Last Updated on 20th February 2024 by Sophie Nadeau
At 19, I took my first trip to Italy. And from the moment I step foot in the boot-shaped country, I was enthralled by the land of pizza, pasta, and plenty of wine. I loved the monuments, the history, the architecture. I loved the beautiful weather. And of course, I loved the people! Here’s your ultimate 2 weeks in Italy itinerary and travel guide!
Things to know before visiting Italy for two weeks
This 14 day travel guide encompasses a lot of distance, and so if you prefer travelling more slowly, you may well want to miss out on a few of the smaller towns and spend longer amounts of time getting to know the larger cities on a more local level.
The easiest, quickest, as well as undoubtedly cheapest way to take this trip is to voyage by train or bus. Italian transport is largely fast and affordable, meaning that it’s easy to travel between all the places mentioned in this itinerary.
When you reach the Amalfi Coast, however, you may well want to rent a scooter or small car (check here for the best car rental comparison prices) to transport yourself via all the small towns and cliff side villages this beautiful stretch of Italian coastline has to offer!
If you’re looking for even more inspiration about the boot-shaped country, then be sure to check out our best travel quotes about Italy. And if you need to know more information before heading to the South of Europe, check out our top Italy travel tips.
When it comes to the best time to travel to Italy, the choice is really up to you! In the summer months, the crowds and heat are at their highest, meaning that if you prefer exploring in a cooler climate with fewer people around, then heading to Italy in the European shoulder seasons (late spring/ early autumn) is probably your best best.
Finally, you’ll soon discover that everyone speaks great English, especially in the tourism industry. However, it’s only polite to learn some basic Italian. I personally recommend learning how to say ‘please,’ ‘thank you,’ ‘hello,’ and ‘sorry’ to get you started.
Otherwise, you might want to bring along an Italian phrasebook like this one. For travelling around Europe, a universal adaptor like this one is a must, so you can keep your essentials (phone, kindle, tablet) charged as you travel.
Suggested itinerary for 2 weeks in Italy
Venice/ Venezia
Stay: 1 night
Where to stay: Hotel Moresco
Ah, the picture-perfect canals and waterways of Venice! The meandering cobbled lanes of Venice are the ultimate starting point for an Italian adventure. Though it’s better to spend 3 or 4 days in Venice, here’s a guide on how to spend one perfect day in Venice.
Nearby international airports mean that budget airlines fly into the city from all across Europe and beyond and rail connections away from the city mean that Venice is the perfect location for reaching other Italian cities.
If you truly want to make the most of the Venetian scene, you’ll want to stay at least one night, either in the city or close by. This way, you’ll be able to experience the city without the crowds of day trippers who only come to the floating city during daylight hours.
Once there, Venice offers oodles of small bars, little museums and endless streets in which to get lost. In order to make the most of your budget, avoid eating in the tourist areas (and never eat or drink anything in Piazza San Marco).
Essential tour: Doge’s Palace & St. Mark’s Basilica 2-Hour Tour
Verona
Stay: 1 night
Where to stay: Hotel Moresco
Home to world-famous fated lovers Romeo and Juliet, Verona is not only a city for lovers, but a city to fall in love with. This is a particularly popular destination among those planning a honeymoon in Italy but is regardless a must-see for any first timer to the country.
Head to Verona if you’re a literary lover or history buff- the city offers plenty of things to do whether you want to see Roman remains or wander the streets which have since become intertwined with the story of Juliet. For even more inspiration, be sure to check out our suggestions for one day in Verona.
Essential tour: Verona Food Tour with Wine Tasting
Bergamo
Stay: 1 night
Where to stay: Hotel Moresco
The hidden gem of the Lombardy region, beautiful Bergamo is a beautiful settlement characterised by its many ancient churches and small off the beaten path eateries.
Best seen in the spring, summer or early autumn when green blankets the slopes and it’s possible to dine outside into the early hours of the morning, the city has plenty of museums, and even more traditional trattorias where you can sample local Lombardian cuisine!
Milan/ Milano
Stay: 1 night
Where to stay: Hotel Moresco
While many tourists miss out on a trip to Milan in favour of other more iconic tourist hotspots, if you love design, art, and fashion, you certainly don’t want to miss Milan!
Highlights of the city include the impressive Duomo dedicated to Saint Mary of the Nativity (a gothic-renaissance masterpiece) and the Galleria Vittorio Emanuele II (Italy’s oldest shopping mall).
Other Milanese pastimes include wandering the colourful streets of the Brera district, picnicing in one of the city’s expansive parks, and consuming countless coffees in small Italian cafés, as well as a bar designed by Wes Anderson.
Essential tour: Milan: Last Supper Guided Tour
Pavia
Stay: 1 night
Where to stay: Le Stanze del Cardinale
The stunning university town of Pavia is not necessarily a must-see when it comes to Italy, but it’s one of those small, secluded, and not-yet-overrun-with-tourists kind of city that gives you a real feel for authentic Italian life.
After all, Pavia was once capital of the Lombardy Kingdom and was where both Barbarossa and Charlemagne were crowned kings of the area.
The town is complete with a Duomo designed by the hand of Da Vinci himself, as well as plenty of ancient buildings which form part of one of the oldest universities in Italy.
Elsewhere in the city, an easy 8km north day trip via train means that you can visit one of the most beautiful Renaissance buildings in Italy in the form of the Certosa di Pavia.
Cinque Terre
Stay: 2 nights
Where to stay: Hotel Moresco
Otherwise known in English as the ‘five lands’, Cinque Terre is a magical place where the pillow-soft bread of focaccia was invented. Cinque Terre gained its name as it is a collection of five towns and villages, each with a different vibe.
Many are not accessible by car; only by sea, rail or on foot! Monterosso Al Mare is best-known as being the commercial tourist village, whereas Riomaggiore is the most southern, and therefore most remote.
Before visiting the five lands of Italy, make sure you read extensively about each settlement, so as to choose where you want to stay; do you want great food? Or would you prefer perfect views when you awaken each morning?
It is also here in Liguria where a sea-inspired cuisine draws tens of thousands of culinary lovers on an annual basis, and excellent hiking trails set against an azure blue sea attract countless other Italian enthusiasts to return again and again. Make some space on your Cinque Terre within your two weeks in Italy itinerary and you certainly won’t regret it!
Essential tour: Cinque Terre Wine Tour
Pisa
Stay: Don’t! Visit Pisa as a day trip en route to Florence from Cinque Terre.
Best-known for its iconic leaning tower of Pisa, this small Italian city doesn’t necessarily merit a nights stay, especially if you’re looking to pack as many Italian adventures as possible into this 2 weeks in Italy itinerary! As such, I recommend visiting Pisa en route to Florence from Cinque Terre.
Essential tour: Reserved Entrance to Leaning Tower of Pisa & Cathedral
Florence/ Firenze
Stay: 2 nights
Where to stay: The Moon Boutique
Birthplace of Dante Alighieri (you know, author of the Divine Comedy and the Inferno!), Florence is a magical city and probably my favourite place in all of Italy.
Filled with secret passages, off-the-beaten-tourist-track coffee shops, and countless museums, you could spend ten lifetimes trying to decode the secrets of Florence, and still never uncover them all.
Florentine highlights include the domed Duomo Santa Maria del Fiore and its countless artworks and architecture dating back to the time when Florence shot to fame as the place of the Cradle of Renaissance (la culla del Rinascimento).
To really make the most of Firenze, you’ll definitely want to dedicate at least two nights staying in the city! For more inspiration on planning a trip to Florence, be sure not to miss out on the wine windows in Florence and here’s our Florence suggested itinerary.
Essential tour: Florence Dome Climb
Rome/ Roma
Stay: 2 nights
Where to stay: G-Rough
As the capital of Italy, you’ll want to spend at least two nights in Rome during this two weeks in Italy itinerary! While you could spend just one day in Rome, this definitely won’t allow you to even scratch the surface of what the Eternal City has to offer.
If possible, you may well want to dedicate a little longer to uncover even more of the secrets of this ancient city. After all, Rome was once at the heart of the Roman Empire and has seen over three millennia worth of human inhabitation.
Highlights of Rome include throwing a coin or two in the Trevi Fountain (one to return to Italy, two to return to Rome, and three if you want to meet an Italian lover!) and entering the gigantic Colosseum.
When in Rome do as the Romans do, and make sure to dedicate at least half a day to exploring Vatican City, as well as all of its treasures. The smallest City State in the world is home to treasures such as the Sistine Chapel and St Peter’s Basilica.
Essential tour: Vatican Museum, Sistine Chapel & Saint Peter’s Guided Tour
Naples/ Napoli & Pompeii
Stay: 1 night
Where to stay: La Ciliegina Lifestyle Hotel
Lovers of pizza simply must head to Naples for the best pizza in all of Italy! Though a little rougher round the edges than some other Italian destinations, this gritty city has plenty of Baroque architecture to enjoy and an impressive labyrinthine underground to explore. For even more inspiration, here’s our suggested one day in Naples itinerary.
Nearby, the Roman ruined towns of Herculaneum and Pompeii give an insight into what life would have been like for ordinary people living and working within the Roman Empire almost two millennia ago.
Essential tour: Pompeii Skip-The-Line 2-Hour Private Guided Tour
Amalfi Coast
Stay: 2 nights
Where to stay: La Ciliegina Lifestyle Hotel
To end your Italian adventure, you’ll want to spend a little bit of time soaking up some Italian sunshine along the Italian coastline.
Stay in a pretty port town such as Positano or Sorrento to ensure that you wake up each morning basking in the sunshine and within easy reach of many of the day trips the region has to offer. If you have time, then I recommend spending at least one day of your two weeks in Italy to exploring the stunning Island of Capri!
Essential tour: Day cruise to Capri
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Sophie Nadeau loves dogs, books, travel, pizza, and history. A Francophile at heart, she runs solosophie.com when she’s not chasing after the next sunset shot or consuming something sweet. She splits her time between Paris and London and travels as much as she can! Subscribe to Sophie’s YouTube Channel.
