Planning a Trip to Italy in 15 Easy Steps

Planning a trip to Italy for your next dream vacation to experience la dolce vita? We have a special love for Italy and have written tons of articles on our favorite Italian destinations over the years — we consider it an ideal one-stop destination for exquisite art, inspiring architecture, breathtaking scenery, and amazing cuisine.

The food in Italy alone is so good in fact, it’s often why we travel there in the first place!

Planning a Trip to Italy: a How-To Guide 

We’re often asked about planning a trip in Italy and what are our favorite places to visit in Italy. Amazingly, the first question is easier to answer than the others — and it may surprise you to hear it’s quite simple to plan a trip to Italy on your own.

In the interest of full disclosure however, you should know that we travel slowly and independently. We believe in loosely-structured travel itineraries, and Italy is a place where a car and a loose itinerary are all you really need.

We think that part of the beauty of travel is crafting your own trip in real time, rather than following the same general schedule everyone else is doing. We recommend a few small group tour experiences with local guides here and there, and fill in the rest as you go with whatever moves you at the time. Discover the small italian towns and undiscovered hidden gems few others dare to go.

This doesn’t mean we travel without itineraries. We simply plan to arrive, arrange a few slow travel tours ahead of time, and arrange to get home. Why have a pre-made itinerary purchased for you by a travel advisor, only to find you have no interest in following it once you get there?

Our Favorite FLY BY THE SEAT OF YOUR PANTS Travel Tip?

If you’re safe and settled into your accommodations, go out for coffee or breakfast, and ask the locals what you should do that day!

Strike up a conversation with a shopkeeper, maybe even buy a little something from their shop. Then ask then their must-see recommendations for things to do, sights to see, local food to try!


Planning a Trip to Italy — What’s in this Guide?

(click to jump ahead)

How Long Should You Stay in Italy?

Save Some Italy For Next Time

Budgeting for Italy

Best Time to Visit Italy

Required documents to Visit Italy

Book Your Trip to Italy

Driving in Italy

Planning a Road Trip in Italy

Your Italy Itinerary

Italian Language and Customs

Dining Out in Italy

Packing for Italy

Shopping in Italy

Intercity and Public Transportation

Make an Arrival Plan

Planning an Italy Trip in 15 Easy Steps

Listed here, in chronological order, are the basic steps you need to follow to plan an Italy trip. Some steps are things to consider, while others are actionable steps. But as Lao Tzu said, “the journey of a thousand miles begins with a single step” and planning a trip to Italy is no exception.

So consider this guide your starting point — how to plan a trip to Italy in 15 basic steps. 

1. How Long Should You Stay in Italy?

The first thing to consider when you’re planning a trip to Italy is how much time you have or how long you should stay. And honestly, our best answer is always as long as you can! Whether this is your first trip to Italy or your 50th, always stay as long as you can. ;-)

While there are endless quick tour options, Italia is definitely best savored slowly. Travlinmad is a slow travel blog, and it all started in Italy because we believe in exploring any place at a relaxed pace.

If you have more time to travel, great. But most travelers have a week to 10 days for their trip to Italy. Therefore, we recommend you pick one or two regions (max) to explore in one to two weeks rather than trying to see the entire country in one trip. Our travel philosophy is always “slow down and stay longer”.


2. Save Some Italy for Next Time

On that note, let’s talk for a minute about slow tourism or slow travel. It always baffles us why people try and see an entire country in a week or so.

We get it — you’ve waited a long time for this trip. Still, trying to cram in all the major sites in one holiday will only lead you to the point of exhaustion, stress, and frustration when you get home that you barely remember the moments in between.

Trust us when we say, you’ll want to remember that amazing pasta dish you ate on the beach in Positano or the cappuccino you shared with new friends one morning in Naples, and not the inside of the tour van that got you there.

So please — resist the temptation to see every major tourist attraction or historic site! Too much of a good thing and things start running together — whether we’re talking duomos, sculptures, vineyards or museums! Unless it’s the Sistine Chapel, or you’re an avid architecture or art history lover, stick with a few bucket list highlights.

Select 2-4 must-see sites in Rome, Naples, Florence, Venice or whatever big city tops your itinerary, then fill in with a few of the lesser-known hidden Italian gems that show a more authentic side of the place itself.

When planning a trip in Italy, start with picking one of the following three regions:

Northern Italy

If you are planning a trip to Italy around food or looking for amazing winter activities, look no further than Northern Italy.

Foodies should look to base themselves near Bologna in Emilia Romagna, the agricultural seat and thus the gastronomic center of Italy. Imperial Venice is just an hour north of Bologna where you can float along the canals of Venice on a gondola ride or take a walking tour of the narrow streets.

Shop in the fashion capital of Milan or unwind along the Ligurian coastline with a hike of the Cinque Terre. And don’t forget a visit to the gorgeous Italian lakes or Verona, the city of the star-crossed lovers Romeo and Juliet!

There’s more to northern Italy than the mystical Dolomites and the blue-green alpine lakes that surround them.


Central Italy

For those who are passionate about art, history and architecture, plan at least a 3 day visit to Florence, once the cradle of the Renaissance. If you’re planning on exploring Tuscany, allow yourself a full week for this ginormous region!

There are historic cities and villages to see like Siena, Montepulciano, and UNESCO Pienza, relaxing thermal spa towns like Saturnia, and of course the iconic landscape of the Tuscan Val d’Orcia. Then spend a day taking in the scenic views in Perugia.

And you certainly can’t plan a trip to Italy without seeing Rome and her many sites, not to mention the Roman food!

Siena, a beautiful medieval town in Tuscany, with view of the Dome & Bell Tower of Siena Cathedral (Duomo di Siena), landmark Mangia Tower and Basilica of San Domenico,Italy

Siena, a beautiful medieval town in Tuscany, with view of the Dome & Bell Tower of Siena Cathedral (Duomo di Siena), landmark Mangia Tower and Basilica of San Domenico,Italy

Southern Italy

Visit the opera house in Bari, bask in the chaotic energy for several days in Naples, and road trip through Sicily drinking wine and eating chocolate in Modica.

And if you want sand, sun and good food, there are plenty of things to do on the Amalfi Coast for some relaxing times in quaint and colorful towns.

This is the Mediterranean side of Italy where fragrant lemons grow huge in the sun, volcanos dominate the surrounding landscape, and foods take on a distinction all their own.

3. How to Budget for Italy: YOLO vs Common Sense

While you only live once, do make smart money choices on your trip to Italy. Whether you spend $1,000 or $10,000 on your trip, we guarantee you’ll love it either way. And taking a $1,000 trip means you get to take 9 more trips back while the Gotrocks family sits at home saving for their next vacation.

Making sound financial decisions while planning a trip to Italy ensures that you won’t have to check your bank account every hour! 

Some important things to remember are:

  • Estimate your daily expenses (in addition to lodging) for where you plan to visit. Here’s a good rule of thumb for tourist cities like Rome, Venice, or Florence: city tours generally run around $25-$50 USD per person. Add in lunch and dinner, and your day could run between $75-$100 per person/per day.

  • Save money where you can — you can easily lessen the cost of things like meals by saving money where you can. Stay in lodging that has a kitchenette or complimentary breakfast, get lunch on the street, and dine in out-of-the-way trattorias.

  • Always buy travel insurance

  • Book in advance — flights, lodging, and rental cars are always cheaper when you book ahead.

  • Keep a financial failsafe ready just in case — always carry a small hidden stash of cash in a money belt or hidden purse for unplanned events or emergencies.

  • Passport copy — always carry a copy of your passport with you, while the original stays in a secure place or safe in your room.

4. The Best Time to Visit Italy

Let’s talk about the timing of your trip to Italy, and remember that while time is an illusion, timing is an art.

One of the first things you’ll discover when you start to plan a trip to Italy is that the country is a year round, traveler-friendly destination, even in the colder climates. Meaning, many of the most popular destinations like Rome, Venice, and Florence stay busy with tourists all year long.

In fact, Italy in the winter is not only beautiful — there’s also lots to do. It’s a favorite destination for Christmas markets (Bolzano and Florence are two of our favorite cities), and northern Italy is perfect for snow bunnies.

Peak tourist seasons for most places are the spring and early summer months of April through June and the fall months of September-October.

Mid-summer months of July and August can get very hot, so coastal areas like the Cinque Terre and southern Italy — especially the Amalfi Coast and Puglia — see more activity especially with Italian residents on holiday.

However, if you want to visit the bigger cities yet wish to avoid the heavy crowds while you luxuriate in pleasant weather, spring shoulder season (April-May) and late summer are the perfect times to visit Italy.

Trips during these two windows are far cheaper too!


5. Check Visa and Documents Required to Visit Italy

Before you start planning a trip to Italy, you should familiarize yourself with the official information you need to travel to Italy legally and safely.

First, you’ll need a valid passport and visa in hand. Italy is a Schengen country, and as part of the Schengen Agreement, be sure and check that your passports are valid for up to 6 months after departure from the Schengen area.

Visitors from the United States, Australia, Canada and New Zealand can enter Italy and stay up to 90 days without a visa within an 180 day period.

Second, be aware of any health risks of traveling to Italy before you go. This includes any responsibility you bear as a traveler such as innoculations, quarantine requirements, and mask mandates. Head to the CDC website for newly updated COVID guidelines for travelers.


6. Book Your Trip to Italy: The Early Bird Gets the Worm

When you are planning a trip in Italy, early bookings help you by getting the most economical options, and also in working out your budget well in advance.

Look for budget-friendly flights and inter-city train travel if you have a tight schedule and want to quickly move across the country. 

Skip the queue and book tickets online for activities or guided tours, e.g., Pompeii or Rome. As certain major attractions are booked weeks in advance, make sure you reserve your tickets online. These include heritage spots like The Colosseum, The Vatican Museums, the Basilica, and more.

Planning a trip to Italy includes picking comfortable lodgings with specific amenities for a more fulfilling vacation. Stay overnight in a bed-and-breakfast to sample the local cuisine, or in alberghis and family-run pensioni hotels in the bigger towns and cities.

Renting a villa is the perfect way to celebrate the slow paced life of the countryside or coast. Book an agriturismo and reconnect with nature on a farmhouse stay.

For great locations with schedule-flexible choices that offer breakfast and a cancellation policy we recommend and use

7. Driving in Italy: Plan a Solo Trip to Italy or With Friends

They say No road is long with good company, so whether you’re planning a trip to Italy solo or with friends, it’s a great destination for both.

Drive along picturesque terrains, aquamarine coastlines, snow capped mountains, and lush green valleys, and watch Italy come to life around you as you drive from the cosmopolitan cities to the sleepy coastal towns and verdant countryside.

Renting a Car in Italy

To explore Italy on your own time schedule, we highly recommend renting a vehicle of your choice. Rental cars are available at major airports, train stations, and in some smaller towns too. Before you reserve one, here are a few tips to remember before renting a car in Italy:

  • International driving permits are a must before renting a car. You’ll need it if you get stopped by local police. It’s quite easy to obtain a permit especially if you are a AAA member.

  • Remember to ensure that your insurance policy covers driving in Italy. We always recommend that you also take the insurance coverage offered by the rental company. If you are involved in a mishap, you’ll be glad you did.

  • For those traveling with small children, do remember to carry approved car seats for children, or just request them from the rental agency in advance.

  • A GPS is invaluable for finding the places you most want to visit. Either include it in your rental or bring along your own.


8. Planning a Road Trip in Italy

Thinking of doing an Italian road trip? We don’t blame you — it’s one of our favorite ways to see bella Italia!

But when in Rome, do as the Romans do — always remember to drive on the right side of the road!

Italy seems to have electronic speed-control devices just about everywhere, so do keep your speed dragon in check as you drive around. It’s good to know a few of the rules for driving in Italy beforehand. Fines for violations will reach you even across continents, sometimes up to a year later — and we speak from our own unfortunate experience.

Driving on the motorway is subject to toll fees, so keep that entry ticket safe, be sure to have some small bills and change, and pay as you exit.

In cities, always keep a close eye out for signs marking ZTL zones or restricted zones, where no cars are allowed. If your hotel is located in a ZTL, enquire with the hotel to see if they can help you get a permit in advance to help park your car close to your accommodations.

Here are just a few of our favorite regions and places to see on an Italian Road Trip:


Planning a trip in Italy begins when you stop dreaming about your bucket list and start living it! The center of art, architecture, spirituality and culture, the Eternal City promises you the experience of a lifetime. History comes to life in the Colosseum, the Pantheon, and St. Peter’s Basilica. 

Roam through the city of love holding hands with your partner and visit the Sistine Chapel, Vatican Museum, and toss a coin in the Trevi Fountain, with a promise to return!

Rome was a poem pressed into service as a city
— Anatole Broyard


When you plan a trip to Italy, your mind instantly conjures up the iconic Michelangelo’s David. For art-lovers, Florence is a veritable art gallery where you can spend hours.

Wander amongst the murals in the Duomo and the Uffizi Gallery, and watch the sun set at the Basilica San Miniato al Monte.



Planning on visiting Tuscany on your trip to Italy? Tuscany is perfect for a good road trip with plenty of places to leisurely drive along beautiful country roads, rent bikes or Vespas for the afternoon, and take a cycling tour through vineyards. Don’t forget to sample some Chianti Classico or a bold Nobile di Montepulciano when you’re out on a picnic with your kids.


If you love rural landscapes, charming Italian small towns, and good Italian food, you’ll find them on nearly every road trip in Italy.

What you’ll also find in Emilia Romagna along the roads outside Bologna are medieval castles, Michelin-star restaurants, poignant World War II history, thermal hot springs, and the hottest performance cars ever made. Slow food and fast cars is what this region is known for, and it makes a great road trip destination!


This city, with its maze of waterways and narrow alleys, is a fantasy come to life. You can spend your days taking canal rides on gondolas or walking the narrow streets around St. Mark’s Square.

But don’t discount the Veneto on your road trip. There are lots of cool places to see from the northern reaches of the Venetian lagoon to Chioggia, a charming small town at the southern tip of Venice bay.

Milan and the Italian Lake District

This shopaholics’ paradise is home to some of the greatest fashion trends in the world. Keep your wallet ready as you explore the magical realm of high fashion design, haute couture, and stylish upscale boutiques! 

Amazingly, the stunning Italian Lake District is close to Milan and exploring them with your trip to Milan makes for one of the best road trips in Italy.

Lake Maggiore and Lake Como are an hour drive from the fashion city, and the spectacular blues of Lake Orta and Lake Garda aren’t far from there. Recreate historical romances as you wander through the halls of medieval castles and shop to your heart’s content at the fashion boutiques.

Famous luxury villa Monastero, stunning botanical garden decorated with mediterranean oleander flowers, lake Como

Famous luxury villa Monastero, stunning botanical garden decorated with mediterranean oleander flowers, lake Como

Naples and the Amalfi Coast

Take a trip to the colorful city of Napoli with the largest number of architecturally renowned churches and the best pizza in the world! Your plans should include a visit to see “The Flagellation of the Christ” by Caravaggio at the Capodimonte Museum and the Naples Archeological Museum. And of course, there are the ruins of Pompeii and Herculaneum.

Located at the foot of Mt. Vesuvius, which erupted in 79 AD, these port towns are pieces of history infamously known for the tragedy that befell them. Watch the story of ancient Rome unfold about you in this time-frozen vista.


Famous for the Greek ruins, this land has been ruled by many civilizations, all of whom have left their stories behind them for you to witness. From the Valley of the Temples, to the Aeolian Islands and Mt. Etna, you’ll be donning your Indiana Jones hat and getting ready to find adventure.

For a comprehensive guide of heritage sites, browse the UNESCO Italy site for a complete list of places to see. 

9. Your Italy Itinerary: Plan An Italy Trip With Flexibility

While good things come to those who travel, good experiences come to those who have a solid, yet flexible, travel itinerary.

For first-time visitors, traveling can be quite overwhelming and confusing with so many options on offer. You’ll want to make sure you visit some of the famous Italy attractions on your bucket list. If you’ve always wanted to see the Statue of David up close, take a gondola ride, or book a test drive in a Ferrari — you should definitely look into buying tickets upfront for those kinds of tours and experiences.

Another great idea is to purchase city attraction cards for a particular place, which offer discounts and skip-the-line tours to card holders. The city of Florence for instance has the Firenze card, and Bologna has their Bologna Welcome card — both are worth purchasing if you plan on seeing a lot of the city highlights.

Be sure and check out some of our Italy posts and itineraries for specific cities and regions around Italy.

10. Italian Language and Customs

Italian culture is deeply rooted in an appreciation of the good things in life. While Italian is the official language, most tourist places speak a bit of English too. So while you can communicate pretty easily — or enjoy trying — learning a smattering of Italian will go a long way in impressing locals. 

Practice some common Italian phrases while you plan a trip to Italy to make your travel and stay a bit easier. After all, knowing how to ask where the bathroom is in Italian might save you a lot of embarrassment when you’re in a rush!

We also love using the Learn Italian course by Pimsleur — it’s what we’ve used to gain a working knowledge of basic Italian, and we get them back out for every subsequent trip to brush up a bit.

11. Dining in Italy

In Italian life, work comes second to family, food and wine. And isn’t that how it should be? ;-)

While breakfast is often in a private setting, lunch and dinner tend to be fairly elaborate meals. Italian food and drink varies by region, so don’t shy away from new food adventures. Just because you tried a particular food in one area doesn’t mean you’ve had it in another. Keep eating! That’s the fun of dining in Italy — it’s always a new and unique experience.

Home to the best pizza, insanely delicious pasta dishes, and some of the finest wine in the world, your trip to Italy will undoubtedly include way too much Italian food. Try the local specialities at family-run hotels, natural foods on a farm-to-table experience, or haute cuisine at a Michelin restaurant.  

And for the caffeine aficionados, espressos are available round the clock!


12. Packing for Italy

One who travels happily must travel light. The topmost items in your suitcase like toiletries, medicine, and documents are always your essentials.

Next comes choosing an appropriate wardrobe after checking the weather of the regions you plan to visit. Always carry sunscreen, umbrellas, and a reusable water bottle

Adaptors for your electronic devices are essential for keeping your devices charged. 

For kids, packing their favorite toys makes sense to keep them entertained during in-between times.

13. Shopping in Italy

Nothing haunts us like the things we didn’t buy, and a trip to Italy is incomplete without shopping! Make a list of items or gifts you’d like to buy from the places you visit. 

Be it food, wine, cheese, jewelry, or clothes, a checklist of Italian souvenirs can make your trip so much easier. Markets are a fun way to discover local products and artists, and don’t forget to purchase tiny souvenirs for friends and family back home.


14. Intercity and Public Transportation

Italy has an excellent public transport system that can take you from points in northern Italy down to Florence and Rome, to further south all the way to Calabria if you’re traveling on to Sicily.

Public transport like buses and trains are good options when traveling between cities. And if you’re an early bird booking your trains, you’ll find more economical pricing on your tickets too. 

If you’re short on time, inter-city flights are also a good idea for those booking in advance and on shorter vacations.


15. Make an Arrival Plan for Your Trip

An arrival plan is always a good idea no matter where you’re headed. This includes movement from the moment you arrive to when you reach your accommodations.

After a long day on the road, the last thing you need is to be stuck without transportation when you get there. Having an arrival plan will help you deal with jet lag and also gives cranky toddlers the breathing room they need to de-stress from all that travel.

No matter which region or city you choose, Italy is a fantastic place to visit. Whether for a week, or more (we recommend at least 2 weeks), planning well will make the difference between a hectic trip and a lifelong memorable visit.

If this checklist does nothing else, we hope it makes your Italy planning less daunting. Planning a trip to Italy should be exciting, not exhausting. You can do it! And when you’re back home and remembering, you’ll know just what to do to plan your trip in Italy for next time.

Because there’s no such thing as only one trip to Italy!

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