There is an excellent reason why Italy tops the checklist of countless travelers. It has a distinctive historical importance even though Italy itself is actually one of the youngest countries in Europe thanks to the escapades of the Roman Empire, it has an admired food culture not to mention the wine, and it has gorgeous scenery.
Italy has spent hundreds of years developing its brand which has millions of people longing to visit Italy.
However, throughout our nearly two months in Italy over the past two years, we`ve learned that focusing only on a few things the country is renowned for means neglecting aspects that truly make it exceptional.
From an American perspective, we have a very specific view of what it means to be “Italian” that involves numerous stereotypes including some combination of chicken parmigiana, garlic bread, and speaking with hand gestures (in our experience, only one of those is genuinely found in Italy – which one is it?).
However, after several trips where we’ve been able to investigate more deeply than you typically do on that initial trip, we’ve come to realize an important fact.
Italy is a surprisingly diverse country.
Not necessarily in regards to race or ethnicity, which is how the word “diversity” often gets translated, but in terms of regional variances that have been formed over thousands of years.
The variances in culture, dialect, and cuisine stemming from centuries as independent (often opposing) city-states are what attract us to Italy, and this diversity is what creates such a fascinating place to visit.
As you transition between regions, you’ll notice that the food and wine selections change greatly, as do the accents and cultural norms.
With so much to learn, experience, eat, and drink in Italy, how does one even go about arranging a two week trip in Italy?
In this guide, we will thoroughly examine what embodies, based on our perspective, an ideal 14 day itinerary for Italy
It covers Italy’s major urban areas – Rome, Florence, and Venice – combined with some time devoted to less acclaimed places like Bologna that most visitors overlook, however we believe is well deserving of a stop.
This guide is aimed at individuals participating for the first time who want to see those main cities, but we also have an entire section below the main itinerary full of ideas on how to modify it, which you may find useful if you`ve done the whole Venice experience previously and are looking for something novel.
However it works out, grab a cup of coffee (or a spritz?) and brace yourself for a lengthy journey – here is precisely (and we mean precisely) how we would spend two weeks in Italy.
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Table of Contents
Is 14 Days Enough Time in Italy?
In summary, no it is not. Certainly not. However, we do think it’s sufficient time to experience parts of the country that will offer a good overview and aid your selection of places to explore more deeply on a subsequent trip.
In this itinerary – which is primarily for first timers – we’re going to cover both the main cities (Rome, Florence, and Venice) and some of our favorite places that don’t usually make the list (Bologna and Verona).
P.S. If you have a shorter trip, be sure to check out our guide to 10 days in Italy, which centers on Rome, Florence (and the surrounding area), and Venice, or our guide to spending a week in Italy, which presents five ideas for a week in Italy that you can combine and match to develop your own itinerary.
Two places absent from this itinerary had to be excluded due to various reasons.
First is southern Italy – specifically Naples, Pompeii, and the Amalfi Coast.
The reason is not that they aren’t beautiful or worth seeing, but that we think your time is better spent in northern Italy, which is our favorite part of the country.
Getting between Naples and northern Italy is going to take a significant amount of time that would be better spent exploring!
The second place is the Cinque Terre, and it`s for a comparable reason. The Cinque Terre is stunning. But it`s not particularly convenient to access.
We condensed our hike over the course of three days with overnight lodging between, and it proved to be quite challenging terrain.
If you do want to include the Cinque Terre, you’ll need at minimum two full days. We have some ideas on how to add it below the main itinerary.
If you’re interested in visiting Cinque Terre, make sure to read our guides for Cinque Terre.
Where to Fly In and Out Of?
If you follow the itinerary below as written, which takes you on a tour around Italy from Rome to Venice, you’ll want to fly into Rome–Fiumicino International Airport (FCO) and out of Venice Marco Polo Airport (VCE).
An alternative would be to fly out of Milan (either LIN or MXP – we like LIN better because it’s closer to the city and a newer airport), which generally has more flight options than Venice, but it requires an extra day or two and a train.
Getting Around Italy
Traveling around Italy by train is the best approach. At least for fulfilling the goals on the itinerary below It’s going to be less expensive, quicker (once you account for travel time and security at the airport), and more eco-friendly than taking short flights.
There are a few elements you should be aware of about trains in Italy before we proceed any further.
Initially, there are (essentially) two types of trains operating differently in Italy – high speed and regional.
High speed trains are more expensive, significantly faster, and less adaptable. To save time since you’ve only got a confined amount of it in Italy, you’ll want to take the high speed trains between cities.
You’ll want to book your ticket as far in advance as possible, which usually will save you some money, but will be less adaptable. If you want the adaptability, you’ll have to be prepared to pay a little extra.
Regional trains are slower, more affordable, and more adaptable. They’re usually used for connecting nearby smaller cities to one another (for example, there’s a regional train between Florence and Pisa).
You can buy these tickets when you arrive at the station, and they’re more adaptable. You need to make sure you validate them before boarding.
The best way to reserve train tickets in Italy is straight through Trenitalia, the company that operates most of the trains in Italy. The only downside is that you’ll need to know the title of the station you want to travel to in Italian.
We’d take high-pace prepares between Rome and Florence, Florence and Bologna, Bologna and Verona, and Verona and Venice. For day trips from Florence and Bologna, nearby prepares will do.
The Itinerary / Route
What follows is the itinerary for spending two weeks exploring Italy.
One quick note: Generally, when you’re moving between cities, we`d recommend taking an afternoon train, which will give you some extra time to explore the city you’re leaving in the morning before heading to the train station.
Here is how we could plan a trip spanning two weeks to experience the top places in Italy, starting in Rome and finishing in Venice:
- Day 1: Arrive in Rome
- Day 2: Rome
- Day 3: Rome
- Day 4: Spending Time in Rome and Taking a Train to Florence
- Day 5: Florence
- Day 6: Florence
- Day 7: Florence Day Trip
- Day 8: Train to Bologna
- Day 9: Bologna
- Day 10: Day Trip to Verona
- Day 11: Train to Venice
- Day 12: Venice
- Day 13: Venice
- Day 14: Venice + Fly Home
You may notice some differences in how we`ve structured this suggested itinerary.
First, we favor allocating a minimum of 2-3 days in major cities to prevent feeling like you’re hastily moving between sights. That will provide some time for exploration to uncover a new favorite neighborhood, coffee shop, wine bar, or restaurant.
Second, we dislike packing and changing accommodations. It`s unpleasant. Which is why we’re advising staying somewhere like Florence or Bologna to use as a home base for exploring the surrounding vicinity.
Third, we’ve allocated a considerable portion of time in Bologna. Which is our preferred city in Italy not called Rome or Florence (Lucca and Verona are also in contention).
The following text discusses why Bologna is an excellent place to visit in Italy: Bologna is the capital of the prime food region in Italy, home to the generation of tasty products like Parmesan-Reggiano cheese (we greatly enjoyed touring a little Parmesan-Reggiano producer with Claudio on this tour), prosciutto di Parma, mortadella, balsamic vinegar, Lambrusco (a bubbly red wine), tortellini, ragu, and plenty more.
Not only is the food exceptional, but the city – which has a noticeably younger, less “touristy” feel than places like Rome, Florence, and Venice – provides a refreshing change of pace.
Bologna also makes an excellent base for day trips because it is so well linked.
Whatever you do, we’d implore you NOT to cut Bologna. It’s an amazing city, and you won’t regret spending a day or two there.
Fourthly, the proposed duration in Venice may appear extended but equates to just over two and a half days factoring a midday train arrival and early morning departure.
If you have a full 14 days (you’re flying out on day 15, for example), we’d add an extra day either in Florence to do another day trip, or in Rome.
2 Weeks in Italy: A Perfect 14 Day Italy Itinerary for First Timers
And now, on to the detailed itinerary.
Our goal here is to provide you with the guidance deemed essential to orchestrating an amazing excursion to Italy.
We will explore these locations more deeply than a brief description, sharing some favorite activities, sights, eats, and drinks from our own Italian adventures (and, equally key, what to avoid – looking at you, Juliet`s House in Verona!).
We accept those subtleties – like specific wine bars, tours, and coffee shops we cherished – are the difference between an agreeable trip and an extraordinary trip, and hope you’ll discover a few places that you wouldn’t necessarily have otherwise found alone.
Another intention here is to avoid simply providing the same routine itinerary found in every travel resource.
Of course, we’re going to include Rome, Florence, and Venice, because visiting those places is absolutely worthwhile during a first trip to Italy.
However, we’ll also feature some of our favorite locales (like Bologna) that don`t usually get mentioned. Matt is quite fond of Rick Steves (who hails from Seattle too!) despite Steves not covering Bologna in his Italy guide – quite an omission.
Rome: Days 1-3
I mean, if you’ve never visited Rome before, you’re in for a real treat. Rome is one of our favorite cities in Europe, and there’s something special about walking past architecture over a thousand years old on your way to a hip natural wine bar in the evening.
While the city of Rome is renowned for its historic sights, it’s also an excellent city for food and drinks (as will be discussed below) and as I was sitting writing this last night, I literally made an Italian pasta dish (amatriciana) for dinner.
We’d recommend spending a minimum of three days in Rome, which will allow enough time to see both the main attractions, dive into the history of Italy’s capital city, and also indulge in some of Rome’s great food and drinks.
What to Do in Rome
Look, there are two primary attractions in Rome that, if it’s your first trip, you probably shouldn’t miss.
They are, of course, the Vatican and the Colosseum and Roman Forum. While popular and “touristy,” being tourist destinations does not necessarily diminish their worth.
However, you should absolutely separate them and avoid doing them on the same day. It will simply be too much information if you try to knock them both out on the same day, and you will be exhausted, which means you won’t get the most out of them.
Do them on different days. Trust us.
Let’s examine those first two areas in more detail. However, this will only provide a brief overview.
For a more thorough depiction of how we recommend experiencing them, explore our guides to the best things to do in Rome, our guide to planning your Rome itinerary, and our review of the Colosseum and Forum tour we enjoyed (and, preview alert, loved).
The Colosseum and Roman Forum are perhaps the finest instance in Rome of the magnificence that the Roman Empire was capable of generating nearly two millennia ago.
The Colosseum, in particular, is an architectural triumph to us.
The Forum is mainly just stones scattered about at this point, so it’s harder to envision what it resembled roughly two thousand years ago at the height of Rome’s power.
Which brings us to an important point: you should definitely participate in a guided tour of the Colosseum and Roman Forum.
We have a strong perspective here, mostly informed by the fact that we did an amazing tour of the Colosseum with our favorite Italian tour company (you can read all about it here) where we learned that some (really, most) of the things we thought we knew about the Colosseum were actually just myths.
We have individually undertaken (and enjoyed) TakeWalks’ Reserved Colosseum Tour with Roman Forum & Palatine Hill – you can read about our experience here(hint: we loved it!). It is an excellent tour option that encompasses both the Colosseum and Forum.
Before or during your visit, there exists an outstanding perspective of the Roman Forum from outside its boundaries located here.
The Vatican is basically one of the most noteworthy art galleries on the planet. For sure, there’s St. Peter’s Basilica, however that as well is exceptionally about the craftsmanship (which ultimately is only a method to demonstrate that you have cash and intensity).
Especially considering its length and Michaelangelo facing the ceiling to paint, the Sistine Chapel is profoundly impactful.
It’s worth touring the Vatican too, if finances allow. We’d do the “Pristine Sistine” early entry tour with Take Walks, which includes early access.
We have not personally done that specific tour, but we have participated in four separate Take Walks tours so far, and all have been excellent because the guides have extensive expertise in their fields.
If you can only do one tour, we’d do the Colosseum and Forum because the added context and historical perspective from a guide is more useful when you’re looking at ruins.
Since we’ve already digressed at length in this section, here’s a brief list of other things to do in Rome.
The vista from the Orange Garden (Giardino degli Aranci).This is one of our favored perspectives in the city, and we’re not alone. Head up here around sundown for a treat, but it’s similarly magnificent in the early morning hours (perhaps preferable, because the sun is generally behind you), and there are far fewer people.
Trastevere in the evening.Our favorite neighborhood in Rome comes alive at night. It’s pleasant in the morning, especially if you check out the outdoor market at Piazza de’ Renzi, but evening is when it awakens. Folks spill from bars and restaurants onto the roadways, and the plazas fill with drinkers having fun
Wine! Enoteca il Piccolo within the Centro Storico ( here) is as remarkable as it is well-liked. The proprietor emerged to the terrace the place I tried to elucidate in my poor Italian what kind of wine I needed (dry white), and he walked away with out a phrase, and returned with two exceptional glasses of precisely what I requested for. If you happen to’re trying to find a bottle, Les Vignerons in Trastevere is the location to go (excellent beer and cider selection, too!).
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If you enjoy quality coffee, head directly to Pergamino Caffè near the Vatican, where some of the best baristas in Rome brew a variety of Italian specialty coffees for patrons.
It’s the favored coffee choice of coffee aficionado Matt in Rome.
There are clearly many worthwhile facets in the Eternal City for experiencing, seeing, and indulging in cuisine. For additional information, refer to our guide on the top attractions in Rome, containing a collection of our preferences.
Where to Stay in Rome
While there are numerous areas you could reside in Rome, we have two robust recommendations for you to assist you in narrowing it down.
We also provide an extensive, thoroughly detailed guide on where to lodge in Rome if you want additional details to help make your decision.
Our overall recommendation is staying in Trastevere, which is far and away our favorite area of the city.
We stayed there during our last trip, and it truly is magical.
It’s a great place to eat and drink, and it really comes alive when night falls, full of lively squares and small bars and restaurants that fill up on a nightly basis and spill out into the cobblestone streets.
The entrance fee will need to be paid, as it is a Utah State Park and is not covered by the America the Beautiful Pass. As of 2021, it is $20 per vehicle – check the most recent fees here.
It’s a indulgent option compared to where we normally reside, but the stylish accommodations, comfortable beds, and incredible breakfast spread were worth the cost.
A more budget-friendly (though equally highly rated) choice would be Ripagrande a Trastevere, which is essentially situated right on the River Tiber and within a five minute walk of everything in Trastevere.
The sole downside to Trastevere is its moderate distance from the train station, which matters less with three days but is somewhat inconvenient (you’ll likely need a taxi).
There are three potential places of lodging on the Grand Canyon’s South Rim, and it mainly relies on your budget and preferences.
Remaining here positions one in the center of all the activity, with a walkable distance to just about every aspect of the city.
It’s most convenient, though crowded and potentially loud. Don’t miss an early morning walk from Piazza Navona to the Trevi Fountain and Spanish Steps!
We stayed five nightsnearPiazzaNavona at
Coronari Palace and Casa Pietra were also on our list, though we opted for more space and a kitchen for our time in Rome.
Florence: Days 4-6
While Rome may have been the crown jewel of the Roman Empire, Florence could reasonably be seen as the second most pivotal city in Italian history due to its seminal role in the Renaissance`s beginning.
During a guided walking tour in Florence ( this particular tour, which we recommend below because it’s a great introduction to the city), as we were strolling through Piazza della Signoria, our guide made an observation I hadn’t fully considered before that moment.
Florence was one of the richest cities in Europe (if not the world) in the 15th Century through the Renaissance.
Many people – including myself – may think that wealth originated from the amazing art produced in Florence leading up to and during the Renaissance.
However, the reality is that Florence was already a wealthy city thanks to silk production, and it was this affluence that enabled it to become a cultural icon still attracting thousands of visitors five centuries later.
Wandering Florence`s streets, it`s easy to understand the city`s power to captivate many visitors.
It’s charming. The Duomo is incredible, both because of how imposing it is, and the fact that it’s an architectural marvel. There are two world class museums.
The cuisine and vino are both excellent (definitely try the wild boar if you see it on a menu – pappardelle al cinghiale – which was our favorite find on our Tuscany road trip schedule).
I could continue discussing Florence – I’ve spent over a week in Florence between two trips in the past year (at the time of writing) – but let’s leave it there and get into how to make the most of your time in the Tuscan capital.
In this itinerary, we have you spending two and a half days in Florence itself, and then using it as a home base for a day trip into Tuscany.
What to Do in Florence
There are two principal attractions in Florence that you`ve likely heard of before, and both richly deserve your time.
They include the Uffizi Gallery, which chronologically journeys through Renaissance art in Florence, and the Galleria dell’accademia, where you will find Michaelangelo’sDavid.
However, attempting to do them on separate days is best, as taking it all in at once may overwhelm.
Believe me, my mother and I attempted to accomplish both activities in a single day in Florence during my recent trip to Italy, however it proved to be too ambitious.
The other thing I would say – and again, I’m speaking from experience here having done both museums with and without a guide – is that it is advisable to invest in an informative guided tour led by an art historian if possible.
After some great recent experiences, I`ve decided I likely won`t visit huge art galleries like the Uffizi or Louvre without a guide again in the future.
The guide can add significantly more in terms of context, details, and storytelling that will provide a deeper understanding of just about any museum visit.
Otherwise, we would look at the art, comment that it looks pleasant, and then move on without truly understanding the context behind what we are observing.
If you only have a budget for one activity, make certain to join the guided tour of the Uffizi, where your guide will be able to explain precisely what you’re viewing, and what it signifies about the changing nature of society and culture during the Renaissance period.
We did this guided tour of the Uffizi Gallery, and it was fantastic.
For what it’s worth mentioning, I (Matt) also undertook this guided tour of the Galleria dell’Accademia on my last visit with my mom, and we also truly enjoyed it.
However, as mentioned above, if you only have time or budget for one tour, you`ll benefit more from the Uffizi.
For more details, including how to independently visit both galleries, check out our guides to the top things to do in Florence and our guide planning your Florence itinerary.
As recommended earlier, visiting one museum on each of the two complete days in Florence allows adequately spacing out attendance. This extra time could then be applied as follows.
We highly recommend experiencing Andrea`s tour of Florence on foot. Walking tours can effectively introduce you to a new city and allow meaningful engagement with a local individual who can offer guidance regarding food, drink, and shopping suggestions. We thoroughly enjoyed Andrea`s walking tour, which provides a two hour immersive overview of Florence`s rich history, covering the Medici family in great detail. Andrea additionally provides an extended version of the tour that allocates an extra hour and crosses the river to Oltrarno.
Ascend to Piazzale Michelangelo. Across the river from Florence’s Centro Storico lies arguably the finest vista of the city at Piazzale Michelangelo. Views encompass the Arno River and intact Ponte Vecchio bridge, the Duomo cathedral, plus additional locations. Sunset presents a nice time, though crowds can gather. Dawn provides an even more favorable experience with the rising sun behind and minimal other present 
Explore Brunelleschi`s domed cathedral. The immense Duomo in Florence is best experienced, in our assessment, by ascending to its heights. Progressing upward, visitors are granted views of the dome`s interior adornments as well as some rather unsettling artworks. Further climbing leads through the area between the inner and outer dome shells, providing perspective on the monumental structure`s construction over six centuries past which is thought-provoking. Reaching the crown offers panoramic vistas across all of Florence. For minimized crowds, opt for an early morning ascent after booking in advance here.
Immerse yourself in Tuscany’s food and beverage offerings. We`d strongly advise you to avoid the pizza in Florence, and instead indulge in some of the local delicacies. We love Pappardelle al ragu di cinghiale (a pasta with a wild boar sauce that my mom fell fond of), pappa al pomodoro (tomato and bread soup), and the Schiacciata (sort of like a focaccia sandwich, but slightly different). We enjoyed the cuisine at Trattoria da Garibardi. Most of the Florentine fare pairs well with the Tuscan reds like Chianti Classico and Brunello, which are a couple of the more prestigious red wines to seek out.
Where to Stay in Florence
Similar to above for Rome, we have two recommendations for areas to stay in Florence.
Also similar to Rome, your choice is going to be between the coolest neighborhood (in our opinions, anyway) and the most convenient area.
Practicality considers a small amount more here because you will be taking a day excursion, which means you’ll be going to and from the train station.
, which is a five minute walk east of the Duomo. It has the best cuisine (we feel), fewer tourists, and is close to everything in the city.
We stayed at Pietrapiana Unique Apartments for nearly a week, and it offered all we sought and more: access to a kitchen, a little extra space to spread out, a peaceful refuge from the hustle and bustle, and a comfortable place to rest. Highly advised!
La Maison du Sage is another suitable option located near – it’s more of a conventional hotel than serviced apartments.
Another option, which is best if you want to be very central to everything in Florence, is Florence’s Centro Storico, which is focused around the Piazza del Duomo and nearby Piazza della Signoria (home to the Uffizi Gallery).
It’s bustling, it’s loud, but it’s highly convenient. It’s also nearer to the train station for your day trip.
Day Trip from Florence (Choose Your Own Adventure): Day 7
Florence is the capital of Tuscany, which might be Italy’s most famous region for its wine and general atmosphere of dolce vita feeling. And, after spending a week in Tuscany, we can definitively say it delivers on both.
Florence is an excellent base to explore Tuscany from, with most of the highlights accessible within 90 minutes by train. However, the main issue with Tuscany is that you really need a car to be able to see certain things properly.
Here are the three day trips from Florence we’d recommend, and which one you choose totally relies on your interests.
If combining San Gimignano, Chianti, and Siena into a single day, it will be a lengthy day, but this tour with Take Walks (which, as mentioned previously in this guide, is one of our favorite tour agencies globally), covers San Gimignano, Chianti, and Siena in one action-packed 10 hour schedule.
Day Trip 1: Siena for the Cathedral (and the History)
Siena is a popular day trip from Florence, involving a 90 minute train journey south in the heart of Tuscany.
There is perhaps no better example of a classic hilltop town than Siena, which is a red city perched on a hill overlooking lush green countryside.
The cathedral in Siena is awe-inspiring, and we say that as individuals who generally don’t become highly energized about enormous opulent places of worship.
The iconic dark green and white stripes of Siena`s Duomo are just the beginning of what makes it exceptional.
The interior is where the real enjoyment begins, particularly if you’re around when the floors are uncovered (usually in the summer), and the intricate art and tilework on the floors is on full display.
We recommend ascending to the Facciatone, which is a viewpoint within the Museo del Duomo that has an excellent view of both the cathedral and the surrounding landscape.
Another can`t-miss location in Siena is Piazza del Campo, rivaling Piazza Maggiore in Bologna (more on that shortly) as our favorite Italian plaza.
In regards to dining and drinking, head to Torrefazione Fiorella for a morning beverage at a stand-up counter (very Italian tradition), Panificio Il Magnifico to sample sweet Tuscan delicacies like ricciarelli, Du’ Cose Da Berna for customary sandwiches at lunchtime (a suggestion from our friendly host at the agriturismo we stayed outside Siena), and Ristorante Gallo Nero, which was one of the finest meals we had in Tuscany.
Transportation options. Regional trains connecting Florence`s central Santa Maria Novella station to Siena take approximately an hour and a half. Bus route 131 (or the quicker 131R) also provides transportation from Florence`s bus terminal ( here on Google Maps – it`s situated next to Santa Maria Novella), requiring a comparable duration. Both options offer reasonable fares.
Day Trip 2: Chianti for the Wine
Chianti is the place to go for wine. Chianti classico is a premier variety here, which is a Sangiovese-based red wine that adheres to strict production standards, and is one of Italy`s most famous exported varieties.
If visitors to Tuscany do not enjoy wines with a red color, I have some unfortunate news – the area is largely focused on red varieties of wine (with the sole exception of vernaccia, a white wine that originates from San Gimignano!).
Assuming you don’t have a car, your only option here is to do an organized tour because doing a self-guided tour of Chianti wineries would require both a rental car and a designated non-drinker.
In terms of guided tours, you have two options.
You have the choice of either a tour that delves deeply into a single winery, usually including a cellar tour and thorough tasting (but you`ll need to make your way out to the winery), or a tour that takes you around to multiple wineries, which will be somewhat less personalized, but give you more breadth where you`ll get to see various approaches AND usually includes transportation from and to Florence.
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The experience was highly personal and intimate, and we gained significant knowledge about cultivating grapes (and olives) in the Chianti region.
We would strongly advise visiting it, and the welcoming part is that it`s easily accessible from Florence where the hosts can help you figure out transportation options, like station pickup.
Regarding the alternative option involving visiting multiple wineries with provided transportation to and from Florence, this highly rated excursion incorporates a wine expert.
You`ll visit three wineries, all closed for public access, indicating it is a unique experience as the host clearly has relationships with those specific wineries.
If you want to see more of Chianti, including the super charming Badia a Passignano, we’d go with this guided tour.
Day Trip 3: Lucca For the Views
You may have anticipated observing Pisa somewhere on this rundown of day trips from Florence, and we’re here to tell you that while, indeed, the leaning tower is somewhat cool, we would absolutely suggest avoiding Pisa (which is swarmed past belief with individuals needing to see the recently referenced tilting tower) and heading to Lucca rather.
There are a couple of reasons we love Lucca.
Firstly, remnants of the medieval walls completely encircle the city, still intact. It’s well worth traversing the entire loop on foot, where you’ll gain nice perspectives of the city and the surrounding mountains from above.
With all the hotels and beaches at Rincón, visitors seeking time near the sea have easy access to transition between the shore and bars where they can enjoy tropical drinks while watching the sun lower in the sky.
During a day excursion to Lucca, one may choose to spend time circumnavigating the historic city walls, ascending the tower for panoramic views, and savoring some local Luccan cuisine for a midday meal (such as at Trattoria L` Angolo Tondo, conveniently located on Piazza dell`Anfiteatro where a Roman amphitheater was once situated), distinguished from Florentine fare owing to Lucca`s proximity to the coast, lending itself to fresher seafood options.
How to arrive: Regional trains run frequently between Florence`s main station, Santa Maria Novella, and Lucca, taking approximately an hour and a half. They`re very affordable for transport between the two cities.
Bologna: Days 8 & 9
You may be somewhat taken aback to see Bologna on this itinerary, since it’s not exactly renowned as one of the “must-see” cities in Italy. However, we’re here to tell you that it absolutely should be on your list, particularly if you love food.
One of the most compelling parts of visiting Italy is having expectations about “Italian” cuisine entirely transformed.
Here, Italian food (now knowing Italian–American is separate) involves dense sauces with lots of garlic, garlic bread, and chicken parmigiana.
The truth is that Italian food culture differs vastly from region to region, and relies heavily on the fresh ingredients available in close proximity.
For example, in Sicily, you’ll find lots of fresh seafood because you’re on an island and are continuously near the shoreline. In Tuscany, it’s olives, wild boar, and sheep cheese (pecorino) because those are the ingredients that are readily accessible.
If making us choose our preferred Italian cuisine region, we’d select Emilia-Romagna, where you’ll find Bologna.
Here’s an exercise: write down your five favorite Italian ingredients (rather than dishes). Chances are at least one of the things you listed comes from Bologna’s region, Emilia-Romagna.
There`s good reason the city is known as “La Grassa” (“the plump one”). It`s about as close to heaven for foodies as you can get.
There are, of course, other aspects we truly appreciate about Bologna. It’s a city of towers overlooking the distinctive reddish brick buildings (most are only facades, though).
It’s a University town (one of its other nicknames is “La Dotta” which means “the learned one”) and it has a distinctly younger vibe than just about any other major city in Italy. There are far fewer tourists than any other city you’ll visit.
And the country has very good transportation options that connect to almost every part of Italy.
We think you should spend three nights in Bologna, using one of those nights to do a day trip up to Verona, which is another one of our favorite cities in Italy.
What to Do in Bologna
Here are a few of our favorite things to do in Bologna. For more details, please check our guide about spending a day in Bologna
Ascend the Asinelli Tower for Stunning Views. We know friends residing in Bologna, and on our first visit there, this was one of their first outings with us. It`s a long climb upwards, but ultimately you`ll reach the top of the taller of the Due Torre towers, where expansive views of Bologna await. Book advance tickets for a time slot.
Surpass your expectations. Mortadella and stuffed pastas like tortelloni originate from Bologna, but the more extensive region is home to virtually every delectable food we relate to Italy. Parmesan, balsamic vinegar, prosciutto di Parma, lambrusco, and ragu alla bolognese. Go to any of the locations in Quadrilatero, which is right off of Piazza Maggiore, to taste and shop. Particularly, we like Tamburini for tagliere (a plate of meats and cheeses) and a glass of wine (lambrusco!), Cremeria la Vecchia Stalla for exceptional ice cream (which is NOT the same as gelato), and Vineria Favalli for their excellent Italian wine list.
Partake in a sustenance guided tour with a neighborhood guide. While you can completely get a sentiment for Bologna’s sustenance contributions independently, a sustenance directed tour is going to be the best way to plunge somewhat more profound. This sustenance guided tour in Bologna was on our list, yet after learning they couldn’t accommodate gluten free diets (which, truth be told, makes complete sense), we chose to forgo it.
Take time exploring Piazza Maggiore and Basilica di San Petronio. Piazza Maggiore is the pulsating core of Bologna, and is considered one of Italy`s finest squares in our view (as mentioned earlier, Siena`s Piazza del Campo closely compares). Events nearly every afternoon and evening range from rallies to concerts, and even when no formal occasions, some of Bologna`s best performers can be found on the square (along with an admiring crowd). The church is worth visiting inside, but remains partially unfinished since attempts to surpass the magnificence of St. Peter`s Basilica in Rome, who objected saying “that can`t be done.” Hence part of the facade displays bare brick where work was left unfinished, in contrast to the covered sections of polished marble.”
Gain altitude by ascending to the religious site of Santuario Madonna di San Luca. Bologna is renowned for its covered walkways known as porticoes, which enable traverses of the 666 arched passageways (an amusing numerical reference) to reach this hilltop church. According to close acquaintances from Bologna, this destination merits foremost recommendation.
Where to Stay in Bologna
There is no uncertainty in our minds – you should stay nearPiazza Maggiore during your time in Bologna. It is the heartbeat of the city, and will be both the most convenient and coolest place to rest your head.
I spent a few days in Bologna solo on my last trip to Italy, and stayed at Bibliò Rooms and Guesthouse. It’s essentially a small bed and breakfast taking up one floor in a residential building approximately five minutes from Piazza Maggiore.
The rooms offer ample space with cozy beds and private bathrooms, and it’s a good home base for a few nights in Bologna.
Which brings us to our second proposed location, which is Rome’s Historic Center (the Centro Storico).
While further from Bologna`s main attractions, it is a beautiful hotel with many fine amenities (a pool, a well-equipped gymnasium, a lounge, an events calendar, and table tennis, to name a few). Additionally, it`s about a five-minute walk from the train station, so is convenient in that sense.
If you’re looking for lodging, check out Canonica Suites, which is where I kind of wish we had stayed.
We have an entire guide focused on assisting you in identifying where to stay in Bologna with significantly more detail, if you want a more in-depth view of your choices.
Day Trip to Verona: Day 10
On this day, we’d highly recommend leaving your belongings in Bologna and doing a day trip up to Verona, heading back to spend the night in Bologna.
Verona is renowned for being the setting of Romeo and Juliet, but it tied with Bologna for our favorite discovery in Italy when we spent six weeks exploring the country in 2021.
One may be wondering why we’d do it this way, considering Verona is somewhat on the route to Venice (the subsequent stop in this itinerary).
The rationale is that we want you to be free of worrying about juggling your bags, and instead focus on obtaining an early train from Bologna without concerns of check-in times and baggage storage.
Take the high speed train, which takes approximately 45 minutes (book tickets in advance for cheaper fares!).
Rather than provide extensive details about what to see and do with a day trip up to Verona, we direct you to a separate blog post where we thoroughly outline exactly that. This is how we would spend a day in Verona.
Venice: Days 11-14
Venice is a place that elicits mixed emotions from us. We`ve each visited Venice previously, and in reflection, we`re truly uncertain if we necessitate another visit.
While Venice remains the best-preserved model of a canal city in Italy, it`s also essentially a scenic disaster.
The numbers are simply too great for Venice`s infrastructure to adequately accommodate, and cruise ships play a major role in the issue, with enormous tourist groups arriving for only part of a day and contributing very little to the local economy while overtaxing Venice`s facilities.
Remember in 2020 when the canals were all of a sudden empty and pristine, and the swans came back to Venice? It’s safe to say that’s over now.
However, it’s not really fair to say that visitors shouldn`t experience Venice because too many people go there.
Instead, we’d advise going to Venice, but doing so deliberately.
Spend multiple days there so you’re not anxious about the crowds and whether or not you’ll be able to do every activity. Enjoy local restaurants, and remain in Venice so that your money continues to aid the local economy.
The best way to explore Venice is not to spend a day (or less) seeing the main attractions and calling it finished.
Venice is at its best in the early morning and evening, when it’s notably less crowded. If you only spend a day in Venice, you’re likely going to miss out on that precious time spent exploring during those hours.
That’s why we’d strongly suggest allocating two and a half days in Venice, providing a couple mornings and nights to genuinely soak in the atmosphere of Venice when crowds are not wall-to-wall.
What to Do in Venice
There are a few main sights in Venice that shouldn`t be missed, and two days is more than enough time to see them. Like we said above, part of the fun of exploring Venice is wandering the canals in the early morning and evening.
Piazza San Marco is the main square in Venice, with a couple primary sights directly on the plaza.
First is the Doge’s Palace, which is a sizable Gothic building (you know because of the pointed arches) on the lagoon. Over its long history, it served as military fortification, a jail, and living quarters for the most powerful person in Venice, the Doge.
The version you see today was built in the 1100’s, and has been renovated a few times since as the needs of its inhabitants changed.
It housed the Doge of Venice (somewhat similar to a Duke, but not exactly the same) during the Republic of Venice, which lasted for over 1,000 years beginning in the 8th Century and was one of the most powerful city-states in modern day Italy for extended periods because of its location on the water.
The most ideal part about the Doge’s Palace is that it’s an awesome spot to become more acquainted with Venice’s set of experiences. For instance, I had no clue that there was a Republic of Venice, not to mention how intense they were.
You can purchase your tickets in advance here.
The second major attraction on San Marco Square is the basilica of Saint Mark (Basilica di San Marco), which is the largest church in Venice.
In a surprising twist that surprises no one, the church is attached to the Doge’s Palace, indicating the relationship between secular and religious power in Venice over the centuries. It’s located on the site of two previous churches, which is a story that you hear repeatedly again at some of Italy’s largest and most important churches.
Similar to other churches in Italy, it was constructed over such an extensive period that it`s one large amalgamation of architectural styles and artistic eras.
It’s an impressive building from the exterior, and the interior is unique because of the mosaics that cover nearly every surface. The Pala d’Oro, which is essentially a large golden altarpiece from the Byzantines, is also quite interesting.
Information on tickets and opening hours here.
If wanting to view both with a guided tour, we’d (again) advise doing the St. Mark’s and Doge’s Palace tour with Take Walks, who we’ve participated in multiple tours with in multiple Italian cities, and enjoy. It’s three hours in length, includes both the church and the palace, and will take you to a deeper level than just visiting independently.
The islands located north of Venice namely Burano and Murano are absolutely worthwhile to visit, and the vast majority of visitors don’t make it out there.
Glassblowing is known from these tiny islands, and they are achievable to reach via water taxi from Venice. From this ferry terminal, it`s a quick 20 minute ride over to Murano, the closer of the two islands (it`s a significantly longer boat ride out to Burano).
You can read more about things to do in Venice in our guide to spending 2 days in the city of Venice.
What to Do with More Time in Italy
If you’re blessed with more than 14 days in Italy, we have (lots of) thoughts on what to do with extra time. Whether it’s one or two days or a full extra week, we have ideas for you based on our own explorations.
Keep in mind that this is not an exhaustive list – we haven’t visited everywhere in Italy, and it’s difficult to recommend something we haven’t experienced ourselves.
For example, the Dolomites and Lake Como are on our list, but we didn’t include them below. Once we make it there, we’ll definitely add them!
You’ll notice that there`s one very popular destination missing from this list that you might be anticipating seeing: Naples, Pompeii, and the Amalfi Coast.
We debated adding it to our recommendations knowing how often others have viewed pictures of the site and wish to see it personally, but we would not choose to visit owing to overcrowding issues and related overtourism problems.
Just this past summer, we saw about 30 images of acquaintances on Instagram who all visited the Amalfi Coast within the same two month period.
Which, upon further consideration, is quite remarkable.
We trust there are preferable coastal destinations in Italy (like the Cinque Terre – that has its personal over tourism issues – and Sicily) that we’d recommend well before the Amalfi Coast. You’ll find the two of people on the listing below.
Add Another Day Trip from Bologna
The first thing we`d add if you only have an extra day or two is another night in Bologna to explore more of Emilia-Romagna.
Cities like Parma (renowned for prosciutto and parmesan-reggiano) and Modena (renowned for balsamic vinegar) are an easy train ride away, and are certainly worth spending time exploring.
We’d highly advise making a day excursion that initiates with Claudio’s trip through a functioning parmesan-reggiano dairy, which obviously incorporates a sampling of various aged parmesans, and a vacuum sealed chunk to bring back home with you.
It was an especially memorable part of our last trip, and Claudio is very friendly, charismatic, and absolutely phenomenal as a host.
That tour occurs in the morning, going until approximately noon.
We would then spend the leftover piece of the day in Modena, which is the capital of balsamic vinegar creation and is a simple 20 moment ride from the train station in Reggio-Emilia (where you’ll get dropped off by Claudio). That is what we did.
We savored sampling small production balsamic vinegar at La Consorteria 1966 (you should know that the tasting costs money unless you purchase a bottle afterwards, which are expensive because this is the good quality).
We also had multiple people recommend Osteria Francescana, which is a world-famous fine dining experience that you’ll need to book well in advance.
You can also sample chef Massimo’s cuisine at nearby Franceschetta58, which is less pricey and more accessible (you still want a reservation, though!).
Another great stop is the Mercato Storico Albinelli, which is Modena’s central marketplace.
Add Another Day Trip from Florence
The second thing we’d add is spending an additional day making an extra trip from Florence. If you took our earlier suggestion, you`ve already visited one of the three options provided. Spend another day exploring a second (or even third!) location.
Cinque Terre (2-3 Days)
For my mother`s sixtieth birthday, we took her on a two week trip to Italy. Her two must-experience activities were the Cinque Terre and seeing The Last Supper in Milan.
Therefore, we spent a few days exploring the scenic Cinque Terre region, and we really enjoyed our time there.
However, we strongly discourage a day trip to the Cinque Terre, which seemed to be what about 90% of people were attempting.
The primary reason is that it’s quite a distance from places like Florence and Milan, requiring three hours of travel time.
That means you won`t arrive until midday, which is when all the other day visitors come, and the streets and routes are crammed wall-to-wall. It`s no wonder some say it`s too crowded!
The magic of the Cinque Terre is in the early mornings and late evenings, when day visitors clear out and it becomes a tranquil, slow paced coastal retreat. That means you’ll need at minimum one night (two nights or more is preferable).
The Cinque Terre, literally translating to `Five Towns,` is a series of charming villages nestled between mountains and coast in northern Italy.
It`s known for hiking, terraced vineyards, and colorful towns perched on rocky outcroppings above the sea.
You’ll definitely want to hike along parts of the Blue Trail (we especially like the section from Corniglia to Vernazza), immerse yourself in the wines of Cinque Terre, take in superb sunset perspectives, and explore all five villages.
We have a bunch of guides dedicated to helping you plan your Cinque Terre trip. Here are some links for you:
Milan (2 Days)
Milan is a city that provides something slightly different from other major Italian cities like Rome and Florence.
That’s not to say that it’s not a historic city, but it feels less “Italian” than Rome and Florence mostly because it has been trading control between the Spanish, French, Italians, and Austrians for centuries.
There is a disparity that will be noticed immediately, likely upon exiting the train station.
Milan seems to have a more contemporary appearance and ambiance, which can be primarily attributed to its status as a core financial center where nearly every prominent fashion corporation in the country makes their headquarters.
There are two world-renowned attractions in Milan – the Duomo di Milano which took six centuries to finish and is a blend of different styles that somehow still works together, and Da Vinci’s Last Supper.
However, it’s worth lingering for an extra day to investigate some of Milan’s less famous attractions and the vibrant food and drink scene.
Roam Parco Sempione and pop into Castelo Sforza, and experience aperitivo in the Navigli District, which is home to some of Milan’s last uncovered canals (it used to look like Venice!).
Where to add it: You could either do Milan after Bologna by high speed train or after Venice potentially departing via Milan.
We have a number of guides dedicated to helping you strategy a voyage to Milan. Here are some connections for you:
- One Day in Milan: The Best of Milan in a Day
- Guide for accommodations in Milan
- The Best Things to Do in Milan
- Locations to Find the Best Specialty Coffee in Milan
- A guide for finding safe gluten free dining options in Milan for those with celiac disease
With merely a day, these are some of the best activities to do in Rome.
Sicily (7 Days)
With about a full extra week available, we would highly recommend exploring the landscape and culture of Sicily.
We enjoy Sicily greatly (Alysha’s kin originate from a little town in southeastern Sicily), and spent three weeks on the island in the fall (which somehow was still not enough time).
However, you should be aware that Sicily is enormous, making it impossible to experience the entire island thoroughly within a single week.
For that reason, we’d focus on southeastern Sicily (Catania, Mount Etna, and Syracuse). Regrettably, that means you’ll miss Palermo, which is an incredible city in northwestern Sicily.
The other reason to focus on southeastern Sicily is that public transportation connects the corridor from Taormina to Syracuse through a regional train line, which isn`t necessarily available throughout the rest of the island.
To get there, you’ll need to fly. The best place to fly into is Catania (Catania–Fontanarossa Airport).
Definitely don’t neglect a day trip from Catania up to Mount Etna, which was among the highlights of our trip (you can read about it in our guide to the best activities to do in Catania) and a trip to the amphitheater in Taormina, which has a spectacular view.
Also, consume all of the pistachio and almond granitas you are able.
We have a full guide focused on assisting with a Sicily itinerary, containing some ideas for spending 7 days on the island (By the way, we recently wrote a guide specifically for 7 days in Sicily, which is even more relevant here).
Where to add it: We’d add it after Venice, flying from Venice to Catania (which may necessitate a connection) and flying home from Catania.
What to Do with Less Time in Italy
We will not delve deeply into how to spend less time in Italy, as we have already covered this topic in some of our other guides.
We have a guide to 10 days in Italy focused on first-timers visiting Rome, Florence, and Venice, and making the most of your time in those areas.
We also have a guide to spending 7 days in Italy, which is a little different because it provides numerous ways to do a weeklong trip to Italy.
Those seeking suggestions for a brief getaway should consider reviewing those options.
When to Visit Italy
Having spent some time in Italy over two consecutive fall seasons, I’m here to tell you that it’s absolutely my favorite time to be in Italy.
Summer is problematic for two key reasons. First, the heat levels are quite intense. My initial visit to Italy in late July while in Rome proved to be uncomfortable due to this. Secondly, it`s simultaneously crowded with visitors yet relatively empty of locals who tend to use this time for vacationing elsewhere. Having both those scenarios occur simultaneously creates less than ideal circumstances. Expenses also tend to be comparatively higher during summer months.
Fall brings more moderate conditions in both regards. By late October and November toward the end of fall, it starts to get a little chilly, especially farther north. However, the months of September and October overall provide an incredibly pleasant time to be in Italy.
Winter will be chillier and gloomier, but significantly less expensive. Another thing to watch out for is certain establishments – bars, restaurants, shops, tours – closing, especially in smaller destinations highly dependent on tourism like the Cinque Terre and beach towns in Sicily.
Spring is just a hair behind fall in terms of the best time to be in Italy, and anytime between Easter and the end of May would also be an excellent balance of weather and crowds.
