No matter what type of traveler you are or what kind of vacation you enjoy, Italy is a destination that will interest everyone. From gorgeous museums to outstanding archaeological sites, hiking trails, coastal towns, cosmopolitan cities, and delicious food, a trip to Italy will remain impressed in your memory for ever.
Two weeks in Italy offers plenty of time to explore different corners of the country, from the picturesque seaside views in the South, to stunning cities of art in the North.
This 14-day itinerary for Italy packs all the perfect destinations to enjoy a fantastic escape.
This post contains compensated links and Solo Trips and Tips may receive a commission for purchases made through links. See our disclosure about affiliate links
Flying to Italy
We suggest you plan the trip according to your airport of arrival. Ideally, it’s a good idea to fly into Rome or Milan.
And from there start moving around the peninsula, either by car or by train (for some connections, bus travel can be a valid alternative).
As a general rule, if you arrive to Rome, you can travel down to the South (Naples) for the first days of your trip, and then start making your way up towards Milan.
By doing so, you will be following the exact route of this itinerary. Instead, if you fly to Milan, you can easily follow this itinerary from the end to the beginning.
2 Week Italy Itinerary
Day 1: Rome to Naples
The busiest airport in the country is Rome Fiumicino Airport, that means that you’ll probably land in Italy’s capital, especially if you’re flying from within Europe.
From the airport, jump on a train to Rome Termini Central Station in order to board a train to Naples, which will be our first stop in this itinerary.
A highspeed train is a good alternative to get to the capital of the Campania region in a bit more than an hour.
If you drive, remember that traffic tends to be heavy, so consider at least 2-3 hours on the road.
Depending on how early you reach Naples, you can devote the first day to simply stroll in the city center, a cup of espresso and a traditional Neapolitan pizza for dinner.
Afterall, the food in Italy is one of the highlights of visiting this country.
You will probably be tired and jet-lagged, so keep a slow pace in order to gather energy for the next morning.
Day 2: Pompeii and Sorrento
Whether it’s by train (Circumvesuviana), or driving, the first thing you should do on the second day in the region is pay a visit to the impressive archaeological findings in Pompeii.
The trip is about 45 minutes, and a morning visit will allow plenty of extra time to visit another gem in the area, the coast of Sorrento.
In order to enjoy it without wasting time, I strongly suggest booking a guided tour to Pompeii that will take you to the best places in the site (which is huge and quite difficult to navigate on your own).
Booking a tour guided by an archaeologist or a knowledgeably official guide will help make sense out of a lot of otherwise anonymous ruins!
In the afternoon, head directly to Sorrento (again by train or car, although there is a bus service available too which can be a good alternative), one of the most beautiful traditional towns in southern Italy.
Although it is not officially part of the Amalfi Coast, it is as charming as many of the other seaside villages facing this portion of Mediterranean coast.
Once in Sorrento, have a delicious dish of gnocchi alla Sorrentina for lunch and try a small glass of Limoncello…trust me, it cannot get more Italian than that!
You can spend the rest of the afternoon discovering the beautiful historical district.
However, if you want to know more about the best things to do in Sorrento, check this Amalfi Coast itinerary that includes Sorrento among the places to visit.
After visiting the small town, you have two choices.
You can either spend the night in Sorrento in order to be ready for the coast of Amalfi early on the next morning.
Or you can go back to your hotel in Naples and set up a very early alarm clock to take the train back to the Amalfi Coast. I strongly suggest the first option.
Day 3: Amalfi and the Costiera Amalfitana
Although exploring the whole coastal area can take much more than just a day, you can shorten the itinerary by visiting only the most remarkable villages.
Or you can spend more time here instead of going back to Naples at night.
The best way to do the Amalfi Coast on your own is by driving or with the special bus that connects the villages.
However, driving will offer much more flexibility in terms of the time you want to spend in each place.
If you don’t feel like driving the jaw-dropping bends of the coastal road, then a guided one-day tour is the perfect compromise to see the best of the area in a day.
This full day tour departing from Naples is super value for money.
If you’re driving your way along the coast, you can begin your day heading to the enchanting Positano, the first small town on the coast.
The official starting point of the Amalfi Coast, there are lots of things to do in Positano.
Made of picturesque colorful alleys, the place is perfect to stroll around souvenir shops and art galleries or to spend about an hour at the beach.
Spiaggia Grande is the most popular beach in Positano and an excellent place for a morning coffee with the local cake, pastiera napoletana.
I highly recommend stopping in Amalfi next and pay a visit to the gorgeous city cathedral or discover the interesting and unique Paper Museum.
The city is known for the excellent quality paper that it has produced for centuries.
Amalfi is a perfect place for lunch as well, head to one of the many trattorias in the center of town for a real Italian treat.
The next village you want to explore is Ravello, a mountain settlement known for its international music festival and some of the most picturesque villas with gardens that you can find in the area.
Finally, depending on how tired you are, you can spend the rest of the afternoon in Cetera, a small but super picturesque fishing village where you can relax and spend the afternoon at the pace of the locals.
Or you can make your way back to Positano by boat and then catch the train again back to Naples.
Day 4: Naples and Rome
It is a good idea to leave from Naples to Rome in the early afternoon.
If you travel with a high-speed train, you will have enough time to see the best of Naples before the departure.
And you’ll still get to Rome early enough to take advantage of the rest of the day in the capital of the country.
During your last morning in Naples, devote some time to visit the Archaeological Museum.
Or, if you prefer, reach Castel dell’Ovo for some medieval sites by the sea.
Spend a few hours discovering Piazza del Plebiscito and the amazing Galleria Umberto Primo, a classic meeting point for locals.
Right in the heart of Piazza the Plebiscito, enjoy a cup of local espresso with a baba al rum, one of the most famous Neapolitan desserts.
From there, reach the train station and board you fast train to Rome.
Take advantage of the traveling time to rest your feet, because you will walk a lot once in the capital.
From Rome’s main train station, you can take the metro and get to the picturesque historic center. Read our guide to Rome (including where to stay in Rome).
In order to avoid the crowds of places like the Vatican and the Colosseum, devote the afternoon to places that do not require long lines to access.
For instance, you can check out Piazza Navona, the Pantheon, with its incredible domed-roof, and the Trevi Fountain.
As an alternative, you can walk along via Veneto, visit the Spanish Steps, and the gorgeous church Trinità dei Monti.
It’s a good idea to have a traditional dinner in the center of town, a place like Piccolo Bucco, only steps from Trevi Fountain, is perfecto for comfort food and pizza.
Piccolo Bucco is at 91 Lavatore Street.
Day 5: Rome
If you’ve already booked your skip the line tickets to the Vatican, then you can start your day discovering the spectacular Piazza the Popolo and Saint Peter’s Basilica.
Devote some time to also visit the imposing Sistine Chapel and the Vatican Museum.
In the afternoon, head along Via della Conciliazione to the nearby Castel Sant’Angelo, just a few minutes from the Vatican’s main square.
The castle is a fortified structure of with incredible views of Rome.
Inside you can check out the museum and learn everything about the history of the building over the centuries and different Popes in the Vatican.
From its terrace, you can spot some of the most gorgeous sights in town, including the Tiber River and the charming Bridge of the Angels.
If you want to join a tour in order to skip a few lines, I suggest the Vatican Museums & Sistine Chapel Skip-the-Line Tour
Day 6: Rome
Your morning will be a historic journey in time, visiting the Colosseum as well as the Roman Forum.
Since this is among the most crowded attractions in Rome, buying the entrance ticket beforehand is a must.
Check out this Colosseum, Roman Forum, Palatine Hill Entry Tickets for a skip-the-line fast track entrance to the most stunning Ancient Rome landmarks located in the same area of the city.
In the afternoon, it’s a good idea to jump on a train and spend time exploring the beautiful area of Ostia Antica, Rome’s coastal town and former prosperous Roman port in the imperial times.
This coastal settlement is about 25 km from Rome and the trip takes about an hour – a perfect day trip from Rome.
This large archaeological site is known for the excellent preservation of its ancient buildings, mosaics, and beautiful frescoes.
Day 7: Rome – Florence
Devote your last morning in Rome to visit Trastevere.
This is a beautiful corner on the opposite side of River Tiber full of spectacular piazzas, ancient villas, and quaint bars and restaurants where you can enjoy your last breakfast in Rome: a cornetto and a cappuccino.
After visiting the district, catch the metro or a bus to Rome’s main train station to board the next train to Florence, the next stop in your 14-day Italy itinerary.
You’ll be arriving at Santa Maria Novella train station in a bit less than 90 minutes.
Once in town, you can check you baggage at the hotel and start your day right in the heart of town.
Don’t worry, Florence is a largely pedestrian town with fast and easy access to most attractions in town. Have a look at our guide to Florence (including hotel recommendations).
Once in the historic district, pay a visit to Santa Maria del Fiore, the impressive Cathedral of Florence with the stunning Brunelleschi Dome.
Also check out the Bell Tower and the Baptistery, all of them within steps from each other and part of the same religious complex.
As Florence is a hotspot when it comes to tourists, a skip-the-line guided tour is a perfect time and money saver.
When planning your time in Florence, book your entrance tickets to the Uffizi Gallery for your first day in town in order to visit this spectacular art gallery with enough time to spare.
The gallery is close to Piazza della Signoria, another place to visit in town to snap a few pictures of Florence’s beautiful art adorning squares and streets.
Day 8: Florence – Tuscany
As you’ve been exploring cities during the last days, take a break from art galleries and museums and join a wine tasting tour to the Tuscany region – one of the best day trips from Florence.
Spending a whole day in the green fields and hills, among lush vines and tasting delicious Italian wines is one of the best thing you can do when in Florence.
Check out this Tuscany wine and food tour. It includes a picturesque journey through the wine-producing region, visiting 2 wineries, tasting 6 wines, plus tasting balsamic vinegar, and olive oil. And lunch is included, making this a perfect one-day Chianti tour.
Day 9: Florence – Pisa
Start early in the morning by exploring the Galleria dell’Accademia and the original David Statue by Michelangelo.
After an hour or a bit more in the museum, walk all the way to the Arno River to cross the iconic Ponte Vecchio (or Old Bridge) and visit the opposite side of the river, the tranquil district known as Oltrarno.
Depending on your time and interests, you can either visit the art exhibition hosted in the magnificent Pitti Palace, or simply devote a few hours to explore the palace’s green area, the Boboli Gardens.
In the afternoon, take a local train to check out the small but attractive city of Pisa, a little more than an hour from Florence.
Over there, don’t miss the main cathedral and the impressive leaning tower. Head back to Florence for a traditional Fiorentina Steak dinner or a succulent cone of creamy gelato.
Day 10: Florence – Venice
Board an early train to Venezia Mestre Train Station where you will board the second train that will take you directly to Venezia Santa Lucia.
The total travel time from Florence to Venice is under 2.5 hours.
Once you’ve passed the station gates, you will be enchanted by the views of the Canal Grande, one of the most gorgeous vistas in town.
Get ready for gondolas, romantic landscapes, dozens of bridges and… in a nutshell, one of the prettiest cities in the country.
Strolling along the cobblestoned streets of Venice, one bridge after another, you will slowly make your way to Piazza San Marco.
Here you can spend time discovering the Byzantine and Renaissance architecture of the imposing Saint Mark’s Basilica as well as the Clock Tower, the Square, and the Doge’s Palace.
Also in this spot, crowds are an everyday thing, so booking this skip-the-line experience can save you precious time… after all, there are just four days to go until the end of your adventure, I don’t think you’d enjoy wasting time in lines.
These kind of entry tickets are especially useful when you’re traveling solo, as it’s often easier to accommodate one entrance at an earlier slot on the same day of the tour than a party of many travelers.
Exactly for this reason, arriving at the place of the excursion a bit earlier can prove a great idea.
Stop for a fish and pasta lunch near the waterfront by the Grand Canal and spend the rest of the afternoon wandering the different neighborhoods.
Some of them are reachable by vaporetto as well. Get more information about things to do in Venice including how to move around in town.
I suggest you board a vaporetto and check out the Jewish Quarter. The district is pleasant and small enough to be seen in just an afternoon.
Day 11: Venice
Wake up and reach any Vaporetto station in order to sail to two of the most iconic destinations in Venice.
The first of these two stops is the small island of Murano, where you will be able to learn everything about the artisan production of glass, an art that has made Venice famous since ancient times.
In Murano you can visit a glass factory and a glass museum to witness glass making in real time!
Your next stop will be the tiny but colorful island of Burano, another picturesque gem famous for the vivid fishermen houses lining the waterfront.
Burano is also famous for the artisan lace production and for serving some of the best sardines in the north of Italy. Stopping here for a late lunch is never a bad idea.
Once back in Venice, pay a visit to the Rialto Bridge, the most iconic stone bridge in town.
You can snap a few photos of Venice from the top of the bridge – you will be amazed at the stunning views, especially if you get there by sunset.
For the evening, why not having a fancy dinner by the lagoon? Check out Algiubagio Restaurant, serving modern Venice cuisine, with gorgeous lagoon views and quite affordable prices.
Day 12: Milan
Board an early morning train to Milan, as this trip can take from 2 to 3 hours depending on the train you pick.
Once you’ve reached the city, head to the main Duomo Square to visit some of the most iconic buildings in town.
Milan’s imposing Gothic Cathedral, the Vittorio Emmanuelle Gallery and, right at the back of this last building, you will also be able to check out the spectacular Teatro alla Scala the famous opera house of this northern Italian town.
Remember that it is possible to visit the roof of the cathedral from where you can admire the city landscape and the small statue of the virgin that shines on top of the church.
Grab a quick lunch in one of the many cafeterias around the Duomo Square and then jump on the metro to reach the Navigli District.
This is a place where you can spend endless hours checking out quirky shops and bookstores, or simply walking along some of the oldest water canals in the country.
Navigli District is perfect at sunset for an aperitivo that will often extend into the evening for dinner, where you can choose among the many affordable restaurants that populate the area.
Day 13: Milan
On your second day, book a morning tour of one of Italy’s most admired masterpieces belonging to the UNESCO’s World Heritage List: The Last Supper by Leonardo da Vinci.
The fresco is located in the so called Cenacolo Vinciano, situated in the church and monastery of Santa Maria delle Grazie.
The visit is very strict in terms of visiting hours, visiting time, and time inside the Cenacolo, therefore booking the visit beforehand is the only way to access the building.
The visitors are admitted a few days a week and in small groups, so plan your visit in advance and buy a ticket at the official website for 15 euros as of this writing.
After the tour, explore the nearby streets of Brera, the artistic and literary quarter of Milan or take the metro to Castello Sforzesco, one of the most impressive medieval structures in town.
End your last day in Italy exploring the back gardens of the Castle, Sempione Park (Parco Sempione), grab a few panini from a local nearby bakery and enjoy a picnic on the immense greenery of this huge public garden.
Day 14: Fly Home from Milan
You can either travel home from Milan Malpensa Airport, about one hour from the center of town by train (a bit more by car due to Milan’s heavy traffic), or you can fly out from Italy, in which case you will need to consider a few extra hours to reach the airport by train from Milan.
Final Thoughts on Italy in Two Weeks
As you can see, from south to north or from north to south there is a lot to do in Italy, you just need some good organization, a sturdy carry on, and an adventurers spirit. Italy will take care of the rest!
More Italy Travel Articles
About the Author
Gabi Ancarola is a translator and travel journalist living in Crete. She regularly writes about Europe for several magazines about travel, gastronomy, and hospitality. She has published several travel guides about Greece and plans customized trips to the Greek islands. She loves cooking local dishes, taking photos, and driving on the mountain roads of Crete.