Italy: A Comprehensive Two-Week Itinerary for First-Timers

Puglia – Two week Italy itinerary

With two weeks in Italy, how do you maximize your time? We can’t all travel the world indefinitely and spend endless time on holiday in Italy. Regarding any Italian itinerary, there is no perfect plan, and everyone has their own interests. So we wanted to assemble this amazing two-week Italy Itinerary anyone can steal.

Italy is the one country that we have repeatedly returned to. This next winter, we will make it our fifth time touring around Italy! Something about the culture, history, and food 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 suggest stepping a bit off the simple route, and I’ve suggested several 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 some must-see places in Italy, so pack your bags and pick what you like for your trip.

A Two Week Italy Itinerary


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 who wreak havoc on the city’s crumbling infrastructure.

The sinking city is a network of 118 islands connected by bridges. Buildings here are old, and if you manage to escape the crowds, it feels like you’ve stepped back five centuries. It is surreal, and we do have a love for Venice.

One of our top tips for Italy is that Venice is best in the shoulder and off-seasons. The canals of Venice are notorious for harboring a lot of waste; 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.

Venice is a must-see place in Italy, except in the summer months.

What to do in Venice?

Piazza San Marco

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

Ca’ Macana

Mask shops rule the streets of Venice, but most of these are cheap imports marketing to tourists. Ca’Macana is a fabulous genuine mask shop in Venice that makes all its 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 allow you to dress up and have 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.


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 be on your two-week Italy 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 you to get lost in its historic heart.

Florence is known for being the birthplace of the Renaissance and full of history. Walking the narrow, cobblestone streets, 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 its 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 eat fantastic bites 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 since that day and is lined with shops and buildings. Make sure to catch it from the riverside and cross 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.


Italy hardly has a more famed region than the rolling hills of the Tuscan countryside. It’s well worth adding the region to your two-week Italy itinerary. You can take day trips from Florence, stay in one of the numerous towns, and enjoy a few great Italian road trips from the region.

The region is geographically diverse, with beautiful beaches, 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?


It’s only a two-hour train ride from Florence and 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.


Be warned, Pisa is underwhelming. Many visitors feel drawn to come here for its famed tower. The most entertaining part of a stop in Pisa is watching everyone air five the tower while they 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.


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 Terre

Italy has many must-see places, but Cinque Terre 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 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. A trail connects the five towns, and it’s a 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. When wondering where to stay in Tuscany Cinque Terre is a great option!


The capital of Umbria does not make enough traveler lists, but it should be added to a 2 week Italy itinerary. 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? 


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


Home of St Frances, the patron saint of Italy, and a site of pilgrimage for Italians. It’s one of Italy’s most beautiful hilltop towns, 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.


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 not enough time in any two-week Italy itinerary to explore all Italy offers. Not even a month would suffice!


Milan should be on anyone’s two-week Italy itinerary. Milan (Milano) is the world’s fashion capital and is home to greats like Prada, Valentino, Versace, and Dolce & Gabbana. However, most tourists do not shop for these clothing brands, which isn’t a reason to go unless you’re into high-class fashion.

In any case, the city does pack a fair amount of sights, museums, and restaurants worth visiting, and in general, there are plenty of things to do in Milan.

It’s a city full of style and known for being posh. This means hip bars, well-dressed locals, and many great places to eat. The city also serves as a great base for exploring 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 a 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. Book your tickets in advance if you’re traveling in the summer months.

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. 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 in Italy and the world.

Galleria Vittorio Emanuele II

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


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 Italy – and the world. History haunts its every corner, littered with historic sites 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.”

Rome at sunset, a great destination for photography lovers

Rome at sunset, a great destination for photography lovers

What to do in Rome?

Trevi Fountain

We all know the saying that if you throw 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 the lines, entering St Peter’s Basilica could take a while, 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, where you can admire the Sistine Chapel. If you want to avoid lines, it helps to buy tickets in advance.

Explore Trastevere

Cross the Tiber river to Trastevere. The bohemian and hip neighborhood is 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 half of your day. The good news is they are close to the subway station, and right beside 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 ranging 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.


This city is the opposite of Milan, you either love 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. 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 Italy? Producing the world’s best pizza, pasta, coffee, seafood, snacks, and sweets, Naples has it all. This is thanks to the fact fertile countryside, a bountiful sea, and a culinary attitude surround the city.

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 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. You can get a pizza in less than five minutes, even with two-hour-plus waits. 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 out 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 harbor views from its ramparts.

National Archaeological Museum

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

Related read: Is Pompeii worth a visit?

Train Travel in Italy

Traveling around Italy by train is the easiest and best way to maximize your time there and complete everything on your Italy itinerary. Every destination on this list is connected via train – many of them via scenic train rides! – and they’re all easily accessible. If you want to save 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 in the South and cheaper than Trenitalia.

If you link all the cities in the post, you should 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!

I hope this guide helped you out. It’s a general post covering many of Italy’s main sights and cities. There is so much more to Italy that is not on this starter list. We particularly love The Dolomites, Lake Como, and Sicily in Southern Italy! See the rest of our Italian guides.

Transport To and Around Italy

Getting to Italy has never been cheaper, with budget airlines like RyanAir operating out of many Italian cities. If you fly 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, booking beforehand with Trenitalia and reserving a seat is best. If traveling shorter distances, you can also show up at the train station and buy a ticket there.

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 as €45 a day in the low season and up to €100 a day in the high seasons and will ensure you get to all the best places in Italy. Knowing how to drive a manual car will often get cheaper rates in Europe. If you’re traveling as a group, hiring a car for your trip is worth your while.

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

Italy’s allure is undeniable, and as your two-week adventure ends, the memories you’ve made will beckon you to return. Until then, carry the beauty of Italy with you. Arrivederci!