How to Plan a Trip to Italy: The Best Itinerary Planner

updated 19.08.2024

Radiating vitality from its natty north to its stylish southern heel, there are plenty of reasons Italy attracts a remarkable range of traveler types. And, given its fabulous food, sun-soaked coastline, picture-perfect panoramas, and all those extraordinary ancient sites, it’s no wonder the country usually sparks a desire to return. But how do you plan a perfect trip to Italy? Keep reading, for starters — here we present key steps in planning your Italy vacation.

Step 1 — Best time to go to Italy
Step 2 — Decide where to go in Italy
Step 3 — Pre-book flights, accommodation and tours
Step 4 — Prepare to depart
Step 5 — Plan your Italy itinerary
Step 6 — Leave time to seize the day
Take a trip designed by local travel experts

Step 1 — Best time to go to Italy

The question "how to plan a trip to Italy" is often related to weather and budget, so let's cover that first.

Best time to visit Italy

When it comes to visiting Italy, timing is everything, and the best time to visit largely depends on your preferences and what you hope to experience.

If you're looking for pleasant weather, manageable crowds, and cost-effective travel, spring (April and May) and fall (September and October) are the best times to visit Italy.

Conversely, peak season, which runs from June to August, sees a spike in temperatures, crowds and prices.

Cinque Terre, Italy © Shutterstock

Step 2 — Decide where to go in Italy

Best cities to visit

When it comes to cities in Italy, the options are boundless. Here are our suggestions for cities to prioritize, especially if you're a first-time visitor.

Rome: known as the 'Eternal City'. Rome's iconic attractions include the Colosseum, Palatino, Roman Forum, and Pantheon. For a real taste of the capital, visit Trastevere, which is known for its bohemian vibe and authentic food.
Venice: one of the most picturesque cities in the world, Venice is renowned for its canals and ornate architecture. Taking a gondola ride through the narrow canals, and strolling the labyrinth of winding streets are must dos.
Florence: birthplace of the Renaissance, Florence is an art-lover's paradise. Don't miss the Uffizi Gallery and the Duomo.
Naples: if you love history, coastal scenery and food, Naples — the birthplace of pizza — is a must-visit. Take trips to Pompeii and Herculaneum, sail down the scenic Amalfi Coast, and choose the perfect place to stay with our guide to the best areas to stay in Naples.

Best areas to visit

The following regions of Italy should be considered when planning your vacation to Italy.

Tuscany: known for its rolling, rural landscapes, history, and viticulture, here you can visit medieval towns, and tour vineyards to taste fine wine.
Amalfi Coast: don't miss visiting colorful towns like Positano, Amalfi and Ravello in one of Italy's most breathtaking regions.
Cinque Terre: the coastal trails along this string of five centuries-old villages are sublime.
Lake Como: surrounded by mountains and speckled with beautiful villages, Lake Como combines luxury and tranquility.

View of Montalcino town, Tuscany, Italy © Shutterstock

Montalcino, Tuscany, Italy © Shutterstock

Best vineyards to visit

Here are some of the best Italian regions for wine-lovers, with an abundance of wine tours available in each of them.

Tuscany: Tuscany produces some of the world's most notable wines, including Chianti, Brunello di Montalcino, and Vino Nobile di Montepulciano.
Veneto: known for its Prosecco and Soave wines, the Veneto region offers splendid views over terraced vineyards.
Barbagia, Sardinia: the island's climate and rugged terrain make for some distinctive world-class wines.

Best lakes to visit

Italy is famous for its picturesque lakes. Here are some of the best.

Lake Como: surrounded by mountains and studded with charming villages and villas, Lake Como is a must-visit for its beauty and tranquillity.
Lake Garda: Italy's largest lake is home to charming medieval towns, thermal bath towns, vineyards, and the family-friendly Gardaland amusement park.
Lake Maggiore: less crowded than Como and Garda, Lake Maggiore is something of a peaceful retreat.

Varenna old town in Como lake © Boris Stroujko/Shutterstock

Varenna old town, Lake Como © Boris Stroujko/Shutterstock

Step 3 — Pre-book flights, accommodation and tours

How to get to Italy from the US

Traveling to Italy from the U.S. is straightforward, with numerous flights to choose from.

Many major U.S. cities offer direct flights to Italy, including New York (JFK, EWR), Miami (MIA), Boston (BOS), Atlanta (ATL), Chicago (ORD), Los Angeles (LAX), San Francisco (SFO), Washington, D.C. (IAD), and Dallas (DFW).

At the other end, the most common arrival points in Italy are Rome (Fiumicino Airport - FCO), Milan (Malpensa Airport – MXP), Venice (Marco Polo Airport - VCE), Florence (Peretola Airport - FLR) and Naples (Capodichino Airport – NAP).

If a direct flight isn’t available from your closest US airport, connect through one of the major European hubs, such as London, Paris, Frankfurt or Amsterdam.

Accommodation in Italy

Italy offers everything from high-end luxury hotels, to budget-friendly hostels, and authentic agriturismo farm-stays.

As bookings can fill up quickly during shoulder and peak season periods, it’s always wise to reserve your accommodation well in advance.

City hotels: major cities like Rome, Florence, and Venice offer a multitude of options for all budgets. Websites like Booking.com are excellent for comparing rates and amenities, and for finding deals on hotels and apartments.
Bed and breakfasts/hostels: a comfortable and cost-effective choice, especially for solo travelers or those on a tight budget.
Agriturismo or farm stays: offered by Italian farmers as a way to supplement their income, these are very popular in Italy. Many also offer meals made from fresh farm produce.
Apartments: ideal for family trips or a larger groups.

Traveling to Rome? Be sure to choose from the best places to stay in the city.

You might also want to browse the best hotels in Italy.

Aerial view of famous medieval San Gimignano hill town with its skyline of medieval towers © Shutterstock

Aerial view Italy's famous medieval San Gimignano hill town © Shutterstock

Step 4 — Prepare to depart

Plan your budget

Though costs vary greatly depending on where you go, when you go, how you travel, and your personal preferences, planning a budget will help your trip run more smoothly.

With that in mind, here are some average costs to guide your budgeting process. You'd also be wise to keep some funds aside for unexpected expenses.

Accommodation: a budget hotel for two people ranges from $50 to $150. For a mid-range hotel, expect to pay $150-$350, while luxury hotels tart at $350.
Food: expect to pay $25-$50 per person for meals in decent restaurants.
Travel: for intercity travel, train fares vary from $15 to $60 depending on distance.
Attractions: allow $15-$25 a day for entry fees to the likes of museums and historic sites.

Get a credit card

Getting a credit card that offers travel rewards can be highly beneficial for your trip to Italy. Look for cards with no foreign transaction fees, and good cash back or points systems.

Visa and Mastercard are widely accepted in Italy, while American Express and Diners Club are not.

A word of warning — be aware of foreign currency charges and ATM withdrawal fees in Italy. You could consider getting a foreign currency card like the Wise Mastercard that enables to you convert Euros easily and cheaply from your US dollar account.

Book airport transfers

Given that many Italian airports are located quite a distance from the city center, and public transport might not always be convenient — especially if you're carrying heavy luggage or traveling in a group — pre-arranging airport transfers can save time and hassle.

Compare different transfer services like Suntransfers or Welcome Pickups, which offer several options, from budget to luxury travel.

Stay connected

Even if you've decided to avoid work emails during your vacation (good for you), having access to affordable data will definitely enhance your experience.

For starters, it'll make navigation a breeze and keep you connected with the folks back home. You might also want to share live updates and photos of your vacation — to do this, you need fast access to data.

In all likelihood, you're already aware of these advantages, but may have concerns about paying over the odds.

The good news is, with an international SIM card or eSIM from SIMCorner — a trusted Rough Guides' partner — you don’t have to worry about high or hidden costs.

Thanks to partnerships with top telecom providers worldwide, SIMCorner offers products for every type of traveler in dozens of countries, including Italy.

And, if you're not keen on long-term commitment, SIMCorner's data plans and services are contract-free. This means you can use your SIM card or eSIM as needed, and put it on hold when not in use. It's that simple.

Old Town of San Leo - Italy © Shutterstock

If you plan a trip to Italy, make sure to check the Old Town of San Leo © Shutterstock

Step 5 — Plan your Italy itinerary

How many days do you need in Italy?

While the ideal length of a trip to Italy depends on your travel wish-list and time constraints, we suggest aiming for 7-10 days as a minimum.

With careful planning, many of Italy's highlights can be covered during a 10-day whirlwind tour. If your time is limited to 3-5 days, you'll need to choose one region or city.

Read on to discover rewarding ways to spend 5, 7, 10 and 14 days in Italy.

How to spend 5 days in Italy

If you only have five days in Italy, you'll want to focus your trip on one or two destinations.

For example, you could split your trip between Rome and Florence, spending three days in Rome, and two in Florence.

Day 1-3: Rome — immerse yourself in the history of the Eternal City. Visit the Colosseum, Roman Forum, and Palatine Hill. Take a walk through St. Peter's Square, tour the Vatican Museums, and roam around Trastevere before tucking into an authentic Italian dinner.

Day 4-5: Florence — hop on a high-speed train to Florence. Enjoy Renaissance art at the Uffizi Gallery, marvel at the view from Piazzale Michelangelo, and visit the Florence Cathedral. You could also dedicate half a day to Pisa or taking a Tuscan wine tour.

Titus Arch and the Roman Colosseum in Rome, Italy as seen from the Palatine Hill © Shutterstock

How to spend 7 days in Italy

7 days in Italy is (just about) long enough get a deeper taste of Italy.

For first-time visitors, we suggest following an itinerary that covers the classic trio of Rome, Florence and Venice.

Day 1-3: Rome — spend the first few days of your vacation exploring Rome's iconic landmarks.

Day 4-5: Florence — take a train to Florence and spend a day exploring the Uffizi Gallery, climbing the Duomo, and taking a sunset stroll across the Ponte Vecchio.

Day 6-7: Venice — board a train to Venice to visit St. Mark’s Square, tour the Bell Tower, and visit the Rialto Market. Don’t forget to take a traditional gondola ride through the canals.

How to spend 10 days in Italy

In addition to visiting Rome, Venice, and Florence, if you have 10 days in Italy, look to expand your horizons, like this:

Rome (3 days): start by immersing yourself in the historic grandeur of the Eternal City, from the Colosseum and Roman Forum, to St. Peter's Square and the Vatican.
Florence (2 days): head to the birthplace of the Renaissance to visit the Uffizi Gallery and iconic Duomo, and savor Tuscany's culinary delights.
Pisa (1 day): visit the Leaning Tower of Pisa.
Venice (2 days): discover the unique city on water with its famous canals and gondolas.
Milan (2 days): conclude in Milan, Italy's fashion capital. Don't miss the seeing Last Supper by Leonardo da Vinci and visit the majestic Duomo.

How to spend 14 days in Italy

With 14 days in Italy at your disposal, you can cover more ground at a more relaxed pace. Here's a suggested itinerary with train itineraries:

Rome (4 days): spend 4 days soaking up Rome's ancient sites and café culture.
Florence (3 days): discover this cradle of the Renaissance.
Cinque Terre (2 days): explore quaint colorful seaside villages perched along the rugged Italian Riviera.
Pisa (1 day): visit the iconic Leaning Tower and nearby attractions.
Venice (2 days): explore Venice's romantic canals, historic landmarks, and charming cafés.
Milan (2 days): end in Milan to witness its towering skyscrapers, international fashion scene and Milan Cathedral.

St. Mark's Basilica and St.Mark's Campanile above the San Marco square in Venice © Shutterstock

You can't plan a trip to Italy without considering including Venice © Shutterstock

Step 6 — Leave time to seize the day

Don't over-plan and factor in free time

While it's important to have an itinerary, don't pack every minute with activities — Italy is best enjoyed at a slower pace.

It's also essential to be flexible so you can, for example, linger in a picturesque picnic spot that wasn't in your plan, or spend time exploring a market you chance upon.

Having wiggle room will allow you to seize such unexpected opportunities.

Take a trip designed by local travel experts

Planning your trip to Italy? Our local experts can help

Here's why booking a trip curated by local experts will elevate your Italian experience:

Personalized itineraries: our local travel experts craft itineraries to align with your interests and preferences, whether you're an art aficionado, foodie, or outdoor enthusiast
Insider knowledge: local experts can guide you to authentic experiences other tourists might miss.
Efficient planning: local experts streamline your trip through handling the logistics of transport and accommodation.
Cultural immersion: trips designed by local experts are more like to give you insights into local life.
Support: our local experts are on hand to provide advice and assistance before and during your trip.

Travel advice for Italy

To help you make the most of your vacation, here are a handful of insider insights.

Avoid peak season: you might want to avoid July and August, when Italy is hot, crowded, and more expensive.
Use public transport: train travel is highly efficient and cost-effective in Italy. Enjoy the scenery and save on car rental and parking fees.
Water: it's safe to drink tap water in Italy, so you can save money by not buying bottled water.
Eat local: as always, trying local food is half the fun of travel.
Safety: while Italy is generally safe, pickpocketing can be an issue, so be vigilant in crowded areas.

written by
Joanne Owen

updated 19.08.2024

Joanne is a Pembrokeshire-born writer with a passion for the nature, cultures and histories of the Caribbean region, especially Dominica. Also passionate about inspiring a love of adventure in young people, she’s the author of several books for children and young adults, hosts international writing workshops, and has written articles on the Caribbean and inspirational community initiatives for Rough Guides. Follow her @JoanneOwen on Twitter and @joanneowenwrites on Instagram.