In Italy

2 Weeks in Italy Itinerary: Italian Highlights 14 Day Travel Guide

Milan Guide: Best things to do in Milan, Lombardy, Italy

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!

Bergamo City Travel Guide: Hidden gem of Lombardy, Northern Italy. Here are the best things to do in Bergamo, churches, hikes, eateries, history and local tradition.

This 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 to transport yourself via all the small towns and cliff side villages this beautiful stretch of Italian coastline has to offer!

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.

2 weeks in Italy travel itinerary! Your complete guide to exploring the best of and highlights of Italy in just 14 days. Ancient towns, coastal villages, chic cities, and more!

Venice/ Venezia

Ah, the picture-perfect canals and waterways of Venice! The meandering cobbled lanes of Venice are the ultimate starting point for an Italian adventure. 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. 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). 

Stay: 1 night

Best day trips from Milan: the canals of Venice

Verona

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. 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. Read more: The Real Life Letters to Juliet.

Stay: 1 night

Verona River

Bergamo

The hidden gem of the Lombardy region, 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! Read more: A quick guide to the best things to do in Bergamo.

Stay: 1 night

Best things to do in Bergamo, Lombardy, Italy: view of Bergamo

Milan/ Milano

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. Read more: The best of Milan in one day.

Stay: 1 night

Best things to do in Milan, Italy: Duomo di Milano

Pavia

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.

Stay: 1 night

Best spring destinations in Europe: Pavia

Cinque Terre

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, 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!

Stay: 2 nights

2 Weeks in Italy Itinerary: Your ultimate Italian Highlights 14 day travel guide for where to go and when. The best Italian cities and towns to visit during just a couple of weeks in Europe!: cinque terre

Pisa

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.

Stay: day trip en route to Florence from Cinque Terre. 

2 Weeks in Italy Itinerary: Your ultimate Italian Highlights 14 day travel guide for where to go and when. The best Italian cities and towns to visit during just a couple of weeks in Europe!

Florence/ Firenze

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!

Stay: 2 nights

2 Weeks in Italy Itinerary: Your ultimate Italian Highlights 14 day travel guide for where to go and when. The best Italian cities and towns to visit during just a couple of weeks in Europe! florence

Rome/ Roma

As the capital of Italy, you’ll want to spend at least two nights in Rome during this two weeks in Italy itinerary! 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.

Stay: 2 nights

2 Weeks in Italy Itinerary: Your ultimate Italian Highlights 14 day travel guide for where to go and when. The best Italian cities and towns to visit during just a couple of weeks in Europe! rome

Naples/ Napoli & Pompeii

Lovers of pizza simply must head to Naples for the best pizza in all of Italy! 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. Read more: The real graffiti found at Pompeii!

Stay: 1 night

Graffiti from Pompeii, Italy: 2000 year old Graffitti found in Southern Italy, near Naples

Amalfi Coast

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 is 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!

Stay: 2 nights

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2 Weeks in Italy Itinerary: Your ultimate Italian Highlights 14 day travel guide for where to go and when. The best Italian cities and towns to visit during just a couple of weeks in Europe!

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