Are you trying to make the most of a short 5-day trip to Italy but finding it hard to decide what to see?
That’s completely understandable!
It often feels like no matter how much time you spend in Italy, you can never fully explore all its wonderful spots (we’ve collectively spent over a year there, and our wish list keeps growing). Planning the ideal 5-day itinerary can be a daunting task, especially if it’s your first visit to the country.
To help, we’ve compiled several suggestions showcasing what you can—and cannot—do during a brief trip to Italy, along with travel tips to maximize your experience.
Whether you’re eager to see as much as possible or prefer to unwind and enjoy la dolce vita in a selected city, you’ll find a 5-day itinerary here that suits your travel style.
Let’s dive into how you can fall in love with Italy in just 5 days!
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How to Structure a 5-Day Italy Itinerary
When planning your 5-day trip to Italy, consider these three key pieces of advice: limit your overnight stays to two destinations, allow geography to guide your choices, and book as much in advance as possible.
This is crucial for popular attractions like the Colosseum and climbing Florence’s Duomo. If you don’t plan ahead, you might miss out on your preferred spots altogether.
Even for less crowded locations, it’s wise to reserve hotels, tickets, tours, rental cars (if needed), and even train tickets early, to avoid wasting your precious time figuring out your next move.
Avoid cramming your schedule too tightly; allow some time to relax and enjoy the stunning surroundings, as well as the delectable food. The less you have to deal with logistics during your 5 days in Italy, the better.
The Most Intense 5-Day Italy Itinerary We Can Recommend
Want to truly maximize your 5 days in Italy, regardless of how exhausted you feel by the end?
The following itinerary represents the fastest-paced 5-day plan we can suggest, and we advise following it only if this trip exclusively focuses on Italy (i.e., if your flight arrives at 3 PM, it shouldn’t count as a full day).
If your trip to Europe spans weeks and includes Italy alongside places like France and Switzerland, this fast pace may not be sustainable—you’ll likely become burnt out.
However, if you’re ready for a whirlwind tour through Italy’s must-see destinations, here’s your plan.
This itinerary assumes you’re traveling round-trip to Rome, but feel free to adjust it according to your arrival and departure airports (though you may also want to change the cities you visit accordingly).
Day 1: Florence
To kick off this itinerary, we assume you’ll arrive in Rome in the early morning—a common travel time, especially for visitors from North America.
Grab your first Italian coffee, shake off the jet lag, and head straight for the high-speed train to Florence (don’t forget to reserve your train tickets in advance).
Upon arrival, drop off your luggage at your hotel and start exploring!
Your day in Florence will likely include visits to either the Galleria dell’Accademia (home to Michelangelo’s David) or the Uffizi Gallery, climbing to capture a stunning view of Florence, visiting the Duomo, crossing the Ponte Vecchio, and strolling through the city’s vibrant piazzas and markets.
For an optimized day in Florence, you can follow our one-day Florence itinerary and adjust according to your arrival time and energy levels after traveling.
Where to Stay in Florence
For this fast-paced itinerary, we suggest staying two nights in Florence (you’ll take a day trip tomorrow).
Here are a few excellent lodging options within walking distance of the Santa Maria Novella train station:
Budget
Hotel Dali — This charming, budget-friendly hotel is just a minute’s walk from the Duomo. With thousands of positive reviews, it offers free on-site parking for those with a car.
Keep in mind, however, that it lacks air-conditioning, which may be a concern in summer!
Check rates & book your stay at Hotel Dali today!
Mid-range
Hotel Silla — Just a short walk from the Arno River, we greatly enjoyed our stay at Hotel Silla.
The hotel is charming and peaceful, the complimentary breakfast is a nice plus, and you’re in a prime location to explore all that Florence has to offer without confronting crowds or noise.
It’s a place we would gladly return to!
Check rates & book your stay at Hotel Silla!
Luxury
Hotel Lungarno — Situated right along the Arno River, this hotel provides one of the best views of the Ponte Vecchio in Florence—as well as breathtaking city views from its terrace. Hotel Lungarno is our go-to “splurge” option in Florence.
You can’t go wrong selecting Hotel Lungarno as your base during your Italy journey!
Check rates & book your stay at Hotel Lungarno!
Day 2: The Tuscan Countryside
After enjoying the best of Florence, it’s time to venture into the hills!
There are numerous options for day trips from Florence (check out some of our favorites), but with just 5 days in Italy, we suggest visiting at least two charming towns, ideally one offering stunning views of the Tuscan landscape.
For convenience, consider this very popular organized day trip. It’s a fantastic value for sampling different aspects of this beautiful region without the hassle of transportation (including a designated driver for those wine tastings!) and parking.
This excellent day trip typically includes visits to the picturesque city of Siena and the classic hill town of San Gimignano, capped off with lunch at a family-run vineyard in Chianti.
Prefer to explore independently? If you rent a car for the day, consider combining visits to San Gimignano and Volterra.
For train travelers, Siena and Lucca are both stunning cities accessible by rail. If you’re set on seeing a famous tower, consider combining your visit to Pisa with Lucca.
Whichever towns you choose to visit, we recommend spending the night in Florence.
Book your day trip to the Tuscan countryside today!
Day 3: Rome
Get an early start and head to the train station to catch the high-speed train back to Rome (and don’t forget to book your tickets in advance).
By selecting the high-speed option, you can reach Rome in about 2 to 2.5 hours. After dropping off your luggage at the hotel, you’ll have a good part of the day to start your Roman adventure!
Since you’ll spend another day in Rome, we recommend following our detailed 2-day Rome itinerary.
Today, make sure to visit the Colosseum and the Roman Forum (unless you prefer to enjoy the night tour of the Colosseum, in which case the Forum will be closed), stroll through Piazza Venezia and Campo de’ Fiori, and take the time to explore the charming district of Trastevere.
If you’re interested in experiencing a delicious culinary tour during your time in Italy, we highly recommend this Trastevere food tour—it’s a fantastic way to sample several Roman pastas for dinner without having to choose just one!
Where to Stay in Rome
After leaving Florence, we recommend that you focus the remaining days of your itinerary in Rome.
Here are several well-reviewed hotels within walking distance of some of Rome’s most notable attractions:
Budget
Hotel Casa Valdese — Located within a 25-minute walk from the Spanish Steps and just a 2-minute walk to the metro, Hotel Casa Valdese offers a lovely atmosphere that balances affordability and proximity in Rome.
With great reviews and a peaceful terrace, this hotel provides a welcome escape in the heart of the city.
Check rates & book your stay at Hotel Casa Valdese!
Mid-range
Pantheon Inn — If you desire a hotel with classic Italian charm in central Rome, Pantheon Inn is the place.
Located immediately behind the Pantheon, it offers a serene retreat within the energetic city. While you will need to walk a bit to the metro stop, you will enjoy traversing the beautiful Centro Storico.
Check rates & book your stay at the Pantheon Inn!
Luxury
Hotel Condotti — Situated just two blocks from the Spanish Steps (and the adjacent Piazza di Spagna metro station), this hotel offers an ideal location in Rome!
Well-rated and boasting luxurious suites and exceptionally clean accommodations, Hotel Condotti is perfect for those wanting to explore the Centro Storico while having quick access to the metro station.
Its popularity and convenient setting make checking into Hotel Condotti a smart choice.
Check rates & book your stay at Hotel Condotti!
Day 4: The Amalfi Coast & Pompeii
If your goal is to make the most of your 5 days in Italy, an epic day trip from Rome will make for an unforgettable experience.
An organized tour, such as this popular option, will allow you to visit the historic Pompeii and even catch a glimpse of the Amalfi Coast in a single day.
Be prepared for a long day, but it’ll be a memorable trip, allowing you to explore one of Italy’s most significant historical sites while enjoying some of its breathtaking natural beauty.
If you’ve been dreaming of Pompeii and the Amalfi Coast, this tour is a fantastic way to include them in your 5-day itinerary.
If organized tours aren’t your thing, you can visit Pompeii independently from Rome but we wouldn’t advise trying to see the Amalfi Coast as well in one day if you’re unfamiliar with the area.
Alternatively, there are plenty of other fascinating day trips from Rome that are closer to the city!
Book your day trip to Pompeii & the Amalfi Coast today!
Day 5: Rome
Start with the Vatican Museums and St. Peter’s Basilica to experience this iconic micro-state.
We highly recommend booking an early-access tour of the Vatican, which allows you to start your sightseeing before most of Rome has had their first caffè.
If you’re a fan of breathtaking views, take the time to climb to the top of St. Peter’s dome; the view is exceptional and it’s one of our favorite tower climbs in Italy!
After your Vatican visit, head to Castel Sant’Angelo and stroll across the angel-lined Ponte Sant’Angelo (be sure to pause and enjoy the buskers for a moment!) into Centro Storico to see some of Rome’s top attractions.
Piazza Navona, the Pantheon, the Trevi Fountain, the Spanish Steps, and Piazza del Popolo, among others, are all within walking distance!
This route mirrors the second day of our suggested 2-day Rome itinerary; depending on how quickly you sightsee, you may even have some time to explore Rome’s lesser-known hidden gems like Galleria Sciarra, Vicus Caprarius, the Capuchin Crypt, and Galleria Spada.
More Ways to Experience Italy in 5 Days
If a fast-paced itinerary doesn’t appeal to you, we understand completely.
Here are a few alternative itinerary ideas for 5 days in Italy that strike a balance between the rapid pace outlined above and a more relaxed approach of focusing on one city or region.
We’ll keep these suggestions concise, but be sure to check out our specific articles on each destination here on Our Escape Clause!
Feel free to use the search bar on the top right of the page (or at the top of the mobile menu) to find more information on any of the suggested locations.
Here are some rewarding options for structuring a 5-day trip to Italy:
Rome + Florence + Cinque Terre
Instead of taking two day trips (the Tuscan countryside and the Amalfi Coast/Pompeii), consider spending 2 days each in Rome and Florence, with a day trip to Cinque Terre from Florence.
We recommend booking an organized day trip to Cinque Terre—here’s why.
By spending 2 days in Florence and limiting yourself to one day trip, you’ll have the opportunity to delve deeper into Florence’s treasures and discover some of its hidden gems.
Rome + the Amalfi Coast + Pompeii
If you want to spend more time in the Amalfi Coast area rather than just as a day trip, consider spending 2 days in Rome and 3 days based in Campania (or vice versa).
When in the south, you can stay directly on the Amalfi Coast or choose Sorrento and Naples as convenient bases that give you access to the coast, Pompeii, and the islands like Capri—plus they simplify transitions to and from Rome.
Milan + Lake Como + Venice
If you’re flying in and out of Milan or Venice and prefer to explore northern Italy, you can have a delightful 5-day trip by spending one day in Milan, one day in Lake Como (consider visiting Varenna and Bellagio), and a couple of days in Venice.
As for the fifth day, you can choose based on your travel style: either spend a second day relaxing in Lake Como with a hike or a boat tour, or enjoy another day in Venice by exploring its unique attractions. You could even extend your trip to a nearby city like Bergamo, Verona, or Padua.
Milan is also a conveniently connected hub facilitating day trips to many northern Italy towns.
Florence + the Tuscan Countryside + Cinque Terre
If your goal is to stay within close proximity while experiencing diverse landscapes, we recommend combining a trip to Florence, the Tuscan countryside, and Cinque Terre.
Split your time between 2 days in Florence and either 2 days in another Tuscan city with a day trip to Cinque Terre, or 2 days in Cinque Terre with a day trip to a different Tuscan destination.
If you desire to visit Cinque Terre independently rather than through a tour, consider basing yourself in a Tuscan city near the coast, like Lucca, for easier access.
Venice + Verona + the Dolomites
If you’re dreaming about exploring the Italian Alps, you can easily combine a couple of days in Venice with a visit to the Dolomites, staying in Cortina d’Ampezzo, Bolzano, or a charming town in the area.
Your 5-day itinerary could also include a day trip to Verona (it’s convenient to stop by while driving from Venice to Bolzano), or even a day for wine tasting in the Prosecco region.
Rome + Florence + Venice
Finally, you can indeed sample the trio of Rome, Florence, and Venice within a 5-day itinerary—but be aware that this will only allow for a brief taste of each city.
We recommend avoiding overnight stays in all three; instead, consider basing yourself in Rome + Florence and making a day trip to Venice from Florence (here’s our full guide to that day trip for details on its benefits and challenges), or in Rome + Venice with a day trip to Florence.
This isn’t the ideal way to explore all three, but if you can’t bear to choose just one and think this might be your only opportunity to visit Italy for a while, it certainly is doable.
Alternative 5-Day Italy Itineraries: Choose a City and Relax
Looking for a more leisurely 5-day Italy itinerary while still seeing plenty?
You can have a fulfilling trip to Italy by selecting one well-connected city as your base and incorporating 1-3 day trips.
My grandparents have adopted this travel style, often renting a place in the Tuscan countryside and embarking on day trips almost every day, resulting in fantastic vacations!
The options for your base city are endless: iconic cities like Rome, Florence, and Venice are always delightful, but less-visited yet charming cities like Bologna, Verona, Naples, Palermo, Siena, Bolzano, and more are also great choices.
Smaller cities can offer peaceful escapes from crowds (especially off-peak). Parma and Lucca have been some of our favorite central Italian basing points recently.
If you’re more interested in the day trip potential than ensuring your base city has enough attractions for full 5 days, consider smaller towns like Sorrento (great for Pompeii and the Amalfi Coast), serene beach towns like Monopoli in Puglia, any of the Cinque Terre towns or close locales like Levanto, or mountain towns like Ortisei.
If you want to experience the most popular regions while enjoying lower costs, consider basing yourself slightly outside of the busier locations—for example, stay in Bergamo instead of Milan, or Padua instead of Venice for access to the best sights with less traffic.
This choice can come with some trade-offs in connectivity, but it could be a great strategy 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.
Regardless of which region(s) you wish to explore, we suggest selecting a major city for your base, preferably one that serves as its region’s capital.
These cities are typically the best connected by train, offering easy access to other destinations within the area and across the country.
For example, by staying in Florence, you’ll have direct train connections to various Tuscan cities and even larger hubs like Milan, Rome, and Bologna.
Conversely, if you choose Lucca, while still accessible, it generally requires at least one train change to reach these popular destinations, which eats into your precious time.
Curious about how to navigate? You can check routes and compare ticket prices using Omio, a transportation aggregator we frequently use throughout Europe.
Don’t try to change hotels more than once.
Imagine this scenario: you awaken excited about moving to your next city (and changing hotels).
You pack your bags, move luggage downstairs, check out, navigate to the train station (on foot, via public transport, by car?), load your luggage onto the train, and wait for departure.
Once you arrive at your next destination, you unload your bags, find your hotel, drop off your luggage at the front desk, or check-in, and then finally set off to explore.
The reality is even with manageable distances, like between Rome and Florence or Venice and Verona, changing locations can significantly consume your day—while it may make sense on a longer trip, it takes up a larger proportion of your limited time during a short stay!
That’s why we recommend only changing lodging once during your Italy trip—or even avoid it entirely if possible.
Lean heavily on day trips.
Fortunately, you don’t have to switch hotels to enjoy a diverse array of destinations in Italy!
Essentially, you have two feasible strategies for experiencing three Italian cities within your 5-day time frame: base yourself in two cities and plan for 1-2 day trips, or stay in one location and spend 2-3 days on outings.
While the latter option may limit how expansive your explorations can be, it’s undoubtedly the more relaxed and adaptable approach for a short trip.
And since every prominent city in Italy (and honestly many of the smaller ones too!) offers enough fantastic day trips to fill your itinerary, you will never run out of options to explore.
Look up train schedules and book your tickets in advance.
While trying to optimize your 5-day itinerary, you won’t have any extra time for transportation, meaning planning in advance is essential.
High-speed trains in Italy employ dynamic pricing. Prices increase as travel dates approach (plus, there’s always a risk of selling out on popular routes, especially during holidays or large groups).
Conversely, local or regional trains (often termed “slow trains”) have fixed pricing, but the time difference can be substantial (approximately 2 hours by high-speed versus almost 4 hours via local train from Rome to Florence).
Our suggested itineraries typically incorporate high-speed train travel to get between major cities efficiently.
As you formulate your plans, make sure to check prices, schedules, and route details for each segment of your journey, helping you set expectations.
Browse train schedules + shop for train tickets in Italy today!
Don’t pressure yourself to “see it all”.
Not only is this unrealistic, but attempting to fit in too many destinations—especially ones you wish to explore more thoroughly or those that are distanced from each other—results in more train rides than leisurely sightseeing.
While it makes sense to seek variety, a good rule of thumb is that *less is more* when you have just 5 days in Italy.
Use your arrival and departure city to shape your itinerary.
If you’re struggling with which Italian destination to prioritize, let your flight path help guide your decision.
Your arrival and departure city should feature at the beginning and end of your itinerary, especially if you’re on a round-trip ticket.
Fill in the gaps with destinations easy to reach in less than half a day—so maybe skip the Amalfi Coast if you’re flying into and out of Venice.
If your budget allows, splurge on experiences that matter to you.
While you can enjoy a wonderful trip to Italy on a budget, if there’s room in your plans for a few splurges, they will enhance the experiences you value the most.
If Pompeii has been on your bucket list for ages and you’re visiting from Rome, consider opting for a guided tour rather than stressing over train transfers and arrival times.
Similarly, if food is a primary motivation for your visit, taking a food tour (we loved this one in Rome and this one in Florence) ensures you’ll enjoy a wide range of dishes while learning more about them.
If avoiding crowds is important to you, splurging for early access to the Vatican Museums (or even a unique experience like the Key Master tour) or visiting the Colosseum at night will create lasting memories.
Read More About Visiting Italy
Excited about your upcoming 5-day Italy adventure and ready to keep planning?
We’re here to help!
You can explore our 100+ Italy blog posts here, or check out these insightful guides:
