Exactly How We’d Spend 2 Weeks In Italy If It Was Our First Trip

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, Milan, 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 or three 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, getting time off work, trip pacing, and how much you can see.

In this guide we show you how we would plan a 14-day Italy itinerary including the Amalfi Coast if it was 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 we’ll show you how to cut one or two places to calm the itinerary down if you’d rather go slower. People travel in all kinds of ways – this is how we would tick off most of Italy’s major destinations in 2 weeks.

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Our 2-Week Italy Highlights Itinerary At A Glance: Why This Route Wins

Other than deciding on a timeframe, the major challenge we faced both times (and you’re facing right now) was deciding which places to visit in Italy. There’s almost too many excellent options, and there’s so many different ways people plan out a first time 2-week Italy itinerary. So before diving into our preferred itinerary, we want to explain why we chose this route.

First, we had to include the core of Rome, Florence and Venice because they’re the three major bucket list Italian cities. We love Rome and Florence – they’re absolute gold and deserve three days each (our Florence portion includes Tuscany), and even though we didn’t love Venice we would still 100% include it if it was our first time again. For us, Venice was a one-and-done deal, but we’re glad we saw it.

Next, we utterly adored our time hopping along the Amalfi Coast so there’s no way we’d plan a first Italy trip without including the likes of Pompeii, Sorrento, Capri and Positano. But this region comes at a cost. Not financially, but in time and effort. The Amalfi Coast is by far the hardest place on our itinerary to visit from a logistics perspective. We’ll explain more later.

Then it’s all about filling in the gaps, and for us, short stays in Milan and Lake Como make the most sense for a well-rounded first experience in Italy. Yes, that means we’re missing places like the Cinque Terre, Pisa, Lucca, Assisi, Bologna, Verona, the Alps, the Dolomites, Sardinia and Sicily. But it’s important to remember, this is a highlights itinerary. The goal is to see the most popular places, figure out which places you like or don’t like, and then fan out to the less visited spots next time. Let’s dive in.

Flights in and out of Italy: We would plan to arrive at Naples airport the day before day 1 of this itinerary, spend 14 full days on the ground, then fly out of Venice on the 15th day. But if there were no direct flights into Naples or the prices were silly, we’d fly into Rome instead, do Rome first, then take a train down to Naples and pick up the Amalfi Coast portion of the itinerary. Similarly, at the end of the trip, if Venice didn’t work for flights home, we’d go from Florence to Venice, then Venice to Milan and fly home from Milan instead.

Pompeii & Sorrento: Day 1

After landing in Naples the day before our itinerary began, we’d hope to have enough time to check out the archeological museum to see tons of original Pompeii artifacts. We did it in 2018 and it was well worth visiting. Then 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). And we’d stay at a hotel like 319 al Duomo or Amadomus Luxury Suites near the Duomo for easy access to Naples train station on day 1.

Now, the first day of our itinerary proper would be all about choosing to visit one of or a combination of Herculaneum, Pompeii and Vesuvius. Visiting all three sites in one day is technically doable but it would be a mad rush and stressful to organize because the logistics and tickets don’t sync well. Not to mention everything would have to run like clockwork – and it probably wouldn’t.

We’ve done all three sites twice, and our advice is to prioritize Pompeii ruins because it’s genuinely amazing to see. A mistake we made both times was doing Pompeii independently with audio guides. Next time we’d definitely join this top rated Pompeii tour with Walks of Italy. Then if you want to squeeze in more sites, add in Herculaneum ruins if you prefer history or Vesuvius if you enjoy hiking or want views over the Gulf of Naples.

How we’d do Herculaneum and Pompeii: Take the Circumvesuviana train from Napoli Garibaldi to Ercolano Scavi, leave our luggage in storage lockers at the station, spend 2 hours walking around Heruclaneum, grab a delicious pizza at Ro.Vi for lunch (it’s right outside the ruins), collect our luggage, take another train to Pompei Scavi (red line), spend around 4 hours exploring Pompeii, take the same Circumvesuviana train on to Sorrento.

How we’d do Pompeii and Vesuvius: Take the Circumvesuviana train from Napoli Garibaldi to Pompei Scavi, leave our luggage in storage lockers at the station, spend the morning exploring the ruins, take a local bus to Vesuvius (we’d already have pre-bought tickets to enter Vesuvius online before arriving), hike up to the crater, return to Pompeii, take the same Circumvesuviana train on to Sorrento. We found the hike easy enough but it was enough to break into a real sweat in hot weather. Oh, and the flies up there are terrible.

Another great option for hiking Vesuvius is to take this popular 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 yet another alternative that might work for bigger travel budgets is 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 the three famous sites in the Gulf of Naples, after finishing we’d arrive into Sorrento, check into a hotel like La Villetta or Elys Suites, and head out for dinner and a few Aperol Spritz among its lovely cobbled streets like Via S. Cesareo. Here’s our guide to the unmissable things to do in Sorrento to see more of the small city.

Kristen’s “easier start” tip: If that all sounded like too much effort after a long flight to Italy, we’d skip Naples and instead take a taxi straight from Naples airport to Sorrento after landing. Then on day 1 we’d just take a 30 minute train to Pompeii, tour the ruins, head back to Sorrento and join this farm and food experience with olive oil, limoncello and wine or this pizza making class with wine and limoncello tasting. We absolutely loved Sorrento so it would be nice to have enough time to soak up the fun atmosphere.

Amalfi Coast: Days 2-4

We’d get an early start on day 2, head down to the Porto di Sorrento and take a 25 minute ferry to Capri. By arriving early (before 9:00 AM), we’d avoid the chaos that takes place around Capri’s Marina Grande port each day between 10:00 AM – 2:00 PM. Trust us, it’s a mess! After arriving, we’d take the funicular up to Capri town and walk to a hotel like Hotel Mamela or Hotel la Floridiana (here’s our guide on where to stay in Capri to learn more). The cheap funicular would allow us to skip taxis and porter services with outrageous prices.

We actually spent 3 days in Capri but there’d only be time for one day on this 2-week Italy itinerary. Capri is up there with our top picks 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 we’d have to be selective with our 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, drop our bags at a hotel like Hotel Marincanto, and set off exploring. 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 highly 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). Alternatively, we’d love to take this top rated cooking class to make our own Gnocchi and Tiramisu.

We spent a night in Praiano during our Amalfi Coast trip, but it was super quiet so we’d skip it if we only had 2 weeks to see Italy. Instead, we’d take a ferry to Amalfi the next morning and drop our bags off at a hotel like Amalfi Centro. After seeing Amalfi’s Duomo and town, 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 in Ravello 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.

Mark’s Amalfi Coast alternative: A lot of the travelers Mark has helped plan Italy trips said this Amalfi Coast part of our itinerary had too much moving around for them. We totally get it. This was an amazing way to really feel and experience more of the Amalfi Coast but it was tiring. The solution is to use Sorrento as a base. We’d spend day 1 exploring Sorrento and days 2-4 taking day trips to Pompeii, Capri and Positano independently using public transport from Sorrento. And there’s tons of tours you can join from Sorrento like this popular day trip that goes to Positano, Amalfi and Ravello, or this Capri boat tour which includes time on the island.

Rome: Days 5-7

Getting to Rome from Amalfi the next morning would be a bit of a pig, so we’d get up very 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 like Albergo del Senato near the Pantheon or Dimora ai Fori near the Colosseum (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 time to see the highlights at a quick pace. So after arriving on day 5 we’d start with the Colosseum, Roman Forum and Palatine Hill (we’d love to join this special access Gladiator’s Gate tour or this cheaper express tour next time with Walks of Italy). Next we’d see Circus Maximus, the Orange Tree Garden 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 in Trastevere that we’d book next time.

On day 6 we’d join the 7:15 AM start time on this extremely popular guided tour of the Vatican Museums called “Pristine Sistine” – we took this exact tour in May 2022 and had a much better experience than when we did the Vatican ourselves in 2018. It got us inside 1 hour before public opening, but the Vatican changed it’s opening hours in 2024 so the tour now begins as the museum opens. After our Vatican tour, we’d go to Castel Sant’Angelo before exploring the super touristy Centro Storico areas like Piazza Navona, Pantheon and Trevi Fountain.

Kristen’s Vatican tour tip: Even though it now begins at public opening time, we still think the Pristine Sistine tour we took and loved is the best tour option available for visiting the Vatican because the group is among the first inside, the expert guide took us straight to the most important artworks, we got into the Sistine Chapel when it was quiet, and we took advantage of the “secret passage” between the museum and St. Peter’s Basilica which is only accessible on guided tours and saved us leaving the museum to join a 1-2 hour line for the basilica. This is the tour our friends, family and clients book.

On day 7, 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 (we’d book tickets as soon as they were released 5 weeks in advance – and if they were sold out we’d try to book 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

The Amalfi Coast is logistically challenging but Tuscany is where most people tear their hair out when planning an Italy itinerary. Is it worth doing? Is a rental car essential? Is it better to just do Florence? The answer to all those questions is it totally depends on what you want to get out of your trip.

For us in 2022, we spent 3 days in Siena relaxing and 3 days in Florence exploring non-stop. We didn’t even take a single day trip into Tuscany at all. You know why? Because eventually we’ll rent a car for a week, plot a long and slow 7-day road trip through Tuscany, throw back the local wine and take cooking classes at farmhouses. You know, do it properly.

But on a 2-week Italy highlights itinerary, we’d skip Siena and doing Tuscany independently, and go straight from Rome to Florence. Why? Because Florence is amazing. It deserves at least two full days. Plus, there’s tons of day trip tours going from Florence to wineries and foodie spots. So we’d take an early 1 hour 20 minutes high speed train straight from Rome to Florence and drop our bags at a hotel like Portanera or Hotel Calimala (here’s our guide on where to stay in Florence to see the different neighborhoods).

After arriving on day 8 we’d explore the cobblestoned historic center, see the Medici Chapels and Mercato Centrale, go up the Torre di Arnolfo for awesome Florence Duomo views, see famous tombs inside the Basilica di Santa Croce, book a late afternoon Uffizi Gallery time slot, cross the Ponte Vecchio and watch sunset from Piazzale Michelangelo. Then we’d grab dinner in the lively Santa Croce.

On day 9 we’d tick off a few more of the top things to do in Florence. We’d start with an 8:15 AM time slot at the Accademia Gallery to see David, and then we’d visit all five “extra” sites included with the Brunelleschi Pass at Florence Duomo, making sure our Dome climb time slot was booked for much later in the afternoon. Then we’d finish our day by joining this sunset food and wine tour in the trendy Oltrarno neighborhood on the south side of the Arno.

But we’d also seriously consider joining this top rated guided tour with Walks of Italy to see Florence’s top attractions in one day, which would give us a full day half way through the 2-week Italy trip to actually unwind and recharge. Florence is the perfect place to have this “rest day” too because it’s small, compact, beautiful, fun, and filled with exceptional eateries.

Then on day 10 we’d take that day trip into Tuscany to see some of those dreamy rolling hills and cypress trees. One option would be to rent a car and drive ourselves, and the other option would be to take a guided tour like this top rated Tuscany day trip. Doing it ourselves would obviously give us more flexibility to visit further out spots like Val d’Orcia and Montalcino, whereas the guided tour with Walks of Italy only visits Siena, San Gimignano and Chianti, but it would be a stress-free day with no car rental or map reading, and we could drink more wine.

Mark’s Tuscany rental car alternative: The other way we’d consider doing the Tuscany part of the trip is to rent a car in Rome (Tiburtina) early on day 8 and drop it off in Florence (Novoli) at the end of day 9 – these specific locations are by design to avoid fines in traffic congestion areas. Again, there’s so many ways to do it, but we’d go for a route along the lines of Montalcino, Val d’Orcia, Bagno Vignoni, Pienza, Montepulciano, Siena, San Gimignano, Greve in Chianti and Panzano before arriving into Florence. We’d spend the night of day 8 in either Montepulciano or Siena. Then on day 10 we’d do the Florence in a day tour with Walks of Italy so we didn’t miss anything.

Milan: Days 11-12

Early on day 11 we’d take a 1 hour 40 minute high-speed train to Milan, then hop on a yellow line metro to a hotel near the Duomo like the aptly named Duomo Hotel or Palazzo Segreti to drop our bags off. Then we’d start with Milan’s stunning Duomo. Basic entry tickets cost €22 with steps to access the terrace. That would be fine for us, but for a few euros more you can buy lift access or skip the line with lift access. There’s also an official guided tour option for €38 with lots of start times throughout the morning that we’d consider.

With just one full day in Milan we’d skip the Palazzo Reale di Milano unless we were especially interested in a specific exhibition. From the Duomo we’d walk to see the photogenic Basilica di Sant’Ambrogio before continuing our walk to the nearby Basilica di Santa Maria delle Grazie to see The Last Supper. Now, remember when we said tickets for Rome’s Borghese Gallery sold out fast? Well, The Last Supper tickets sell out even faster. They go on sale 2 months before the next “season”, so for example around mid-March tickets for May through August go on sale. We missed this during our visit, so next time we’d be ready to buy afternoon slot tickets for this date, the minute they were released.

After successfully seeing Da Vinci’s The Last Supper we’d head back towards our hotel and take a walk through the famous Galleria Vittorio Emanuele II shopping mall. There’s 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 love watch an opera at La Scala if something was on (again we’d book this long in advance).

On day 12 we’d take an easy day trip to see Lake Como. 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.

If we couldn’t be bothered with the Lake Como day trip and wanted another relaxing day in Milan, we’d start in Pinacoteca di Brera art gallery, which opens at 8:30 AM every day (closed on Mondays). This would be 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 it’s well worth it to see Michelangelo’s Pieta Rondanini sculpture. And finally, later in the day we’d join this early evening foodie tour to see a different side to Milan.

Kristen’s Milan planning tip: If tickets to see The Last Supper were sold out by the time we looked into it, we’d try to take advantage of this highly rated guided tour of Milan Duomo with skip the line tickets to The Last Supper with Walks of Italy. Even when the official site is sold out, this tour sometimes has a few tickets available but it seems like only on Thursdays and Saturdays with morning start times. We’d consider adapting our Italy itinerary to fit this iconic site in if we snagged tickets. Maybe switch the Milan day and Lake Como day trip, or even switch Venice and Milan around (as long as it worked with flights out).

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 very real downsides, we still thought it was a place that everyone should include on a first-time Italy itinerary. Why? Because it was incredibly fun to walk around, it had superb restaurants, and it had a unique “get lost among the canals” vibe that we haven’t experienced anywhere else.

So, we’d get another early start on day 13 and take the fast train for 2 hours and 15 minutes from Milan to Venice. We’d take a water boat from the train station to drop our bags at a hotel like Palazzo Veneziano or Palazzo Keller. Then we’d basically hit the canals and plot a rough path to see the Basilica di Santa Maria Gloriosa dei Frari, the Ponte di Rialto, and the Basilica Santa Maria della Salute. We’re not massively into modern art but the Peggy Guggenheim Collection would be an option, and we’d love to end the day with a show in the Teatro La Fenice (which we’d have booked in advance).

Then on the last day of our 14 day Italy itinerary we’d walk the canals to St. Mark’s Square, spend a few hours visiting St. Mark’s Basilica, the Doge’s Palace, and the Bridge of Sighs. That would be enough of the crowds for us, we thought St. Mark’s Square was a bit like Times Square but without the flashing lights. So we’d either spend the rest of the day eating and drinking around the Rialto Bridge, or we’d join this popular boat tour to Murano and Burano to see glassblowing and lace being made. Then the next morning we’d take a boat taxi straight to Venice airport and fly home.

Mark’s top Venice tour: Next time we go to Venice we will 100% join this award winning 6-hour Venice in a day tour with Walks of Italy that includes skip the line entry at St. Mark’s Basilica and Doge’s Palace, a 30-minute gondola ride, and a walk around most of Venice’s famous sites. We’d say it’s one of the best tours on the classic Italy route, and we recommend it to all our clients.

Next Steps

We hope our 2-week itinerary 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. See our reviews and schedule a video call.

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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