Here’s How to Plan an Amazing Trip to Italy!

Planning a trip to Italy? Magnifico!

From the delights of pizza and pasta to the remnants of a grand ancient empire and a world-renowned fashion scene, Italy caters to every traveler’s dream.

Stretching for 736 miles from top to bottom – with dramatic northern mountains and idyllic beaches in the south – this European country is also as diverse as it is beautiful. 

In fact, count up all the grand cities and beautiful places in Italy, and you could spend a lifetime here!

But with attractions like the gondolas of oh-so-romantic Venice, the Leaning Tower of Pisa, the ancient sites of Rome, islands like Sicily and Capri, and stunning coastlines like the Amalfi Coast and Cinque Terre – well, how do you choose where to go?

And what do you need to know if this is your first trip to Italy?

Planning your trip to Italy

Things to know when visiting Italy for the first time 

Italy travel requirements

Before you get too excited about planning your Italy trip, make sure you have the right documentation.

To visit Italy, you need a passport with at least six months’ validity from your arrival date. USA and Canadian passport holders can stay in the country for 90 glorious gelato-filled days without a visa. 

Bear in mind that Italy is a Schengen country. That means your 90 days here count towards any other days that you wish to spend in the Schengen area.

So, if you spend 60 days in Italy, you’ll only have 30 more to spend in countries like France and Spain. You’ll then need to spend 90 days out of the Schengen area before traveling back into it. 

The entry rules are similar for visitors from countries like the UK and Australia.

But EU nationals can come and go from Italy as they please. Some passport holders from other countries will need to acquire a Schengen visa before traveling to Italy. 

Getting to Italy

Italy has nine major international airports dotted around the country. You can usually find affordable flights (and often cheap flights) to Rome, Milan, Florence and Venice from European and even North American cities. 

If you want to fly non-stop from the United States, New York is your best bet, although there are routes from Chicago and some other large cities. You can also change elsewhere in Europe, for example in London or Paris. 

If you’re already in Europe, taking the train to Italy is easy and affordable. International routes connect the nation with Switzerland, Austria, Germany and France. There are also long-distance coach services. 

Renting a car in Italy

Driving in Italy isn’t for the timid. (The traffic in Sicily shook us up so much that we returned our rental car just an hour after we got it!)

Still, many travelers love the flexibility that comes with renting a car. 

Rental offices are available in most of Italy’s cities and even some smaller towns. Popular rental companies include Europcar and Hertz. 

Currency

The Euro is the official currency in Italy, like it is in most of the European Union.

For the most part, U.S. dollars aren’t accepted – but you can easily exchange them for Euros in Italy. If you have leftover Euros when you leave Italy, it’s easy to exchange them for other currencies anywhere in the world too.  

To make life easier, most places in Italy accept credit cards. Visa and Mastercard are the preferred cards.

Visiting Italy in the spring and fall

For us, the shoulder season is the best time to visit Italy. The months in spring (March to May) and autumn (September to November) are particularly great times.

Visiting Italy in summer

It’s a good idea to avoid the summer months. The weather is hot and humid in July and August, and hotel prices soar.

Visiting Italy in winter

You’ll find the best deals in the winter months.

But then you have to contend with cold and possibly wet weather. And many hotels and restaurants in tourist areas that aren’t major cities shut down in winter.

Where to go in Italy for the first time?

Now for the tricky (and fun!) part – deciding the best places to go on your visit to Italy.

You won’t be able to tick off the whole country on your first Italian trip. 

Instead, we recommend choosing maybe two or three of the country’s top destinations – and returning for the rest at a later date.

The following are some of our favorite places to visit in Italy:

Venice

A bucket list activity is to take a gondola ride along the city’s canals and under its bridges. 

We also love traveling down the Grand Canal on a vaporetto (a public transit “water bus”). It’s a great way to view the magnificent palaces and grand old mansions along the canal.

But try to avoid Venice in the peak season. It’s one of the busiest cities in Europe in the summer!

Rome

Ahhh, the eternal city of Rome! Every cobblestone and corner has a story to tell. And of course, it’s the heart of Catholicism today.

And don’t forget to toss a coin into the 18th century Trevi Fountain to ensure your return to this magical city!

In Rome, you can also cross the border into another country – Vatican City.

The Pope’s residence, the Vatican is home to gorgeous art museums and the ornately decorated Sistine Chapel, which dates back to 1473.

No doubt about it. Rome is simply one of the best cities to visit in Italy for the first time!

Let’s talk logistics too. Rome’s Fiumicino Airport (Leonardo da Vinci International Airport) is Italy’s largest airport and the major gateway for travelers flying in from the U.S. and other countries.

So Rome is also the perfect first stop in Italy.

Florence

The capital of Tuscany, Florence is an Italian city that’s perhaps most famous for its renowned museums, art galleries, Renaissance architecture and food scene. 

Plus, you’re in beautiful Tuscany, so venturing into the countryside and doing a vineyard tour with wine tastings is also a great option! 

Tired after a busy day of exploring? Relax in the Piazzale Michelangelo, the ideal place to sit for a while and take in Florence life. 

Amalfi Coast

In contrast to the historic cities, the Amalfi Coast (near Naples) is made up of a glorious collection of colorful smaller towns and villages overlooking the turquoise Mediterranean Sea. 

The crowning jewel is the sun-soaked village of Positano – where narrow steps snake up cliffs around boutiques and cafés with drop-dead views.

(Positano is where we first tried limoncello – to go with our chocolate cake and cappuccino on a morning break. How’s that for eating in Italy!)

Cinque Terre

The rainbow-hued villages of Monterosso, Vernazza, Corniglia, Manarola and Riomaggiore spill down rugged cliffs into the heart of the Italian Riviera. 

Whether you want to sit and sample oh-so-fresh pasta or step out on some of the incredible hikes in the area, there’s plenty on offer in Cinque Terre. 

The main villages are a bit touristy, but walk a little further away from the center of each and you’ll come across traditional Italian farms and small locally-owned restaurants. 

Lake Como and Lake Garda

Italy’s two favorite northern lakes, Lake Como and Lake Garda are popular destinations summer and winter. 

Sip on an Aperol spritz as you look over Lake Como after a busy day exploring. Here, you’ll find wondrous places like Tremezo’s Villa Carlotta and the village of Menaggio, which dates back to the Roman era and boasts a picturesque lake promenade. 

While Lake Como is famous for its celebrity residences (George Clooney is one such celeb who owns a mansion here), Lake Garda is more wild and rustic.

That’s not to say that it doesn’t have lots of tourist infrastructure. For example, it’s home to the Gardaland amusement park, one of Italy’s most popular tourist sites for families. 

Sicily

In many ways, Sicily feels like an entity unto itself. 

Much of Italy is well-groomed, from its fashionable cities to its lovely showbiz-appeal lakes. 

Sicily, on the other hand, is more rugged, with a massive volcano, ancient ruins, a laidback atmosphere and seriously tantalizing food. 

The island has been at the crossroads of Europe for millennia, and to this day you’ll notice much more of a fusion of cultures here (Greek, Roman, African, Arabian, Norman) than elsewhere in the nation. 

Most tourists don’t visit Sicily on their first Italian trip. But if you prefer off-the-beaten-track destinations, you’ll be rewarded by visiting this island.

Sample 2-week Italy itineraries

For your first time in Italy, we recommend visiting the three top Italian cities – Rome, Florence and Venice. Or at least pick two of these cities. If you’re an art and museum lover, go with Rome and Florence.

You’ll need at least three days in Rome. For Venice and Florence, you could get away with two days in each city.

You can then add other places in Italy, depending on your interests.

For example, if picturesque coastal towns appeal to you, add the Amalfi Coast. To immerse yourself in Italy’s food-and-wine scene, include a culinary journey through Tuscany or Piedmont.

You could go with a tour operator for all or part of your trip who organizes everything for you. (A couple we met on our recent Sicily trip had built a one-week cooking school vacay into their longer DIY Sicily visit.) 

Book your hotels in Italy

Italy’s position as a top tourist destination means that it has some fabulous luxury hotels. Be sure to book in advance to get the best possible prices.

The following are some of the best hotels in Italy:

St. Regis Rome

You can’t beat the opulence of the reinvented St. Regis Rome – one of our favorite romantic hotels in all of Europe! Rome’s first luxury hotel, it opened in 1894 as “The Grand.” 

Its location right in the heart of the city is ideal too.

Margutta 19 (Rome)

A member of Small Luxury Hotels of the World, this five-star boutique hotel is an intimate abode less than a 10-minute walk from the Spanish Steps. 

It has just 16 rooms decorated in trendy modern decor. Choose a classic room with a luxurious bathroom or a full suite with a terrace looking out over the bustling city center. 

As Margutta 19 is such a small hotel, it’s often booked up in the peak season – so reserve your spot early to avoid disappointment. 

Hotel La Calcina (Venice)

There’s no shortage of romantic hotels in Venice – one is the historic Hotel La Calcina. And you don’t have to break the bank to stay here either.

Located in the historic Zattere area, this delightful 3-star hotel is a little oasis on the Giudecca Canal.

Rooms all feature parquet floors and wooden furniture, but some are quite teeny. It’s worth spending a bit more for a larger room with a canal view.

We especially liked starting our days with breakfast on the canal-side terrace – sipping cappuccinos and nibbling on homemade cakes while watching boats glide by.

JW Marriott Resort and Spa (Venice)

Venice can be of hectic at the best of times. And while enjoying the dynamic city is usually top of most Italy traveler’s bucket lists, sometimes you just want to get away from it all. 

Enter the JW Marriott Venice Resort & Spa. 

It’s a huge resort hotel on its own island, Isola delle Rose, just off the coast of Venice. Enjoy strolling around the manicured gardens, soaking in the spa or relaxing on the rooftop pool deck. 

Some rooms have wall-to-ceiling windows, complete with plush furniture and luxury linens. And when you get itchy feet, Venice is only a short boat ride away.

Monastero Santa Rosa Hotel (Amalfi Coast)

A trendy but charming hotel located in a 17th-century former monastery, Monastero Santa Rosa Hotel & Spa is perfect for a luxury stay. 

Located on the edge of a cliff, this adults-only spa hotel has some of the best ocean views of the entire Amalfi Coast.

Indulge in a relaxing massage at their wellness center, then sip on a glass of Prosecco at the hotel bar while taking in the incredible views! 

Principe di Salina (Sicily)

Most guests are content to relax in double cabanas sprinkled around the infinity pool. But excellent public mini-buses can also take you to rocky and pebble beaches around the island.

Because the candlelight 4-course dinners are so good at the hotel, we ate in most nights. From pasta with swordfish, flavored with mint, to pistachio ice-cream (and Mount Etna wine, of course!), we tasted the best of Sicily here.

Hotel Porto Roca (Cinque Terre)

Over 40 rooms, most with breathtaking sea views, are on offer at the Hotel Porto Roca. Located in Monterosso al Mare, this elegant villa-style hotel is one of the best places to stay in Cinque Terre. 

Enjoy some of the region’s local gastronomy on your private balcony or take a dip in the villa’s infinity pool. For beach time, you’re taken care of with complimentary loungers and parasols on the beach below. 

Buy tickets to major attractions in advance

When doing your Italy travel planning, you should purchase your tickets for popular attractions in advance.

Some of Italy’s hotspots can be very busy, especially during peak season. If you wait until you arrive in the country, you might be turned away or hit with higher prices.

Be sure to book these attractions in advance: 

Vatican City

One of the best ways to see this micro nation is by a guided tour, which usually includes skip-the-line tickets. 

This Vatican Museums tour lets you skip the ticket line to see the Vatican Museums and Sistine Chapel.

Or pay a bit more for a live tour guide on this popular small-group tour of the museums, Sistine Chapel and St. Peter’s Basilica.

Colosseum

Another popular Rome attraction, the Colosseum still stands as the largest amphitheater in the world and is well worth seeing. 

As lines are heaving here in the summer months, it’s essential to pre-book your tickets. Book a Colosseum guided tour, and you’ll get priority access. You can also book tickets from the Colosseum’s official retailer.

Pompeii

The ancient city of Pompeii, buried under ash and pumice when Mount Vesuvius exploded in 79 A.D., makes for an excellent day trip from Naples. 

You’ll learn all about this tragic historical event and see some fascinating remains. Since Pompei was buried so quickly under volcanic ash, much of it is well-preserved.

This small-group tour with an archaeologist is top-rated.

Capri Island

With beautiful blue Mediterranean waters and secret grottoes, the island of Capri is nature’s delight (though we caution you not to visit in the summer high season if you don’t like crowds).

Capri is an easy day tour from Sorrento, Naples and elsewhere along the Amalfi Coast. Its fantastic swimming spots and photo opportunities make it an immensely popular attraction. 

Milan Cathedral

This is the largest church in Italy (since St. Peter’s is located in Vatican State).

It took a whopping six centuries to complete – its foundations were laid out in 1386, but it was only deemed complete in 1965. 

Visiting the cathedral is like taking a journey through 600 years of Italian history. You can also climb to the top for an immense view over the city. 

Tours range from self-guided Milan Cathedral tickets (with an optional audio guide) to this combination guided tour of Milan’s Duomo and “The Last Supper” at the Santa Maria delle Grazie Church.

Water taxi into Venice

This is, without a doubt, the coolest way to enter Venice. It beats sitting on a stuffy bus! 

Be whisked straight from the international airport to the city center as you take in canal views from the water on this airport-to-Venice water taxi transfer.

(If you’re arriving from the Venice cruise port, read our post on getting to Venice or the train station from the port.)

Make reservations for top restaurants

Italian food is, without a doubt, legendary.

But if you’re visiting during peak season (May to September or during any European holidays), you’ll need to make restaurant reservations in advance for some places. 

This is because meals in Italy are typically longer affairs – it’s one of the Italian food traditions you’ll quickly come to appreciate! Enjoying food in Italy like a local means many courses, with long gaps between

So tables need to be reserved early – generally a week in advance. Book more popular restaurants two weeks ahead (three in peak season). 

Most restaurants have online booking systems. So as you plan your trip to Italy, you can make quick reservations through OpenTable and similar platforms.

Do you need to book everywhere you’re eating in Italy? No. Hole-in-the-wall type places and most pizzerias don’t require bookings and usually have a high table turnover. 

So what are some of the best restaurants Italy?

Da Vittorio (Bergamo)

This family-run restaurant in the north of the country serves fresh seafood and delicious wine straight from its cellar. 

Despite its unassuming countryside location, Da Vittorio has racked up three Michelin stars over the years. Visitors flock here to try specials like king crab salad and tomato-and-basil paccheri pasta. 

Ristorante de Ivo (Venice)

Sample soft tagliatelle with truffles or mussels in a garlic sauce when dining at George Clooney’s favorite Venice restaurant. While the cuisine is firmly on the fine dining spectrum, Restorante da Ivo is unpretentious, and you’re guaranteed personable service in a relaxed atmosphere.  

Perseus (Florence)

Florence is arguably the culinary capital of Italy. So you must try Florentine steak in Florence. And there’s no place better than Perseus for meat dishes. 

A tip: The meat is served rare, and as Florentines are very proud of how it’s cooked, don’t ask for it well-done. 

Aja Mola (Palermo)

Just when you think you’ve explored enough of Italian cuisine, head to Sicily. 

With rich pasta dishes to tantalize even the most well-traveled taste buds, the island’s cuisine offers its own take.

In the Sicilian capital, Aja Mola is one of the best seafood restaurants, serving dishes like marinated mackerel with citrus fruits as an appetizer and linguine with clams as a main. 

Archestrato di Gela (Palermo)

If you fancy pizza in Palermo, look no further than Archestrato di Gela, widely regarded to have the best pizza on the island. 

While you don’t need to book for many Italian pizzerias, this is a particularly popular spot, so book a table at least two days in advance. 

10 Other Italy travel tips

1) It’s better to do two weeks in Italy than one

Don’t cram everything into a one-week trip. Aim for two weeks and choose only three to four places. Otherwise, you’ll be traveling too much – with no time to appreciate the land of pasta, pizza and Parmigiano.

2) Balance the big and small

Mix it up. Plan your Italy itinerary to include some big cities (like Rome and Bologna) and some relaxing places or small towns (like Alberobello, Capri and Polignano a Mare) to get the best of both.

As for the major centers, you’ll probably want to visit at least two of the must-see cities in Italy – perhaps Rome and Venice, or Rome and Florence?

3) Do day trips

It’s better to base yourself in, say, three or four places and do day trips – rather than stay overnight in a whole bunch of places.

4) Don’t try to do and see everything

Depending on how much time you have, keep your itinerary full. But don’t overload it.

5) Take the train in Italy

Italian drivers are known to regard traffic rules as mere suggestions. 

The best way to visit Italy and get around the country is by train, in our view. High-speed trains make short work of the long distances between Italy’s bigger cities.

Unless you’re visiting rural areas like Tuscany or Puglia, you’d be wise not to rent a car.

6) In summer, book hotels with air-conditioning

If you decide to visit Italy in the summer months (especially June to August), make sure you book a hotel with air conditioning. If you can’t find one, at least ask for a fan. You’ll need it.

7) Drink wine!

Because when in Italy, you have to! Tuscany, Sicily and Cinque Terre are all famous for their wines.

Wine is an integral part of your meal, not an enhancement – and it’s often cheaper than soft drinks or bottled water!

8) Understand the coperto charge

The coperto charge is a small fixed fee (typically between €1 to €5 p.p.) that’s added to your bill at most restaurants. It’s also said to cover free items like bread (even if bread isn’t served), the cost of washing the table linens and other similar costs associated with dining at a restaurant.

On the plus side, the coperto avoids embarrassments associated with tipping. Tipping isn’t expected in Italy. But for good service, you can round up the bill or leave an additional Euro or two.

9) Expect to eat dinner late

Restaurants aren’t usually ready for dinner before 7:30 to 8:00 pm. Italians eat dinner late, typically around 9:00 or even 10:00 pm.

And don’t expect a full American breakfast with eggs and bacon in the morning. For most Italians, breakfast in Italy consists of cappuccino and a croissant or sweet pastry.

Mind you, the better hotels and B&B’s typically offer lovely breakfast spreads with sliced meat, cheese, fresh fruit, yogurt and the like, in addition to breads and pastries.

10) Cover up when visiting churches

Both men and women need to cover their knees and upper arms. That means no sleeveless dresses or tops, and no skirts or shorts above the knee.

Pants are your best bet, but long skirts are permitted.

So pack appropriately – which leads us to the next section!

That’s it for Italy trip planning guide!

With mouthwatering cuisine, amazing art galleries, dramatic landscapes and centuries of rich history, it’s no surprise that the European nation known for la dolce vita is one of the world’s most popular tourist destinations. 

It’s a relatively easy country to visit. You shouldn’t need a travel agent for help with planning an Italian vacation the first time you go. 

Hopefully this Italy travel guide has proved to be a good starting point for mapping out your trip.

Ciao for now!

See our other travel guides on Italy

• 11 Top Italian Cities to Visit
• 23 Most Beautiful Places in Italy (Not Big Cities)
• 17 Most Romantic Things to Do in Venice
• 10 Most Romantic Hotels in Venice
• Getting From the Venice Cruise Port to the Train Station
• The Beautiful Bridges of Venice
• The Leaning Tower of Pisa is Worth Visiting!

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Photo credits: 10, 11, 17, 22, 28 © Janice and George Mucalov, SandInMySuitcase

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