5 Days in Italy: Itinerary Ideas for a (Very) Quick Trip

Hoping to make the most of a brief 5 days in Italy and struggling to narrow down your choices?

That’s completely understandable!

While it seems that no amount of time spent traveling Italy will ever be enough to uncover all of the delightful corners of the country (we’re up to more than a cumulative year in Italy each and have longer wish lists than when we started), planning the perfect 5 day Italy itinerary is definitely a challenge–especially if it’s your first time in the country.

We’ve put together several ideas here to show what can (and can’t) be accomplished on a short trip to Italy, plus included travel tips to help you make the most of your time.

Whether you’re a go-getter determined to see as much as possible or are just hoping to relax and dive into la dolce vita in one carefully chosen city, there’s an itinerary for 5 days in Italy here that will hopefully work for you.

Here’s how to fall in love with Italy in 5 days!

How to Structure a 5 Day Italy Itinerary

When it comes to structuring a 5 day Italy trip, here are the 3 most important tips we can recommend: stay overnight in no more than 2 destinations, let geography at least partially guide where you go, and book as much in advance as possible.

That’s especially important for incredibly popular attractions like touring the Colosseum and climbing to the top of Florence’s Duomo, where failing to plan ahead might mean not getting to see your desired spots at all.

Even for less-competitive spots, though, you’ll still benefit from booking hotels, tickets, tours, rental cars (in the unlikely event you need one), and even train tickets in advance as much as possible, to ensure you’re not eating up any of your very limited time researching what to do or where to go next.

While you don’t want to schedule your trip down to the hour or minute–you’ll need time to relax and soak in the beauty of your destinations, not to mention savor the delicious food–the less you need to think about logistics during your 5 days in Italy, the better.

The Most Intense 5 Day Italy Itinerary We Can Recommend

Want to make the absolute most of your 5 days in Italy, regardless of how tired you are by the end of it?

The itinerary outlined here is the absolute fastest-pace 5 day Italy itinerary we can recommend–and even then, we only suggest doing this if your time in Italy is a standalone trip and you have 5 whole days to work with (in other words, if your flight arrives at 3:00 PM, it can’t really count as a day here).

If you’re taking, say, a 2 week trip to Europe that sandwiches Italy between France and Switzerland, this is a much faster pace than we recommend keeping up (you’ll almost certainly get burned out along the way).

That being said, if you’re ready for a speedy blitz through as many of Italy’s classic tourism destinations as you can squeeze into one trip, here’s how to do it.

This itinerary assumes that you’re flying round-trip through Rome, though you can also adjust things to make the itinerary work using other airports (though you might want to adjust which cities you visit then, too).

Day 1: Florence

To make this itinerary work, we’re assuming that you’re landing early in the morning in Rome–but that’s a very common flight schedule, especially if you’re arriving from North America.

Grab your first Italian coffee, shrug off the jetlag, and immediately hop on the high-speed train to Florence (you will want to book these train tickets in advance).

Once you arrive, drop your luggage at your hotel and get to exploring!

With one day to focus on Florence, you’ll likely want to visit either the Galleria dell’Accademia (where David is housed) or the Uffizi, climb up to one of the best views in Florence, visit Florence’s Duomo, cross the Ponte Vecchio, and hop through the city’s piazzas and markets.

We go into detail on optimizing a day in Florence in our one day Florence itinerary, and recommend more or less following it, adjusting as needed based on what time you arrive and your energy levels after traveling.

Where to Stay in Florence

For this fast-paced itinerary, we recommend spending two nights in Florence (tomorrow, you’ll take a day trip).

Here are a few great places to stay within walking distance of the Santa Maria Novella train station:

Budget

Hotel Dali — With an impeccable location a 1-minute walk from the Duomo, thousands of excellent reviews, and even free on-site parking for anyone planning a road trip, Hotel Dali is simultaneously charming and budget-friendly–a true rarity in central Florence.

The catch? No air-conditioning, so keep that in mind if you’re planning a summer trip to Italy!

Check rates & book your stay at Hotel Dali today!

Mid-range

Hotel Silla — Located just a hop, skip, and jump from the Arno River, we loved our stay at Hotel Silla!

The hotel itself is lovely and quiet, the included breakfast a nice touch, and the location perfect: you have easy access on foot to all that Florence has to offer, without having to worry about crowds or noise.

We’d be happy to check in again!

Check rates & book your stay at Hotel Silla!

Luxury

Hotel Lungarno — Nestled right against the Arno River and home to one of the best views of the Ponte Vecchio in Florence (not to mention some of the best views of the rest of Florence from their top deck), Hotel Lungarno is our personal “if we ever really want to splurge” hotel in Florence.

You can’t go wrong using Hotel Lungarno as your base during your Italy vacation!

Check rates & book your stay at Hotel Lungarno!

Day 2: The Tuscan Countryside

After sampling the best of Florence, it’s time to take to the hills!

While there are countless ways to structure a day trip from Florence (here are some of our favorite ideas), with only 5 days in Italy, we recommend sampling at least a couple of different towns, with ideally at least one of them featuring gorgeous views of the Tuscan countryside.

For ease of travel, consider this extremely popular organized day trip, which can be an incredible value if your goal is to sample a variety of what makes this part of the world so special, without worrying about transportation (including a designated driver for those wine tastings!), parking, or time.

This excellent day trip includes visits to the beautiful city of Siena and the classic hilltop town of San Gimignano, plus lunch at a family-operated vineyard in the Chianti wine region.

Prefer to travel independently? If you rent a car for the day, San Gimignano and Volterra make for a delightful combination.

Want to travel by train? Siena and Lucca are both stunning cities that are fairly easily accessible by train–and if you have your heart set on seeing a very famous tower, you can combine Pisa and Lucca into one day trip.

Regardless of where you decide to visit, we recommend spending the night in Florence.

Book your day trip to the Tuscan countryside today!

Day 3: Rome

As early as you can bear to jump out of bed this morning, make your way to the train station to catch the high-speed train back to Rome (as we mentioned above, you’ll want to book these tickets in advance).

Assuming you take the high-speed train instead of the local one, you’ll arrive in Rome between 2 and 2.5 hours after leaving, which after dropping your luggage at your hotel, will hopefully leave you well over half a day to start exploring Rome!

This itinerary will include a second day in Rome, and we recommend more or less following our detailed 2 day Rome itinerary.

Today, you’ll want to pay a visit to the Colosseum and the Roman Forum (unless, of course, you decide to visit the Colosseum at night, in which case the Forum will be closed), wander through places like Piazza Venezia and Campo de’ Fiori, and enjoy some time in Trastevere.

If you want to take an excellent food tour during your 5 days in Italy, we adored this Trastevere food tour (and it will save you from having to choose just one Roman pasta to enjoy for dinner).

Where to Stay in Rome

After leaving Florence, we recommend spending the rest of this itinerary based in Rome.

Here are a few well-reviewed hotels within walking distance of some of Rome’s best sights to consider.

As a much larger city than Florence, no matter where you stay, you’ll need to use trains/buses/taxis to get around some–but ideally, not every time you leave.

Budget

Hotel Casa Valdese — Located within a 25-minute walk of the Spanish Steps and (importantly) a 2-minute walk to the metro, Hotel Casa Valdese offers a beautiful atmosphere that balances price point and location when visiting Rome.

With excellent reviews and an on-site terrace, Hotel Casa Valdese offers a quiet escape within the city.

Check rates & book your stay at Hotel Casa Valdese!

Mid-range

Pantheon Inn — If you’re looking for a building with classic Italian charm in the heart of Rome, this is it.

Located right behind the Pantheon and within reach, the Pantheon Inn offers a quiet, peaceful escape in the middle of bustling Rome.

You will need to walk a bit to the metro stop–but since the walk will take you through the heart of the beautiful Centro Storico, we doubt you’ll mind.

Check rates & book your stay at the Pantheon Inn!

Luxury

Hotel Condotti — Located just a couple of blocks from the Spanish Steps (and consequently the Piazza di Spagna metro station), you couldn’t ask for a better location in Rome!

Well-reviewed and boasting incredible suites and exceptionally clean rooms, Hotel Condotti is the perfect choice for a traveler who would like to be within walking distance of the best that Centro Storico has to offer while also having easy access to a metro stop.

Enduringly popular and perfectly positioned, you can’t go wrong with checking into Hotel Condotti.

Check rates & book your stay at Hotel Condotti!

Day 4: the Amalfi Coast + Pompeii

If you’re looking to cover as much ground as possible in Italy in 5 days, the ultimate day trip from Rome is one that makes for a very long–but memorable–day.

With the help of an organized tour (this one is wildly popular for good reason), it is possible to tour the legendary Pompeii and even get a taste of the Amalfi Coast in a single day.

While it’s not the easiest day trip option (be prepared for long van rides), it is an incredibly memorable one, and will allow you to tour one of Italy’s most legendary historic sites and also sample a slice of natural beauty unlike any other that you’ve seen on your trip so far.

If Pompeii and the Amalfi Coast are on your bucket list, this tour is a fantastic way to fit them into a 5 day Italy trip.

(Not a fan of organized tours?

With some careful planning, you can absolutely tour Pompeii independently from Rome, but we wouldn’t recommend also trying to see the Amalfi Coast in one day alone, especially if you don’t know the area well.

There are plenty of other cool day trips from Rome that are closer to the city, though!).

Book your day trip to Pompeii + the Amalfi Coast today!

Day 5: Rome

On your very final day in Italy, it’s time to… leave Italy! Sort of.

Start your morning with a visit to the Vatican Museums and St. Peter’s Basilica for a look at one of the world’s micro countries.

To make the most of your time, we highly recommend booking an early-access tour of the Vatican, which will allow you to start your sightseeing before most of Rome has finished their first caffè.

(And, if you’re a big fan of excellent views, hopefully it means you’ll have time to squeeze in a climb to the top of St. Peter’s dome before leaving Vatican City–the view is phenomenal, and it’s one of our favorite tower climbs in Italy).

From there, make your way over to Castel Sant’Angelo and cross the angel-lined Ponte Sant’Angelo (though first, pause and enjoy the buskers for a moment!) into Centro Storico to hit up some of Rome’s top sights.

Piazza Navona, the Pantheon, the Trevi Fountain, the Spanish Steps, and Piazza del Popolo–plus many more–are at your fingertips from here.

This route more or less follows the second day of our suggested 2 day Rome itinerary, but depending on how fast you sightsee, you may also have time to squeeze in visits to some of Rome’s nearby hidden gems like Galleria Sciarra, Vicus Caprarius, the Capuchin Crypt, Galleria Spada, and more.

More Ways to Experience Italy in 5 Days

Looking for less of a breakneck pace than what we outlined above?

We can’t blame you–personally, we’d generally opt for a slower pace ourselves these days.

Each of the following itinerary ideas for 5 days in Italy offers a balance between the intense pace of the itinerary outlined above and the more relaxed nature of picking one city or immediate area to focus on (which we’ll cover below).

We’ll keep these options brief in order to keep this blog post from becoming the size of a guidebook, but we do have specific articles on each of these destinations here on Our Escape Clause!

I’ll link to them where relevant below, and you can also use the search bar at the top right of the page (or at the top of the pop-out menu on mobile) to find what you’re looking for.

Here are some other rewarding ways to structure a 5 day trip to Italy!

Rome + Florence + Cinque Terre

Instead of taking two day trips (the Tuscan countryside + the Amalfi Coast/Pompeii), instead opt to spend 2 days in each Rome and Florence, and then get a taste of the coast with a day trip to Cinque Terre from Florence.

We recommend booking an organized day trip to Cinque Terre from Florence–here’s why.

By spending 2 days in Florence and only having one day trip to navigate, you’ll have a chance to dive deeper into Florence’s charms and hopefully even get away from the crowds and visit some of its hidden gems.

Rome + the Amalfi Coast + Pompeii

Want to spend more time in the Amalfi Coast area, as opposed to just taking a day trip?

Spending 2 days in Rome and 3 days based in Campania (or vice versa) can make an excellent short trip to Italy.

When down south, you can opt stay on the Amalfi Coast itself, but Sorrento and Naples are both also excellent options that have access to both the coast and Pompeii, plus islands like Capri–and staying one of them will make your transition to and from Rome a bit simpler.

Milan + Lake Como + Venice

Flying in and out of Milan or Venice, and want to stick to northern Italy?

If so, you can enjoy a gorgeous 5 day Italy vacation by spending one day in Milan, one day in Lake Como (we recommend Varenna and Bellagio), and a couple of days in Venice.

What should you do for the fifth day?

That depends on what kind of traveler you are: personally, we would either opt to spend a second day relaxing in Lake Como and possibly enjoying a hike or boat tour, a third day in Venice checking out some of the city’s offbeat gems, or possibly adding another day trip to a city like Bergamo, Verona or Padua.

Milan is geographically and economically ideally situated for train travel in Italy, so you have many of northern Italy’s most fascinating cities at your fingertips when staying there.

Other travelers would love to savor a second day in Milan, which absolutely works as well!

Florence + the Tuscan Countryside + Cinque Terre

Want to stick to a fairly close geographic range while seeing a wide variety of landscapes?

If so, combining a trip to Florence, Tuscany outside of Florence, and Cinque Terre is the perfect option!

Divide up your time by spending 2 days in Florence, and either two days in another Tuscan city with a day trip to Cinque Terre, or 2 days in Cinque Terre and one day taking a day trip to another destination in Tuscany outside of Florence.

If you would like to opt for taking a day trip to Cinque Terre but don’t want to visit as part of an organized tour, choosing another Tuscan city to base yourself in that’s closer to the coast, like Lucca, will allow you to visit independently more easily than you can from Florence.

Venice + Verona + the Dolomites

Dreaming of the Italian Alps?

If so, a couple of days in Venice can easily be combined with a visit to the Dolomites by basing yourself in Cortina d’Ampezzo, Bolzano, or a smaller town in between the two.

From there, you can launch yourself into the mountains via trail, gondola, or both!

To round out your 5 day itinerary, you can add on a day trip to Verona (you’ll pass right by if you choose to drive from Venice to Bolzano, for example), or even a day spent going wine tasting in the Prosecco region.

Rome + Florence + Venice

And, finally: yes, it is possible to sample the trifecta of Rome, Florence, and Venice in a 5 day trip to Italy… but with the caveat that it will truly be a sample.

We absolutely don’t recommend spending the night in all 3 places, and instead recommend either basing yourself in Rome + Florence and then taking a day trip to Venice from Florence (here’s our full guide to that day trip–complete with the pros and cons of doing so), or basing yourself in Rome + Venice and taking a day trip to Florence from Rome.

Is this the ideal way to see all 3 cities?

No, but if you can’t bring yourself to choose between them and think this will only be your chance to visit Italy for quite a while, it is doable.

Alternative 5 Day Italy Itineraries: Pick a City and Slow Down

Want to plan a more relaxing 5 day Italy itinerary, but still see quite a bit of the country?

You can absolutely have a rewarding trip to Italy by simply picking one fairly well-connected city, keeping it as your base, and adding 1-3 day trips to your list.

My grandparents are a big fan of this style of travel, and have often rented a place in the Tuscan countryside and then taken day trips nearly every day to different places within reach. It makes for wonderful vacations!

The options of where to stay are endless: icons like Rome, Florence, and Venice are of course delightful, but less-visited-but-still-popular cities like Bologna, Verona, Naples, Palermo, Siena, Bolzano, and more are great options as well.

Even quieter cities can be incredibly rewarding in terms of escaping the crowds (especially outside of day-tripping hours), while still offering plenty to see: Parma and Lucca have been two of our favorite base cities in central Italy in recent years.

If you are more interested in the day-trip potential and the natural topography of the area than in making sure the actual limits of the city hold enough things to do to keep you busy for 5 days, smaller towns or cities like Sorrento (a great jumping-off point to Pompeii, the Amalfi Coast, Capri, and more), Monopoli (a captivating beach town in Puglia), any of the Cinque Terre towns or nearby bases like Levanto, or mountain towns like Ortisei are all wonderful ideas.

Want to see some of the most popular parts of the country, but enjoy more affordable prices?

Choosing a city located just outside of the more popular one as a base–for example, Bergamo instead of Milan, Padua instead of Venice, Pisa or Pistoia instead of Florence–can give you access to all the best of the same region with a much lower price tag and a somewhat more offbeat feel.

This comes with a trade-off in terms of connectivity, which we’ll cover below, but can be a great option depending on your priorities.

Tips for Spending 5 Days in Italy

Choose a major city as your base, ideally the capital city of its region.

No matter which region(s) you plan to focus your trip around, if you want to see a wide variety of destinations during your 5 days in Italy, we recommend choosing a major city as a base–and ideally, a city that’s the capital of its region.

Why?

Because these cities tend to be the best connected by train, both to other destinations within their region and to the country as a whole.

For example, if you stay in Florence, you’ll have direct train access to plenty of Tuscan towns and cities, but also places like Milan, Rome, and Bologna.

If you decide to stay in, say, Lucca, you’ll still have access to all of those places–but you’ll generally need to make at least one train change in order to reach them, eating up more of your extremely limited time with logistics.

Curious about getting around?

You can search routes and price out tickets between different cities on Omio, a transportation aggregate we often use throughout Europe.

Don’t try to change hotels more than once.

Picture this: you wake up in the morning, ready to change cities (and hotels) for the next leg of your short trip to Italy.

You pack your bags, move the luggage downstairs, check out at the front desk, navigate to the train station (on foot, via public transport, via car?), load your bags onto the train, and wait.

After arriving in the next city, you unload your luggage, make your way to your hotel, either drop off your bags at the front desk for storage or check in, and then you’re free to see the city.

The reality is that even when dealing with two cities that don’t take too long to travel between, like Rome and Florence or Venice and Verona, you’re still eating up a sizable chunk of your day by changing overnight locations–and while that may be worth it on a longer trip, it takes a much longer percentage of your limited time in Italy on a shorter one!

For that reason, we really recommend only changing hotels once during your trip to Italy–or even not changing one at all.

Lean heavily on day trips.

Luckily, you don’t need to change hotels in order to see a wonderful variety of places in Italy!

Essentially, there are two reasonable options for seeing 3 Italian destinations over the course of 5 days in Italy: either base yourself in 2 places and take 1-2 days trips, or base yourself in one place and take 2-3 day trips.

While the second option narrows your scope a bit in terms of how far-flung each of your destinations will be, it is without a doubt the more laid-back and flexible option for a short Italy itinerary.

And, as each of Italy’s major (and minor, let’s be honest) cities has far more than 3 excellent day trips to choose from, there’s absolutely no way you’ll run out of things to see.

Look up train schedules and book your tickets in advance.

When trying to optimize a 5 day Italy itinerary, you won’t have any extra time to waste on transportation–which means planning ahead.

High-speed trains in Italy use dynamic pricing, meaning that prices rise as your dates get closer (and of course, routes selling out is always a risk, though not a very big one unless you happen to travel on a holiday, are with a big group, etc.)

Local or regional trains, also sometimes called the “slow trains”, have static pricing–but the difference in travel times can be significant (for example, just over 2 hours versus just under 4 hours to get between Rome and Florence, on average).

For most of the recommended itineraries in this blog post, we assume you’re using high-speed trains to get between each major destination.

As you brainstorm, we recommend searching for prices, train times, and route options for each transition to get a feel for what to expect.

Browse train schedules + shop train tickets for Italy today!

Don’t put pressure on yourself to “see it all”.

Not only is it impossible, but trying to fit too many destinations–especially ones that you want to enjoy overnight or that are far apart from each other–in one short trip is a recipe for seeing more of the inside of a train or car during your vacation than the cities themselves.

While balancing a desire to see a variety of destinations makes perfect sense, a good rule of thumb is that less is more with only 5 days in Italy.

Let your arrival and departure airport(s) guide your itinerary if you’re unsure.

Can’t seem to choose which of Italy’s top destinations you want to prioritize?

If so, letting your flight path guide your choices is an excellent way to narrow it down.

Unless you truly have no interest in seeing a particular place, your arrival and departure city should feature at the beginning and end of your itinerary (assuming you’re flying on a round-trip ticket).

From there, fill in the gaps with destinations that are fairly simple to reach over half a day or less–so don’t opt for visiting the Amalfi Coast if you’re flying in and out of Venice, for example.

If it fits in your budget, splurge on an experience or two that’s important to you.

While you can have a fantastic trip to Italy on a budget, if there’s room in your planning for a splurge or two, one of the best ways to spend that money is to upgrade your most sought-after experiences.

If seeing Pompeii has been on your bucket list since childhood and you want to visit on a day trip from Rome, for example, that’s a great reason to opt for a guided tour from Rome instead of stressing about changing trains and negotiating arrival and departure times.

Similarly, if you’re primarily coming to Italy for the food, signing up for a food tour (we adored this one in Rome and this one in Florence, just to name a couple) is a great way to ensure you sample a wide variety of dishes–and learn a bit about them on the way!

Is avoiding crowds your priority?

If so, springing for early access to the Vatican Museums (or even unlocking the doors with the Key Master if you’re up for a serious splurge) or visiting the Colosseum at night, for example, will make sure those moments stick out in your memory for all the right reasons.

Read More About Visiting Italy

Excited to visit Italy for 5 days soon and ready to keep planning your trip?

We would love to help!

You can browse our 100+ Italy blog posts here, or check out these guides:

• How to Enjoy 3 Days in Tuscany: Itinerary Ideas With or Without a Car!
• Venice or Rome: Which Italian Masterpiece is Right for You?
• 17 Wildly Romantic Places in Italy
• Amalfi Coast or Cinque Terre: Which Sublime Italian Coastline is Best?
• 25 Best Movies Set in Italy (By Genre!)