Two Weeks in Italy: Magical 14 Day Italy Itinerary Ideas for 2021

A two weeks in Italy itinerary is a bucket list travel experience for many. It is not really difficult to understand why.

Italy boasts a fascinating history, UNESCO-protected cuisine, beautiful landscapes, and some of the friendliest people in Europe. It is, without hesitation, one of the most charming places that you could visit.

Suggested two weeks in Italy itinerary ideas

Italy itinerary: The medieval town of Treviso
Italy itinerary: The medieval town of Treviso

It can be overwhelming to decide precisely where you want to go and what you want to do when planning a trip to Italy. This guide outlines several different Italy itineraries, each focusing on different areas of the country.

They are intended to cover a 10-14 day duration. However, you can extend or omit activities as you see fit.

To summarise, the Italy itineraries enclosed here are:

  • Italy Highlights Tour – A cross-country route to Italy’s main attractions

  • Emilia Romagna –  A foodie adventure, through the heart of Italy’s gastronomical centre

  • Southern Italy – Travel through the rugged south, from Amalfi to Puglia

  • Northern Italy – A journey through the elegant cities and nature of Northern Italy

First time visitors to Italy may wish to consider a cross country Italy itinerary. This enables you to see all of the most famous sights and cities. The regional itineraries focus on more off the beaten track destinations.

14 Day Italy Itinerary:
Italy Highlights Tour

Italy itinerary: Rome
2 week Italy itinerary: Rome

This 2 week Italy itinerary is perhaps the best choice for those wanting to cover a lot of ground in a short space of time and to see the sights and sounds of quintessential Italy. For instance the Colosseum, the Amalfi Coast, etc.

Venice (Days One and Two)

Venice has been capturing the hearts of travellers for centuries. Two days in Venice is ample to see all of the city’s highlights.

With its labyrinth-like network of canals, its quaint gondola taxis, and its grand palaces that seemingly float on water, the city boasts a magical, almost ethereal ambiance.

In Venice, be sure to board a boat that cruises the grand canal. The journey is especially beautiful at night when the elegant palaces and structures are illuminated by twinkling lights.

Stop to admire the breathtaking architecture of the Ponte di Rialto bridge and Saint Mark’s basilica. Then, be sure to sample some Venetian delicacies such as the locally adorned baccalá mantecato and cicchetti.

Rome (Days 5 – 7)

After Venice, venture down to Rome. This is Italy’s capital and the birthplace of the Roman civilization.

Rome has plenty to offer. The sun-bleached ruins of the Colosseum and the breathtaking frescoes of the Vatican and its Sistine Chapel, are among the most famous attractions in the country.

Another highlight of visiting Rome is exploring the city’s quartieri. Each of the citys districts are unique and have their own personalities.

Essentially, they are like little villages in themselves. Don’t miss Trastevere – a hip area filled with eclectic bars, restaurants, and art galleries. Equally notable is the Jewish ghetto, whose crumbling buildings have been renovated into quirky art galleries and coffee shops.

It is easier than you may realise to get off the beaten path in Rome. The Spanish steps and the Colosseum may be perpetually crowded.

However, there are many lesser-known attractions that few tourists are aware of. The Capuchin crypt, the Abbazia delle Tre Fontane, and the Per Grazia Ricevuta shrine are a few Rome attractions you have likely never heard of!

Where to Stay in Rome

  • La Cornice Guesthouse – Excellent budget choice in Rome

  • Pantheon Inn – Luxury choice situated right behind the Pantheon

Naples (Days 8 & 9)

Punky, gritty, and bursting with attitude, Campania’s capital of Naples may just well be one of the most underrated travel destinations in all of Italy. Head to the Antica Pizzeria Port’Alba to eat pizza at the place that invented it. While you’re there, blend in with the locals by ordering yourself a slice of pizza portafoglio.

Venture down Spacca Napoli. This is the main promenade that runs along the length of Naples. Take the time to get lost among the ramshackle alleys and markets that veer off from it.

Enjoy a sea front walk along Via Caracciolo e Lungomare in the city’s upscale Chiaia neighbourhood. Then, for incredible views over the bay of Naples, take the funicular up to Castel Sant’Elmo.

There is also, of course, the option to take a day trip from Naples to hike nearby Vesuvius. The volcano looms over the city and can be seen from virtually all areas of old Napoli.

Several excellent vineyards specialising in red wine can be found on the foothills of Vesuvius. Ascend to the craters at the top and then round off your day with an Italian wine tasting.

Where to Stay in Naples

  • Caruso Palace Boutique & Wellness Suites

  • Grand Hotel Saint Lucia

Capri (Day 10)

The glamorous island of Capri has become synonymous with luxury travel and the jet-set lifestyle. This has been the case ever since Roman times. Roman Emperors Tiberius and Augustus had several summer homes here and raved about the natural beauty of Capri.

It is easy to get to Capri from Naples. Ferries depart hourly.

Try to venture to Capri early in the morning in order to make the most out of your day there. As your boat pulls in to Marina Grande, purchase a ticket to the Grotta Azzurra.

This is Capri’s “blue grotto”  and one of the island’s highlights. Explore the whitewashed stores of charming Anacapri, admire the former mansion residences of Roman leaders and take the chair lift up to the peak of Monte Solaro.

Finally, spend an elegant evening enjoying an aperitif and some fresh seafood in downtown Capri. If your schedule is flexible, you could extend this Italy itinerary and also visit Procida and Ischia.

Where to Stay in Capri

The Amalfi Coast (Days 11-13)

Take the boat from Capri to Sorrento in order to kick off your exploration of the Amalfi Coast. This region is so charming that you could easily dedicate an entire week of your Italy itinerary to exploring it. That said, three days is ample.

Dedicate one day to visiting Sorrento, exploring its winding passageways, and sampling handmade Italian gelato beneath the cover of lemon groves. Don’t miss the Church of St. Francesco whose location offers incredible views out to the Sea and the Bay of Naples.

Spend your other two days in the Amalfi Coast exploring the adorable little seafront towns and villages. Start with glamorous Positano, and continue on to the mountaintop town of Ravello. Finally, end with the medieval town of Amalfi.

For incredible views, consider taking on the somewhat challenging “path of the Gods” hike. The route offers breathtaking panoramas over the pastel-coloured towns of the Amalfi Coast and out to Capri.

There are several Cinque Terre hiking routes that weave throughout the region. You will find something to suit every hiking ability.

Departure (Day 14)

As your Italy itinerary draws to a close, head to the airport for your flight home or onwards. Both Rome and Naples international airports offer a range of low-cost flights around the globe.

If you are flying further afield, one of the Rome airports may be the most convenient option. Fiumicino or Ciampino service a wider array of destinations.

10 day Italy Travel Itinerary:
Foodie travels through Emilia Romagna

Emilia Romagna itinerary: Bologna
Bologna, Emilia Romagna

Italian cuisine is so good that it has obtained a UNESCO protected status. The country may be known for pizza, pasta, and gelato. However, the reality is that Italian food goes way beyond that.

Any Italy itinerary is a great opportunity to sample Italian food. However, if you are looking for the creme de la creme of Italian foodie destinations, Emilia Romagna is it.

Different Italian regions have different specialty dishes. Emilia Romagna is the birthplace of notable delicacies such as balsamic vinegar, parmesan cheese, tortelloni, and parma ham.

Most Italians have a strong sense of pride in their food and where they come from. Yet many will begrudgingly admit that some of the best food in the country can be found in Emilia Romagna.

This area is often overlooked. Even if you venture here in the height of summer, the cities of Bologna, Parma, Modena, etc are seldom crowded. This is a great place to venture off the beaten path in Italy.

Days One to Three:

2 weeks in Italy itinerary
2 weeks in Italy itinerary

Beautiful Bologna is the capital of Italy’s Emilia-Romagna region. It is often referred to as “the Red City”.

This is on account of the countless terracotta-colored medieval buildings that line Bologna’s promenades and porticoed streets.

As the capital of Italy’s foodie capital, Bologna is a great place to attend a Bologna cooking class. This is a great way to learn the secrets of the local delicacies.

What better way to wow your dinner party guests than by cooking them recipes that you learned during your Italy itinerary? Don’t miss the leaning towers of the Torre Degli Asinelli, or the traditional food markets at the Quadrilatero.

Day Four:

Parma is the second stop of this Italy itinerary. The city was the birthplace of several notable Italian delicacies, including the city’s namesake Parma ham, and Parmigiano Reggiano cheese.

While in town, take the time to visit a Parmesan cheese factory. Parmigiano Reggiano is a product of designated origin, meaning that it can only be produced in this part of Italy.

Several cheese factories await on the outskirts of Parma. Many tour companies offer day trips to visit them, and the experience is more interesting than it may sound!

Here, great wheels of parmesan are stacked from floor to ceiling and branded according to age and quality. The Master Cheesemaker discusses the manufacturing process with you.

Then, you can watch the parmesan move through various stages of creation. At the end of the tour, indulge in a little sampling of various types of parmesan served with excellent quality jars of honey, condiments, and local wine.

Parma is a compact town. However, wandering its medieval streets is certainly a pleasant way to spend an afternoon.

Enjoy lunch in the Piazza Duomo, and admire the architecture of the Parma cathedral and baptistery. Take a stroll through the leafy Parco Ducale and enjoy an evening aperitif before watching the sunset.

Day Five:

Despite its tiny size, Modena has made grand contributions to Italy’s culture and history. It is here where Pavarotti was born.

So too were some of the most notable Italian luxury car brands. Ferrari, Lamborghini, Maserati, and others all originated here.

If you are interested in the opera or in cars, you can take a day trip to Pavarotti’s former house, or stop by the Enzo Ferrari museum.

The cobbled central piazza of Modena (Piazza Grande) is surrounded by narrow streets that provide the perfect opportunity for window shopping. The chic stores sell the most exquisite of Italian styles.

Many of the stores sell exquisite, handmade Italian leather shoes. These are unlike anything you would find elsewhere. Others sell gorgeous silk dresses and apparel items.

Modena was the birthplace of Balsamic vinegar. Many of the stores here offer complimentary balsamic tastings.

That may sound peculiar. However, taste a few and you will note that the quality variations are more significant than you may have thought.

Enoteca Ducale, Mercato Albinelli, and Acetaia di Giorgio are among the best-regarded sellers in the region. Stop by these stores if you are interested in trying or buying Modena PDO balsamic.

Modena does not fall short on foodie delicacies. To dine like the locals, consider ordering a Cotechino Modena (local pork sausage).

If you’re feeling brave, try a zampone (stuffed pig’s foot). Osteria Francescana has acquired international acclaim as an exquisite fine dining restaurant, albeit a little expensive.

If your budget does not stretch to a meal here, there are plenty of excellent trattorias throughout Modena. Just ask the receptionist at your hotel to recommend their favourites.

Day Six:

From Modena, we backtrack past Bologna and head to Ferrara. In general, Emilia Romagna remains relatively off-the-beaten-path as far as travel in Italy goes.

However, Ferrara even more of an unknown. This is not a touristic destination, yet the medieval town provides a wonderful glimpse into traditional life in Italy.

Ferrara dates back to the 14th century. Its entire town centre is a UNESCO protected site.

Simply wandering the centre of Ferrara with gelato in hand is a nice way to spend a day. Look out for the ancient Castello Estense which is remarkably well-preserved and boasts a beautiful courtyard and moat.

Like the other spots in Emilia Romagna, Ferrara too boasts its local delicacies. At a local patisserie, be sure to order a slice of Tenerina Ferrarese or a Pampapato.

A Tenerina Ferrarese is a rich, indulgent local chocolate cake. The pampapato is a very dense, dark chocolate treat filled with chopped almonds and hazelnuts.

Day Seven:

Ravenna is the next stop on this Italy itinerary. This is a city famed for its vibrant mosaics.

Every twist, turn and street entrance in Ravenna greets you with colourful 5th-century tiles. They depict various scenes from religion and history.

Ravenna may not look like much at first. However, the town was once one of the capitals of the Roman empire.

There are dozens of churches and basilicas in Ravenna. Exploring them should rank high on your to-do list. In particular, don’t miss the Basilica di San Vitale, the Neonian Baptistery, and the Sant’Apollinare Nuovo.

Days Eight and Nine:

Rimini is a beautiful coastal town perched on the shores of the Adriatic Sea. It is characterised by translucent azure waters and white sandy beaches.

These combine to make little Rimini a go-to getaway destination for Italians during the hot summer months. Rimini beach itself is a lovely place to relax and unwind, although it does get crowded between June and September.

If you prefer to escape the crowds, you can also consider heading to the nearby village of Riccione. This is a stunning rural area known for its natural thermal springs and spas.

Beaches aside, Rimini town offers beautiful architecture and history. Stroll along the banks of the Ponte di Tiberio, and indulge in local delicacies at the grand piazzas of Cavour and Tre Martini.

Day Ten:

2 weeks in Italy itinerary
2 weeks in Italy itinerary

Gulp down your last limoncello, and scoff your last gelato as you wave goodbye to Emilia Romagna. Both Bologna and Venice airports are easily accessible from here and offer good, low-ost flight routes around the world.

14 Day Italy Itinerary:
Southern Italy Adventure

Naples, Italy Itinerary
Naples, Italy Itinerary

Southern Italy is perhaps the most rugged, underrated, and unexplored region of Italy. This is the real, authentic, Mediterranean.

At the stopping points on this Italy itinerary, you will see Italian nonnas preparing pasta and hanging their washing out on the streets, Vespas whizzing along narrow streets, and true signs of Italian life. Many of the scenic medieval hill towns here are bypassed by most tourists.  

It can be tricky to get around Southern Italy. Public transport links are not so good. Consider renting a car for this Italy itinerary if you are comfortable in doing so.

Days One and Two:

The gritty Campania capital is perhaps one of the most underrated travel destinations in Italy. Information can be found in the Italy highlights itinerary above.

Days Three to Five:
Amalfi Coast

Three days is ample to obtain an introduction into this beautiful region of Southern Italy. Divide your time between Sorrento, and the quaint towns of Amalfi, Ravello, and Positano.

You can also incorporate a day in Capri into this leg of your schedule if you like.  

Days Six and Seven:
Reggio Calabria

Reggio Calabria is one of the least-visited regions in Italy. It can be found at the very bottom of the “boot” of Italy.

This region is surrounded by translucent turquoise waters, miles of pristine coastlines, lush green national parks, and rolling hills filled with lemon trees and olive groves. It is a wonder that Reggio Calabria has escaped the eyes of tourists for so long.

This region is often used as a stopping point for those crossing over to Sicily. You can see Sicily across the narrow Messina Strait.

Messina and Eastern Sicily glimmer across the water. On a clear day, you can see as far as Catania.

The region dates back to the 4th century and was founded by the ancient Greeks. Don’t miss the Museo Nazionale della Magna Grecia.

If you have rented a car, spend a day exploring the sleepy medieval villages and beautiful coastal areas of the region. Tropea, for example, is every bit as beautiful as the Amalfi Coast, yet without the crowds.

Days Eight and Nine:

From Reggio Calabria, follow the boot of Italy around to the beautiful baroque city of Lecce. A lot of the appeal of exploring Lecce is simply taking the time to get lost among its narrow streets and passageways.

Amid your wanderings, there are several historic buildings to look out for. Notably, the crumbling remnants of the Roman amphitheatre in Piazza Sant Oronzo, the scenic Piazza del Duomo, and the extravagant baroque church of the Basilica di Santa Croce.

Day Ten:

The beautiful port city of Brindisi offers a little something for everyone. Take the time to explore the port area, and stroll the palm tree lined promenade that runs from Via Dorotea to the Virgil monument.

If you want a little rest and relaxation after a tiring Italy itinerary, relax on the picturesque shores of Brindisi’s Lido Azzurro beach.

Days Ten to Thirteen:

Puglia is slowly emerging as a sought-after Italian travel destination. The region is home to medieval hilltop villages and some of the most unique landscapes in the country.

Spend a day in Gallipoli, getting lost among its serpentine-like network of streets. Admire the gorgeous architecture of the dreamy whitewashed city of Ostuni, and spend a day in Alberobello. The latter is one of the prettiest towns in all of Italy, home to unique houses that look like little seashells.

Day Fourteen:

As you wrap up your Southern Italy itinerary, you have a number of options in terms of getting a flight out of the country, depending on where you are headed to next. The airport at Brindisi/Salento offers limited flight routes.

Drive back to Naples or onwards to Rome if you are flying farther afield/outside of Europe.

Extending Your Italy Itinerary

Alberobello, Italy
Alberobello, Italy Itinerary

You may wish to chop, change, and adapt your Italy itinerary to your liking. One thing to keep in mind though is that these routes are already pretty jam-packed.

It is easy to look at Italy and feel that you want to go EVERYWHERE. However be cautious about cramming too much in.

Distances between cities may be farther than you realise. You don’t want to spend 50% of your time travelling from A to B, and come back from your vacation feeling like you need another vacation!

When to travel to Italy

Beach towns of Reggio Calabria
Beach towns of Reggio Calabria

Italy is a wonderful year-round travel destination. There is no such thing as a bad time to spend 2 weeks in Italy.

Italy enjoys a warm, pleasant Meditteranean climate. Even winters here are milder and more manageable than most places in Europe.

However, that being said, some times are better for planning your 2 weeks in Italy itinerary than others. The summer months (June to September) are the high season for travelling to Italy.

Travelling during this period almost guarantees that you will be met with a sea of tourists wherever you go. Furthermore, accommodation and flight prices are at their highest during this time.

Try to avoid the high season if you can. A nice time for your 2 weeks in Italy itinerary are the shoulder seasons of spring or autumn.

In spring, the temperatures are still warm but not unbearably so. You can enjoy warm enough conditions to go swimming from the end of April and May.

During this time, flowers are in bloom, and crowds are few. Autumn is another good time to visit. Italian cities look spectacular adorned with fall foliage

Getting around during your 2 weeks in Italy Itinerary

Italy travel itinerary: Naples
Italy travel itinerary: Naples

Public transport is generally very good in Italy. The only exception is in Southern Italy and Sicily were transport links are virtually non-existent.

Renting a car in Italy offers you the most freedom and flexibility during your 2 weeks in Italy itinerary. Comprehensive bus and train routes are available in most of the country.

Travel Italy by Rail

If you are hoping to get around Italy by public transport then opting to do so by rail is the easiest method. Italian trains run on regular schedules and tickets do not need to be booked in advance.

There are two main train operators in Italy. Namely, they are Trenitalia and Italo.

When you are covering large distances, you can also take the “frecciarossa”. This is Trenitalia’s high-speed train service.

Renting a Car in Italy

Attitudes to driving and road rules are a little different in Italy, especially in the south. That said, opting to rent a car in Italy allows you a lot more freedom and is not as daunting as you may imagine.

You must have an International Driving Permit (IDP) in order to rent a car in Italy, and you must keep this with you at all times. Major operators such as Hertz, Avis, and Sixt provide services in Italy

It is possible to pick up your rental car immediately upon arrival at the airport. Roads are often narrower (and more chaotic!) in Italy, and there are areas where you are not permitted to drive.

In particular, look out for Zona traffico limitato. Historical areas within cities are often flagged as such and accidentally passing through them can mean incurring a hefty fine.

Parting Words

Do you have any further queries or concerns about organising your Italy itinerary? Feel free to reach out to me via the comments below, or pop me an email.

I lived in Naples for several years while working as an English Teacher in Italy. have travelled Italy extensively so it’s safe to say that I know the country relatively well.

Safe travels! Melissa xo

Melissa Douglas

Melissa Douglas is a British Travel Writer and Blogger based in Athens, Greece. She writes for numerous high profile travel publications across the globe - including Forbes Travel Guide, Matador Network, The Times of Israel and The Huffington Post.

2 thoughts on “Two Weeks in Italy: Magical 14 Day Italy Itinerary Ideas for 2021”

  1. Hi Melissa, these are some great ideas of how to see the best of Italy. I love the country and I’d like to see more, but am continually distracted by other places. I’ve been to Rome so many times and would still go again but I’d really like to see the south as I’ve never been to that area. Thanks for sharing.

  2. some great ideas. what month do you think is best for visiting Emilia Romagna ? I don’t like tourist crowds but need to take holidays during school breaks.

    Do you think last week of June will be too busy?


Leave a Comment