Health and Travel Alerts Learn More Left arrow

There’s a lot to consider when planning a trip to Italy, one of Europe’s most irresistible destinations. Its abundance of history, culture, and spellbindingly beautiful cities mean that it’s also one of the best places to visit more than once.

As such, it’s important to carefully research how to plan a trip to Italy so your journey attains the heights that one expects of this Old World favorite. Once you’re an expert at the preparation, you can begin planning your next trip as soon as you’re home.

Here are the steps you need to plan your trip.

Consider Where You’d Like to Go

How to plan a trip to Italy - Portofino


Figuring out which part of the country you’d like to visit is probably the most difficult part of traveling to Italy. From the northern top of the “boot” to its southerly pointed “toe”, the Italian peninsula is a unity of sunny Mediterranean landscapes, remarkable cities, and blissful beaches.

Whether you’re a first-time visitor to the country or are simply unsure where to go in Italy next, here’s a quick overview of the perennially popular options.

Umbrellas lined up on Monterosso Beach in Cinque Terre

Monterosso al Mare, Cinque Terre

From the north, the Italian Riviera is a mountain-backed swathe of pastel-colored seaside resorts. Part of the Italian region of Liguria, headline destinations here include Portofino and the Cinque Terre. Besides these picturesque fishing villages, Liguria is also home to gems such as its capital Genoa, home to Europe’s largest medieval center.

It’s (almost) always sunny in Liguria, so this region is superb for beach vacations, soaking up the Italian way of life, or dining al fresco on supersized red shrimp.

How to plan a trip to Italy - Tuscany


Journey south along the west coast and you quickly arrive in Tuscany. While, like Liguria, Tuscany is blessed with a wonderful coastline (only with more sand), this region is better known for its hinterland. There you’ll find rolling hills, Chianti vines, and stunning medieval cities such as Florence, Pisa, and Siena.

If you’re interested in Italian culture, Tuscany is second only to Rome in this regard.

Florence is a must for Italophiles, the cradle of the Renaissance, with the famous Uffizi Gallery and even public squares like Piazza della Signora home to world-famous sculptures such as a replica of Michelangelo’s David (head to the Accademia Gallery to see the original).

Travel south and you arrive in Lazio, the region that’s home to Rome, the country’s capital. An astonishing intersection of ancient history, religion, cuisine, and culture, a visit to the Eternal City is a bucket list adventure. Come for the Vatican, stay for the wine bar aperitivi.

Couple inside a restaurant in Naples

Restaurant in Naples

Naples to the south of Rome is one of the best food cities in Italy. The home of pizza, this charismatic southern city throbs with life, its eponymous bay overlooked by looming Mount Vesuvius.

The best views of the volcano are probably found on the southern edge of the Gulf of Naples, from beneath the prolific lemon trees of Sorrento. Perched on cliffs above the Tyrrhenian Sea, this gloriously handsome town has been a popular seaside holiday destination since Roman times.

How to plan a trip to Italy - Amalfi Town

Amalfi Town

Take a winding coastal road a short distance south of the Sorrentine Peninsula and you arrive at the iconic architecture of the Amalfi Coast.

This famous run of punchbowl-bright seaside towns acts as colorful ornamentation for some of Italy’s most spectacular coastal scenery. A place to see and be seen, it’s an epicenter for fashionistas, and the region’s famous for its handmade leather sandals and ceramics.

Scenic waterfront of Palermo, Sicily

Palermo, Sicily

Across the cerulean Tyrrhenian Sea rise the mountainous profiles of Sicily and Sardinia. Both islands are officially part of the Italian state, yet both are truly unique destinations. Each has a multi-layered history, social idiosyncrasies, and Italian cuisine inflected with flavors that speak to their intriguing past.

Cross the Apennine spine of the mainland, and you’ll reach Italy’s eastern Adriatic coastline. Highlights here include the grand café culture of the northern port of Trieste, the sun-bleached quays of southerly Brindisi, and, in between, Italy’s most romantic place: Venice.

Choose Your Route

Gondola ride in Venice


It is possible to see a number of Italy’s top-tier destinations in a short space of time. Many of its major cities and cultural sights are clustered relatively closely together in the adjoining regions of Lazio (Rome), Tuscany (Florence, Pisa), and Campania (Naples, Amalfi Coast).

Beware of burnout, however. So great is this country’s store of lifelike sculptures, mosaic-filled cathedrals, and legendary pizza places that saturation by the sublime is a real risk.

If you’re planning a multi-destination trip, don’t feel you have to choose two places with similar qualities such as cultural big hitters Rome and Florence on the same visit. You could even save one for the next trip, and travel to a city like Venice instead, where you have time to process what you’ve seen in Florence while sipping prosecco on a relaxing gondola ride.

Couple at a restaurant in Sorrento

Restaurant in Sorrento

Try to marry up a cultural city visit with a period in somewhere more laid-back like Liguria or Sorrento, where you can, at your own pace, absorb the unique charms of the Italian coastal town experience.

Above all else, Italy’s people are its greatest treasure. It’s tempting to rush from place to place ticking off immortal landmarks, but it’s the chic, scooter-gunning mortals surrounding you that make Italy what it is. Ensure you’re making time for the kind of encounters that transform a good trip into a story you never tire of telling.

Plan When to Go

How to plan a trip to Italy - Florence


This southern European country languidly stretches from the Alps towards the center of the Mediterranean. So while the mountains cradling Lake Como and even the country’s central Apennine range often see snow in the winter, Italy mostly enjoys a moderate and mild Mediterranean climate. Of course, this becomes warmer the further south you travel.

In early spring, however, the weather can be overcast. For your surest bet of sunshine filtering through blooming wisteria and onto your al fresco breakfast, travel from May onwards.

From the sun loungers on the Genoese quayside to the coastal archaeological parks of Agrigento in southern Sicily, May offers warmth and the sensory explosion of Italy’s flora. Medieval walls billow with bougainvillea and high street flower boxes glow with marigolds in fragrant blossom.

May also offers the possibilities of fewer crowds in the cities, prior to the start of the high season in June. And while mosquitoes aren’t a major issue, they are more prevalent during summer in Italy.

Couple strolling Amalfi Town

Amalfi Town

Once summer fully kicks in, Italy is at its most fully realized. The sunlight illuminates Sardinian shallows the green of cats’ eyes, bounces off the majolica-tiled domes of the Amalfi, and shines up the chrome of parked Vespas in Trastevere. In the evening, the warmth lingers into the small hours.

June and July are perfect months for an Italian beach vacation, although the main beaches will be busy. The situation gets even more crowded during August when the entire country goes on vacation. The Italians, escaping the sweltering inland heat, migrate to the limpid breakers of the Tyrrhenian and Adriatic seas.

Even as late into fall, the weather remains reliably pleasant. During this shoulder season, as autumn begins to color the Sangiovese vine leaves of Tuscany, trattoria menus embrace truffle season. It’s an excellent time to journey out into the countryside, as fall is also one of Italy’s festival high seasons.

Street view of Piazza Navona, Rome

Piazza Navona, Rome

You’ll find towns hung with pennants, celebrating the locality’s medieval heritage. Traditional games are played in piazzas, the townspeople march in costume blowing long fairytale trumpets, and a good deal of aromatic black truffle is shaved onto melt-in-your-mouth pasta.

Think About Extending Your Stay

Couple strolling Aix-en-Provence, France

Aix-en-Provence, France

The pros of Italy’s mid-Mediterranean positioning aren’t just connected to the blissful climate.

While considering how to plan a trip to Italy, be sure to spread out your map and examine which countries are close by. You’ll see how thinking about how to plan a trip to Italy can easily blossom into considering how to plan a trip for a multi-destination Old World extravaganza.

Bordering Liguria to the west is France. Hop across the border and you quickly arrive in Provence and the French Riviera. A destination of timeless glamor and allure, this coastline is a mix of flower-filled medieval hill towns like Èze and glitzy coastal spots like Cannes and San Tropez.

Beautiful landscape of Calanques National Park

Calanques National Park, France

Go west again and you arrive amid the crystalline waters of the Calanques National Park and Marseilles, France’s engaging second city.

Or look south. A short boat ride from Brindisi and you arrive among the whitewashed villages of the Greek archipelago. Isles of myth and magnificent meals on the quayside, an island-hopping odyssey here is not to be missed.

Journey a little further east again, and Turkey’s honey-colored beaches and elegant minarets come into view.

If you’re visiting Venice or Trieste, it’s a quick journey across the Adriatic to neighboring Croatia. There you’ll find sun-kissed islands like Hvar, fortified medieval towns such as Dubrovnik, and an archipelago of serene unspoiled islands.

Make Sure Italy Is For You

Couple in La Sorgente Farm, Sorrento

La Sorgente Farm, Sorrento

When considering how to plan a trip to Italy, consider why you’re going. What do you want out of your experience? It’s such a varied destination that it’s hard not to find some part of this spectacular country that’ll be a good fit.

Whether you like a vacation in the great outdoors, a cultural pilgrimage, or a laid-back beach holiday, the Bel Paese has you covered.

It’s also wonderful for families. If you’re traveling with picky eaters, Italy generally doesn’t offer the dinnertime hurdles offered by countries with less familiar cuisine. Additionally, Italians, as a rule, tend to dote on the younger generation. Traveling with younger children can see you mobbed by twinkly-eyed nonnas (grandmothers).

If you’re concerned about the language, you’ll usually find that most Italians have a good working knowledge of English. Hopefully, you’ll feel brave enough to try a few phrases of your own, and the locals are usually encouraging and appreciative of such efforts.

Read: Best Things to See & Do in Italy With Teens

Time to Pack

Couple strolling Piazza Navona, Rome

Piazza Navona, Rome

Italy’s Mediterranean climate means that you’ll want to have plenty of breathable fabrics in your wardrobe. That’ll ensure your comfort as you’re navigating Rome’s centro storico, especially in the warmth of the summertime.

In the shoulder seasons, pack another layer for the evenings. If you’re traveling in the summer, a sun hat, sunscreen, sunglasses, and bug spray are all helpful inclusions in your suitcase.

Couple strolling Piazza del Plebiscito, Naples

Piazza del Plebiscito, Naples

Comfortable shoes with good grips are important. The timeworn cobbles and flagstones of somewhere like Naples’ Spanish Quarter can be slippery even if there’s only a hint of rain.

When visiting the cosmopolitan cities, there’s scope for the full range of your wardrobe amid the Italian love for fashion and color. Pull out the garments that you always loved but never felt that you had the right occasion to put them on for. This is the occasion. When thinking sartorially about how to plan a trip to Italy, put your best and boldest foot forward.

Cultural Considerations

Couple visiting a church in Amalfi

Amalfi Town

Navigating Italy’s cultural nuances is a fairly straightforward business. However, if you’re visiting more traditional areas of the countryside, it’s important to be sensitive to the more conservative outlooks that can be found in the smaller communities.

To that end, if you can dress more modestly while exploring small villages then it’s respectful to do so. Think shirts with sleeves and long pants for men, and trousers, below-knee skirts, and covered shoulders for women. These kinds of outfits are appreciated by locals when you step in to see the 1,000-year-old frescos ornamenting their local places of worship.

How to plan a trip to Italy - Vatican City

Vatican City

That dress code is even more emphasized at the illustrious entrance to the Vatican in Rome. Admittance will only be granted if you’re wearing clothes deemed fit for the Catholic holy site, so be sure to check for the requirements ahead of your visit.

Italians strive for a concept called bella figura, which is more than just looking elegant. It’s about a bigger picture of a person who shows self-respect, decency, good manners, and a positive attitude as well as taking care of their appearance.

Prepare Yourself for Not Wanting to Return Home

Beautiful landscape of Vernazza, Cinque Terre

Vernazza, Cinque Terre

Before planning a trip to Italy, it’s probably a worthwhile exercise to jot down a quick list of what responsibilities you’ll be leaving at home and that you absolutely must return to. This is because life in Italy, on the right evening, with Spritz in hand, can seem like the absolute ideal.

The lifestyle in this fascinating country, from toes-in-the-sand dining to diving from the rocks in the Cinque Terre is alluring. It’s not unknown for visitors to be so enchanted by the Italian stile di vita that they simply stay.

Your face and heart will be warmed by the balmy weather and friendly locals, and you’ll quickly join in with social traditions such as the passeggiata. Italy remains a favorite destination for idly dreaming of a full-life transfer to its pasta-rich shores, which is why it’s important to know how to plan a trip to Italy so a swift return is a piece of torta.

Celebrity Cruises sailing to Portofino


Feel like you’re ready to start planning a trip to Italy? A cruise is the perfect way to explore. Browse our Italy cruises and book your incredible adventure today.

Free Vacation Planning Services

Free Vacation Planning Services