Exactly How To Spend 2 Weeks In Italy

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 so 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!

Fear not, we went back for another 3-week trip to Italy in May 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), the Amalfi Coast extensively, Rome, Siena and Florence. That makes 5 weeks experience traveling through Italy 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. It’s fast and furious with lots of stops, but you can easily cut one or two places to calm this itinerary down if you’d rather go slower. Read more about us.

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Gulf Of Naples: Day 1

After flying into Naples the day before our itinerary began, we’d head straight out into the Centro Storico for the best Neapolitan pizza in Italy (we ate at Donna Sofia but there’s so many amazing options along Via dei Tribunali). If we had enough time we’d also check out the archeological museum to see tons of Pompeii artifacts, and we’d stay in the Centro Storico for easy access to the train station on day 1.

Now, the first day is all about choosing 2 of 3 options between Herculaneum, Pompeii and Vesuvius. Visiting all three sites in one day is doable but it would be a mad rush and stressful to organize because of public transport and entry tickets. Not to mention everything would have to run like clockwork – and it probably wouldn’t!

If you’re more interested in history or you don’t want to hike, visit Herculaneum ruins and Pompeii ruins. Take a train from Napoli Centrale to Ercolano Scavi, leave your luggage in storage lockers and spend a few hours walking around the ruins. Grab a fantastic pizza at Ro.Vi for lunch (it’s right outside the ruins), then get your luggage and take another train to Pompei (red line) or Pompei Santuario (green line). We love Pompeii, it’s not a tourist trap so don’t miss it – here’s a fantastic guided tour of the ruins with Walks of Italy.

The alternative is to take a train from Napoli Centrale to Pompeii, tour the ruins in the morning and then take a bus to Vesuvius in the afternoon. You must buy tickets for Vesuvius online before arriving, and the only way to reach the crater is by hiking up a steep gravel path from where the bus drops you off. 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.

Or another great option for Vesuvius is to take this top rated guided tour from Pompeii which includes transport, skip the line entrance tickets and a guided hike. It’s amazing value, so take a look at it. And another alternative if you have a bigger budget is to take this private tour that goes to Herculaneum, Vesuvius and Pompeii in one awesome day. It’s not cheap but it gets you to all three sites.

No matter which way we did those three famous sites in the Gulf of Naples, after finishing we’d take another train to Sorrento, check into our hotel and head out for dinner and a few Aperol Spritz among its lovely cobbled streets. Here are the unmissable things to do in Sorrento.

Tip: If you have more time, Sorrento is a lovely place to spend an extra day and it has amazing foodie tours like this farm and food experience with olive oil, limoncello and wine or this pizza making class with wine and limoncello tasting.

Amalfi Coast: Days 2-4

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 (here’s our guide on where to stay in Capri), skipping taxis and porter services because the prices are outrageous.

We actually spent 3 days in Capri but you’d only have time for one day on this itinerary. Capri remains one of our favorite places to visit in Italy thanks to ultra-scenic attractions like the chair lift 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. Here’s our guide on what you can’t miss in Capri to learn more. You can also buy a pdf version of our 3-day Capri itinerary if you decide to stay on the island longer.

The next morning we’d take this early ferry to Positano. Our favorite things to do in Positano were to 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 the incredible Path of Gods Trail, which is accessed via this staircase near Arienzo Beach Club or by bus to Nocelle (bus timetable). Or you could take this top rated cooking class to make your own Gnocchi and Tiramisu.

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.

Here’s our 10 days Amalfi Coast itinerary in case you want to spend more time on the coastline. And here’s our guide on the best places to stay on the Amalfi Coast to see exactly where to book your hotels.

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

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. Then we’d check into a hotel near the Pantheon (here are the most popular places to stay in Rome) and get started with Rome’s top attractions!

We think 4 days in Rome would be better, but 3 days is enough. We’d start with the Colosseum, Roman Forum and Palatine Hill (here’s a top rated guided tour with Walks of Italy). 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 fantastic pasta making class with Devour Tours in Trastevere.

The next morning we’d start with this early bird special guided walking tour of the Vatican Museums, we took this exact 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’d 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 – if sold out take a look at this guided tour). Then later in the day we’d go back into the Centro Storico for more pizza, wine and gelato. Read our guide on what it’s like to visit Rome in May if you’ll be going in the late spring.

Florence: Days 8-10

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 days in Siena and 3 days 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 those places as part of a guided tour from Florence instead.

Let’s assume you go straight from Rome to Florence on day 8. It only takes 1 hour 20 minutes by train so that allows for pretty much 3 full days in the City of Flowers. Here’s our guide on where to stay in Florence so you book a hotel in the right neighborhood.

Now, if we wanted to tick off the top things to do in Florence – we’d spend the first day doing Florence Duomo and Accademia, the second day walking around the stunning historic center and going up the Torre di Arnolfo, and the third day visiting the Uffizi, Ponte Vecchio and Piazzale Michelangelo for sunset. Here’s a top rated guided tour with Walks of Italy hitting the city’s major highlights in one day.

But we think condensing attractions and awesome foodie tours like this sunset food and wine tour in Oltrarno by Devour Tours or boozy winery tours like this one with Viator could be a more balanced way to enjoy the best of Florence. How many wine tours we could handle would depend on how bad our hangover was from the day before!

Milan: Days 11-12

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 (here’s a highly rated guided tour of the city’s top highlights and skip the line to The Last Supper with Walks of Italy).

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 bustling 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’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, and 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 few hours visiting the St Mark’s Basilica, the Doge’s Palace and the Bridge of Sighs. Here’s an award winning half day guided tour with Walks of Italy hitting the major highlights of Venice – and it 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.

Next Steps

We hope our itinerary example helps with planning your trip to Italy.

Two weeks sounds like plenty of time until you start planning – you’ll have tough choices to make. Book a 1-on-1 call with us and we’ll help you design the perfect route based on your travel pace, exactly what you want to see, and mistakes to avoid. Plan your ideal itinerary.

Still researching for your trip?

• Here are our top places to visit in Italy.
• Read our action packed 4 days in Rome itinerary.
• Don’t miss these fun things to do in Rome.
• Here’s what you can’t miss in Capri.
• This is our 10 days Amalfi Coast itinerary.
• Here’s exactly what to do in Florence.

Finally, if you’ll be visiting more places on the same trip, we recommend reading our Italy travel guide for helpful tips and advice.

Happy Travels,

Mark and Kristen

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