How many days do we need in Italy? This was the big question on our minds as we began planning our first visit back in July 2018. Mark had already done tons of trips to Italy because his dad lived in Varese for a few years, had a small boat in Sardinia and they skied in the Aosta Valley. But Kristen hadn’t been and was super excited to finally explore one of the countries that had always been near the top of her bucket list.

We would happily have done a full month, but we were traveling on a shoestring budget because Italy was just one part of our 18 month trip around the world. So we decided to balance things out by doing 2 weeks instead, which isn’t a lot of time when there are so many great places to see. And those 14 days were eaten up quickly by Pisa, Rome, Naples, Pompeii, Cinque Terre, Lake Como and Venice. Now, what’s the first thing you notice? There’s no Florence or Amalfi Coast!

This is us at the top of Monte Solaro in Capri

Fear not, we went back for another 3-week trip to Italy in 2022, and this time we had a healthier travel budget. We visited fewer places with more days, which meant staying longer in each spot with more money to actually enjoy ourselves. We did Pompeii (again), 10 days on the Amalfi Coast, Rome, Siena and Florence. So our combined Italy experience is 5 weeks at different paces with different budgets.

So how many days do you need? Well, in an ideal world you’d have 3 or even 4 weeks free to tour the country. But really, who has 4 weeks going spare? With one week you can only see two places comfortably, and while 10 days is better, it’s still not enough to cover all the must-visit spots. That leaves 2 weeks as the magic number. This timeframe strikes the best balance between expenses, pace and how much you can see.

In this guide we show you how we would plan a 14 day Italy itinerary if it were our first time visiting again, based on everything we’ve learned after spending 5 weeks in the country. Read more about us.

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Naples: Day 1

Here we are in Pompeii with Mt Vesuvius behind

After flying into Naples the day before our itinerary began, we would head straight out into the Centro Storico for the best Neapolitan pizza in Italy. We ate in Donna Sofia but there’s so many popular options along Via dei Tribunali. And if we had enough time we’d also check out the archeological museum to see tons of Pompeii artifacts.

Now, the first day is a bit chaotic but it’s honestly the best way to do this area. We’d hop on an early train to Herculaneum and arrive for opening time at 8:30am. After quickly exploring the ruins we’d take this coach at 10:00am from outside the ruins to Mt Vesuvius. The only way to reach the crater is by hiking up a steep gravel path, it’s not too hard but it’s enough to break into a real sweat in hot weather. Oh, and the flies up there are terrible, but it’s still worth going.

Once the coach dropped us back off in Herculaneum, we’d jump on another train or take a ride share to Pompeii and spend at least 3 hours walking around because it’s enormous. We love Pompeii, it’s not a tourist trap so don’t miss it. Once finished, we’d take another train to Sorrento and head out for dinner among its lovely cobbled streets.

Tip: We recommend booking entry tickets to Herculaneum, Vesuvius and Pompeii before arriving. You can visit them all individually like we did, or you can take a top rated guided tour like this one that takes you to all three places without having to figure out transport. You’d still need to buy entry tickets to the three sites, but it streamlines the day and you get a local guide.

Amalfi Coast: Days 2-4

This is Mark hiking the Path of the Gods near Praiano in the Amalfi Coast

After breakfast we’d get another early start, head down to the Porto di Sorrento and take a 25 minute ferry to Capri. And by arriving early, we’d avoid the chaos that takes place around the port each day between 10:00am-2:00pm. Trust us, it’s a mess! We’d take the funicular up to the town center and walk to our hotel, skipping taxis and porter services because the prices are outrageous.

Then we would spend a full day exploring the gorgeous island of Capri (we spent 3 days here but you’d only have time for one day). We loved the chairlift to Monte Solaro, Marina Piccola Beach, Via Krupp, Giardini di Augusto and hiking the full west side of the island from the blue grotto to Faro di Punta Carena. There’s loads to do, but you’ll have to be selective with your time.

The next morning we’d take an early ferry to Positano. This would be a more relaxing day because there’s not much to do in Positano except lounge around on the beach, walk through the shops, taste limoncello, eat great food and drink cocktails. If you’re active travelers like us, we recommend using the afternoon to hike Path of Gods which is accessed via this staircase near Arienzo Beach Club.

We spent a night in Praiano but it was super quiet so we’d skip it if we only had 2 weeks. Instead, we’d take a ferry to Amalfi the next morning. After exploring Amalfi, we’d walk through the tunnel to see Atrani then more importantly we’d take a bus up to Ravello, which we think is unmissable. Our favorite places were Villa Rufolo and Villa Cimbrone.

Tip: If you’re short on time or don’t want to deal with all the moving around, take a day trip tour like this one that goes to Positano, Amalfi and Ravello from Sorrento. You could also do a day trip to Capri from Sorrento, then get a train straight up to Rome.

Rome: Days 5-7

Here’s Kristen at the crowded Spanish Steps in Rome

Getting to Rome the next morning is a bit of a pig, so we’d get up early and just get on with it. We’d hop on a cheap bus that takes around one hour from Amalfi to Salerno and then take a train straight up to Rome, which only takes 1 hour 30 minutes. Next we’d check into a hotel near the Pantheon in Rome, or at least drop our bags off at the hotel if it’s too early to check in.

Then it’s time to start exploring the Eternal City! We’d start with the Colosseum, Roman Forum and Palatine Hill (here’s a great guided tour). Next we’d see Circo Massimo, Giardino degli Aranci and Aventine Hill. Then we’d loop around into the charming neighborhood of Trastevere for dinner, drinks and a vibrant atmosphere. Here’s a top rated food tour you could try in Trastevere.

The next morning we’d start with this early bird special guided walking tour of the Vatican Museums, we took the tour in 2022 and had a much better experience than when we did the Vatican ourselves in 2018. Afterwards, we’d go to Castel Sant’Angelo before exploring the super touristy Centro Storico areas like Piazza Navona, Pantheon and Trevi Fountain.

On our third day in Rome, we’d head north up Via del Corso towards Piazza del Popolo with a side trip to see the Spanish Steps. Next, we go up to the Terrazza del Pincio, before heading into Villa Borghese to walk around the park with the end goal of going into the Borghese Gallery (book tickets in advance). Later in the day we’d go back into the Centro Storico for more pizza, wine and gelato.

Florence: Days 8-10

This is Kristen looking at the Ponte Vecchio not long after sunrise in Florence

So far the itinerary hasn’t had any flexibility, but it becomes less rigid after Rome because there’s more than one way you can do Tuscany. In 2022, we spent 3 nights in Siena and 3 nights in Florence with day trips through the Tuscan rolling hills and wineries, but on a 2 week Italy itinerary we would skip Siena and go straight to Florence.

Why? Because there are far more tour options available from Florence going to wineries, foodie spots and Siena than there are doing the same thing starting in Siena. But it all depends on whether you hire a car or not. With a car we would drive from Rome to Siena, Monteriggioni, San Gimignano and Greve in Chianti on the way to Florence. Otherwise, we’d do them as part of a guided tour from Florence.

Let’s assume you go straight from Rome to Florence on day 8. It only takes 1 hour 20 minutes so that allows for pretty much 3 full days in the City of Flowers. We’d spend the first day walking around the stunning historic center, going up the Torre di Arnolfo, taking a self guided tour of Florence Duomo, crossing the Ponte Vecchio and watching sunset from Piazzale Michelangelo.

The second day we’d take a long tour through Tuscany, either a foodie tour like this one or a winery tour like this one. Then on the third day we’d either take another Tuscany tour with more wine or food, or we’d spend a relaxing day visiting museums and walking the cobbled streets in Florence. It would depend on how much money was left in our travel budget and how bad our hangover was from the day before!

Milan: Days 11-12

This is the famous Galleria Vittorio Emanuele II shopping arcade in Milan

Early on day 11 we’d take a 1 hour 40 minute train to Milan, hop on a yellow line metro to a hotel near the Duomo and drop our bags off. Then we’d start with a self guided tour of the Duomo and the Palazzo Reale di Milano. Next, we’d make our way over to Basilica di Sant’Ambrogio and Basilica di Santa Maria delle Grazie to see the Last Supper painting.

Later that day we’d head back near the hotel and take a walk through the famous Galleria Vittorio Emanuele II shopping mall. There’s almost a 0% chance of us buying anything from the high end designer stores, instead we’d find a top rated restaurant in the area to grab dinner and drinks. And to close out a fantastic day in style, we’d watch an opera at La Scala.

The next day we’d start in Pinacoteca di Brera art gallery, which opens at 8:30am every day (closed on Mondays). It’s a slower day so we’d take our time and enjoy the lesser known works before walking the short distance to Castello Sforzesco. The grounds are free to enjoy but there’s a small $5 fee to go inside the museum. And finally, later in the day we’d take an early evening foodie tour to see a different side to Milan.

Tip: The alternative is to combine more attractions in Milan into day 11 and then take a day trip to Lake Como on day 12. You can either do it yourself by train from Milan (don’t get off in Como, get off in Bellano and take ferries to Varenna and Bellagio) or book a guided tour like this one to Lake Como instead. We spent a few nights at a hotel in Varenna in 2018, and while it was lovely, we don’t think it’s essential on a first Italy itinerary.

Venice: Days 13-14

We took this photo of the Doge’s Palace from a boat

We’ll be totally honest, we didn’t love Venice when we spent 3 nights there in July 2018. It was hot, expensive and ridiculously overcrowded. But despite those downsides, we still think it’s a place that you just have to include when planning your first Italy itinerary. Why? Because it’s an incredibly fun place to walk around, it has superb restaurants and it has a unique buzz that you won’t get anywhere else.

So, we’d take the fast train (2 hours 15 minutes) from Milan to Venice, then check into a hotel near the Ponte di Rialto. Then we’d visit the Basilica di Santa Maria Gloriosa dei Frari and the Basilica Santa Maria della Salute, see the Peggy Guggenheim Collection and watch a show in the Teatro La Fenice.

Then on the last day of our 14 day Italy itinerary we’d start by walking the canals of Venice between Rialto Bridge and St Mark’s Square, spending a good few hours visiting the Basilica di San Marco, the Doge’s Palace and the Bridge of Sighs. Here’s a top rated half day guided tour option that hits the highlights of Venice and even includes a gondola ride.

But we wouldn’t stick around too long because St Mark’s Square is a bit like Times Square without the flashing lights. Instead, we’d take a ferry over to Lido and spend a few hours in the afternoon relaxing on the beach. Then we’d splurge on a fancy dinner with one last bottle of wine to finish the trip in style.

We hope our 2 week Italy itinerary helps with planning your trip!

Please let us know if you have any questions in the comments below.

Happy Travels,

Mark and Kristen

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Mark and Kristen spent 6 years traveling the world, visiting over 40 countries across 4 continents and more than 30 US states. They created Where Are Those Morgans in 2018 to help others plan the best possible vacations by writing authentic travel and hiking guides based on their real experiences.

Since the arrival of baby Maya in late 2024, Mark and Kristen’s extensive travels have slowed down but they still take plenty of trips. Where Are Those Morgans now helps millions of travelers each year to visit new places and hike new trails through information-packed blog posts and expert travel guidebooks. Read more about Mark and Kristen.

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