Taste of Italy! 2 Week Italy Itinerary from North to South

Italy is one of the most traveled to countries on the planet and deservingly so! It’s one of our favorites in Europe and the absolute winner when it comes to our taste buds’ opinion. But where do you start in planning your trip? Deciding between all the major cities and the scenic in-betweens is challenging, to say the least. To help out and get you started, we’ve put together this 2 week itinerary for your amazing trip to Italy!

What Kind of Itinerary is This?

View of Piazza del Campo in Siena

Most itineraries out there for Italy will have you going from city to city to city without stopping.

Some two week itineraries we’ve found even suggest going from Rome to Naples, then retracing your steps back to Rome, then to Florence, then Milan and ending in Venice. Phew!

We think that’s just too much on your plate for a two week itinerary. Florence itself can keep you wonderfully entertained for several days with its awe-inspiring architecture and museums. There is so much to do!

While cramming all the major sights into two weeks sounds like a great time in theory, the reality is traveling non-stop from place to place can exhaust you.

What about finding those off-the-beaten-path types of places? The ones you’ll be dying to tell everyone about? It’s important to leave time for those too!

Instead of rushing you from one popular Italian destination to the other, we’ve built this two week Italy itinerary to guide you to the must-see sights but to also allow for some adventure time.

Whether your adventure means discovering more than just a city’s tourist attractions or roaming the Tuscan countryside and sampling all the Chianti and pecorino you can, we’re big fans of seeing a lot at an enjoyable pace. That sweet spot of traveling.

Is it your first time to Italy? Is it your first time to Europe? If so, the urge to fit as much as you can in your itinerary is strong. However, skipping a city or two allows you the opportunity to see more than what most other tourists do in your destination. You’ll likely return to Europe again so don’t try to fit it all in at once!

If it is your first time on the continent then read up on some tips for first-timers in Europe. We’ve traveled it non-stop for 13 months and share our advice!

We give an overview of each region below before diving into the details of your trip. Why do we do this? We feel it helps you understand why we chose this itinerary for a two week trip to Italy.

Italy Itinerary Overview and Quick Tips!

Dante Alighieri statue in Naples

Getting Around

Driving in Italy isn’t for the faint of heart, especially in bigger cities and towns. That’s not to say you shouldn’t drive around the Tuscan hills or along the Amalfi Coast. It would be a beautiful drive and in many ways more convenient.

But if you’re not up for sharing the road with drivers on narrow streets or parking in tight spaces then Italian trains are the best way of getting around. They’re much more reliable and more enjoyable than buses in Italy.

Should I Follow This Itinerary Exactly?

Of course not! At the end of the day, these two weeks in Italy are all yours. We’re just here to suggest a guide to help you plan a great trip. We do think our itinerary is pretty awesome, though.

We think that flying into Rome or Florence (odds are the cheaper flight will be Rome) makes the most sense for our itinerary but if you find a cheap flight deal to Milan or Venice or elsewhere instead then, by all means, start there!

Whether you’re coming from the United States or you’re already in Europe, flight deals are constantly coming and going. You just have to be diligent.

Read up on some tips to find cheap flights before booking! A cheaper flight means more spending money in Italy!

Tuscany and Florence for 5 days

Tuscan town on a hill

This region of Italy is famous for its beautiful villages, rolling hills, and vineyard after vineyard. The most famous city in Tuscany is, of course, Florence!

Florence is teeming with history, art, and architecture. Many of the great Renaissance artists you know and love spent some time in Florence.

When researching Florence you might stumble across the Firenzecard. This card covers the entry costs (and offers fast track tickets) for many of Florence’s museums and galleries. Even so, you may want to pass on it.

We say this because visiting enough museums and galleries to make the price of the card worth it will burn you out. The thing about art (and a majority of Florence’s attractions revolve around art) is that you need to appreciate it, which takes time and a lot of brainpower. If you see multiple museums in one day then you’ll likely be a zombie by the end of it.

There’s also so much more to see in Tuscany than Florence, which is why we recommend spending 3 days in Florence and the rest of your time amongst the smaller Tuscan towns like Siena and San Gimignano.

Rome for 2 days

The Trevi Fountain in Rome

Rome is massive city and is a must for first-timers and veterans to Italy alike! You can’t see everything in Rome in 3 days but you can knock out a few of the main sites like the Colosseum, the forum, and the Vatican.

Our biggest tip for Rome? Book a tour in advance for the Colosseum and the forum

Most tours include both attractions for one price. The reason we recommend a guide is because you’ll be looking at a bunch of ruins and structures and it’s nice to have some context.

With this said, be careful about the guide you book! We’ve been on two guided group tours of the Colosseum and the forum. The first guide was engaging, entertaining, and informative while the second guide was informative but so dry and boring that we felt like falling asleep where we stood.

Another bonus about booking a guided tour is that you get to skip the long lines.

Campania (Naples, Pompeii and the Amalfi Coast) for 4 days

View of Naples and Mount Vesuvius from Castel Sant'Elmo

Many people think that Naples is dirty and unsafe, so they leave it off their itinerary. We think this is a huge mistake!

We found Naples to be authentic, charming, vibrant, and full of some of the most incredible food during our time in Italy. You’ll see as much trash in Naples as you’ll see in other parts of Italy and there may be more graffiti and some buildings could use some restoration but that’s all part of the charm of Naples.

In addition to Naples, you’ve got Pompeii and the stunning Amalfi Coast next door. This is just a sample of southern Italy but it’s a great place to start!

Finally, That’s Over! Let’s Talk About a Memorable Two Weeks in Italy

Day 1 – Arrival and Travel to Florence

Florence at sunset

Florence is smack dab in the middle of Venice, Rome, and Milan so it’ll be easy for you to hop on a train and get to Florence. If your flight lands in Venice or Milan then you can adjust the itinerary to do a little sightseeing before heading to Florence.

What about jet lag? Yes, if coming from afar you’re going to experience jet lag. It’s unavoidable, unfortunately, but you can minimize it. Read up on some of Skyscanner’s tips so you don’t have a rough arrival!

If you arrive in Florence in the early afternoon then this would be the perfect time to visit Cattedrale di Santa Maria del Fiore (Il Duomo di Firenze) and the bronze doors on the Baptistry of Saint John. Known as the Gates of Paradise by Lorenzo Ghiberti, these beautiful doors depict scenes from the Bible.

Day 2 – Uffizi Gallery, Ponte Vecchio, Bardini Garden

Ponte Vecchio in Florence on a cloudy day

Your first full day in Florence! Start off at the Uffizi Gallery. Make sure to book your tickets in advance (and pay extra for your entrance reservation). Lines for this museum can be very long and no wonder!

Some worthwhile pieces of art to keep an eye out for:

Tickets are 12€ and Entrance Reservations are 4€

Just observing the art is always great but sometimes you want a little context. There are many audio guide apps available for the Uffizi Gallery. Many are free or offer affordable in-app purchases.

After you’ve had your fill of art at the Uffizi Gallery, it’s time to get your fill of Italian street food! All’Antico Vinaio is great for a quick and delicious bite to eat. The line can be long but it’ll move quickly.

If you can wait to eat, make your way to Bardini Garden for lunch with a view! These beautiful gardens will give you an incredible vista of Florence.

Ponte Vecchio! This is the oldest bridge in Florence and the only bridge that wasn’t destroyed in World War II. Along the bridge you’ll find gold shops. It can be pretty crowded during the day so it’s best to go at night, unless you’re wanting to do some shopping.

While walking along the bridge can be a pleasant experience, the best way to view it is from below! Take a boat cruise on the Arno and see Florence from a new perspective.

After a long day of exploring it’s time to enjoy some Italian food! In all honesty, you can wander into almost any decent looking restaurant and have a great meal in Florence.

Once you’re full and glowing from a couple glasses of wine you can wander around the beautiful streets of Florence at night!

Day 3 – Accademia, San Lorenzo Market, and Medici Chapel

The David by Michelangelo

Let’s start today with another important art museum! Ever heard of The David by Michelangelo? Of course you have! This impressive sculpture can be seen in person at the Accademia Gallery.

Like the Uffizi, it’s best to order your tickets online and pay the extra fee for reserved entrance. This way you can skip the line and spend your day enjoying art instead of the backside of the people in front of you.

Once you’ve seen all the masterpieces you can stand, make your way to San Lorenzo Market for lunch and some shopping!

San Lorenzo market is a great place to buy souvenirs. Outside you’ll find high-quality leather goods like purses, wallets, gloves, jackets and more. Don’t be afraid to haggle!

Once you’ve thoroughly explored outside, make your way indoors to the food market for lunch (and more souvenirs). There are many food vendors selling fresh produce, cheese, and meats. In addition, you can find specialty shops selling sauces, oils, and vinegars! Once you’ve built up an appetite it’s time to eat lunch at the food court.

After the market you have your choice of visiting the Medici Chapel to see Dawn and Dusk by Michelangelo, wandering around the streets of Florence or, if you didn’t see it on your first day, visiting il Duomo di Firenze.

Finish your day with a pasta making class for dinner!

Day 4 – Day Trip to Siena

Facade of Duomo in Siena

Siena is an essential Tuscan town about an hour and a half outside of Florence by train. Spend the day wandering around the beautiful streets of Siena, taking in the immense Piazza del Campo and exploring the Cathedral complex, which includes the baptistry, Museo dell’Opera, and a great view of Siena!

Look no further than our one day in Siena itinerary that hits all the main sights but also takes you to some lesser-traveled gems!

Day 5 – Wine Tasting and Gelato in San Gimignano

Shops lighting up the streets of San Gimignano

This is a day you may want to rent a car; otherwise, you’re probably stuck on an Italian bus, which can be a stressful experience.

We’ve yet to mention wine in our 2 week Italy itinerary so we think a wine tasting is in order! We had an intimate and educational experience at Villa Spoiano, tasting their organic wines and oils and learning about the process of growing and making Chianti and other varieties of wine.

While we recommend Villa Spoiano’s wine tasting, you can find many others on Airbnb and TripAdvisor.

If you rent a car, make sure you have a designated driver or you’ve waited long enough to drive afterwards. Know your limits!

After your wine tasting it’s time for some medieval charm! San Gimignano is a medieval town, perfectly perched on the top of a Tuscan hill. Be sure to explore its streets, visit its duomo and grab some world-famous gelato. Read our post to find out more about what to do in San Gimignano.

Day 6 – Arezzo or Pisa

Piazza grande in Arezzo

It’s your last day in Tuscany! Sad day.

You have 2 choices for day trips out of Florence. You can hold up the Tower of Pisa and explore the other buildings in the Square of Miracles, which includes the Duomo, Baptistry, and the ancient monumental cemetery (Camposanto).

Or you can visit the less-traveled Arezzo. Not only is this town full of art, history and delicious food but it’s also on your way to Rome (whereas Pisa is a little out of the way).

If you find yourself in Arezzo on the first Sunday of the month and the Saturday before then you’re in for a treat! The monthly antique market takes over Piazza Grande and the surrounding streets.

Otherwise, make your way to the top of the hill to visit the duomo as well as get a view of the surrounding countryside. Then enjoy a hot piadina from La Tua Piadina before seeing Piero della Francesca’s Legend of the True Cross Frescoes inside Basilica di San Francesco.

Day 7 – Ancient and Free Sights in Rome!

The Colosseum and the Forum in Rome during a two week trip in Italy

All roads lead to Rome and so does our itinerary! It’s a city packed full of art, history, and world-famous food.

Start your day off at one of the most iconic sights of Rome: the Colosseum. Built between 70 and 72 AD, this structure has seen gladiatorial fights, chariot races and other spectacles. We recommend booking a tour in advance that includes the Colosseum, the Roman Forum, and Palatine Hill so that you can learn all about these ancient sights! They’re all next door to each other.

Be sure to pick your tour wisely by checking reviews. As we mentioned in our overview, there are good guides and there are boring guides.

Once you’ve had your fill of ancient Rome you might be feeling a bit peckish but before you settle down for some lunch make your way to Basilica di San Pietro in Vincoli. You can enter for free and make your way to the back right of the church where you’ll see the Horned Moses by Michelangelo.

From here you can grab lunch and then continue exploring some of the (free) highlights of Rome like the Trevi Fountain, the Pantheon, and Spanish Steps. See them in that order and as you walk from the Pantheon to the Spanish steps stop at Giolitti for some well-earned gelato.

Day 8 – Explore the Vatican and Get Lost in the Trastevere Neighborhood

Begin your day on the other side of the Tiber River at the Vatican. Start off with the Vatican Museums. Lines can be long so either book a guided tour or buy skip-the-line tickets online. Once finished with the museums you can enter Saint Peter’s Basilica for free.

If you can still feel your legs after all the walking, head to the Trastevere neighborhood where you can grab a bite to eat and step inside some beautiful churches like the Basilica di Santa Maria, with its golden mosaics, or the Basilica di Santa Cecilia.

Exploring the Trastevere neighborhood is the perfect way to spend the afternoon and evening of your second day in Rome.

Day 9 – 11 – Explore the Amalfi Coast and Surrounding Areas

Colorful town on the Amalfi Coast during two weeks in Italy trip

This 2 week Italy itinerary has been a little on the busy side so far (mainly cities) so now we think it’s time for a bit of a break on the beautiful Amalfi Coast. You can set up base in Sorrento to explore the area or pick one of the towns in the Riserva Statale Valle delle Ferriere. Either way, it’s the perfect place to take it slow and recharge.

From Positano to Salerno, there’s so much natural beauty and history to discover. We’re leaving these next three days up to you but we think it’s best spent on the Amalfi coast.

You could easily:

  • Hike the Path of the Gods
  • Visit the island of Capri
  • Snorkel or dive in the Green or White grottos
  • Spend your days on the beach
  • Explore Riserva Statale Valle delle Ferriere
  • Go on a sailing excursion
  • Stroll around Sorrento’s Old Town

Day 12 – Pompeii & Naples

Basilica in the Pompeii forum

After you’ve had your 3 relaxing days along the Amalfi coast it’s time to dive back into history and eat some of the best food in Italy. We recommend spending your morning exploring Pompeii. Tour groups are everywhere so the earlier you start the better. You can visit Pompeii with a guide (TripAdvisor or Airbnb have a ton of Pompeii tours) or wander around on your own.

We preferred seeing it on our own (with the help of a free Rick Steves app). Be sure to read our guide on how to see Pompeii on a budget if you’d like to save a little and go at your own pace!

Then it’s time to head to Naples!

If you arrive in Naples before 4:30 pm then you should book a free walking tour with Napoli That’s Amore. They keep their groups small so that your experience is enjoyable. Be sure to reserve your spot online ahead of time!

If you want to pass on the free walking tour then head to the Royal Palace of Naples and Piazza del Plebiscito. Here you can explore Basilica Reale Pontificia San Francesco da Paola or tour the San Carlo Theatre.

Dinner is up to you but you can’t go wrong with pizza in Naples. But there’s more than just the pizza pie in this foodie haven. Get the down-low on what to eat in Naples!

Day 13 – Explore Spaccanapoli in Naples

Spaccanapoli in Naples

This is the perfect day to explore Spaccanapoli, the main thoroughfare of Naples, to its fullest! From the Museo Cappella Sansevero to Castel Sant’Elmo and all the bites in between, we’ve got you covered in our one day in Naples itinerary.

Day 14 – Flight Home

Depending on your flight, you may have more time to wander around Naples. You could take a tour of Naples Underground or view some art at the Gallerie d’Italia near the Toledo Metro Station.

If day 14 is your last day then say your sweet goodbye to beautiful Italia before heading out. Of course, if you’re flying out of a different city than Naples, you may want to adjust a day so you’re prepared for your departure!

Summary of Our 2 Week Italy Itinerary

There’s a lot of info packed into the post and we thank you for reading! We sincerely hope it’s helped you in your search for a memorable two weeks in Italy. If you have any questions please feel free to reach out to us! We’d love to help!

Buon viaggio!

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Pin showing Piazza del Campo in Siena

Where Food Takes Us

We’re Darah and Garrett. Our life has been an adventure ever since we eloped in a pink Cadillac in Las Vegas. Now we’re running around the world, working online, and eating everything we can.

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