseum, don’t waste time and don’t miss out on this awesome Italian attraction!

Rome: Street Food Tour with Local Guide – Italians take food very seriously, the best way to discover true Roman cuisine is with a local!

Exploring Piazza Navona in Rome

Exploring Piazza Navona in Rome

Day 4: Travel from Rome to Florence

On your 4th day in Italy, you’ll travel from Rome to Florence. You can get to Florence either by plane or train. I personally recommend the train.

The flight might be one hour, but you still have to factor in travel time to and from the airport, and you usually have to be at the airport at least one hour before.

If you get the fast train from Rome to Florence this takes you from the centre of Rome straight to the centre of Florence in roughly the same amount of time as the total flying travel time.

Once you arrive in Tuscany, you’ll have plenty more activities to take part in and areas to explore. No matter how many days in Florence you have, you’re sure to fill up your Italy itinerary with a multitude of awesome things to do.

Your first stop in Florence should be the grand Florence Cathedral. It’s possibly the most celebrated cathedral in the world, making it one you don’t want to miss!

Known as Duomo or the jewel of the city, the incredible building was built in 1436 but wasn’t finished being built until the 19th century. 

The architecture is amazing and is an absolute must-see if you’re looking for Italian vacation ideas!

Click here to book your skip the line guided tour of the Florence Cathedral!

Getting up close to the majestic Duomo of Florence

Getting up close to the majestic Duomo of Florence

Next, you should visit Ponte Vecchio, which is a historically significant bridge that stretches across the river Arno. The bridge is enclosed and has become famous for the many quaint shops built into its sides.

The earliest recordings of the bridge date back to 996, but nobody really knows its true origins. Take a meander along the bridge as you browse the shop windows.

Light reflections at the Ponte Vecchio in Florence

Light reflections at the Ponte Vecchio in Florence

You can end your first day in Florence at Piazzale Michelangelo. This is a park with a beautiful view over Florence. The huge dome of the cahedral towers over the rooftops of the houses, and makes for a stunning sunset spot.

When I visited Florence with my mum we stayed at Palazzo Riblet.

This hotel is a family-run business with only a few room within a historical building, with beautiful decorated bedrooms and original Renaissance affrescos on the ceilings.

It’s also very conveniently located close to both the train station and centre of Florence. 

Check out the latest prices and availability at Residenza d’Epoca Palazzo Riblet here!

Sunset over Florence from Piazzale Michelangelo

Sunset over Florence from Piazzale Michelangelo

Day 5: Florence – Gallery and Gardens

On your second day in Florence, you should aim to fill your day with as many beautiful Florence sights as possible.

Galleria dell’Accademia is a wonderful gallery that houses some of the most incredible sculptures from the Renaissance period. 

You can expect to see original sculptures from Michelangelo, as well as masterpieces from a multitude of other incredible artists. 

After a visit to the wonderful gallery, spend the afternoon exploring the Boboli Gardens! The gardens cover an area of 45 000 square metres, making them the largest gardens in Florence.

If you love being out in nature, this is the perfect Italy vacation idea. The gardens were created in the 16th century and feature rolling lawns with a scattering of beautiful sculptures to admire.

A stroll through these gardens is the perfect escape from the hustle and bustle of the city!

Street markets in Florence, Italy

Street markets in Florence, Italy

Best tours in Florence

Here are some tours with awesome reviews to check out for your time in Florence.

Florence: Uffizi Gallery Timed Entrance Ticket – Skip the queue for your visit to the Uffizi!

Florence: City Walking Tours with entry to Accademia – Discover Florence on foot with a local guide, and then explore the Accademia with them!

Florence: Small-Group Tour on E-Bike – Try something a little different and discover Florence by bike!

Aerial view of Florence - Photo by Garrit Wes Anderson on Scopio

Aerial view of Florence – Photo by Garrit Wes Anderson on Scopio

Where to stay in Florence

Besides Palazzo Riblet, I wanted to suggest a few places to stay for every budget.

Budget: Plus Florence – This hostel has spacious dorms, a sociable atmosphere and a spectacular rooftop with views over the Florence skyline.

Mid-range: Palazzo Riblet – I stayed here when I visited Florence with my mum and can highly recommend it. This family run hotel is situated in a historical building, with affrescos on the ceiling and in a great location.

Luxury: Firenze Rentals Corso 12 – This lovely apartment has a balcony directly overlooking the Duomo of Florence. It doesn’t really get any better than this!

The view from the top of the dome of the Duomo of Florence - Photo by Giuseppe Trimarchi on Scopio

The view from the top of the dome of the Duomo of Florence – Photo by Giuseppe Trimarchi on Scopio

Day 6: Explore the Old Town of Siena

But Tuscany isn’t just about Florence, so travel on to Siena on day 6. In Siena you’ll discover a different side of Italy, as you explore the well preserved medieval city. 

There are plenty of things to see and places to explore in this wonderful town in the middle of the Tuscany region.

Start your tour of Siena at the central square, called Piazza del Campo, and learn about its great historical significance before paying a visit to the Gothic town hall.

Every year they run an important horseriding competition in this square, called Palio di Siena, and it’s a huge event much loved by the local people of Siena. 

Visiting the Cathedral of Santa Maria Assunta is an absolute must when you’re in the beautiful town.

It was constructed in the 13th century, and just like many of the other wonderful buildings in Italy, it has incredible architecture that rivals the worlds best. 

You can take a guided tour that will take you to both the Piazza del Campo and the Siena cathedral.

Click here to book your Siena highlights guided tour!

Piazza del Campo in Siena

Piazza del Campo in Siena

You’ll also want to visit the Siena national gallery, which is housed in a former palace, making for a wonderful destination to tour.

Inside the gallery, you’ll find wonderful artworks from famed artists between the 12th and 16th centuries.

If you don’t feel like being indoors, spend some time wandering around the streets of Siena. Siena has one of the best preserved medieval old town centres and even just getting lost in its quaint streets will be a fun experience. 

We only spent one night in Siena and we stayed at Hotel Athena, within the old town walls.

The rooms were spacious and they included a tasty breakfast, but the highlight for me was by far the stunning view they had from the rooftop restaurant of the Tuscan countryside.

Click here to see the latest prices and availability at Hotel Athena

View over the Tuscan countryside

View over the Tuscan countryside from our hotel in Siena

Best tours in Siena

Here are some tours in Siena with excellent reviews.

Siena: Guided City Tour with Cathedral Skip-the-Line Entry – Discover the beauties of Siena with a local guide and without wasting time in a queue.

From Siena: San Gimignano, Montalcino & Wine Tasting – Explore the surroundings of Siena and taste delicious local wine!

From Siena: Vespa & Chianti Tour in the Tuscan Hills – Live your Italian travel movie dreams and zoom around the Tuscan countryside in a traditional Italian vespa!

View over the rooftops of Siena, Italy - photo by Roberto Destarac on Scopio

View over the rooftops of Siena, Italy – photo by Roberto Destarac on Scopio

Where to stay in Siena

Besides Hotel Athena, I wanted to include a few accommodation options for every budget.

Budget: Camping Siena Colleverde – For something a little different, you can stay in this unique camping with epic views of Siena!

Mid-range: Hotel Athena – The hotel I stayed at, it has cozy rooms and great views of the Tuscan countryside.

Luxury: Grand Hotel Continental Siena – If you want to treat yourself, this is the place to do so!

Sunset views in Siena - Photo by Giuseppe Trimarchi on Scopio

Sunset views in Siena – Photo by Giuseppe Trimarchi on Scopio

Day 7: Travel to Pisa & explore Piazza dei Miracoli

After a week in Italy, you’re sure to have fallen in love with the beautiful country! However, there’s still plenty more to see if you’re feeling up for it!

On your 7th day in Italy, I recommend you travel from Siena to the wonderful town of Pisa. 

As soon as you arrive you should head straight for the famous Leaning Tower of Pisa, which was completed in 1372, and yes, it was leaning then too.

It’s incredible that this tower has managed to stand for hundreds of years at what seems to be a dangerous angle.

| READ MORE: ONE PERFECT DAY IN PISA |

The Leaning Tower of Pisa

The Leaning Tower of Pisa

The Leaning Tower of Pisa is located in Piazza Dei Miracoli, which houses also the Baptistery and Duomo of Pisa. With one visit you can tick off all the main landmarks and attractions of Pisa.

These aren’t as famous as the tower (nothing crooked or unusual about their architecture after all) but they’re still important parts of Italian history.

You can do a guided tour of Piazza Dei Miracoli where they will take you into both the Leaning Tower, the Baptistery and the Duomo, so that you can learn everything about this stunning city. 

Click here to book your Pisa guided tour!

The baptistery of Pisa in Piazza dei Miracoli, Italy

The baptistery of Pisa in Piazza dei Miracoli, Italy

The Duomo of Pisa with the Leaning tower in the back

The Duomo of Pisa with the Leaning tower in the back

You should then head to Borgo Stretto, a street that combines magnificent architecture and high-end shopping.

The street is located in the heart of the city and features many branded stores, boutique shops, designer clothing labels and quaint cafes that offer the perfect break from your shopping experience. 

After an incredibly scenic shopping experience, head to the Mezzo bridge that spans over the river Arno. It’s a great place to take pictures during sunset and it provides beautiful views of the sleepy town.

River Arno in Pisa, Italy

River Arno in Pisa, Italy

Where to stay in Pisa

I haven’t slept in Pisa myself but here are some suggestions for places to stay.

Budget – Hotel Cecile: A good budget option, with finely decorated rooms and conveniently located in Pisa

Mid-range – Grand Hotel Duomo: This mid-range hotel is in an amazing location, with a rooftop terrace with a stunning view over the rooftops of Pisa and you can also get a glimpse of the Leaning Tower of Pisa. The rooms are also spacious and finely decorated

Luxury – Allegroitalia Pisa Tower Plaza: This luxury hotel is a bit outside Pisa but has a beautiful swimming pool, for those searching for a quiet place to take a break in the middle of this busy Italy itinerary

Click here to see the latest prices and availability for accommodation in Pisa

Exploring the off the beaten track courtyards of Pisa

Exploring the off the beaten track courtyards of Pisa

Day 8: Pisa to Cinque Terre

After spending a wonderful night in Pisa, it’s time to move on to another wonderful part of Italy! Cinque Terre is a string of ancient sea-side villages that stretch along the Italian Riviera coastline.

Travelling from Pisa to Cinque Terre by train will take you between 1 – 2 hours, and gives you the chance to enjoy spectacular views along the way.

If you want to stay in Cinque Terre I recommend staying in either Monterosso or Riomaggiore. These are the two towns at the two ends of the Sentiero Azzurro, and as such are great starting points for your hike tomorrow.

It’s cheaper to stay outside Cinque Terre and travel in, but these towns really are beautiful and if you’re only going to spend 2 weeks in Italy, I get it if you want to absorb more of their atmosphere. 

The First – La Vista di Marina in Riomaggiore is a lovely apartment with absolutely gorgeous views. They’re right on the sea front and have epic views both of the sea and the colourful houses of Riomaggiore.

Click here to see the latest prices and availability at The First – La Vista di Marina!

Admiring the colourful houses of Riomaggiore in Cinque Terre, Italy

Admiring the colourful houses of Riomaggiore in Cinque Terre, Italy

By day 8 I imagine you’ll be pretty knackered with all this intense sightseeing, so I suggest that after your train journey to Cinque Terre you take some time to relax.

Riomaggiore seemingly rises out of the ocean, leaving the entire town with exquisite views! You can spend some time exploring the town, wandering around the harbour or basking in the sun.

The coastline in Cinque Terre is rugged, but there are a few beaches in Riomaggiore worth exploring. Batteria beach is one of them. 

Fegina Beach in Monterosso al Mare in Cinque Terre

Fegina Beach in Monterosso al Mare, Cinque Terre

Hiking along the Sentiero Azzurro in Cinque Terre in one day

Hiking along the Sentiero Azzurro in Cinque Terre

Day 9: Hike the Sentiero Azzurro in Cinque Terre

You should spend a full day in Cinque Terre hiking the Sentiero Azzurro, a wonderfully scenic hike.

The trail passes passes through Monterosso, Vernazza, Corniglia, Manarola and Riomaggiore, giving you the option to explore each town individually.

The trail is 12 kilometres long, but if you’re not up for the entire hike, you can do segments of it instead. You can start at either end of the trail, depending on where you’re staying, and then take a train back.

All the towns are connected via train. Access to the Cinque Terre national park and the Sentiero Azzurro hike costs 8 EUR for just entry, or 15 EUR for a combined park plus hop-on hop-off ticket to the trains.

Wineries somewhere along the Sentiero Azzurro in Cinque Terre, with Monterosso in the distance

Wineries somewhere along the Sentiero Azzurro in Cinque Terre, with Monterosso in the distance

Admiring the colourful houses of Vernazza, one of the five towns along the Sentiero Azzurro in Cinque Terre, Italy

Admiring the colourful houses of Vernazza, one of the five towns along the Sentiero Azzurro in Cinque Terre, Italy

If you can handle 12km in a day, I highly recommend doing the hike. While the colourful houses of Cinque Terre are the highlight of this trail, there are stunning views all throughout.

Along the way, you’ll enjoy the beautiful scenic views of the ocean and sheer rock faces that rise up out of the sea. It’s a wonderful hike for photographers or Instagrammers looking for the perfect shot. 

Be sure to find a great spot to watch the sunset in the evening, as the views from the trail are absolutely exquisite. Although it’s easy enough to head down to a seaside restaurant and watch the beautiful views from there.

The beautiful streets of Manarola in Cinque Terre, Italy

The beautiful streets of Manarola in Cinque Terre, Italy

View over Vernazza from the start of the Sentiero Azzurro, enroute to Corniglia

View over Vernazza from the start of the Sentiero Azzurro, enroute to Corniglia

Best tours in Cinque Terre

You can explore Cinque Terre on foot by hiking the Sentiero Azzurro, but these highly rated tours can add a special something to your holiday!

Cinque Terre Sunset Boat Tour – Admire the coloured houses of Cinque Terre as the sun goes down and the sky turns golden!

From Monterosso: Cinque Terre Kayak Tour – Combine a workout with a unique experience, and see Cinque Terre from a completely different angle!

From La Spezia: Cinque Terre Full-Day Boat Tour – Spend a whole day sailing along the beautiful Ligurian coastline.

Sunset over the perched colourful houses of Riomaggiore in Cinque Terre, Italy

Sunset over the perched colourful houses of Riomaggiore in Cinque Terre, Italy

Where to stay in Cinque Terre

I’ve already given you my opinion on the best place to stay in Cinque Terre, but here are some optons for every budget.

Budget: Grand Hostel Manin – This hostel has spacious dorms, a friendly atmosphere and is located in the heart of La Spezia. It’s the perfect place to use as base to explore Cinque Terre on a budget!

Mid-range: ALTIDO Villa Monterosso Apartment Bellavista – This modern villa is tastefully decorated, with gorgeous views of the Ligurian coastline and sea. It’s also in an excellent position in Monterosso.

Luxury: La Vista di Marina by The First – This apartment combines modern furnishing with exposed bricks for a rustic vibe, plus spacious rooms and white décor for an airy feel. It also has a spectacular terrace with view over the sea and iconic perched houses of Riomaggiore.

The harbour and colourful houses of Porto Venere

The harbour and colourful houses of Porto Venere

Day 10: Cinque Terre to Milan

After your hiking and seaside break it’s time to take the train from Cinque Terre to Milan (my hometown)!

By now you’ll be very familiar with taking the train in Italy, and learning to enjoy the journey as the views are usually spectacular!

The slight delays that often happen on Italian railways are just part of the journey.

The train trip should take you around 3 hours, leaving you with plenty of time in the afternoon and evening to explore the wonderful city of Milan and its nightlife.

Girl in a red jumper sat on the red railways of the Metro in Milan, with the Duomo Cathedral behind her

Piazza del Duomo in Milan, Italy

This city is one of the fashion capitals of the world, so you can be sure its a creative city with loads to explore!

The best way to start a trip to Milan is by visiting the Brera District. You can walk through the charming cobbled streets, admiring the architecture and taking in all the wonderful sights and smells.

Sit down for a meal at one of the charming cafes or restaurants before exploring some of the amazing art galleries in the area. And, if you need a little retail therapy, there’s plenty of high-end shops that can provide you with just that!

Galleria Vittorio Emanuele seen from across Piazza del Duomo in Milan, Italy

Galleria Vittorio Emanuele seen from across Piazza del Duomo in Milan, Italy

Where to stay in Milan

Wondering where to stay in Milan? Being from Milan I’ve never had any need to stay in a hotel there, however there are a couple thatI’ve had friends stay at before that I can recommend:

BudgetOstello Bello: There are two hostels of this chain around Milan and both are good budget options, with a lively atmosphere, spacious dorms and convenient central locations

Mid-range – Ibis Milano Centro: Part of the Ibis chain this is a good mid-range hotel, with a guaranteed standard of room set up and a great central location

Luxury – Galleria Vik Milano: If you’re looking to splurge a bit, this is the place to do so. Located in Galleria Vittorio Emanuele this luxury hotel couldn’t get any more central than this, with stunning views over the galleria just outside your window

Click here to see the latest prices and availability for accommodation in Milan!

The inside courtyard of the Accademia di Brera, Milan

The inside courtyard of the Accademia di Brera, Milan

Day 11: Explore Piazza del Duomo in Milan

You should spend your full day in Milan around Piazza del Duomo, this is the central square in Milan and all the main tourist attractions are located around it. It’s a great meeting place amongst locals and tourists alike.

You’ll see unbelievable architecture, intricate sculptures and the wonderful Duomo itself.

You can start with a guided tour of the cathedral which is very informative, however the highlight of the tour for me is the rooftop tour that comes along with it. 

It allows you to enjoy a view over the city while seeing the spires and architectural intricacies of the rooftop sculptures and designs.

This is also a great place to take photos, especially as the sun is rising or setting in the background!

Book your fast track tour of the Milan Duomo here!

Exploring the rooftop of the Duomo cathedral in Milan, Italy

Exploring the rooftop of the Duomo cathedral in Milan, Italy

Sunset over Milan from the rooftop of the Duomo, Italy

Sunset over Milan from the rooftop of the Duomo, Italy

After exploring the wonderful interior of the Duomo, it’s time to head outdoors and enjoy the scenery that Milan has to offer!

From Piazza del Duomo you can easily visit Galleria Vittorio Emanuele, the Teatro della Scala and Castello Sforzesco, two must-sees that are close in the area.

Some of my favourite food places can also be found close to he Duomo; Luini for panzerotti (these are tiny fried calzone) and Spontini for pizza.

You can end the day by going for a stroll around the navigli. Not many people realise that Milan has canals (yes like Venice!) even if it only has two.

The Naviglio Grande canal was built in 1177 and has been expanded since then. This is one of the hip areas to hang out in evenings, where you can have a lovely aperitivo or dinner out amongst locals.

Admiring the perfect symmetry of Galleria Vittorio Emanuele in Milan, Italy

Admiring the perfect symmetry of Galleria Vittorio Emanuele in Milan, Italy

Best tours in Milan

Here are some of the best tours you can’t miss during your time in Milan.

Milan: Fast-Track Milan Cathedral and Terraces Guided Tour – Discover the beautiful Duomo and its stunning rooftop, without having to waste time queuing!

Best of Milan Tour with Skip-the-Line to Duomo & Last Supper – For the art lovers, no visit to Milan would be complete without seeing the Last Supper!

Milan: Grand City Highlights E-Bike Tour – Discover all the highlights of Milan on bike!

Girl walking in front of Castello Sforzesco in Milan, Italy

Castello Sforzesco in Milan, Italy

Day 12: Travel from Milan to Venice

Travelling by train from Milan to Venice offers some amazing views along the way.

The trip should take just over 2 hours, if you set off in the morning it will give you plenty of time to start getting your bearings around the famed city of Venice.

As soon as you get to Venice, after you drop off your bags, you should visit San Marco square, where you’ll find some some of the most beautiful basilicas in Venice.

If you love exploring old churches, why not take a tour of the basilica and the palace? This will give you a chance to learn a great deal about Venetian history and the culture of the city. 

Click here to book your skip the line tour of St Mark’s Basilica and the Doge’s Palace!

Piazza San Marco in the early evening

Piazza San Marco in the early evening

On the way back from San Marco square you will come across Ponte di Rialto, which is the most famous of the 400 bridges that are scattered throughout Venice.

The bridge offers magnificent views over the romantic city and it’s a wonderful spot to enjoy the sunset.

I spent one night in Venice with my mum and we slept at Hotel alle Guglie. This was ideal since it was located just outside the main touristy area of Venice, but was still within short walking distance of all the attractions.

The rooms were a bit small but they made up for it with an abundant breakfast, good price for value and great location.

Click here to book your stay at Hotel all Guglie!

Sunset on the grand canal in Venice

Sunset on the grand canal in Venice from Ponte di Rialto

Day 13: Explore Venice

Seeing as you only have one full day in Venice, you need to make the most of it by doing as many sightseeing activities as possible.

You can start the day with a gondola ride through the canals of Venice. These are a bit expensive but it’s such a traditional Venetian experience, how could you possibly miss it?

It will give you a unique and lovely view from the waterways, since you can see the ancient buildings that seemingly rise up out of the water.

I recommend starting your gondola cruise by Rialto Bridge, as it offers the best views and calmest waters.

There’s no need to book beforehand, since there are plenty of gondolas all over Venice waiting to take tourists around (kind of like taxi stands in any other city) and the price is standardised.

However if you want to be sure to have your experience confirmed you can also book online.

Click here to book your private gondola cruise in Venice!

Enjoying my gondola cruise around Venice

Enjoying my gondola cruise around Venice

Our gondola ride in Venice took us close to Rialto Bridge

Our gondola ride took us close to Rialto Bridge

After your gondola cruise you should visit the Bridge of Sighs or Ponte dei Sospiri, which is a very famous bridge in Venice. Despite popular stories, the name isn’t inspired by love stories.

The bridge connects the interrogation room to the prison, and it’s said that prisoners would sigh while crossing the bridge, as they took in their very last sight of Venice.

Not as romantic as you’d think right? But it’s still a beautiful spot in Venice and definitely worth a visit.

The Ponte dei Sospiri in Venice, Italy, one of the main things to see in the city

The Ponte dei Sospiri in Venice

From here you can take a tour of the Basilica di Santa Maria Della Salute. It’s a beautiful church with some of the best architecture you’ll ever find in the city (which is really saying something).

You can explore it yourself, or take a guided tour if you’d like to learn a little more about its history. Just across from the Basilica there’s also a killer sunset spot so you can sit here and enjoy the end of your Italy itinerary.

Best tours in Venice

Book one of these highly rated tours for your time in Venice!

Venice: Private Gondola Ride to Rialto Bridge – Go for a private gondola ride amongst the most beautiful canals of Venice!

Venice: Doge’s Palace Priority Admission Ticket – Skip the queue and visit this iconic site in Venice!

Venice: Small Group Wine Tasting and Food Tour with a Local – Go for a guided tour of all the best places to eat and drink in Venice with a local guide!

Sunset at the Basilica di Santa Maria della Salute in Venice, with gondola boats cruising in front it

Sunset at the Basilica di Santa Maria della Salute in Venice

Where to stay in Venice

I’ve already mentioned my great stay at Hotel alle Guglie, but I wanted to include some more accommodation options for every budget.

Budget: Combo Venezia – This hostel has a combination of modern dorms and a traditional courtyard. It’s also in a great location and has a very sociable atmosphere.

Mid-range: Hotel alle Guglie – I stayed here with my mum and found it a perfect compromise for those looking for a comfortable room, great location and affordable price.

Luxury: Ai Patrizi di Venezia – These luxury apartments are the perfect place to treat yourself during your Venice stay.

Cruising the canals of Venice, Italy, in our gondola

Cruising the canals of Venice in our gondola

Day 14: Fly home from Venice or extend your trip

It’s the 14th and final day of your Italy trip! The time has sadly come to fly home. However, if you manage to get a few extra days in, there is still so much more of Italy to see!

After hitting all the main cities and tourist landmarks, I imagine you’ll be ready to head out off the beaten track!

If you’re not ready to leave Venice just yet you can go on some awesome day trips from Venice. You can easily get to beautiful cities like Verona, Bologna and more.

If you want to see a completely different side to Italy, it’s time for a nature escape!

Exploring the Greek amphitheatre of Taormina at sunset

Exploring the Greek amphitheatre of Taormina at sunset

If you’re looking for beautiful beaches, I recommend you head to Sardinia for a boat trip, where you’ll get the chance to explore the beautiful archipelago and see a more tropical side to my wonderful country.

I’ve seen a lot of beaches all over the world, but I’m yet to see beaches that are better than the ones in Sardinia. If you’re looking for a mixture of sea and culture, you can also head to Sicily.

Here you can spend your afternoons with the sunshine warming your skin and your toes in the sand, before cooling off in the turquoise waters, but also exploring the food scenario and wandering around the cute towns. 

Relaxing on the nets of the catamaran we cruised in Maddalena Archipelago with at the Cavaliere Beach

A relaxing boat trip day in Sardinia, Italy

If you’re not a beach bum, or you’re visiting Italy during the cold months, you can head to Trentino for an adventurous escape.

In summer you can entertain yourself with some magnificent hikes, whilst in winter you can ski in world famous slopes.

Either way, you’ll get your heart pumping and your blood flowing. I’ve visited Trentino loads of times as a kid in winter, but only recently in summer and I can honestly say this region is stunning at any time of year.

It’s the perfect place for a nature escape after 2 weeks of city sightseeing in Italy.

Hiking at Rolle Pass in Trentino

Hiking at Rolle Pass in Trentino

You could also head to the south and visit the Sassi of Matera. This city went from being considered the “Shame of Italy” to being the European Capital of Culture in 2019. 

Don’t have two weeks to travel around Italy? Check out this Italy 10-day itinerary or my 7 days in Italy itinerary instead.

Enjoying the view over the Sassi of Matera in Italy

Enjoying the view over the Sassi of Matera in Italy

How to travel around Italy

Travelling within Italy is fairly easy.

We have a pretty decent railway system (Trenitalia is often late but it always gets you where you need to go), lots of bus companies, internal flights that connect most major and minor cities to each other, and pretty good roads for driving.

My personal favourite way to get around, as you may have guessed from this itinerary, is by train.

On long distances the Frecciarossa (the high speed train here in Italy) is often faster than flying, if you were to factor in also travel time to the airport, airport faff time and then travel time from the airport to home.

Driving in Italy is also great if you have a licence and friends to share the journey with, as it gives you more flexibility than the trains.

Exploring the rooftop of the Duomo cathedral in Milan, Italy

Exploring the rooftop of the Duomo cathedral in Milan, Italy

What to pack for 2 weeks in Italy

I’ve written a full Italy packing list with all the essential items you might need in Italy, however if you don’t want to open a new tab (I get it, it’s the end of the article, you’re tired and excited to start planning your trip) here’s a couple absolute must haves you don’t want to forget.

International adaptor – depends on where you come from but I like to always carry with me an international adaptor just to be sure.

It’s a bit more expensive than the one country adaptors but at least I only need one that I can take everywhere

Power bank – you don’t want to be wandering around the medieval streets of Siena and then all of a sudden your phone dies! You want to always be charged both for Google Maps and let’s be real, photo opportunities!

Steel water bottle – In Italy we’re not as ahead as other countries with water dispensers in restaurants and other public places, but generally speaking the tap water is drinkable everywhere, so if you want to cut down on your plastic consumption and save some cash in the process, don’t forget your own water bottle!

Exploring the side streets, canals and bridges of Venice, Italy

Exploring the side streets, canals and bridges of Venice, Italy

Final thoughts on the best Italy itinerary

If you’re looking for the best way to visit Italy in 2 weeks, you’ve just found it! I’ve made sure that this Italy itinerary is jam-packed full of exciting entertainment, sightseeing opportunities and adventures you’ll treasure forever.

Yes it’s a bit of a touristy itinerary, but after all tourist places are so for a reason, usually because they’re beautiful! 

Travelling to all the major cities and tourist destinations is a must during your 14 days in Italy trip. However that doesn’t mean you shouldn’t venture a little off the beaten track to find the hidden gems that will keep you coming back. 

If quaint cities, beautiful architecture and ancient history all sound right up your ally, then Italy is the place for you to roam. I hope you find this 2-week Italy itinerary useful in planning your own trip.

From an Italian point of view, I tried my best to include all the most beautiful cities that I would want any new traveller to visit. I hope you’ll fall in love with my country as much as me! 

If you’re still looking for more Italy advice, check out my guide on the 10 things to know before travelling to Italy.

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Collage of Manarola in Cinque Terre, the duomo of Florence and Ponte di Rialto in Venice with text overlay saying "how to see Italy in 14 epic days"

The colourful houses of Manarola in Cinque Terre with text overlay saying "how to spend 2 weeks in Italy"

Collage of Rome, Venice and Cinque Terre with text overlay saying "explore Italy in 2 weeks"

The colourful rooftops of the Amalfi Coast with text overlay saying "how to spend 2 weeks in Italy"

Photo collage of the leaning tower of Pisa, the Colosseum and Piazza del Duomo in Milan with text overlay saying "how to see Italy in 2 epic weeks"

The Duomo of Florence lit up during blue hour with text overlay saying "Italy in 2 weeks"

The BEST Milan 1-Day Itinerary (Written By A Local!)

Wednesday 8th of September 2021

[…] READ MORE: 2 EPIC WEEKS IN ITALY […]

Nancy

Sunday 21st of March 2021

Great article!

Jeff

Thursday 26th of December 2019

Thanks for the fabulous guide! We are going to try a 2 week trip to Italy next summer and your guide is very close to what we want to do. We were thinking though of replacing one city with Naples/Amalfi Coast. If we did that, would the best way to add it is between Rome and Florence? Grazie!

Irene Carroll

Sunday 13th of October 2019

Dear Greta, Your blog is amazing! Very interestingly written with amazing photographs. I will be booking my 10th (and last - money will have dried up then) in 2021 or 2022 and I will certainly consider doing bookings through your blog page. I will be visiting some places I did not have enough time to see (I always had co-travellers) with me eg top of Milan Duomo, Sforza, Teatro Scalo in Milan, Siena, Pisa city beyond the Duomo and tower :) :) Yours is the first blog that has kept me interested from start to finish - thank you!!!