A Two Week Italy Itinerary • Don’t Miss the Best Cities in Italy

Italian Itinerary

With two weeks in Italy, how do you maximize your time? We can’t all travel the world indefinitely and spend an endless amount of time on holiday in Italy. When it comes to any Italian itinerary there is no perfect plan and each person has their own set of interests.

Italy is the one country that we have repeatedly returned to. This next winter will make it our fifth time touring around Italy! There is something about the culture, history, and food that warrants deep exploration. If it’s your first time in the country you’ll want to hit all the main tourist destinations such as Venice, Florence, and Rome.

We would suggest stepping a bit off the simple route and I’ve suggested a number of smaller towns that are well worth the trip. The way we plan trips is to pick the destinations we find of interest and go from there. You won’t hit everything here in just a two week trip to Italy, but hopefully, it inspires you to return! This guide has a number of must-see places in Italy and you can pick what you like for your trip.


A Two Week Italy Itinerary


Venice

Is Venice worth a visit

Love or hate Venice there is no denying its popularity. It may be one of the most beautiful historic cities on the planet, but it is also besieged by tourists with a crumbling infrastructure. The sinking city is a network of 118 islands connected by bridges. Buildings here are old and if you manage to get away from the crowds it feels as if you’ve stepped back five centuries. It is surreal and we do have a love for Venice.

In our opinion, Venice is best in the shoulder and off seasons. The canals of Venice are notorious for harboring a lot of waste and in the summer the smell can get pretty bad; however, in the cooler months there are fewer tourists, less waste, and the smell is at bay. If you were to ask us Venice is a must see place in Italy, except in the summer months.

What to do in Venice?

Is Venice worth a visit
Piazza San Marco

This is one of the focal points in the city and the main square. It’s likely you’ve seen countless photos of this iconic square lined by cafes, shops, and museums. You can also sip a cafe at Cafe Florien which claims to be the oldest cafe in the world (but also crazy expensive).

The Grand Canal

The central artery to the city and often packed with boats. It has some beautiful buildings along the canal and it’s one of the most famous views in all of Venice.

Ca’ Macana

Mask shops pretty much rule the streets of Venice, but most of these are cheap imports marketing to tourist. Ca’Macana is a fabulous genuine mask shop in Venice that actually makes all their own products. You can even find masks used in Stanley Kubrick’s Eyes Wide Shut, as the shop produced the masks for the film. The shop owners do allow for you to play dress up and have some fun!

Spritz & Cicchetti

Enjoying an afternoon of spritz and Cicchetti is a must in Venice. A Spritz Veneziano is an aperitif in Northeast Italy and Cicchetti are bite-sized entrees similar to tapas often on a slice of bread. Our favorite Spritz is at Bacareto Da Lele for a cool €1.50 and it’s right around the corner from Osteria Al Squero, an excellent spot for Cicchetti. There’s little to no seating room so come prepared to stand and relax along the canal.


Milan

Milan Two Week Must See Italy Itinerary

Milan (Milano) is the fashion capital of the world and is home to greats like Prada, Valentino, Versace, and Dolce & Gabbana. However, the vast majority of tourists do not shop for these clothing brands and isn’t a reason to go unless you’re into high-class fashion. However, Milan does pack a fair amount of sights, museums, and restaurants worth visiting.

It’s a city that full of style and known for being posh. This means hip bars, well-dressed locals, and plenty of great places to eat. The city also serves as a great base if you want to explore the Southern Italian Alps and famous lakes like Como and Garda.

That being said it’s our least favorite city in Italy and easy to give a skip with only two weeks in Italy or limited time.

What to do in Milan?

Santa Maria Delle Grazie

The historic church is a fabulous piece of architecture, but it is most famous for what is inside. The church houses one of Leonardo da Vinci’s last paintings, The Last Supper. If you’re traveling in the summer months be sure to book your tickets in advance.

Teatro alla Scala

We are fans of opera and ballet so enjoying a show at the Teatro la Scala was a must in our lifetimes. It’s famed for being one of the best theaters in the world and has some of the best talents in the world. Just be warned tickets are expensive.

Duomo of Milan

It’s the largest cathedral in the world. The foundation was laid in 1386 and it took nearly 500 years to complete the herculean task. It’s an architectural wonder and a sight to be seen in Italy and the world.

Galleria Vittorio Emanuele II

The famous galleria is a shopping arcade that links the Duomo Square with Teatro Alla Scala. The massive glass roof is mind-boggling and the tiles of the interior are gorgeous. I wouldn’t plan on too much shopping as the galleria houses high-end brands.


Florence

Florence Two Week Italy Itinerary

Florence (Firenze) is the capital of Tuscany and a highlight of any tour of Italy. Even if you only have two weeks in Italy, Florence should definitely be on your itinerary. You have to add this city to your Italy itinerary if it’s not already.

The city is famous for its world-class cuisine, museums, works of art, and the surrounding countryside. The architecture in Florence pulls you in and begs for you to get lost in its historic heart.

Florence is known for being the birthplace of the Renaissance period and packed full of history. When you walk the narrow cobbled stone streets it appears as if little has changed with marble basilicas, dark chapels, gas lanterns, and enchanting frescos.

What to do Florence?

Duomo –  Santa Maria del Fiore

It’s the most beautiful cathedral in Italy. The size and scale of the interior along with the frescos housed inside will humble anyone. It is breathtaking with it’s white, pink, and green marble exterior. We love that despite being world famous the Duomo remains free to the public.

Mercato Centrale

If you’re looking to eat head to the Mercato Centrale. You can get some fantastic bites to eat with counters and a few tables. The energy only adds to the environment and the beautiful food products of Tuscany are on full display.

Pont Vecchio

This was the first bridge to cross the Arno River in 1348. It’s been standing ever since that day and is lined with shops and buildings. Make sure to catch it from the riverside and to cross over the bridge on foot.

All’Antico Vinaio

Grabbing a panini from this famous sandwich shop is a must in Italy. All’ Antico Vinaio has even been named one of the best sandwiches in the world. The original shop is only a storefront and you’ll have to enjoy a cheap glass of wine and a sandwich along the street. It’s a cheap eat that won’t disappoint anyone.


Tuscany

Tuscany - Two Week Italy Itinerary

There is hardly a more famed region in Italy than the rolling hills of the Tuscan countryside. It’s well worth adding the region to your Italy itinerary. You can take day trips from Florence or stay in any one of numerous towns.

The region is geographically diverse with beautiful beaches and islands, rolling hills, and the Apennine Mountains. You can find some of Italy’s best products such as beautiful wines, olives, mushrooms, cheese, legumes, and bread. There are whole trips spent in Tuscany and for good reason.

Where to go in Tuscany?

Siena

It’s only a two-hour train ride from Florence and it’s everything you can hope for in a Tuscan town. This is the Italy romanticized in countless movies and books. It’s packed full of medieval buildings and offers the Italian countryside at its doorstep.

Pisa

Be warned Pisa is underwhelming. Many visitors feel the draw to come here for its famed tower. In our opinion, the most entertaining part of a stop in Pisa is watching tourist air five and pretend to hold the 180 ft bell tower. Pisa is walkable and offers a great place to grab a gelato and sit by the Arno River. However, it’s not the prettiest city.

Lucca

This is the walled Renaissance city and where I suggest heading instead of Pisa if you’re short on time. It’s full of cobblestoned streets, lovely piazzas and street side cafes. Take a day to stroll along the city ramparts and hop from one cafe to the next.

Cinque Terra

There are many must-see places in Italy, but I think Cinque Terra is close to number one. It’s not technically in Tuscany, but it’s an easy day trip from Tuscany. It’s a photogenic collection of five towns that are on almost every traveler’s Italy must-see list.

The five towns are accessible by train from La Spezia. The towns are colorful and perched along a series of cliffs. There is a trail that connects the five towns and it’s summertime favorite to hike, be prepared for some steep descents and ascents. If the hike is too much all the towns are accessible by train or boat.


Umbria

What To Wear In Italy, Perugia

The capital of Umbria does not make enough travelers lists. However, it is well worth a stop. The region is full of fantastic food and wine just like Tuscany and was long known to tourists as Tuscany’s little sister. It has amazing hilltop towns, fantastic food, and half the tourists.

It’s known as the Green Heart of Italy because of the amazing countryside. To make it all better the sights are easy to explore and only require a few days to see. It also saves you a long train ride from Florence to Rome, making a nice stop in between.

Where to go in Umbria?

Perugia

This is the capital of Umbria, but it’s a manageable hilltop city. The city is loaded with historic sites and buildings and makes for a fun day exploring. The city center is a maze of steps, cobbled alleys, and arched stairways. At its heart, you’ll find a number of large piazzas and mansions.

Assisi

Home of St Frances, the patron saint of Italy, and a site of pilgrimage for Italians. It’s one of the most beautiful hilltop towns in Italy with Mount Subasio rising above the town with wooded valleys. As the town’s cobblestone streets ascend to the Cathedral or “heaven” you’ll pass along the well-preserved building and hear the clatter of footsteps from nuns and pilgrims.

Orvieto

You’ll be hard-pressed to find a town more beautiful than the hill topped Orvieto. As you approach the city it is breathtaking and the cathedral is out of this world. As with all towns in the region expect cobbled lanes, large piazzas, churches and lots of history. There is just not enough time in any two-week Italy itinerary to explore all Italy has to offer. Not even a month would suffice!


Rome

Rome - Italy Itinerary

All roads lead to Rome. It is the beating heart of Italy and a city that begs to be explored again, and again, and maybe one more time. It’s known as the Eternal City and one of the most romanticized cities in the world. History haunts its every corner and it is littered with historic site spanning several millennia. There is no city on earth like Rome.

Rome has amassed great wealth over the years as the seat of power of the Catholic church the result is stunning architecture. Vatican City is unparalleled in its beauty and scale. We are not big city people or into museums and churches, but the Vatican will humble you.

Where Rome truly shines is the ability for a tourist to get lost and immerse themselves. Just pick a direction and keep walking. It’s not always about ticking off the sights or old buildings. Stop and enjoy un caffè, here’s our guide to coffee in Italy.

What to do in Rome?

Trevi Fountain

We all know the saying that if you a coin in the Trevi Fountain you’re destined to return. Well, we’ve done that and we’ve been back… four times. Until next time Roma!

Vatican City

Prepare to spend a half-day or more in Vatican City. Depending on lines it could take you a while to enter St Peter’s Basilica, especially in the summer. Once inside you’ll want to take the time to appreciate your surroundings.  Bring a shawl to cover your shoulders here, this is also where you will get to admire the Sistine Chapel. If you want to avoid lines it does help to buy tickets in advance.

Explore Trastevere

Cross the Tiber river to Trastevere. The bohemian and hip neighborhood long known for its working-class roots and unique vibe. Rome is constantly reinventing itself, for example, you check out a great beer bar at Ma Che Siete Venuti A Fà. Relax have a beer, watch a football match, and mingle with locals and expats.

Roman Forum & Colosseum

Exploring the Colosseum and Roman Forum will also tie up at least a half of your day. The good news is they are close to the subway station and they are also right next to each other.  These should not be missed!

Embrace Aperitivo

At the end of the day Romans meet for aperitivo, it’s essentially the Italian happy hour. Any decent bar supplies food that can range from simple snacks to full-on buffets or beautiful Italian food products.

Knights of Malta

An out of the way literal keyhole to the city.  High on the hills, you can look through a small keyhole, that overlooks peaceful gardens and an outstanding view of St Peter’s Basilica.  If you have extra time this is a sight worth going to.  Visit later in the day for more peace and quiet.


Naples

Naples - Two Week Italy Itinerary

This city is the opposite of Milan, you either love it or hate it. It’s gritty, it’s loud, it’s in your face, and it is Italian. The electricity in the narrow streets of Naples cannot be beaten. Not to mention the city is packed with history, architectural treasures, palaces, castles, art, beaches, and churches.

Did I mention that the city also has some of the best food in all of Italy? Producing the world’s best pizza, pasta, and coffee, seafood, snacks and sweets, Naples has it all. All while being surrounded by fertile countryside, a plentiful sea, and culinary attitude.

Naples is our favorite city in Italy and for good reason. Forget the hype about crime and dirty streets and learn to embrace it. Naples’ flaws are what make it unique and exhilarating.

What to do in Naples?

Gino Sorbillo

If Naples has the best pizza in the world and Gino Sorbillo has the best pizza in Naples then you could say the best pizza can be found at Gino Sorbillo. Expect a massive crowd around the pizza joint and crazy long waits for a table.

However, there is one trick, push through the throngs of people, walk up to the hostess, and order your pie take away. Even with two hour plus waits you can get a pizza in less than five minutes. The best part is it’s €3.50 for a Margherita pizza.

Cafe Culture

Coffee is a serious affair to Neapolitans. You can’t walk down a street in Naples that doesn’t have a cafe bar. A coffee shop in Italy is no Starbucks, it’s standing room only and the drinks are made to be drunk immediately, leave the travel laptop in the hotel room. If you’re looking for a charismatic bar check our Bar Mexico.

Castel Nuovo

It’s a focal point of the city and close to the famous Piazza del Plebiscito. The castle dates back to 1282 and offers amazing views of the harbor from its ramparts.

National Archaeological Museum

We’re not museum people, but this museum boasts an impressive amount of ruins.


Train Travel in Italy

Traveling around Italy by train is the easiest and best way to maximize your time in the country. Every destination on this list is connected via train and they’re all easily accessible. If you’re looking to save some money you can also travel via bus.

There are two train companies in Italy. Trenitalia is largely based in the North and their trains are generally nicer and more expensive. NTV Italo is more widespread towards the South and they are generally cheaper than Trenitalia.

If you link all of the cities in the post you should have to take a train no longer than a couple of hours, with only a handful of changes if any.

If you want more information on train travel in Italy Seat 61 is an excellent guide.


There is so much more to Italy!

Dolomites Superski Pass Trentino

I hope this guide helped you out. It’s a general post that covers many of the main sights and cities in Italy. We have to stress there is so much more to Italy that is not on this starter list. We particularly love Sorrento, the Amalfi Coast, and Sicily in Southern Italy! See the rest of our Italy guides.

Transport To and Around Italy


Getting to Italy has never been cheaper with budget airlines such as RyanAir operating out of many Italian cities. If you are flying from a different continent the main hubs are Rome, Florence, and Milan.

Once in Italy, the best way to get around is via train. For long-distance routes, it’s best to book beforehand with Trenitalia and reserve a seat. If you are traveling shorter distances it’s also possible to show up at the train station a buy a ticket there. Or get around Europe with a Eurail.

We’ve rented a car numerous times in Italy and it’s a great way to get around on your own schedule. An automatic rental car can go for as low €15 a day in the low season up to €45 a day in the higher seasons and will ensure you get to all the best places in Italy. Knowing how to drive a manual car will often get you cheaper rates in Europe. If you’re traveling as a group it is worth your while to hire a car for your trip.

We traveled around Italy for one week and paid about $300 for a car rental in Italy, which was a pretty decent deal in my opinion! I generally like to check comparison sites so I can get the best prices.

My favorites to look at are:



What to Pack for Italy


What to wear in Italy is one of the first things to consider once you plan the basics of your first trip to the country. Packing can be simple.

Generally, Italians are stylish and we recommend dressing casually that way you’re comfortable when hanging out with locals.


Italian Guidebook

We love to have a guidebook when traveling. We spend enough time attached to our phones in everyday life and planning our trips. Once we reach a destination like Italy, we put the phone away and pick up a guidebook to help with our trip.

Travel Insurance

We don’t travel without travel insurance and neither should you. You never know what can happen in a foreign country and it’s best to be prepared. World Nomads provides good short term coverage.

SafetyWing is perfect for digital nomads. See our full review here!

Adapter

Remember that Italy uses both the  “Type L ” Italian adapter and the Europlug. Many adapters are interchangeable, so make sure you find a good one like the one I have to keep you charged.


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