Planning a Trip to Italy: Travel Tips + 2023 Guide

There are so many reasons to visit Italy!

It’s the home of not only pizza and pasta, but one of the world’s most famous ancient empires and an iconic fashion culture. Whatever vacation you desire, Italy has something for you. 

It also has scenery ranging from dramatic mountains in the north to idyllic beaches in the south. Stretching over a length of 736 miles from its northernmost to southernmost point, this European country is as diverse as it is beautiful. 

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

But, if you only have a short amount of time, you may be wondering how to plan an Italian vacation.

With attractions like the gondolas of 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? 

It’s the European nation that encompasses everything – so how do you fit it all into one or two weeks? 

Planning a trip to Italy

Things to know before going to Italy 

Currency:

The Euro is the official currency in Italy, like it is in most of the European Union. (The much-loved Italian lire officially went the way of the dodo bird at the beginning of 2002.)

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.

Italy travel requirements:

Before you start planning a trip to Italy, make sure you have the right documentation.

To visit Italy, all you need is 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. 

Do 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 an experience for the faint-hearted, but many travelers love the flexibility that comes with a rental car. 

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

Pick the right time to go to Italy

You want to pick the right time of year to go – when there are fewer crowds and the weather is good.

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.

It’s a good idea to avoid summers, as the weather starts to get quite hot and humid in July and August, and hotel prices soar.

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.

Decide where to go in Italy

Now for the tricky part – how to decide where to go in Italy!

Italy has countless tourist attractions, and you won’t tick off the whole country on your first trip. 

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

Here are our favorite places to visit in Italy: 

Venice:

There are few cities quite as alluring as Venice. Famous for its waterways connecting the city’s landmarks and its labyrinth of winding streets, the UNESCO city is a photographer’s paradise. 

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

Rome:

Italy’s vibrant capital, Rome is the birthplace of one of the world’s most powerful ancient empires.

And of course, it’s the heart of Catholicism today.

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

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

Back in Rome, don’t miss attractions like the 18th century Trevi Fountain, the Colosseum (the largest ancient amphitheater in the world) and the beautiful Baroque-style Piazza Navona (with Bernini’s famous Fountain of the Four Rivers.)

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 Mediterranean coastline. 

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 places like Tremezo’s Villa Carlotta or villages such as 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 like traveling to more off-the-beaten-track destinations, you’ll be rewarded by visiting this island.

Word has been getting out about Sicily – and its time to shine has come.

Sample 2-week Italy itineraries

To see how all the best Italy attractions can tie together, check out the following sample two-week Italy itineraries.

You may choose to 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.) 

But If you’re wondering how to plan a trip to Italy on your own, these itineraries are really helpful.

Two weeks is enough time to get a flavor for Italian culture and see some of the main sights. 

But of course, you could always spend longer. Italy is a big country, and it’s packed with attractions. We planned almost one month in Sicily alone on our most recent Italy visit.

Book your hotels in Italy

Italy’s position as a top tourist destination means that it has some fabulous luxury hotels. Booking these in advance is highly advisable to ensure you get your chosen option at the best possible price. 

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 terrace jutting out into the canal – sipping cappuccinos and nibbling on homemade cakes while watching boats glide by on the canal.

JW Marriott Resort and Spa (Venice):

Venice can be nothing short 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 do 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. Here you can 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 with some of the best ocean views of the entire Amalfi Coast, this adults-only spa hotel features a swimming pool, wellness center with Turkish bath and the chance to enjoy a relaxing massage or other treatments. 

Or just on turn vacation mode by sip on a glass of Prosecco from the hotel bar, and taking in the incredible views! 

When you want to explore, there’s a free shuttle bus to Amalfi from the hotel. 

Principe di Salina (Sicily):

Principe di Salina has just 12 white-on-white rooms, all with ocean views and large terraces with a hammock.

Most guests are content to relax in double cabanas sprinkled around the infinity pool. But an excellent public mini-bus system 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, the 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 you’re doing your Italy travel planning, 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 to book your tickets, you may either be out of luck or find that the prices are astronomical. 

Make sure that you book the following attractions in particular 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 tour on GetYourGuide includes skip-the-ticket-line tix with entry to the Vatican Museums and Sistine Chapel through the dedicated GetYourGuide entrance, plus an audio guide, so you can explore leisurely at your own pace.

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 (3 to 4 hours long).

Colosseum:

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

Lines can be heaving here in the summer months, so it’s essential to pre-book your tickets, which you can do as part of a guided tour or via the Colosseum’s official retailer.

Pompeii: 

The ancient city of Pompeii, which was 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. As Pompeii was buried quickly under volcanic ash, it remained well-preserved until discovered much later in the 16th century. 

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:

The largest church in Italy (since St. Peter’s is located in Vatican State), the Milan Cathedral took a whopping six centuries to complete. Its foundations were laid out in 1386, but it was only deemed to be completed 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 simple entry tickets (with audio guide, if you choose) to combination guided tours 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.

While it’s replicated all over the globe, few international Italian restaurants can compare to Rome’s top Michelin star restaurants or, when it comes to less fancy places, what you’ll find in Ortigia’s labyrinth of streets in Sicily, say.

We’re talking creamy pastas, authentic pizzas, tantalizing risotto and much, much more.

Italy’s cuisine is famously regional, as Stanley Tucci’s TV series Searching for Italy attests. The flavors are rich and intense, and the ingredients fresh and virtually preservative-free. 

If you’re visiting during peak season (aka May to September all over the country, or during any European holidays), you’ll need to make restaurant reservations for some eateries. 

One of the Italian food rules or traditions you’ll quickly come to appreciate is that meals in Italy are typically longer affairs.

Locals see eating out as a chance to catch up with friends or spend time with family, perhaps enjoying four courses and wine after dinner too, or even just having two courses with long gaps in between. There’s no rush here! 

However, this means that booking is very advisable. If you don’t, you may find that you’re turned away, even if the restaurant has empty tables.

Generally, tables are reserved up to a week in advance. Some of the most popular restaurants are booked up two weeks in advance, or even three in peak season. 

We found most of the “better” restaurants in Sicily have online booking systems, so you can reserve in advance of your trip through OpenTable or other platforms (or even just by emailing).

Some restaurants now require a prepaid deposit too, ranging from 50 to 100 Euros, to guarantee your reservation. (They’re usually cancelable on 24 hours’ notice.)

Then when you arrive in Italy, you can get your hotel to call and make reservations at other restaurants for you.

Do you need to book everywhere you’re eating in Italy? We hear you. You don’t want every moment of your trip planned and pre-digested. It’s nice to have a little spontaneity.

If you’re just dining at hole-in-the-wall type places, you likely won’t need reservations. Plus, most pizzerias don’t require bookings and they usually have a high table turnover. 

But for some of the best restaurants in Italy, particularly those that have Michelin stars, reservations are very advisable! 

So what are some of the best restaurants in the nation? Here’s a list: 

La Pergola (Rome):

This is one of Italy’s only three-star Michelin restaurants. (There are only 143 three-star restos in the whole world!)

Serving dishes like lobster with vegetables and pinzimonio (an oil-based dressing) and deep-fried zucchini flower with caviar, La Pergola basks in elegance with features like an 18th century chandelier and exceptional views over the city center. 

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, ensuring that visitors continuously flock here to try specials like king crab salad or 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):

If you eat meat, Florentine steak is a must in Florence, arguably the culinary capital of Italy. A beautiful traditional spot in the heart of the city, Perseus is one of the best restaurants 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 and enough citrus to tantalize even the most well-traveled tastebuds, the island’s cuisine offers its own take.

In the Sicilian capital, Aja Mola is one of the best seafood restaurants, serving dishes like tagliolini pasta with shrimps for a first course and tuna belly with veal tongue and grilled watermelon as a main. 

Archestrato di Gela (Palermo):

If you fancy pizza in Sicily, 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 you’d be wise to reserve your table at least two days in advance. 

10 Other Italy travel tips

Here’s some more advice for planning an Italy trip:

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

The best way to plan a trip to Italy is to not to cram everything into a one-week trip. Spend at least two weeks in the land of pasta, pizza and Parmigiano to get the most out of your visit.

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 (or cover charge) originated in the Middle Ages, when people would stop at inns, but bring their own food from home because the food sold there was expensive. Unable to make any money, the inn owners started the coperto charge for the seats that guests occupied.

Now, 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.

Everyone gets charged the coperto, whether you’re a tourist or a local.

On the plus side, the coperto avoids embarrassments associated with tipping.

Tipping isn’t expected in Italy. But if you’d like to leave a little something for good service, you can round up the bill or leave an additional Euro or two.

9) Expect to eat dinner late:

North Americans traveling to Italy should note that 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.

10) Cover up when visiting churches:

The basic dress code (for both men and women) is that you need to cover your 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.

Packing for your Italy trip

That’s it for our 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. 

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

Ciao for now!

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

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