Two Week Italy Itinerary: Perfect for First Timers!

Fitting in all you want to see with a two week Italy itinerary can seem daunting, but it’s actually a great amount of time! You can fit so much in to just two weeks, and still find time to relax.

After 16 days in Italy with my family, and returning 4 more times since, I can safely say this is a quality (and yes, BUSY) itinerary!

This has a perfect combination of iconic Italy, while also offering authentic experiences.

My two week Italy itinerary map:

Some links in this post are affiliate links, meaning if you book or buy something through one of these, I may earn a small commission (at no additional cost to you!).

Save these images to help you plan!

DAY 1- MILAN – Italy 10 Days

You might not think it, but Milan has the most populated metro area in all Italy. It’s all about shopping and fashion, and not as much of the “classical” Italy you might envision.

First visit the Duomo di Milano (walk on the duomo rooftop!) and the piazza in front. Nearby, go to the Galleria Vittorio Emanuele II for some scenic shopping! It looks like a grand museum, but it’s actually just a super elegant mall.

Nearby, you can also visit the Castello Sforzesco, and a handful of museums. If you’re an art lover, you can also see the famed “Last Supper” painting by Leonardo da Vinci at the Santa Maria delle Grazie Monastery.

Lodging: Hotel Teco Milano

DAY 2- VENICE

Early in the morning, take the train from Milan to Venice. This will take about 4.5 hours total, and you’ll arrive to the city by water taxi!

Venice is magical, one of a kind, and its gondolas are a true icon of Italy. It’s also a place that many have a “love-hate” relationship with.

Increased tourism (largely thanks to the cruise ships) has made it almost unbearably crowded in summer, so have patience! If you want good photos, getting up early is key!

On your first day, explore the canal filled streets. Stop at the Rialto Bridge, and the Chiesa di San Barnaba (the church from the Indiana Jones movie!). After, go up to the Campanile di San Marco for views of the city below!

Next, hop over to St. Mark’s Basilica, and enjoy the beautiful chaos that is St. Mark’s Square. Also try to visit the Doge’s Palace. This was one of my favorite things in the city!. It also gives you the chance to walk through the famous “Bridge of Sighs”.

Get your Doge’s Palace tickets in advance!

bridge of sighs, venice, doge's palace, two week italy itinerary — *The “Bridge of Sighs”*

Lodging: See a list of Venice hotels

DAY 3- VENICE

On your second day, take a “Grand Canal” cruise of Murano, Burano, and Torcello. You can escape the crowds of the city, and see some truly beautiful places. Make sure to save money for some famous hand-blown glass from Murano!

When you get back to the city, take a gondola ride through the canals. My suggestion is to do a gondola ride in the evening, as you can save money and enjoy a more quiet and romantic experience.

Book your tour to Murano, Burano & Torcello!

Lodging: Corte del Paradiso Venezia

DAY 4- CINQUE TERRE

Very early in the morning (I’m talking 5am), head back to the train station for a 5 hour ride from Venice to Levanto. To visit the famous five cities that constitute “Cinque Terre”, this is a good base to have.

Once settled, navigating the transit system to try and see Cinque Terre in one day is relatively easy. Take a short 20 minute train to Monterosso (or the ferry, weather permitting), and go from there! After Monterosso, you can either hike (about 2 hours) to Vernazza, or take a quick train or ferry.

From there you can hike to Corniglia, then on to Manarola, and end in Riomaggiore. Once you’re ready, take the train back to Levanto for the night. If you have additional time- add an extra day here! The Levanto bike trail is one of the most scenic in the world.

Riomaggiore

Manarola

Monterosso

Corniglia

Manarola Town

***Lodging: Link for hotels in Levanto***

DAY 5- PISA + LUCCA + FLORENCE

Head back to your new favorite place, the Italian train station! From here, head to the town of Pisa! You only need an hour there to see the famous leaning tower, and then move on to the small town of Lucca.

In Lucca, admire the main plaza, then rent a bike for the afternoon. When you’re ready, hop on the train again to Florence!

Florence is chock full of things to do and see. In general though, on your first day you can:

Check out the iconic Piazza del Duomo and admire the cathedral
Visit the Uffizi Gallery and its Renaissance masterpieces
Walk across the famous Ponte Vecchio, a colorful medieval bridge
Stop by the church of Santo Spirito and surrounding neighborhood

duomo, firenze, cathedral, florence, italy — *Il Duomo di Firenze (Florence Cathedral)*

ponte vecchio, florence, firenze, italy — *Ponte Vecchio (Old Bridge)*

Lodging: List of hotels in Florence

DAY 6- FLORENCE

Exploring on foot and happening upon unexpected sites is probably the best part about traveling through Italy, but once you’ve had a chance to eat some world-class meals, here is what you can do on your second day:

Accademia Gallery to see the famous David sculpture
Santa Croce Church, where Michelangelo and Galileo are buried
Visit the beautiful Boboli Gardens
In the evening, check out the Piazzale Michelangelo, a hillside viewpoint, for the best view of the city below (especially at sunset!)

piazzale michelangelo — *View from the Piazzale Michelangelo*

Lodging: List of hotels in Florence

DAY 7- FLORENCE (Tuscany: San Gimignano, Monteriggioni, Siena)

There are of countless companies running Tuscany day trip tours leaving from Florence, so it can be hard to pick. When I visited, my family had a driver take us to the small medieval towns of San Gimignano and Monteriggioni first.

Siena

In the afternoon, we headed to Siena. We had lunch, gelato, and got to admire the church and the main square.

On the way back to Florence, we stopped at Fattoria La Tancia, a local vineyard. We had a private wine tasting and olive oil tour. This was probably one of the most fun days we had (the wine possibly contributed to this!).

Lodging: List of hotels in Florence

DAY 8- ASSISI

The train ride to Assisi takes about 3.5 hours, and if you are Catholic, I especially recommend visiting this city!

Assisi is the home of the famous animal-loving Saint Francis. Visiting the Basilica in his name is the main reason to visit, but the surrounding countryside views are incredible too!

This city is a little less touristy-feeling than others in Italy, and you can get some really quality Italian food here while learning about the 13th century saint’s life and legacy.

Lodging: Hotel ideas in Assisi

DAY 9 – SORRENTO + AMALFI COAST

This is a long travel day! Start day by taking the 5.5 hour train from Assisi to Sorrento. Once you settle in, explore this scenic town! Walk around anywhere and you will see beautiful views (especially at sunset!)

Sorrento, Sunset, Italy — *A Sorrento sunset*

Sorrento, Vesuvius, Sunset — *Mt. Vesuvius – as seen from the hotel window!*

If you want to maximize your time, take a driving tour of the Amalfi coast! It is one of the most absolutely scenic drives you can have in your life.

If you can, stop over in the towns of Ravello and Amalfi! You can rent a car and do it on your own, or check out these Amalfi tours.

ravello, amalfi coast, italy — *View from Ravello*

Lodging: Imperial Hotel Tramontano

DAY 10 – SORRENTO (Capri)

From Sorrento, take a short public ferry out to the island of Capri. Famous for massive yachts and celebrity visits, it’s also where the ancient legend of the Sirens originated. It has so much beauty, but also a fascinating history.

There is enough to do in Capri for a week, but with one day I’d pick 1 or 2 of the following:

Visiting Anacapri, and riding the chairlift to Monte Solaro
Swimming in one of the private beach clubs
Taking a boat tour around the island, and seeing the Faraglioni rocks
Swimming in the eerie and one-of-a-kind Grotta Azzurra (blue grotto)

Blue Grotto Capri

The three “Faraglioni” rocks

It’s very doable on your own, but if you prefer a guide there are options for day tours on Capri!

Lodging: Imperial Hotel Tramontano

DAY 11 – SORRENTO (Positano)

Relax by the beaches of Sorrento, or explore more of its small town. Known for its limoncello, it is all too easy to do!

Alternatively, you can do what I did! We rented a car and headed to the town of Positano for the day. Incredibly beautiful, you can roam around on foot for the whole day and be perfectly content!

Lodging: Imperial Hotel Tramontano

DAY 12- SORRENTO (POMPEII)

Today it’s time to learn about the dark side of that volcano you’ve been looking at all week! Visiting the archaeological site of ancient Pompeii is also one of the most memorable things you can do in central Italy.

In 79AD, the still-active volcano of Mount Vesuvius erupted, burying the small city below in a thick blanket of ash. Nearly 2,000 of its citizens died. The city was abandoned, and lost to history.

It was accidentally “re discovered” in 1748. While a bit sad, and even creepy, it is remarkable to see the plaster “body casts” of the unfortunate victims and the poses they were in at the moment of their deaths.

It’s possible to go on your own, but there are organized Pompeii day trips too. The site is large with little signage, so I recommend getting a guide at least while you’re there. Otherwise, you will miss out on so much context, and won’t fully appreciate what you’re looking at.

All roads lead to Rome, so take the 2 hour train to Rome that evening.

Lodging: Luxury Apartment Campo de Fiori

DAY 13- ROME + VATICAN CITY

I’ve had the privilege of visiting Rome on 4 separate occasions, and I’m still not tired of it!! There is so much to see that it’s hard to chop it down to two days! However, in a nutshell, here’s what I’d suggest. Read on for helpful Rome tips for first time visitors!

The Pantheon (early morning or late evening!)
Trevi Fountain (throw a coin in!)
Piazza Navona
Piazza del Popolo (hike to the hill above it at sunset for epic views!)

Vatican City
- St. Peter’s Basilica (free entry)
- St. Peter’s Square

st peters basilica, vatican, rome — *View of St. Peter’s Basilica*

Want more time in the Vatican? See organized Vatican tours !

Lodging: Luxury Apartment Campo de Fiori

DAY 14- ROME

On your last day in Rome, make sure to knock out these bucket list items:

The Colosseum (buy tickets beforehand!)
The Roman Forum (do the audio tour, or hire a guide!)
The eerie Catacombs and historic Appian Way (tours found here)
Altar of the Fatherland (a.k.a. The “Wedding Cake” monument)
Spanish Steps and Trastevere Neighborhood

roman forum — *Il Foro Romano (Roman Forum)*

If you can’t decide, there is a huge lineup of guided trips and sightseeing options on my Viator day trip page.

Lodging: Luxury Apartment Campo de Fiori

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March 5, 2024 in Italy, Itineraries, Travel

3 Comments

Reply Britney Uehara June 23, 2021 at 9:46 am

What do you do with your luggage for the day when traveling by train(day 5)?

If you had to pick cinque terre or amalfi coast?

Reply Michelle W. June 28, 2021 at 8:59 pm
Hi Britney- That’s a good question! There are usually lockers at train stations that you can rent out by the hour using coins to store your bags in while you explore! Also I think both Cinque Terre and Amalfi are INCREDIBLE, so it really just depends what interests you more. I think Amalfi is better for a short visit, and can be seen more via car whereas in Cinque Terre you’ll want more time to get out and hike and visit the towns via boat or bike.

Reply Travelite Taj Tours July 9, 2022 at 10:09 am

Thanking you for your amazing information really like these places.. and your blog is also a complete package…..

Fitting in all you want to see with a two week Italy itinerary can seem daunting, but it’s actually a great amount of time! You can fit so much in to just two weeks, and still find time to relax.

After 16 days in Italy with my family, and returning 4 more times since, I can safely say this is a quality (and yes, BUSY) itinerary!

This has a perfect combination of iconic Italy, while also offering authentic experiences.

My two week Italy itinerary map:

Save these images to help you plan!

DAY 1- MILAN – Italy 10 Days

You might not think it, but Milan has the most populated metro area in all Italy. It’s all about shopping and fashion, and not as much of the “classical” Italy you might envision.

First visit the Duomo di Milano (walk on the duomo rooftop!) and the piazza in front. Nearby, go to the Galleria Vittorio Emanuele II for some scenic shopping! It looks like a grand museum, but it’s actually just a super elegant mall.

Nearby, you can also visit the Castello Sforzesco, and a handful of museums. If you’re an art lover, you can also see the famed “Last Supper” painting by Leonardo da Vinci at the Santa Maria delle Grazie Monastery.

Lodging: Hotel Teco Milano

DAY 2- VENICE

Early in the morning, take the train from Milan to Venice. This will take about 4.5 hours total, and you’ll arrive to the city by water taxi!

Venice is magical, one of a kind, and its gondolas are a true icon of Italy. It’s also a place that many have a “love-hate” relationship with.

Increased tourism (largely thanks to the cruise ships) has made it almost unbearably crowded in summer, so have patience! If you want good photos, getting up early is key!

On your first day, explore the canal filled streets. Stop at the Rialto Bridge, and the Chiesa di San Barnaba (the church from the Indiana Jones movie!). After, go up to the Campanile di San Marco for views of the city below!

Next, hop over to St. Mark’s Basilica, and enjoy the beautiful chaos that is St. Mark’s Square. Also try to visit the Doge’s Palace. This was one of my favorite things in the city!. It also gives you the chance to walk through the famous “Bridge of Sighs”.

Get your Doge’s Palace tickets in advance!

Lodging: See a list of Venice hotels

DAY 3- VENICE

On your second day, take a “Grand Canal” cruise of Murano, Burano, and Torcello. You can escape the crowds of the city, and see some truly beautiful places. Make sure to save money for some famous hand-blown glass from Murano!

When you get back to the city, take a gondola ride through the canals. My suggestion is to do a gondola ride in the evening, as you can save money and enjoy a more quiet and romantic experience.

Lodging: Corte del Paradiso Venezia

DAY 4- CINQUE TERRE

Very early in the morning (I’m talking 5am), head back to the train station for a 5 hour ride from Venice to Levanto. To visit the famous five cities that constitute “Cinque Terre”, this is a good base to have.

Once settled, navigating the transit system to try and see Cinque Terre in one day is relatively easy. Take a short 20 minute train to Monterosso (or the ferry, weather permitting), and go from there! After Monterosso, you can either hike (about 2 hours) to Vernazza, or take a quick train or ferry.

From there you can hike to Corniglia, then on to Manarola, and end in Riomaggiore. Once you’re ready, take the train back to Levanto for the night. If you have additional time- add an extra day here! The Levanto bike trail is one of the most scenic in the world.

Lodging: Link for hotels in Levanto

DAY 5- PISA + LUCCA + FLORENCE

Head back to your new favorite place, the Italian train station! From here, head to the town of Pisa! You only need an hour there to see the famous leaning tower, and then move on to the small town of Lucca.

In Lucca, admire the main plaza, then rent a bike for the afternoon. When you’re ready, hop on the train again to Florence!

Florence is chock full of things to do and see. In general though, on your first day you can:

Check out the iconic Piazza del Duomo and admire the cathedral

Visit the Uffizi Gallery and its Renaissance masterpieces

Walk across the famous Ponte Vecchio, a colorful medieval bridge

Stop by the church of Santo Spirito and surrounding neighborhood

Lodging: List of hotels in Florence

DAY 6- FLORENCE

Exploring on foot and happening upon unexpected sites is probably the best part about traveling through Italy, but once you’ve had a chance to eat some world-class meals, here is what you can do on your second day:

Accademia Gallery to see the famous David sculpture

Santa Croce Church, where Michelangelo and Galileo are buried

Visit the beautiful Boboli Gardens

In the evening, check out the Piazzale Michelangelo, a hillside viewpoint, for the best view of the city below (especially at sunset!)

Lodging: List of hotels in Florence

DAY 7- FLORENCE (Tuscany: San Gimignano, Monteriggioni, Siena)

There are of countless companies running Tuscany day trip tours leaving from Florence, so it can be hard to pick. When I visited, my family had a driver take us to the small medieval towns of San Gimignano and Monteriggioni first.

In the afternoon, we headed to Siena. We had lunch, gelato, and got to admire the church and the main square.

On the way back to Florence, we stopped at Fattoria La Tancia, a local vineyard. We had a private wine tasting and olive oil tour. This was probably one of the most fun days we had (the wine possibly contributed to this!).

Lodging: List of hotels in Florence

DAY 8- ASSISI

The train ride to Assisi takes about 3.5 hours, and if you are Catholic, I especially recommend visiting this city!

Assisi is the home of the famous animal-loving Saint Francis. Visiting the Basilica in his name is the main reason to visit, but the surrounding countryside views are incredible too!

This city is a little less touristy-feeling than others in Italy, and you can get some really quality Italian food here while learning about the 13th century saint’s life and legacy.

Lodging: Hotel ideas in Assisi

DAY 9 – SORRENTO + AMALFI COAST

This is a long travel day! Start day by taking the 5.5 hour train from Assisi to Sorrento. Once you settle in, explore this scenic town! Walk around anywhere and you will see beautiful views (especially at sunset!)

If you want to maximize your time, take a driving tour of the Amalfi coast! It is one of the most absolutely scenic drives you can have in your life.

If you can, stop over in the towns of Ravello and Amalfi! You can rent a car and do it on your own, or check out these Amalfi tours.

Lodging: Imperial Hotel Tramontano

DAY 10 – SORRENTO (Capri)

From Sorrento, take a short public ferry out to the island of Capri. Famous for massive yachts and celebrity visits, it’s also where the ancient legend of the Sirens originated. It has so much beauty, but also a fascinating history.

There is enough to do in Capri for a week, but with one day I’d pick 1 or 2 of the following:

Visiting Anacapri, and riding the chairlift to Monte Solaro

Swimming in one of the private beach clubs

Taking a boat tour around the island, and seeing the Faraglioni rocks

Swimming in the eerie and one-of-a-kind Grotta Azzurra (blue grotto)

It’s very doable on your own, but if you prefer a guide there are options for day tours on Capri!

Lodging: Imperial Hotel Tramontano

DAY 11 – SORRENTO (Positano)

Relax by the beaches of Sorrento, or explore more of its small town. Known for its limoncello, it is all too easy to do!

Alternatively, you can do what I did! We rented a car and headed to the town of Positano for the day. Incredibly beautiful, you can roam around on foot for the whole day and be perfectly content!

Lodging: Imperial Hotel Tramontano

DAY 12- SORRENTO (POMPEII)

Today it’s time to learn about the dark side of that volcano you’ve been looking at all week! Visiting the archaeological site of ancient Pompeii is also one of the most memorable things you can do in central Italy.

In 79AD, the still-active volcano of Mount Vesuvius erupted, burying the small city below in a thick blanket of ash. Nearly 2,000 of its citizens died. The city was abandoned, and lost to history.

It was accidentally “re discovered” in 1748. While a bit sad, and even creepy, it is remarkable to see the plaster “body casts” of the unfortunate victims and the poses they were in at the moment of their deaths.

It’s possible to go on your own, but there are organized Pompeii day trips too. The site is large with little signage, so I recommend getting a guide at least while you’re there. Otherwise, you will miss out on so much context, and won’t fully appreciate what you’re looking at.

All roads lead to Rome, so take the 2 hour train to Rome that evening.

Lodging: Luxury Apartment Campo de Fiori

DAY 13- ROME + VATICAN CITY

I’ve had the privilege of visiting Rome on 4 separate occasions, and I’m still not tired of it!! There is so much to see that it’s hard to chop it down to two days! However, in a nutshell, here’s what I’d suggest. Read on for helpful Rome tips for first time visitors!

***Lodging: Link for hotels in Levanto***